ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 4, Problem 4.38P

Give the IUPAC name for each compound.

a. Chapter 4, Problem 4.38P, 4.38 Give the IUPAC name for each compound.
a. c. e. g. i. 
b. d. f. h. j. 
 , example  1c. Chapter 4, Problem 4.38P, 4.38 Give the IUPAC name for each compound.
a. c. e. g. i. 
b. d. f. h. j. 
 , example  2e. Chapter 4, Problem 4.38P, 4.38 Give the IUPAC name for each compound.
a. c. e. g. i. 
b. d. f. h. j. 
 , example  3g. Chapter 4, Problem 4.38P, 4.38 Give the IUPAC name for each compound.
a. c. e. g. i. 
b. d. f. h. j. 
 , example  4i. Chapter 4, Problem 4.38P, 4.38 Give the IUPAC name for each compound.
a. c. e. g. i. 
b. d. f. h. j. 
 , example  5

b. Chapter 4, Problem 4.38P, 4.38 Give the IUPAC name for each compound.
a. c. e. g. i. 
b. d. f. h. j. 
 , example  6d. Chapter 4, Problem 4.38P, 4.38 Give the IUPAC name for each compound.
a. c. e. g. i. 
b. d. f. h. j. 
 , example  7f. Chapter 4, Problem 4.38P, 4.38 Give the IUPAC name for each compound.
a. c. e. g. i. 
b. d. f. h. j. 
 , example  8h. Chapter 4, Problem 4.38P, 4.38 Give the IUPAC name for each compound.
a. c. e. g. i. 
b. d. f. h. j. 
 , example  9j. Chapter 4, Problem 4.38P, 4.38 Give the IUPAC name for each compound.
a. c. e. g. i. 
b. d. f. h. j. 
 , example  10

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The IUPAC name for the given compound is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

2. The next step is to identify the groups attached to the longest chain.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

Answer to Problem 4.38P

The IUPAC name for the given compound is 6isopropyl3methyldecane.

Explanation of Solution

The given compound is,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  1

Figure 1

The number of carbon atoms present in longest carbon chain is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  2

Figure 2

The longest carbon chain has ten carbon atoms. The root word used for ten carbon atoms is dec and the suffix used for CC linkage is –ane. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One isopropyl substituents is attached to the sixth carbon atom and one methyl substituent is attached to third position. Thus, the IUPAC name of the given structure is 6isopropyl3methyldecane.

Conclusion

The IUPAC name for the given compound is 6isopropyl3methyldecane.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The IUPAC name for the given compound is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing IUPAC name from structural formula are

1. First identify the longest carbon chain.

2. The next step is to identify the groups attached to the longest chain.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

Answer to Problem 4.38P

The IUPAC name for the given compound is 8ethyl4isopropyl2,6dimethyldecane.

Explanation of Solution

The given compound is,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  3

Figure 3

The number of carbon atoms present in longest carbon chain of the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  4

Figure 4

The longest carbon chain has ten carbon atoms. The root word used for ten carbon atoms is dec and the suffix used for CC linkage is –ane. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One isopropyl substituent is attached to the fourth carbon atom; two methyl substituents are attached to the second and sixth carbon atom, and one ethyl group is present at eighth carbon atom. Thus, the IUPAC name of the given structure is 8ethyl4isopropyl2,6dimethyldecane.

Conclusion

The IUPAC name for the given compound is 8ethyl4isopropyl2,6dimethyldecane.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The IUPAC name for the given compound is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

2. The next step is to identify the groups attached to the longest chain.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

Answer to Problem 4.38P

The IUPAC name for the given compound is 3ethyl3,4dimethyl5propyloctane.

Explanation of Solution

The given compound is,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  5

Figure 5

The number of carbon atoms present in longest carbon chain of the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  6

Figure 6

The longest carbon chain has eight carbon atoms. The root word used for eight carbon atoms is oct and the suffix used for CC linkage is –ane. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One ethyl substituents is attached to the third carbon atom, one methyl substituent is attached to third and fourth carbon atom, and one propyl substituent is attached to fifth position. Thus, the IUPAC name of the given structure is 3ethyl3,4dimethyl5propyloctane.

Conclusion

The IUPAC name for the given compound is 3ethyl3,4dimethyl5propyloctane.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The IUPAC name for the given compound is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

2. The next step is to identify the groups attached to the longest chain.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

Answer to Problem 4.38P

The IUPAC name for the given compound is 3,3,6triethyl7methylnonane.

Explanation of Solution

The given compound is,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  7

Figure 7

The number of carbon atoms present in longest carbon chain of the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  8

Figure 8

The longest carbon chain has nine carbon atoms. The root word used for nine carbon atoms is non and the suffix used for CC linkage is –ane. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One methyl substituents is attached to the seventh carbon atom and two ethyl substituents are attached to third carbon atom and one ethyl substituent is attached to sixth carbon atom. Thus, the IUPAC name of the given structure is 3,3,6triethyl7methylnonane.

Conclusion

The IUPAC name for the given compound is 3,3,6triethyl7methylnonane.

Expert Solution
Check Mark
Interpretation Introduction

(e)

Interpretation: The IUPAC name for the given compound is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

2. The next step is to identify the groups attached to the longest chain.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

Answer to Problem 4.38P

The IUPAC name for the given compound is 3cyclobutylpentane.

Explanation of Solution

The given compound is,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  9

Figure 9

The number of carbon atoms present in longest carbon chain of the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  10

Figure 10

The longest carbon chain has five carbon atoms. The root word used for five carbon atoms is pent and the suffix used for CC linkage is –ane. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One cyclobutyl substituents is attached to the third carbon atom. Thus, the IUPAC name of the given structure is 3cyclobutylpentane.

Conclusion

The IUPAC name for the given compound is 3cyclobutylpentane.

Expert Solution
Check Mark
Interpretation Introduction

(f)

Interpretation: The IUPAC name for the given compound is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

2. The next step is to identify the groups attached to the longest chain.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

Answer to Problem 4.38P

The IUPAC name for the given compound is 1(secbutyl)2isopropylcyclopentane.

Explanation of Solution

The given compound is,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  11

Figure 11

The number of carbon atoms present in longest carbon chain of the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  12

Figure 12

The longest carbon chain has five carbon atoms. The root word used for five carbon atoms is pent and the suffix used for CC linkage is –ane. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One isopropyl substituents is attached to the second carbon atom and one secondary butyl substituent is attached to first carbon atom. Thus, the IUPAC name of the given structure is 1(secbutyl)2isopropylcyclopentane.

Conclusion

The IUPAC name for the given compound is 1(secbutyl)2isopropylcyclopentane.

Expert Solution
Check Mark
Interpretation Introduction

(g)

Interpretation: The IUPAC name for the given compound is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing IUPAC name from structural formula are

1. First identify the longest carbon chain.

2. The next step is to identify the groups attached to the longest chain.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

Answer to Problem 4.38P

The IUPAC name for the given compound is 1isobutyl3isopropylcyclohexane.

Explanation of Solution

The given compound is,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  13

Figure 13

The number of carbon atoms present in longest carbon chain of the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  14

Figure 14

The longest carbon chain has six carbon atoms. The root word used for six carbon atoms is hex and the suffix used for CC linkage is –ane. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One isobutyl substituents is attached to the first carbon atom and one isopropyl substituent is attached to third position. Thus, the IUPAC name of the given structure is 1isobutyl3isopropylcyclohexane.

Conclusion

The IUPAC name for the given compound is 1isobutyl3isopropylcyclohexane.

Expert Solution
Check Mark
Interpretation Introduction

(h)

Interpretation: The IUPAC name for the given compound is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing IUPAC name from structural formula are

1. First identify the longest carbon chain.

2. The next step is to identify the groups attached to the longest chain.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

Answer to Problem 4.38P

The IUPAC name for the given compound is 5isobutyl4isopropyl2methyl6propyldecane.

Explanation of Solution

The given compound is,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  15

Figure 15

The number of carbon atoms present in longest carbon chain of the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  16

Figure 16

The longest carbon chain has ten carbon atoms. The root word used for ten carbon atoms is dec and the suffix used for CC linkage is –ane. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One isopropyl substituents is attached to the fourth carbon atom, one isobutyl substituent is attached to fifth carbon atom, one methyl substituent is attached to second carbon atom, isopropyl substituent is attached to fourth carbon atom, and one propyl substituent is attached to sixth carbon atom. . Thus, the IUPAC name of the given structure is 5isobutyl4isopropyl2methyl6propyldecane.

Conclusion

The IUPAC name for the given compound is 5isobutyl4isopropyl2methyl6propyldecane.

Expert Solution
Check Mark
Interpretation Introduction

(i)

Interpretation: The IUPAC name for the given compound is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

2. The next step is to identify the groups attached to the longest chain.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

Answer to Problem 4.38P

The IUPAC name for the given compound is 5(secbutyl)5ethyl1,1dimethylcyclohexane.

Explanation of Solution

The given compound is,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  17

Figure 17

The number of carbon atoms present in longest carbon chain of the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  18

Figure 18

The longest carbon chain has six carbon atoms. The root word used for six carbon atoms is hex and the suffix used for CC linkage is –ane. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One secondary butyl substituents is attached to the second carbon atom, one ethyl substituent is attached to fifth carbon atom, and two methyl substituents are attached to first carbon atom. Thus, the IUPAC name of the given structure is 5(secbutyl)5ethyl1,1dimethylcyclohexane.

Conclusion

The IUPAC name for the given compound is 5(secbutyl)5ethyl1,1dimethylcyclohexane.

Expert Solution
Check Mark
Interpretation Introduction

(j)

Interpretation: The IUPAC name for the given compound is to be stated.

Concept introduction: The systematic naming of organic compound is given by IUPAC nomenclature. The naming of organic compound is done such that the structure of organic compound is correctly interpreted from the name.

Rules for writing IUPAC name from structural formula are:

1. First identify the longest carbon chain.

2. The next step is to identify the groups attached to the longest chain.

3. Identify the position, location, and number of the substituent bonded to the carbon chain.

4. Use prefix di, tri, tetra if same type of substituent is present.

5. Name the substituents in alphabetical order.

Answer to Problem 4.38P

The IUPAC name for the given compound is 8,9diethyl7isopropyl4methyltridecane.

Explanation of Solution

The given compound is,

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  19

Figure 19

The number of carbon atoms present in longest carbon chain of the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 4, Problem 4.38P , additional homework tip  20

Figure 20

The longest CC chain has thirteen carbon atoms. The root word used for thirteen carbon atoms is tridec and the suffix used for CC linkage is –ane. The hydrocarbons that are attached to the longest chain are called substituents and they are written as prefix in alphabetical order. One isopropyl substituents is attached to the seventh carbon atom, one ethyl substituent is attached to each eighth and ninth carbon atom, one methyl substituent is attached to fourth carbon atom. Thus, the IUPAC name of the given structure is 8,9diethyl7isopropyl4methyltridecane.

Conclusion

The IUPAC name for the given compound is 8,9diethyl7isopropyl4methyltridecane.

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Chapter 4 Solutions

ORGANIC CHEMISTRY

Ch. 4 - Give the IUPAC name for each compound.Ch. 4 - Give the structure corresponding to each IUPAC...Ch. 4 - Arrange the following compounds in order of...Ch. 4 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4 - Prob. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Problem 4.17 a. Draw the three staggered and...Ch. 4 - Problem 4.18 Rank the following conformations in...Ch. 4 - Problem 4.19 Consider rotation around the...Ch. 4 - Calculate the destabilization present in each...Ch. 4 - Problem 4.21 Classify the ring carbons as up or...Ch. 4 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4 - Draw a second chair conformation for each...Ch. 4 - Problem 4.24 Draw both conformations for and...Ch. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.27PCh. 4 - Problem 4.28 Consider . Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.30PCh. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - 4.38 Give the IUPAC name for each compound. a. c....Ch. 4 - 4.39 Give the structure and IUPAC name for each of...Ch. 4 - 4.40 Draw the structure corresponding to each...Ch. 4 - Prob. 4.41PCh. 4 - 4.42 Give the IUPAC name for each compound. a....Ch. 4 - Prob. 4.43PCh. 4 - Prob. 4.44PCh. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - 4.46 Considering rotation around the bond...Ch. 4 - Prob. 4.47PCh. 4 - 4.48 (a) Using Newman projections, draw all...Ch. 4 - 4.49 Label the sites of torsional and steric...Ch. 4 - 4.50 Calculate the barrier to rotation for each...Ch. 4 - 4.51 The eclipsed conformation of is less...Ch. 4 - (a) Draw the anti and gauche conformations for...Ch. 4 - For each compound drawn below: a.Label each OH,Br...Ch. 4 - Draw the two possible chair conformations for...Ch. 4 - For each compound drawn below: a. Draw...Ch. 4 - 4.56 Convert each of the following structures into...Ch. 4 - Prob. 4.57PCh. 4 - Prob. 4.58PCh. 4 - 4.59 Classify each pair of compounds as...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.61PCh. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.63PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.69PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.71PCh. 4 - Prob. 4.72PCh. 4 - Consider the tricyclic structure B (a) Label each...Ch. 4 - Read Appendix B on naming branched alkyl...Ch. 4 - Read Appendix B on naming bicyclic compounds. Then...
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