ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG(LL)
ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG(LL)
4th Edition
ISBN: 9781119659587
Author: Klein
Publisher: WILEY
Question
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Chapter 22.6, Problem 14PTS

(a)

Interpretation Introduction

Interpretation: For a given set of compounds, amines are to be prepared via two different methods of reductive amination

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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , 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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , 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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , 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.

(b)

Interpretation Introduction

Interpretation: For a given set of compounds, amines are to be prepared via two different methods of reductive amination

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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , additional homework tip  4

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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , additional homework tip  5

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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , additional homework tip  6

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.

(c)

Interpretation Introduction

Interpretation: For a given set of compounds, amines are to be prepared via two different methods of reductive amination

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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , additional homework tip  7

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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , additional homework tip  8

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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , additional homework tip  9

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.

(d)

Interpretation Introduction

Interpretation: For a given set of compounds, amines are to be prepared via two different methods of reductive amination

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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , additional homework tip  10

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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , additional homework tip  11

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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , additional homework tip  12

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.

(e)

Interpretation Introduction

Interpretation: For a given set of compounds, amines are to be prepared via two different methods of reductive amination

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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , additional homework tip  13

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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , additional homework tip  14

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-STUD.SOLNS.MAN+SG(LL), Chapter 22.6, Problem 14PTS , additional homework tip  15

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.

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Chapter 22 Solutions

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