Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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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.

Expert Solution & Answer
Check Mark

Answer to Problem 28P

Solution:

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

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  1

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

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  2

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

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  3

d) The structural formula of ethyl cycloheptanecarboxylateis shown below.

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  4

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

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  5

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

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  6

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

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  7

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

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  8

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

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  9

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.

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  10

b) Trifluoroacetic anhydride.

The name of the compound shows that anhydride group (C(O)OC(O)) is present in the compound. The carbonyl carbon atom is bonded to CF3

group. The structure of compound is shown below.

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  11

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.

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  12

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.

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  13

(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.

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  14

(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.

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  15

(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.

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  16

(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.

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  17

(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.

Organic Chemistry - Standalone book, Chapter 20, Problem 28P , additional homework tip  18

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