a) Interpretation: Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized is to be stated. Concept introduction: In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the keto group is a meta directing group. Hence to prepare p-chloroacetophenone, benzene has to be halogenated and the halobenzene obtained should be subjected to Friedal-Crafts acylation. To state: Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized.

Question

16-57 Starting with either benzene or toluene, how would you synthesize the following substances? Assume that ortho and para isomers can be separated. (a) 2-Bromo-4-nitrotoluene (c) 2,4,6-Tribromoaniline (b) 1,3,5-Trinitrobenzene (d) m-Fluorobenzoic acid

Answer 1

Question

Chapter 16.SE, Problem 56AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the keto group is a meta directing group. Hence to prepare p-chloroacetophenone, benzene has to be halogenated and the halobenzene obtained should be subjected to Friedal-Crafts acylation.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized.

Interpretation Introduction

b)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-bromonitrobenzene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare m-bromonitrobenzene, benzene has to be first nitrated and the nitrobenzene obtained should be halogenated.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m–bromonitrobenzene can be synthesized.

Interpretation Introduction

c)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare o-bromobenzenesulfonic acid, benzene has to be halogenated and the halobenzene obtained should be subjected to sulfonation.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized.

Interpretation Introduction

d)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare m-chlorobenzenesulfonic acid, benzene has to be sulfonated and the benzenesulfonicacid obtained should be halogenated.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized.

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16-57 Starting with either benzene or toluene, how would you synthesize the following substances? Assume that ortho and para isomers can be separated. (a) 2-Bromo-4-nitrotoluene (c) 2,4,6-Tribromoaniline (b) 1,3,5-Trinitrobenzene (d) m-Fluorobenzoic acid

How could you convert butanenitrile into the following compounds? Write each step showing the reagents needed. (a) 1-Butanol (b) Butylamine

(a) How will you convert:(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.

Answer 2

Question

Chapter 16.SE, Problem 56AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the keto group is a meta directing group. Hence to prepare p-chloroacetophenone, benzene has to be halogenated and the halobenzene obtained should be subjected to Friedal-Crafts acylation.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized.

Interpretation Introduction

b)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-bromonitrobenzene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare m-bromonitrobenzene, benzene has to be first nitrated and the nitrobenzene obtained should be halogenated.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m–bromonitrobenzene can be synthesized.

Interpretation Introduction

c)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare o-bromobenzenesulfonic acid, benzene has to be halogenated and the halobenzene obtained should be subjected to sulfonation.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized.

Interpretation Introduction

d)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare m-chlorobenzenesulfonic acid, benzene has to be sulfonated and the benzenesulfonicacid obtained should be halogenated.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized.

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Answer 3

Question

Chapter 16.SE, Problem 56AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the keto group is a meta directing group. Hence to prepare p-chloroacetophenone, benzene has to be halogenated and the halobenzene obtained should be subjected to Friedal-Crafts acylation.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized.

Interpretation Introduction

b)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-bromonitrobenzene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare m-bromonitrobenzene, benzene has to be first nitrated and the nitrobenzene obtained should be halogenated.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m–bromonitrobenzene can be synthesized.

Interpretation Introduction

c)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare o-bromobenzenesulfonic acid, benzene has to be halogenated and the halobenzene obtained should be subjected to sulfonation.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized.

Interpretation Introduction

d)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare m-chlorobenzenesulfonic acid, benzene has to be sulfonated and the benzenesulfonicacid obtained should be halogenated.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized.

Expert Solution & Answer

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Answer 4

Question

Chapter 16.SE, Problem 56AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the keto group is a meta directing group. Hence to prepare p-chloroacetophenone, benzene has to be halogenated and the halobenzene obtained should be subjected to Friedal-Crafts acylation.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized.

Interpretation Introduction

b)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-bromonitrobenzene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare m-bromonitrobenzene, benzene has to be first nitrated and the nitrobenzene obtained should be halogenated.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m–bromonitrobenzene can be synthesized.

Interpretation Introduction

c)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare o-bromobenzenesulfonic acid, benzene has to be halogenated and the halobenzene obtained should be subjected to sulfonation.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized.

Interpretation Introduction

d)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare m-chlorobenzenesulfonic acid, benzene has to be sulfonated and the benzenesulfonicacid obtained should be halogenated.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized.

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Answer 5

Chapter 16.SE, Problem 56AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the keto group is a meta directing group. Hence to prepare p-chloroacetophenone, benzene has to be halogenated and the halobenzene obtained should be subjected to Friedal-Crafts acylation.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized.

Interpretation Introduction

b)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-bromonitrobenzene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare m-bromonitrobenzene, benzene has to be first nitrated and the nitrobenzene obtained should be halogenated.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m–bromonitrobenzene can be synthesized.

Interpretation Introduction

c)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare o-bromobenzenesulfonic acid, benzene has to be halogenated and the halobenzene obtained should be subjected to sulfonation.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized.

Interpretation Introduction

d)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare m-chlorobenzenesulfonic acid, benzene has to be sulfonated and the benzenesulfonicacid obtained should be halogenated.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized.

Answer 6

Chapter 16.SE, Problem 56AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the keto group is a meta directing group. Hence to prepare p-chloroacetophenone, benzene has to be halogenated and the halobenzene obtained should be subjected to Friedal-Crafts acylation.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized.

Answer 7

Chapter 16.SE, Problem 56AP

Interpretation Introduction

a)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the keto group is a meta directing group. Hence to prepare p-chloroacetophenone, benzene has to be halogenated and the halobenzene obtained should be subjected to Friedal-Crafts acylation.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized.

Answer 8

Interpretation Introduction

b)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-bromonitrobenzene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare m-bromonitrobenzene, benzene has to be first nitrated and the nitrobenzene obtained should be halogenated.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m–bromonitrobenzene can be synthesized.

Answer 9

Interpretation Introduction

b)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-bromonitrobenzene can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare m-bromonitrobenzene, benzene has to be first nitrated and the nitrobenzene obtained should be halogenated.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m–bromonitrobenzene can be synthesized.

Answer 10

Interpretation Introduction

c)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare o-bromobenzenesulfonic acid, benzene has to be halogenated and the halobenzene obtained should be subjected to sulfonation.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized.

Answer 11

Interpretation Introduction

c)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare o-bromobenzenesulfonic acid, benzene has to be halogenated and the halobenzene obtained should be subjected to sulfonation.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized.

Answer 12

Interpretation Introduction

d)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare m-chlorobenzenesulfonic acid, benzene has to be sulfonated and the benzenesulfonicacid obtained should be halogenated.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized.

Answer 13

Interpretation Introduction

d)

Interpretation:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare m-chlorobenzenesulfonic acid, benzene has to be sulfonated and the benzenesulfonicacid obtained should be halogenated.

To state:

Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized.

Answer 14

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Answer 25

Ch. 16.1 - Prob. 1P Ch. 16.2 - Propose a mechanism for the electrophilic...Ch. 16.2 - How many products might be formed on chlorination...Ch. 16.2 - When benzene is treated with D2SÅª4. deuterium...Ch. 16.3 - Prob. 5P Ch. 16.3 - What is the major monosubstitution product from...Ch. 16.3 - Identify the carboxylic acid chloride that might...Ch. 16.4 - Rank the compounds in each of the following groups...Ch. 16.4 - Predict the major products of the following...Ch. 16.4 - Prob. 10P

Solution Summary: The author explains how p-chloroacetophenone can be synthesized by starting from benzene as the only source of aromatic compounds.

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Chapter 16 Solutions