Chapter 18, Problem 18.12P

(a)

Interpretation Introduction

Interpretation:

The structural formula for the given compound has to be drawn.

Concept introduction:

Nomenclature of esters of carboxylic acids:

The acyl group bonded to $\text{-OR}\text{or}\text{OAr}$ is the functional group of a carboxylic ester.

The naming of an ester of a carboxylic acid is done by naming alkyl or aryl group bonded to oxygen first followed by the name of the acid in which the suffix –ic acid is replaced by the suffix –ate.

Explanation of Solution

The name of the compound is given below:

Dimethyl carbonate

From the name, it is clear that two methyl groups are attached to oxygen atoms in the compound and the parent ester group is carbonate.

Thus, the structure of the compound is given below:

(b)

Interpretation Introduction

Interpretation:

The structural formula for the given compound has to be drawn.

Concept introduction:

Nomenclature of nitriles:

The numbering 1 can be given to the nitrile carbon atom and add nitrile to end of the alkane or aryl chain.

Explanation of Solution

The name of the compound is given below:

The functional group is nitrile and benzene ring is attached to it.

Thus, the structure of the compound is given below:

Benzo nitrile

(c)

Interpretation Introduction

Interpretation:

The structural formula for the given compound has to be drawn.

Concept introduction:

Nomenclature of esters of carboxylic acids:

The acyl group bonded to $\text{-OR}\text{or}\text{OAr}$ is the functional group of a carboxylic ester.

The naming of an ester of a carboxylic acid is done by naming alkyl or aryl group bonded to oxygen first followed by the name of the acid in which the suffix –ic acid is replaced by the suffix –ate.

Explanation of Solution

The name of the compound is given below:

Isopropyl-3-methylhexanoate

The alkyl group attached on oxygen atom is the isopropyl group and the parent chain is the methylhexanoate.

Thus, the structure of the compound is given below:

(d)

Interpretation Introduction

Interpretation:

The structural formula for the given compound has to be drawn.

Concept introduction:

Nomenclature of esters of carboxylic acids:

The acyl group bonded to $\text{-OR}\text{or}\text{OAr}$ is the functional group of a carboxylic ester.

The naming of an ester of a carboxylic acid is done by naming alkyl or aryl group bonded to oxygen first followed by the name of the acid in which the suffix –ic acid is replaced by the suffix –ate.

Explanation of Solution

The name of the compound is given below:

Diethyl oxalate

From the name, it is clear that two ethyl groups are attached to oxygen atoms in the compound and the parent ester group is oxalate.

Thus, the structure of the compound is given below:

(e)

Interpretation Introduction

The structural formula for the given compound has to be drawn.

Concept introduction:

Nomenclature of esters of carboxylic acids:

The acyl group bonded to $\text{-OR}\text{or}\text{OAr}$ is the functional group of a carboxylic ester.

The naming of an ester of a carboxylic acid is done by naming alkyl or aryl group bonded to oxygen first followed by the name of the acid in which the suffix –ic acid is replaced by the suffix –ate.

Explanation of Solution

The name of the compound is given below:

Ethyl (Z)-2-pentenoate

The alkyl group attached on oxygen atom is the ethyl group and the parent chain is the pentenoate. The double bond is having E configuration.

Thus, the structure of the compound is given below:

(f)

Interpretation Introduction

Interpretation:

The structural formula for the given compound has to be drawn.

Concept introduction:

Nomenclature of anhydrides:

The nomenclature of anhydride involves replacement of the word acid with anhydride. In the case of mixed anhydrides, both acids should be named.

Explanation of Solution

The name of the compound is given below:

Butanoic anhydride

From the butanoic acid, acid part can be replaced with an anhydride group.

(g)

Interpretation Introduction

Interpretation:

The structural formula for the given compound has to be drawn.

Concept introduction:

Nomenclature of amides and imides:

The acyl group bonded to a nitrogen atom is the functional group of an amide.

The naming of an amide can be done by giving the suffix –oic acid from the IUPAC name of the parent acid and adding –amide.

The location of the alkyl or aryl group attached on nitrogen atom in an amide is indicated by ‘N-‘

The indication “ N,N-di-“ is used for two identical alkyl or aryl groups on nitrogen atom

Explanation of Solution

The name of the compound is given below:

Dodecanamide:

The functional group is amide and the acyl group attached is the dodecane group.

Thus, the structure of the compound is given below:

(h)

Interpretation Introduction

The structural formula for the given compound has to be drawn.

Concept introduction:

Nomenclature of esters of carboxylic acids:

The acyl group bonded to $\text{-OR}\text{or}\text{OAr}$ is the functional group of a carboxylic ester.

The naming of an ester of a carboxylic acid is done by naming alkyl or aryl group bonded to oxygen first followed by the name of the acid in which the suffix –ic acid is replaced by the suffix –ate.

Explanation of Solution

The name of the compound is given below:

Ethyl-3-hydroxybutanoate

The alkyl group attached on oxygen atom is the ethyl group and the parent chain is the butanoate and a hydroxyl group is present in the third position.

Thus, the structure of the compound is given below:

(i)

Interpretation Introduction

The structural formula for the given compound has to be drawn.

Concept introduction:

Nomenclature of acid chlorides:

The nomenclture of acid chlorides can be done by replacing –oic acid with –oyl chloride.

Explanation of Solution

The name of the compound is given below:

Octanoyl chloride

The acid group from the octanoic acid will be replaced by acid chloride group.

Thus, the structure of the compound is given below:

(j)

Interpretation Introduction

The structural formula for the given compound has to be drawn.

Concept introduction:

Nomenclature of esters of carboxylic acids:

The acyl group bonded to $\text{-OR}\text{or}\text{OAr}$ is the functional group of a carboxylic ester.

The naming of an ester of a carboxylic acid is done by naming alkyl or aryl group bonded to oxygen first followed by the name of the acid in which the suffix –ic acid is replaced by the suffix –ate.

Explanation of Solution

The name of the compound is given below:

Diethyl cis-1,2-cyclohexanedicarboxylate

The alkyl group attached on oxygen atom are two ethyl groups and the parent chain is the dicarboxylate and a cyclohecxane group is present in the 1,2 position.

Thus, the structure of the compound is given below:

(k)

Interpretation Introduction

The structural formula for the given compound has to be drawn.

Concept introduction:

Nomenclature of acid chlorides:

The nomenclture of acid chlorides can be done by replacing –oic acid with –oyl chloride.

Explanation of Solution

The name of the compound is given below:

Methanesulfonyl chloride

The acid group from the methanesulfonic acid will be replaced by acid chloride group.

Thus, the structure of the compound is given below:

(l)

Interpretation Introduction

The structural formula for the given compound has to be drawn.

Concept introduction:

Nomenclature of acid chlorides:

The nomenclture of acid chlorides can be done by replacing –oic acid with –oyl chloride.

Explanation of Solution

The name of the compound is given below:

p-Toluenesulfonyl chloride

The acid group from the p-toluenesulfonic acid will be replaced by acid chloride group.

Thus, the structure of the compound is given below: