OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
8th Edition
ISBN: 9781305582439
Author: Brown, William H.; Iverson, Brent L.; Anslyn, Eric; Foote, Christopher S.
Publisher: Cengage Learning
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Textbook Question
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Chapter 2, Problem 2.28P

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

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

(a)

Expert Solution
Check Mark
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. 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. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 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. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 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. 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. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 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,

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card 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
Check Mark
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. 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. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 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. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 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. 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. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 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,

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card 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
Check Mark
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. 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. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 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. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 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. 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. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 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,

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card 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
Check Mark
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. 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. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 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. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 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. 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. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 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,

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card 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
Check Mark
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. 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. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 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. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 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. 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. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 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,

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card 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
Check Mark
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. 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. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 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. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 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. 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. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 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,

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card 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
Check Mark
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. 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. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 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. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 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. 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. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 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,

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card 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
Check Mark
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. 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. 2) For branched chain alkane, select the longest chain of carbon atoms as the parent chain, its name becomes the root name.
  3. 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. 4) Always number the parent chain in such a way that the carbon bearing substituent gets the lower number.
  5. 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. 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. 7) Alphabetize the names of the substituents first and then insert these prefixes.
  8. 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,

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card 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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Chapter 2 Solutions

OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition

Ch. 2.2 - Do the line-angle formulas in each pair represent...Ch. 2.2 - Draw line-angle formulas for the three...Ch. 2.3 - Write IUPAC names for these alkanes.Ch. 2.4 - Combine the proper prefix, infix, and suffix and...Ch. 2.4 - Write the molecular formula, IUPAC name, and...Ch. 2.4 - Write molecular formulas for each bicycloalkane,...Ch. 2.4 - Prob. 2.7PCh. 2.5 - For 1,2-dichloroethane: (a) Draw Newman...Ch. 2.5 - Following is a chair conformation of cyclohexane...Ch. 2.5 - Draw the alternative chair conformation for the...
Ch. 2.5 - Draw a chair conformation of...Ch. 2.6 - Which cycloalkanes show cis, trans isomerism? For...Ch. 2.6 - Following is a planar hexagon representation for...Ch. 2.6 - Here is one cis,trans isomer of...Ch. 2.6 - Prob. AQCh. 2.6 - Prob. BQCh. 2.6 - Prob. CQCh. 2.7 - Arrange the alkanes in each set in order of...Ch. 2 - Write a line-angle formula for each condensed...Ch. 2 - Write the molecular formula of each alkane.Ch. 2 - Using parentheses and subscripts, provide an even...Ch. 2 - Which statements are true about constitutional...Ch. 2 - Prob. 2.20PCh. 2 - Each member of the following set of compounds is...Ch. 2 - Each of the following compounds is an amine...Ch. 2 - Each of the following compounds is either an...Ch. 2 - Draw structural formulas and write IUPAC names for...Ch. 2 - Draw structural formulas for all of the following....Ch. 2 - Write IUPAC names for these alkanes and...Ch. 2 - Write structural formulas and line-angle formulas...Ch. 2 - Explain why each is an incorrect IUPAC name and...Ch. 2 - For each IUPAC name, draw the corresponding...Ch. 2 - Write the IUPAC name for each compound.Ch. 2 - Prob. 2.31PCh. 2 - Torsional strain resulting from eclipsed CH bonds...Ch. 2 - How many different staggered conformations are...Ch. 2 - Consider 1-bromopropane, CH3CH2CH2Br. (a) Draw a...Ch. 2 - Consider 1-bromo-2-methylpropane and draw the...Ch. 2 - trans-1,4-Di-tert-butylcyclohexane exists in a...Ch. 2 - From studies of the dipole moment of...Ch. 2 - Prob. 2.38PCh. 2 - Following are the alternative chair conformations...Ch. 2 - Prob. 2.40PCh. 2 - Prob. 2.41PCh. 2 - Draw line-angle formulas for the cis and trans...Ch. 2 - Name and draw structural formulas for all...Ch. 2 - Using a planar pentagon representation for the...Ch. 2 - Gibbs free energy differences between...Ch. 2 - Prob. 2.46PCh. 2 - Calculate the difference in Gibbs free energy in...Ch. 2 - Draw the alternative chair conformations for the...Ch. 2 - Use your answers from Problem 2.48 to complete the...Ch. 2 - There are four cis,trans isomers of...Ch. 2 - Draw alternative chair conformations for each...Ch. 2 - 1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans...Ch. 2 - Prob. 2.53PCh. 2 - What generalization can you make about the...Ch. 2 - What unbranched alkane has about the same boiling...Ch. 2 - Complete and balance the following combustion...Ch. 2 - Following are heats of combustion per mole for...Ch. 2 - Following are structural formulas and heats of...Ch. 2 - Without consulting tables, arrange these compounds...Ch. 2 - Which would you predict to have the larger (more...Ch. 2 - Following are structural formulas for 1,4-dioxane...Ch. 2 - Following is a planar hexagon representation of...Ch. 2 - On the left is a stereorepresentation of glucose...Ch. 2 - Prob. 2.64PCh. 2 - Prob. 2.65P
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