Chapter 20.SE, Problem 32AP

Interpretation Introduction

a) cis-1,2-Cyclohexanedicarboxylic acid

Interpretation:

The structure of cis-1,2-cyclohexanedicarboxylic acid is to be given.

Concept introduction:

The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C₁, instead the carbon to which it is attached is numbered as C₁. As a substituent, the –COOH group is called as carboxyl group.

To give:

The structure of cis-1,2-cyclohexanedicarboxylic acid.

Answer to Problem 32AP

The structure of cis-1,2-cyclohexanedicarboxylic acid is

Explanation of Solution

The name shows that the compound has a cyclohexane ring with two carboxylic acid groups in 1,2 positions arranged in the same side of the ring.

Conclusion

The structure of cis-1,2-cyclohexanedicarboxylic acid is

Interpretation Introduction

b) Heptanedioic acid

Interpretation:

The structure of heptanedioic acid is to be given.

Concept introduction:

The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C₁, instead the carbon to which it is attached is numbered as C₁. As a substituent, the –COOH group is called as carboxyl group.

To give:

The structure of heptanedioic acid.

Answer to Problem 32AP

The structure of heptanedioic acid is

Explanation of Solution

The name shows that the compound has a seven carbon straight chain with two carboxyl groups at theb ends.

Conclusion

The structure of heptanedioic acid is

Interpretation Introduction

c) 2-Hexen-4-ynoic acid

Interpretation:

The structure of 2-hexen-4-ynoic acid is to be given.

Concept introduction:

The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C₁, instead the carbon to which it is attached is numbered as C₁. As a substituent, the –COOH group is called as carboxyl group.

To give:

The structure of 2-hexen-4-ynoic acid.

Answer to Problem 32AP

The structure of 2-hexen-4-ynoic acid is

Explanation of Solution

The name shows that the compound has a six carbon straight chain with a carboxylic group, a double bond between C₂ & C₃ and a triple bond between C₄ & C₅.

Conclusion

The structure of 2-hexen-4-ynoic acid is

Interpretation Introduction

d) 4-Ethyl-2-propyloctanoic acid

Interpretation:

The structure of 4-ethyl-2-propyloctanoic acid is to be given.

Concept introduction:

The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C₁, instead the carbon to which it is attached is numbered as C₁. As a substituent, the –COOH group is called as carboxyl group.

To give:

The structure of 4-ethyl-2-propyloctanoic acid.

Answer to Problem 32AP

The structure of 4-ethyl-2-propyloctanoic acid is

Explanation of Solution

The name shows that the compound is an octane derivative and has a carboxyl group, a propyl group on C₂ and an ethyl group on C₄.

Conclusion

The structure of 4-ethyl-2-propyloctanoic acid is

Interpretation Introduction

e) 3-Chlorophthalic acid

Interpretation:

The structure of 3-chlorophthalic acid is to be given.

Concept introduction:

The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C₁, instead the carbon to which it is attached is numbered as C₁. As a substituent, the –COOH group is called as carboxyl group.

To give:

The structure of 3-chlorophthalic acid.

Answer to Problem 32AP

The structure of 3-chlorophthalic acid is

Explanation of Solution

The name indicates that the compound is a benzene derivative with two carboxyl groups on C₁ & C₂ and a chlorine atom on C₃.

Conclusion

The structure of 3-chlorophthalic acid is

Interpretation Introduction

f) Triphenylacetic acid

Interpretation:

The structure of triphenylacetic acid is to be given.

Concept introduction:

The names of simple carboxylic acids which are derivatives of open-chain alkanes are arrived by replacing the terminal –e of the corresponding alkane name by –oic acid. The numbering starts from carboxyl carbon. Compounds with –COOH bonded to a ring are named using the suffix-carboxylic acid. The –COOH carbon in this case is not numbered as C₁, instead the carbon to which it is attached is numbered as C₁. As a substituent, the –COOH group is called as carboxyl group.

To give:

The structure of triphenylacetic acid.

Answer to Problem 32AP

The structure of triphenylacetic acid is

Explanation of Solution

The structure of acetic acid is CH₃COOH. The name of the compound given indicates that it has three phenyl groups instead of the three hydrogen atoms present in methyl group in acetic acid.

Conclusion

The structure of triphenylacetic acid is

Interpretation Introduction

g) 2-Cyclobutenecarbonitrile

Interpretation:

The structure of 2-cyclobutenecarbonitrile is to be given.

Concept introduction:

Simple open chain nitriles are named by adding –nitrile as suffix to the alkane name, with the nitrile carbon numbered as C₁. Nitriles can also be names as derivatives of carboxylic acids by replacing the –ic acid or –oic acid ending with –onitrile. The nitrile carbon is not numbered but the carbon to which it is attached is numbered ac C₁. If another carboxylic acid derivative is present in the same molecule, the prefix –cyano is used for the –CN group.

To give:

The structure of 2-cyclobutenecarbonitrile.

Answer to Problem 32AP

The structure of 2-cyclobutenecarbonitrile is

Explanation of Solution

The name shows that the compound has a nitrile group attached to a cyclobutene ring with a double bond between C₂ & C₃.

Conclusion

The structure of 2-cyclobutenecarbonitrile is

Interpretation Introduction

h) m-Benzoylbenzonitrile

Interpretation:

The structure of m-benzoylbenzonitrile is to be given.

Concept introduction:

Simple open chain nitriles are named by adding –nitrile as suffix to the alkane name, with the nitrile carbon numbered as C₁. Nitriles can also be names as derivatives of carboxylic acids by replacing the –ic acid or –oic acid ending with –onitrile. The nitrile carbon is not numbered but the carbon to which it is attached is numbered ac C₁. If another carboxylic acid derivative is present in the same molecule, the prefix –cyano is used for the –CN group.

To give:

The structure of m-benzoylbenzonitrile.

Answer to Problem 32AP

The structure of m-benzoylbenzonitrile is

Explanation of Solution

The name shows that the compound has a benzene ring attached to a nitrile group and a benzoyl group with meta relationship.

Conclusion

The structure of m-benzoylbenzonitrile is