For the given nitration reaction, orientation of the reaction has to be accounted. Concept Introduction: Activating and deactivating groups: The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups. Activating groups – ortho/para directing groups. The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen. Deactivating groups – meta directing groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.

Question

In an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?

Answer 1

Question

Chapter 22, Problem 22.28P

(a)

Interpretation Introduction

Interpretation:

For the given nitration reaction, orientation of the reaction has to be accounted.

Concept Introduction:

Activating and deactivating groups:

The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.

Activating groups – ortho/para directing groups. The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.

Deactivating groups – meta directing groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.

(b)

Interpretation Introduction

Interpretation:

For the given substitution reaction in step 2, reaction mechanism has to be proposed.

Concept Introduction:

Activating and deactivating groups:

The effect of substituents on the reaction rate of aromatic electrophilic substitution is given by activating or deactivating groups.

Activating groups – ortho/para directing groups. The rate of reaction is increased by an activating groups (electron donating groups) relative to hydrogen.

Deactivating groups – meta directing groups. The rate of reaction is decreased by a deactivating groups (electron withdrawing groups) relative to hydrogen.

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