Chapter 22.7, Problem 18PTS

(a)

Interpretation Introduction

Interpretation: For a given compound set of compounds, the given amines are to be prepared via an azide synthesis, reductive amination starting from sodium azide

Concept Introduction: An azide synthesis involves the reaction between alkyl halide and sodium azide.  Alkyl azide is formed in the first step.  Alkyl azide on reduction with hydrogen in the presence of platinum produces primary amine.  In this way, primary amines are synthesized while secondary and tertiary amines are not formed as by-products.

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.

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.

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.

(b)

Interpretation Introduction

Interpretation: For a given compound set of compounds, the given amines are to be prepared via an azide synthesis, reductive amination starting from sodium azide

Concept Introduction: An azide synthesis involves the reaction between alkyl halide and sodium azide.  Alkyl azide is formed in the first step.  Alkyl azide on reduction with hydrogen in the presence of platinum produces primary amine.  In this way, primary amines are synthesized while secondary and tertiary amines are not formed as by-products.

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.

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.

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.

(c)

Interpretation Introduction

Interpretation: For a given compound set of compounds, the given amines are to be prepared via an azide synthesis, reductive amination starting from sodium azide

Concept Introduction: An azide synthesis involves the reaction between alkyl halide and sodium azide.  Alkyl azide is formed in the first step.  Alkyl azide on reduction with hydrogen in the presence of platinum produces primary amine.  In this way, primary amines are synthesized while secondary and tertiary amines are not formed as by-products.

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.

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.

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.

(d)

Interpretation Introduction

Interpretation: For a given compound set of compounds, the given amines are to be prepared via an azide synthesis, reductive amination starting from sodium azide

Concept Introduction: An azide synthesis involves the reaction between alkyl halide and sodium azide.  Alkyl azide is formed in the first step.  Alkyl azide on reduction with hydrogen in the presence of platinum produces primary amine.  In this way, primary amines are synthesized while secondary and tertiary amines are not formed as by-products.

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.

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.

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.

(e)

Interpretation Introduction

Interpretation: For a given compound set of compounds, the given amines are to be prepared via an azide synthesis, reductive amination starting from sodium azide

Concept Introduction: An azide synthesis involves the reaction between alkyl halide and sodium azide.  Alkyl azide is formed in the first step.  Alkyl azide on reduction with hydrogen in the presence of platinum produces primary amine.  In this way, primary amines are synthesized while secondary and tertiary amines are not formed as by-products.

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.

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.

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.

(f)

Interpretation Introduction

Interpretation: For a given compound set of compounds, the given amines are to be prepared via an azide synthesis, reductive amination starting from sodium azide

Concept Introduction: An azide synthesis involves the reaction between alkyl halide and sodium azide.  Alkyl azide is formed in the first step.  Alkyl azide on reduction with hydrogen in the presence of platinum produces primary amine.  In this way, primary amines are synthesized while secondary and tertiary amines are not formed as by-products.

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.

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.

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.