a) Interpretation: The flaw in the synthesis given is to be stated. Concept introduction: In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO 4 the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected. To state: The flaw in the synthesis given.

Question

The following syntheses have flaws. What is wrong with each?

Answer 1

Question

Chapter 16.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO₄ the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected.

To state:

The flaw in the synthesis given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with aromatic compounds with a deactivating group like NO₂ etc. attached to the ring.

To state:

The flaw in the synthesis given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H₂/Pd the –C=O group gets reduced to –CH₂ group and –NO₂ gets reduced to –NH₂ group.

To state:

The flaw in the synthesis shown.

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The following syntheses have flaws. What is wrong with each?

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Answer 2

Question

Chapter 16.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO₄ the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected.

To state:

The flaw in the synthesis given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with aromatic compounds with a deactivating group like NO₂ etc. attached to the ring.

To state:

The flaw in the synthesis given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H₂/Pd the –C=O group gets reduced to –CH₂ group and –NO₂ gets reduced to –NH₂ group.

To state:

The flaw in the synthesis shown.

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Answer 3

Question

Chapter 16.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO₄ the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected.

To state:

The flaw in the synthesis given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with aromatic compounds with a deactivating group like NO₂ etc. attached to the ring.

To state:

The flaw in the synthesis given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H₂/Pd the –C=O group gets reduced to –CH₂ group and –NO₂ gets reduced to –NH₂ group.

To state:

The flaw in the synthesis shown.

Expert Solution & Answer

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Answer 4

Question

Chapter 16.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO₄ the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected.

To state:

The flaw in the synthesis given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with aromatic compounds with a deactivating group like NO₂ etc. attached to the ring.

To state:

The flaw in the synthesis given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H₂/Pd the –C=O group gets reduced to –CH₂ group and –NO₂ gets reduced to –NH₂ group.

To state:

The flaw in the synthesis shown.

Expert Solution & Answer

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Answer 5

Chapter 16.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO₄ the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected.

To state:

The flaw in the synthesis given.

Interpretation Introduction

b)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with aromatic compounds with a deactivating group like NO₂ etc. attached to the ring.

To state:

The flaw in the synthesis given.

Interpretation Introduction

c)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H₂/Pd the –C=O group gets reduced to –CH₂ group and –NO₂ gets reduced to –NH₂ group.

To state:

The flaw in the synthesis shown.

Answer 6

Chapter 16.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO₄ the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected.

To state:

The flaw in the synthesis given.

Answer 7

Chapter 16.SE, Problem 58AP

Interpretation Introduction

a)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carboxylic acid group are meta directing and deactivating group. While oxidizing with KMnO₄ the alkyl groups in the side chain are oxidized and the aromatic ring remains unaffected.

To state:

The flaw in the synthesis given.

Answer 8

Interpretation Introduction

b)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with aromatic compounds with a deactivating group like NO₂ etc. attached to the ring.

To state:

The flaw in the synthesis given.

Answer 9

Interpretation Introduction

b)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, halogens are ortho and para directing groups. Friedal-Crafts alkylation is not possible with aromatic compounds with a deactivating group like NO₂ etc. attached to the ring.

To state:

The flaw in the synthesis given.

Answer 10

Interpretation Introduction

c)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H₂/Pd the –C=O group gets reduced to –CH₂ group and –NO₂ gets reduced to –NH₂ group.

To state:

The flaw in the synthesis shown.

Answer 11

Interpretation Introduction

c)

Interpretation:

The flaw in the synthesis given is to be stated.

Concept introduction:

In aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups while carbonyl group is a meta directing and deactivating group. When treated with H₂/Pd the –C=O group gets reduced to –CH₂ group and –NO₂ gets reduced to –NH₂ group.

To state:

The flaw in the synthesis shown.

Answer 12

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Answer 13

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Answer 23

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 that in aromatic electrophilic substitution reactions, alkyl groups are ortho and para directing and activating groups.

Chapter 16 Solutions