a) Chlorobenzene, o-dichlorobenzene and benzene Interpretation: The compounds chlorobenzene, o-dichlorobenzene and benzene are to be ranked according to their reactivity towards electrophilic substitution. Concept introduction: Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene. To rank: The compounds chlorobenzene, o-dichlorobenzene and benzene according to their reactivity towards electrophilic substitution.

Question

Wolff-Kishner reduction of compound W gave compound A. Treatment of A with m-chloroperbenzoic acid gave B which on reduction with LiAH4 gave C. Oxidation of compound C with chromic acid gave D (C9H14O). Suggest the structures for A, B, C, and D.

Answer 1

Question

Chapter 16.SE, Problem 48AP

Interpretation Introduction

a) Chlorobenzene, o-dichlorobenzene and benzene

Interpretation:

The compounds chlorobenzene, o-dichlorobenzene and benzene are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds chlorobenzene, o-dichlorobenzene and benzene according to their reactivity towards electrophilic substitution.

Interpretation Introduction

b) p-bromonitrobenzene, nitrobenzene, phenol

Interpretation:

The compounds p-bromonitrobenzene, nitrobenzene and phenol are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds p-bromonitrobenzene, nitrobenzene and phenol according to their reactivity towards electrophilic substitution.

Interpretation Introduction

c) Fluorobenzene, benzaldehyde, o-xylene

Interpretation:

The compounds fluorobenzene, benzaldehyde and o-xylene are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds fluorobenzene, benzaldehyde and o-xylene according to their reactivity towards electrophilic substitution.

Interpretation Introduction

d) Benzonitrile, p-methylbenzonitrile, p-methoxybenzonitrile

Interpretation:

The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile according to their reactivity towards electrophilic substitution.

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Wolff-Kishner reduction of compound W gave compound A. Treatment of A with m-chloroperbenzoic acid gave B which on reduction with LiAH4 gave C. Oxidation of compound C with chromic acid gave D (C9H14O). Suggest the structures for A, B, C, and D.

Two isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. Which of the following isomeric pairs best match this data?

Two isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. What is the isometric pair of A and B that corresponds?

Answer 2

Question

Chapter 16.SE, Problem 48AP

Interpretation Introduction

a) Chlorobenzene, o-dichlorobenzene and benzene

Interpretation:

The compounds chlorobenzene, o-dichlorobenzene and benzene are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds chlorobenzene, o-dichlorobenzene and benzene according to their reactivity towards electrophilic substitution.

Interpretation Introduction

b) p-bromonitrobenzene, nitrobenzene, phenol

Interpretation:

The compounds p-bromonitrobenzene, nitrobenzene and phenol are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds p-bromonitrobenzene, nitrobenzene and phenol according to their reactivity towards electrophilic substitution.

Interpretation Introduction

c) Fluorobenzene, benzaldehyde, o-xylene

Interpretation:

The compounds fluorobenzene, benzaldehyde and o-xylene are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds fluorobenzene, benzaldehyde and o-xylene according to their reactivity towards electrophilic substitution.

Interpretation Introduction

d) Benzonitrile, p-methylbenzonitrile, p-methoxybenzonitrile

Interpretation:

The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile according to their reactivity towards electrophilic substitution.

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Answer 3

Question

Chapter 16.SE, Problem 48AP

Interpretation Introduction

a) Chlorobenzene, o-dichlorobenzene and benzene

Interpretation:

The compounds chlorobenzene, o-dichlorobenzene and benzene are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds chlorobenzene, o-dichlorobenzene and benzene according to their reactivity towards electrophilic substitution.

Interpretation Introduction

b) p-bromonitrobenzene, nitrobenzene, phenol

Interpretation:

The compounds p-bromonitrobenzene, nitrobenzene and phenol are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds p-bromonitrobenzene, nitrobenzene and phenol according to their reactivity towards electrophilic substitution.

Interpretation Introduction

c) Fluorobenzene, benzaldehyde, o-xylene

Interpretation:

The compounds fluorobenzene, benzaldehyde and o-xylene are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds fluorobenzene, benzaldehyde and o-xylene according to their reactivity towards electrophilic substitution.

Interpretation Introduction

d) Benzonitrile, p-methylbenzonitrile, p-methoxybenzonitrile

Interpretation:

The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile according to their reactivity towards electrophilic substitution.

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Answer 4

Question

Chapter 16.SE, Problem 48AP

Interpretation Introduction

a) Chlorobenzene, o-dichlorobenzene and benzene

Interpretation:

The compounds chlorobenzene, o-dichlorobenzene and benzene are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds chlorobenzene, o-dichlorobenzene and benzene according to their reactivity towards electrophilic substitution.

Interpretation Introduction

b) p-bromonitrobenzene, nitrobenzene, phenol

Interpretation:

The compounds p-bromonitrobenzene, nitrobenzene and phenol are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds p-bromonitrobenzene, nitrobenzene and phenol according to their reactivity towards electrophilic substitution.

Interpretation Introduction

c) Fluorobenzene, benzaldehyde, o-xylene

Interpretation:

The compounds fluorobenzene, benzaldehyde and o-xylene are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds fluorobenzene, benzaldehyde and o-xylene according to their reactivity towards electrophilic substitution.

Interpretation Introduction

d) Benzonitrile, p-methylbenzonitrile, p-methoxybenzonitrile

Interpretation:

The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile according to their reactivity towards electrophilic substitution.

Expert Solution & Answer

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Answer 5

Chapter 16.SE, Problem 48AP

Interpretation Introduction

a) Chlorobenzene, o-dichlorobenzene and benzene

Interpretation:

The compounds chlorobenzene, o-dichlorobenzene and benzene are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds chlorobenzene, o-dichlorobenzene and benzene according to their reactivity towards electrophilic substitution.

Interpretation Introduction

b) p-bromonitrobenzene, nitrobenzene, phenol

Interpretation:

The compounds p-bromonitrobenzene, nitrobenzene and phenol are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds p-bromonitrobenzene, nitrobenzene and phenol according to their reactivity towards electrophilic substitution.

Interpretation Introduction

c) Fluorobenzene, benzaldehyde, o-xylene

Interpretation:

The compounds fluorobenzene, benzaldehyde and o-xylene are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds fluorobenzene, benzaldehyde and o-xylene according to their reactivity towards electrophilic substitution.

Interpretation Introduction

d) Benzonitrile, p-methylbenzonitrile, p-methoxybenzonitrile

Interpretation:

The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile according to their reactivity towards electrophilic substitution.

Answer 6

Chapter 16.SE, Problem 48AP

Interpretation Introduction

a) Chlorobenzene, o-dichlorobenzene and benzene

Interpretation:

The compounds chlorobenzene, o-dichlorobenzene and benzene are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds chlorobenzene, o-dichlorobenzene and benzene according to their reactivity towards electrophilic substitution.

Answer 7

Chapter 16.SE, Problem 48AP

Interpretation Introduction

a) Chlorobenzene, o-dichlorobenzene and benzene

Interpretation:

The compounds chlorobenzene, o-dichlorobenzene and benzene are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds chlorobenzene, o-dichlorobenzene and benzene according to their reactivity towards electrophilic substitution.

Answer 8

Interpretation Introduction

b) p-bromonitrobenzene, nitrobenzene, phenol

Interpretation:

The compounds p-bromonitrobenzene, nitrobenzene and phenol are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds p-bromonitrobenzene, nitrobenzene and phenol according to their reactivity towards electrophilic substitution.

Answer 9

Interpretation Introduction

b) p-bromonitrobenzene, nitrobenzene, phenol

Interpretation:

The compounds p-bromonitrobenzene, nitrobenzene and phenol are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds p-bromonitrobenzene, nitrobenzene and phenol according to their reactivity towards electrophilic substitution.

Answer 10

Interpretation Introduction

c) Fluorobenzene, benzaldehyde, o-xylene

Interpretation:

The compounds fluorobenzene, benzaldehyde and o-xylene are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds fluorobenzene, benzaldehyde and o-xylene according to their reactivity towards electrophilic substitution.

Answer 11

Interpretation Introduction

c) Fluorobenzene, benzaldehyde, o-xylene

Interpretation:

The compounds fluorobenzene, benzaldehyde and o-xylene are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds fluorobenzene, benzaldehyde and o-xylene according to their reactivity towards electrophilic substitution.

Answer 12

Interpretation Introduction

d) Benzonitrile, p-methylbenzonitrile, p-methoxybenzonitrile

Interpretation:

The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile according to their reactivity towards electrophilic substitution.

Answer 13

Interpretation Introduction

d) Benzonitrile, p-methylbenzonitrile, p-methoxybenzonitrile

Interpretation:

The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile are to be ranked according to their reactivity towards electrophilic substitution.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

To rank:

The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile according to their reactivity towards electrophilic substitution.

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

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Chapter 16 Solutions