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.