ORGANIC CHEMISTRY (LL)-W/WILEYPLUS
ORGANIC CHEMISTRY (LL)-W/WILEYPLUS
4th Edition
ISBN: 9781119659556
Author: Klein
Publisher: WILEY
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Chapter 22, Problem 90IP
Interpretation Introduction

Interpretation: The given compound of amine is to be prepared via reductive amination and preparation of the starting material via retrosynthetic analysis of the final product.

Concept Introduction: Sodium cyanoborohydride is a strong reducing agent than sodium borohydride.  It reduces the carbonyl group into amine group in a rapid way.  So, it is called as reductive amination reactions.  Aldehyde or ketone group is reacted with ammonia in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce primary amines.

ORGANIC CHEMISTRY (LL)-W/WILEYPLUS, Chapter 22, Problem 90IP , additional homework tip  1

Aldehyde or ketone group is reacted with primary amine in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce secondary amines.

ORGANIC CHEMISTRY (LL)-W/WILEYPLUS, Chapter 22, Problem 90IP , additional homework tip  2

Aldehyde or ketone group is reacted with secondary amine in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce tertiary amines.

ORGANIC CHEMISTRY (LL)-W/WILEYPLUS, Chapter 22, Problem 90IP , additional homework tip  3

There are two ways to get the starting compounds in either left or right side cleavage of all C−N bonds.  After the cleavage, retrosynthetic analysis of the starting materials is done.  If both aldehyde/ketone and amine starting materials are decided, reductive amination is followed in both the ways by placing the suitable reagents.

The starting materials for reductive amination are carbonyl compound and alkyl amine.  The carbonyl compound can be prepared in a number of ways such as radical bromination of alkane, treatment of brominated product with strong base, ozonolysis of alkene.

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Chapter 22 Solutions

ORGANIC CHEMISTRY (LL)-W/WILEYPLUS

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