Chapter 23, Problem 49PP

(a)

Interpretation Introduction

Interpretation: The structures of the major products when aniline is treated with the given set of reagents have to be drawn.

Concept Introduction:

An amino group present in an aromatic ring is ortho-para director.  It directs the entering group into two ortho-positions and one para-position that depends on the nature of the reagent.

To find: Draw the structure of the major product when aniline is treated with the given reagent (a)

Find the director of amino group

(b)

Interpretation Introduction

Interpretation: The structures of the major products when aniline is treated with the given set of reagents have to be drawn.

Concept Introduction:

Acetylation is the reaction in which acetyl group is introduced in the reactive center of the compound.  In most cases, bases are used as the reagents.

To find: Draw the structure of the major product when aniline is treated with the given reagent (b)

Find the nature of aniline and pyridine

(c)

Interpretation Introduction

Interpretation: The structures of the major products when aniline is treated with the given set of reagents have to be drawn.

Concept Introduction:

When excess methyl iodide is treated with the amine group containing compound, that amine group undergoes exhaustive alkylation to give a quaternary ammonium salt.

To find: Draw the structure of the major product when aniline is treated with the given reagent (c)

Find the reactive group in aniline for the reagent (c)

(d)

Interpretation Introduction

 Interpretation: The structures of the major products when aniline is treated with the given set of reagents have to be drawn.

Concept Introduction:

When aniline is treated with NaNO₂ and HCl, the corresponding diazonium salt is formed which is an intermediate for the transformation of various functional groups.

To find: Draw the structure of the major product when aniline is treated with the given reagent (d)

Put the reaction of aniline with NaNO₂ and HCl

To find: Draw the structure of the major product when aniline is treated with the given reagent (d)

Put the reaction of aniline with NaNO₂ and HCl

(e)

Interpretation Introduction

Interpretation: The structures of the major products when aniline is treated with the given set of reagents have to be drawn.

Concept Introduction:

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

Sandmeyer reactions use copper salts as the reagents.  Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

To find: Draw the structure of the major product when aniline is treated with the given reagent (e)

Put the reaction of aniline with NaNO₂ and HCl