ORGANIC CHEMISTRY (LL) W/ACCESS
ORGANIC CHEMISTRY (LL) W/ACCESS
4th Edition
ISBN: 9781119856122
Author: Klein
Publisher: WILEY
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Chapter 22, Problem 44PP

(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

ORGANIC CHEMISTRY (LL) W/ACCESS, Chapter 22, Problem 44PP , additional homework tip  1

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

ORGANIC CHEMISTRY (LL) W/ACCESS, Chapter 22, Problem 44PP , additional homework tip  2

(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.

ORGANIC CHEMISTRY (LL) W/ACCESS, Chapter 22, Problem 44PP , additional homework tip  3

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.

ORGANIC CHEMISTRY (LL) W/ACCESS, Chapter 22, Problem 44PP , additional homework tip  4

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

ORGANIC CHEMISTRY (LL) W/ACCESS, Chapter 22, Problem 44PP , additional homework tip  5

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Chapter 22 Solutions

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