Chapter 20, Problem 28P

Interpretation Introduction

Interpretation:

The structural formula for each of the given compounds is to be drawn.

Concept introduction:

The systematic naming of organic compound is given by IUPAC. The naming of organic compound is done in such a way that the structure of organic compound is correctly interpreted from the name.

Rules for writing the structural formula from IUPAC are:

First identify the word root for the given compound.

The suffix used in the compound like –ane, ene, yne, ol, al and so on.

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

Answer to Problem 28P

Solution:

a) The structural formula of m-chlorobenzoyl chlorideis shown below.

b) The structural formula of trifluoroacetic anhydride is shown below.

c) The structural formula of cis-$1,2$-cyclopropanedicarboxylic anhydrideis shown below.

d) The structural formula of ethyl cycloheptanecarboxylateis shown below.

(e) The structural formula of $1$-phenylethyl acetate is shown below.

(f) The structural formula of $2$-phenylethyl acetate is shown below.

(g) The structural formula of p-ethylbenzamide is shown below.

(h) The structural formula of N-ethylbenzamide is shown below.

(i) The structural formula of $2$-methylhexanenitrile is shown below.

Explanation of Solution

a) m-Chlorobenzoyl chloride.

The name of compound suggests that chlorine group is present at meta position with respect to acyl group on benzene ring. The structure of compound is shown below.

b) Trifluoroacetic anhydride.

The name of the compound shows that anhydride group $\left(\text{C}\left(\text{O}\right)-\text{O}-\text{C}\left(\text{O}\right)\right)$ is present in the compound. The carbonyl carbon atom is bonded to ${\text{CF}}_{\text{3}}$

group. The structure of compound is shown below.

c) cis-$1,2$-Cyclopropanedicarboxylic anhydride.

The name of the compound indicates that two carboxylic groups are present on cyclopropane. Both carboxylic groups are present on the same plane. The structure of compound is shown below.

d) Ethyl cycloheptanecarboxylate

The name of the compound suggests that ester group is present in the structure. The cycloheptane ring is bonded to carbonyl carbon atom and ethyl group is bonded to oxygen atom. The structure of compound is shown below.

(e) $1$-Phenylethyl acetate

The name of the compound suggests that ester group is present in the structure. The methyl group is bonded to carbonyl carbon atom and ethyl group is bonded to oxygen atom. The structure of compound is shown below.

(f) $2$-Phenylethyl acetate

The name of the compound suggests that ester group is present in the structure. The methyl group is bonded to carbonyl carbon atom and ethyl group is bonded to oxygen atom. The second carbon atom is bonded to benzene ring. The structure of compound is shown below.

(g) p-Ethylbenzamide

The name of compound suggests that ethyl group is present at para position with respect to amide group on benzene ring. The structure of compound is shown below.

(h) N-Ethylbenzamide

The name of compound suggests that ethyl group is bonded to amide group which further bonded to benzene ring. The structure of compound is shown below.

(i) $2$-Methylhexanenitrile

The name of the compound indicates that it contains hydrocarbon chain of six carbon atoms. On the second carbon atom methyl group is present and on the first carbon atom nitrile group is present. The structure of compound is shown below.