Explain why each is an incorrect IUPAC name and write the correct IUPAC name for the intended compound. (a) 1,3-Dimethylbutane (b) 4-Methylpentane (c) 2,2-Diethylbutane (d) 2-Ethyl-3-methylpentane (e) 2-Propylpentane (f) 2,2-Diethylheptane (g) 2,2-Dimethylcyclopropane (h) 1-Ethyl-5-methylcyclohexane

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Answer 1

Textbook Question

Chapter 2, Problem 2.28P

Explain why each is an incorrect IUPAC name and write the correct IUPAC name for the intended compound.

(a) 1,3-Dimethylbutane
(b) 4-Methylpentane
(c) 2,2-Diethylbutane
(d) 2-Ethyl-3-methylpentane
(e) 2-Propylpentane
(f) 2,2-Diethylheptane
(g) 2,2-Dimethylcyclopropane
(h) 1-Ethyl-5-methylcyclohexane

(a)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

1,3-Dimethylbutane

Correct IUPAC name:

The structure of 1,3-Dimethylbutane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 1

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

(b)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

4-Methylpentane

Correct IUPAC name:

The structure of 4-Methylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 2

The given IUPAC name is incorrect because in the above structure, the pentane is numbered wrongly.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

(c)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Diethylbutane

Correct IUPAC name:

The structure of 2,2-Diethylbutane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 3

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group and one ethyl group at the third position

Hence, the correct IUPAC name is 3-ethyl-3-methylpentane.

(d)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2-Ethyl-3-methylpentane

Correct IUPAC name:

The structure of 2-Ethyl-3-methylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 4

The given IUPAC name is incorrect because in the above structure, the longest chain is hexane.

The main carbon chain has six carbon atoms and two methyl group at the third and fourth position

Hence, the correct IUPAC name is 3,4-dimethylhexane.

(e)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituents must be chosen as parent chain.

Explanation of Solution

Given data:

2-Propylpentane

Correct IUPAC name:

The structure of 2-Propylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 5

The given IUPAC name is incorrect because in the above structure, the longest chain is heptane.

The main carbon chain has seven carbon atoms and one methyl group at the fourth position

Hence, the correct IUPAC name is 4-methylheptane.

(f)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Diethylheptane

Correct IUPAC name:

The structure of 2,2-Diethylheptane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 6

The given IUPAC name is incorrect because in the above structure, the longest chain is octane.

The main carbon chain has eight carbon atoms and one methyl group and one ethyl group are at the second carbon.

Hence, the correct IUPAC name is 3-ethyl-3-methyloctane.

(g)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Dimethylcyclopropane

Correct IUPAC name:

The structure of 2,2-Dimethylcyclopropane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 7

The ring is numbered incorrectly for the above structure.

The main core of the given compound has a cyclic three membered ring with two methyl groups at one carbon.

Hence, the correct IUPAC name is 1,1-dimethylcylcopropane.

(h)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

1-Ethyl-5-methylcyclohexane

Correct IUPAC name:

The structure of 1-Ethyl-5-methylcyclohexane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 8

The main core of the given compound has a cyclic six membered ring with one ethyl groups at first carbon and one methyl group at third carbon.

The main carbon chain has six carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 1-ethyl-3-methylcyclohexane.

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Answer 2

Textbook Question

Chapter 2, Problem 2.28P

Explain why each is an incorrect IUPAC name and write the correct IUPAC name for the intended compound.

(a) 1,3-Dimethylbutane
(b) 4-Methylpentane
(c) 2,2-Diethylbutane
(d) 2-Ethyl-3-methylpentane
(e) 2-Propylpentane
(f) 2,2-Diethylheptane
(g) 2,2-Dimethylcyclopropane
(h) 1-Ethyl-5-methylcyclohexane

(a)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

1,3-Dimethylbutane

Correct IUPAC name:

The structure of 1,3-Dimethylbutane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 1

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

(b)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

4-Methylpentane

Correct IUPAC name:

The structure of 4-Methylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 2

The given IUPAC name is incorrect because in the above structure, the pentane is numbered wrongly.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

(c)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Diethylbutane

Correct IUPAC name:

The structure of 2,2-Diethylbutane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 3

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group and one ethyl group at the third position

Hence, the correct IUPAC name is 3-ethyl-3-methylpentane.

(d)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2-Ethyl-3-methylpentane

Correct IUPAC name:

The structure of 2-Ethyl-3-methylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 4

The given IUPAC name is incorrect because in the above structure, the longest chain is hexane.

The main carbon chain has six carbon atoms and two methyl group at the third and fourth position

Hence, the correct IUPAC name is 3,4-dimethylhexane.

(e)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituents must be chosen as parent chain.

Explanation of Solution

Given data:

2-Propylpentane

Correct IUPAC name:

The structure of 2-Propylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 5

The given IUPAC name is incorrect because in the above structure, the longest chain is heptane.

The main carbon chain has seven carbon atoms and one methyl group at the fourth position

Hence, the correct IUPAC name is 4-methylheptane.

(f)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Diethylheptane

Correct IUPAC name:

The structure of 2,2-Diethylheptane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 6

The given IUPAC name is incorrect because in the above structure, the longest chain is octane.

The main carbon chain has eight carbon atoms and one methyl group and one ethyl group are at the second carbon.

Hence, the correct IUPAC name is 3-ethyl-3-methyloctane.

(g)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Dimethylcyclopropane

Correct IUPAC name:

The structure of 2,2-Dimethylcyclopropane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 7

The ring is numbered incorrectly for the above structure.

The main core of the given compound has a cyclic three membered ring with two methyl groups at one carbon.

Hence, the correct IUPAC name is 1,1-dimethylcylcopropane.

(h)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

1-Ethyl-5-methylcyclohexane

Correct IUPAC name:

The structure of 1-Ethyl-5-methylcyclohexane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 8

The main core of the given compound has a cyclic six membered ring with one ethyl groups at first carbon and one methyl group at third carbon.

The main carbon chain has six carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 1-ethyl-3-methylcyclohexane.

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Answer 3

Textbook Question

Chapter 2, Problem 2.28P

Explain why each is an incorrect IUPAC name and write the correct IUPAC name for the intended compound.

(a) 1,3-Dimethylbutane
(b) 4-Methylpentane
(c) 2,2-Diethylbutane
(d) 2-Ethyl-3-methylpentane
(e) 2-Propylpentane
(f) 2,2-Diethylheptane
(g) 2,2-Dimethylcyclopropane
(h) 1-Ethyl-5-methylcyclohexane

(a)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

1,3-Dimethylbutane

Correct IUPAC name:

The structure of 1,3-Dimethylbutane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 1

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

(b)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

4-Methylpentane

Correct IUPAC name:

The structure of 4-Methylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 2

The given IUPAC name is incorrect because in the above structure, the pentane is numbered wrongly.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

(c)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Diethylbutane

Correct IUPAC name:

The structure of 2,2-Diethylbutane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 3

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group and one ethyl group at the third position

Hence, the correct IUPAC name is 3-ethyl-3-methylpentane.

(d)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2-Ethyl-3-methylpentane

Correct IUPAC name:

The structure of 2-Ethyl-3-methylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 4

The given IUPAC name is incorrect because in the above structure, the longest chain is hexane.

The main carbon chain has six carbon atoms and two methyl group at the third and fourth position

Hence, the correct IUPAC name is 3,4-dimethylhexane.

(e)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituents must be chosen as parent chain.

Explanation of Solution

Given data:

2-Propylpentane

Correct IUPAC name:

The structure of 2-Propylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 5

The given IUPAC name is incorrect because in the above structure, the longest chain is heptane.

The main carbon chain has seven carbon atoms and one methyl group at the fourth position

Hence, the correct IUPAC name is 4-methylheptane.

(f)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Diethylheptane

Correct IUPAC name:

The structure of 2,2-Diethylheptane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 6

The given IUPAC name is incorrect because in the above structure, the longest chain is octane.

The main carbon chain has eight carbon atoms and one methyl group and one ethyl group are at the second carbon.

Hence, the correct IUPAC name is 3-ethyl-3-methyloctane.

(g)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Dimethylcyclopropane

Correct IUPAC name:

The structure of 2,2-Dimethylcyclopropane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 7

The ring is numbered incorrectly for the above structure.

The main core of the given compound has a cyclic three membered ring with two methyl groups at one carbon.

Hence, the correct IUPAC name is 1,1-dimethylcylcopropane.

(h)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

1-Ethyl-5-methylcyclohexane

Correct IUPAC name:

The structure of 1-Ethyl-5-methylcyclohexane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 8

The main core of the given compound has a cyclic six membered ring with one ethyl groups at first carbon and one methyl group at third carbon.

The main carbon chain has six carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 1-ethyl-3-methylcyclohexane.

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Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 4

Textbook Question

Chapter 2, Problem 2.28P

Explain why each is an incorrect IUPAC name and write the correct IUPAC name for the intended compound.

(a) 1,3-Dimethylbutane
(b) 4-Methylpentane
(c) 2,2-Diethylbutane
(d) 2-Ethyl-3-methylpentane
(e) 2-Propylpentane
(f) 2,2-Diethylheptane
(g) 2,2-Dimethylcyclopropane
(h) 1-Ethyl-5-methylcyclohexane

(a)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

1,3-Dimethylbutane

Correct IUPAC name:

The structure of 1,3-Dimethylbutane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 1

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

(b)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

4-Methylpentane

Correct IUPAC name:

The structure of 4-Methylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 2

The given IUPAC name is incorrect because in the above structure, the pentane is numbered wrongly.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

(c)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Diethylbutane

Correct IUPAC name:

The structure of 2,2-Diethylbutane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 3

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group and one ethyl group at the third position

Hence, the correct IUPAC name is 3-ethyl-3-methylpentane.

(d)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2-Ethyl-3-methylpentane

Correct IUPAC name:

The structure of 2-Ethyl-3-methylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 4

The given IUPAC name is incorrect because in the above structure, the longest chain is hexane.

The main carbon chain has six carbon atoms and two methyl group at the third and fourth position

Hence, the correct IUPAC name is 3,4-dimethylhexane.

(e)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituents must be chosen as parent chain.

Explanation of Solution

Given data:

2-Propylpentane

Correct IUPAC name:

The structure of 2-Propylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 5

The given IUPAC name is incorrect because in the above structure, the longest chain is heptane.

The main carbon chain has seven carbon atoms and one methyl group at the fourth position

Hence, the correct IUPAC name is 4-methylheptane.

(f)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Diethylheptane

Correct IUPAC name:

The structure of 2,2-Diethylheptane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 6

The given IUPAC name is incorrect because in the above structure, the longest chain is octane.

The main carbon chain has eight carbon atoms and one methyl group and one ethyl group are at the second carbon.

Hence, the correct IUPAC name is 3-ethyl-3-methyloctane.

(g)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Dimethylcyclopropane

Correct IUPAC name:

The structure of 2,2-Dimethylcyclopropane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 7

The ring is numbered incorrectly for the above structure.

The main core of the given compound has a cyclic three membered ring with two methyl groups at one carbon.

Hence, the correct IUPAC name is 1,1-dimethylcylcopropane.

(h)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

1-Ethyl-5-methylcyclohexane

Correct IUPAC name:

The structure of 1-Ethyl-5-methylcyclohexane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 8

The main core of the given compound has a cyclic six membered ring with one ethyl groups at first carbon and one methyl group at third carbon.

The main carbon chain has six carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 1-ethyl-3-methylcyclohexane.

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Answer 5

Textbook Question

Answer 6

Textbook Question

Answer 7

(a)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

1,3-Dimethylbutane

Correct IUPAC name:

The structure of 1,3-Dimethylbutane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 1

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

(b)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

4-Methylpentane

Correct IUPAC name:

The structure of 4-Methylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 2

The given IUPAC name is incorrect because in the above structure, the pentane is numbered wrongly.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

(c)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Diethylbutane

Correct IUPAC name:

The structure of 2,2-Diethylbutane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 3

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group and one ethyl group at the third position

Hence, the correct IUPAC name is 3-ethyl-3-methylpentane.

(d)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2-Ethyl-3-methylpentane

Correct IUPAC name:

The structure of 2-Ethyl-3-methylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 4

The given IUPAC name is incorrect because in the above structure, the longest chain is hexane.

The main carbon chain has six carbon atoms and two methyl group at the third and fourth position

Hence, the correct IUPAC name is 3,4-dimethylhexane.

(e)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituents must be chosen as parent chain.

Explanation of Solution

Given data:

2-Propylpentane

Correct IUPAC name:

The structure of 2-Propylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 5

The given IUPAC name is incorrect because in the above structure, the longest chain is heptane.

The main carbon chain has seven carbon atoms and one methyl group at the fourth position

Hence, the correct IUPAC name is 4-methylheptane.

(f)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Diethylheptane

Correct IUPAC name:

The structure of 2,2-Diethylheptane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 6

The given IUPAC name is incorrect because in the above structure, the longest chain is octane.

The main carbon chain has eight carbon atoms and one methyl group and one ethyl group are at the second carbon.

Hence, the correct IUPAC name is 3-ethyl-3-methyloctane.

(g)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Dimethylcyclopropane

Correct IUPAC name:

The structure of 2,2-Dimethylcyclopropane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 7

The ring is numbered incorrectly for the above structure.

The main core of the given compound has a cyclic three membered ring with two methyl groups at one carbon.

Hence, the correct IUPAC name is 1,1-dimethylcylcopropane.

(h)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

1-Ethyl-5-methylcyclohexane

Correct IUPAC name:

The structure of 1-Ethyl-5-methylcyclohexane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 8

The main core of the given compound has a cyclic six membered ring with one ethyl groups at first carbon and one methyl group at third carbon.

The main carbon chain has six carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 1-ethyl-3-methylcyclohexane.

Answer 8

(a)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

1,3-Dimethylbutane

Correct IUPAC name:

The structure of 1,3-Dimethylbutane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 1

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

Answer 9

(a)

Expert Solution

Answer 10

(a)

Expert Solution

Answer 11

Expert Solution

Answer 12

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Answer 13

Explanation of Solution

Given data:

1,3-Dimethylbutane

Correct IUPAC name:

The structure of 1,3-Dimethylbutane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 1

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

Answer 14

(b)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

4-Methylpentane

Correct IUPAC name:

The structure of 4-Methylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 2

The given IUPAC name is incorrect because in the above structure, the pentane is numbered wrongly.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

Answer 15

(b)

Expert Solution

Answer 16

(b)

Expert Solution

Answer 17

Expert Solution

Answer 18

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Answer 19

Explanation of Solution

Given data:

4-Methylpentane

Correct IUPAC name:

The structure of 4-Methylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 2

The given IUPAC name is incorrect because in the above structure, the pentane is numbered wrongly.

The main carbon chain has five carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 2-methylpentane.

Answer 20

(c)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Diethylbutane

Correct IUPAC name:

The structure of 2,2-Diethylbutane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 3

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group and one ethyl group at the third position

Hence, the correct IUPAC name is 3-ethyl-3-methylpentane.

Answer 21

(c)

Expert Solution

Answer 22

(c)

Expert Solution

Answer 23

Expert Solution

Answer 24

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Answer 25

Explanation of Solution

Given data:

2,2-Diethylbutane

Correct IUPAC name:

The structure of 2,2-Diethylbutane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 3

The given IUPAC name is incorrect because in the above structure, the longest chain is pentane.

The main carbon chain has five carbon atoms and one methyl group and one ethyl group at the third position

Hence, the correct IUPAC name is 3-ethyl-3-methylpentane.

Answer 26

(d)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2-Ethyl-3-methylpentane

Correct IUPAC name:

The structure of 2-Ethyl-3-methylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 4

The given IUPAC name is incorrect because in the above structure, the longest chain is hexane.

The main carbon chain has six carbon atoms and two methyl group at the third and fourth position

Hence, the correct IUPAC name is 3,4-dimethylhexane.

Answer 27

(d)

Expert Solution

Answer 28

(d)

Expert Solution

Answer 29

Expert Solution

Answer 30

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Answer 31

Explanation of Solution

Given data:

2-Ethyl-3-methylpentane

Correct IUPAC name:

The structure of 2-Ethyl-3-methylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 4

The given IUPAC name is incorrect because in the above structure, the longest chain is hexane.

The main carbon chain has six carbon atoms and two methyl group at the third and fourth position

Hence, the correct IUPAC name is 3,4-dimethylhexane.

Answer 32

(e)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituents must be chosen as parent chain.

Explanation of Solution

Given data:

2-Propylpentane

Correct IUPAC name:

The structure of 2-Propylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 5

The given IUPAC name is incorrect because in the above structure, the longest chain is heptane.

The main carbon chain has seven carbon atoms and one methyl group at the fourth position

Hence, the correct IUPAC name is 4-methylheptane.

Answer 33

(e)

Expert Solution

Answer 34

(e)

Expert Solution

Answer 35

Expert Solution

Answer 36

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituents must be chosen as parent chain.

Answer 37

Explanation of Solution

Given data:

2-Propylpentane

Correct IUPAC name:

The structure of 2-Propylpentane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 5

The given IUPAC name is incorrect because in the above structure, the longest chain is heptane.

The main carbon chain has seven carbon atoms and one methyl group at the fourth position

Hence, the correct IUPAC name is 4-methylheptane.

Answer 38

(f)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Diethylheptane

Correct IUPAC name:

The structure of 2,2-Diethylheptane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 6

The given IUPAC name is incorrect because in the above structure, the longest chain is octane.

The main carbon chain has eight carbon atoms and one methyl group and one ethyl group are at the second carbon.

Hence, the correct IUPAC name is 3-ethyl-3-methyloctane.

Answer 39

(f)

Expert Solution

Answer 40

(f)

Expert Solution

Answer 41

Expert Solution

Answer 42

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Answer 43

Explanation of Solution

Given data:

2,2-Diethylheptane

Correct IUPAC name:

The structure of 2,2-Diethylheptane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 6

The given IUPAC name is incorrect because in the above structure, the longest chain is octane.

The main carbon chain has eight carbon atoms and one methyl group and one ethyl group are at the second carbon.

Hence, the correct IUPAC name is 3-ethyl-3-methyloctane.

Answer 44

(g)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

2,2-Dimethylcyclopropane

Correct IUPAC name:

The structure of 2,2-Dimethylcyclopropane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 7

The ring is numbered incorrectly for the above structure.

The main core of the given compound has a cyclic three membered ring with two methyl groups at one carbon.

Hence, the correct IUPAC name is 1,1-dimethylcylcopropane.

Answer 45

(g)

Expert Solution

Answer 46

(g)

Expert Solution

Answer 47

Expert Solution

Answer 48

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Answer 49

Explanation of Solution

Given data:

2,2-Dimethylcyclopropane

Correct IUPAC name:

The structure of 2,2-Dimethylcyclopropane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 7

The ring is numbered incorrectly for the above structure.

The main core of the given compound has a cyclic three membered ring with two methyl groups at one carbon.

Hence, the correct IUPAC name is 1,1-dimethylcylcopropane.

Answer 50

(h)

Expert Solution

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Explanation of Solution

Given data:

1-Ethyl-5-methylcyclohexane

Correct IUPAC name:

The structure of 1-Ethyl-5-methylcyclohexane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 8

The main core of the given compound has a cyclic six membered ring with one ethyl groups at first carbon and one methyl group at third carbon.

The main carbon chain has six carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 1-ethyl-3-methylcyclohexane.

Answer 51

(h)

Expert Solution

Answer 52

(h)

Expert Solution

Answer 53

Expert Solution

Answer 54

Interpretation Introduction

Interpretation:

The reason for the incorrect IUPAC name of the given compound has to be explained also the correct IUPAC name for the intended compound has to be given.

Concept Introduction:

IUPAC nomenclature:

The rules for writing IUPAC system of names is as follows,

1) For an alkane with unbranched chain of carbon atoms, prefix the root word showing the number of carbon atoms ad end the name with –ane.
2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
3) Number all the carbon atoms in the parent chain. When a substituent is attached to the chain, the number shows the carbon atom to which the substituent is attached. Use a hyphen in the name to connect the number to the substituent name.
4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
5) If a same substituent is present more than one time, then number the parent chain in such a way that the first encountered substituent gets the lowest number. Prefix di-, tri-, tetra-, penta- and so on to indicate the number of times the substituent occurs. A comma is used to separate position numbers.
6) If there are two or more different substituents, list them in alphabetical order and number the chain from the end that gives the lower number to the substituent encountered first. If there are different substituents in equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.
7) Alphabetize the names of the substituents first and then insert these prefixes.
8) Where two or more parent chains of identical lengths are present, the chain with greater number of substituent must be chosen as parent chain.

Answer 55

Explanation of Solution

Given data:

1-Ethyl-5-methylcyclohexane

Correct IUPAC name:

The structure of 1-Ethyl-5-methylcyclohexane is,

Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition, Chapter 2, Problem 2.28P , additional homework tip 8

The main core of the given compound has a cyclic six membered ring with one ethyl groups at first carbon and one methyl group at third carbon.

The main carbon chain has six carbon atoms and one methyl group at the second position

Hence, the correct IUPAC name is 1-ethyl-3-methylcyclohexane.