EBK ORGANIC CHEMISTRY-PRINT COMPANION (
EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
Question
Book Icon
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.

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, 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.

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, 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.

EBK ORGANIC CHEMISTRY-PRINT COMPANION (, 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.

Blurred answer

Chapter 22 Solutions

EBK ORGANIC CHEMISTRY-PRINT COMPANION (

Knowledge Booster
Background pattern image
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY