ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
4th Edition
ISBN: 9781119745105
Author: Klein
Publisher: WILEY
Question
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Chapter 25.3, Problem 17CC

(a)

Interpretation Introduction

Interpretation:

Reagents required for preparation of methionine, histidine, phenylalanine and leucine by using Strecker synthesis need to be identified.

Concept introduction:

Strecker synthesis is a process in which the aldehyde reacts with ammonium chloride and alkali cyanide to form α -aminonitrile.  The formed α -aminonitrile is undergoes hydrolysis to give the respective amino acids.  The general scheme can be shown as,

ORGANIC CHEMISTRY, Chapter 25.3, Problem 17CC , additional homework tip  1

Steps involved in Strecker synthesis are,

  • Protonation of carbonyl
  • Nucleophilic attack of ammonia to form imine
  • Attack of cyanide to form α -aminonitrile
  • Hydrolysis to give α -aminoacid

To find: the reagents used for synthesis of methionine by Strecker synthesis.

(b)

Interpretation Introduction

Interpretation:

Reagents required for preparation of methionine, histidine, phenylalanine and leucine by using Strecker synthesis need to be identified.

Concept introduction:

Strecker synthesis is a process in which the aldehyde reacts with ammonium chloride and alkali cyanide to form α -aminonitrile.  The formed α -aminonitrile is undergoes hydrolysis to give the respective amino acids.  The general scheme can be shown as,

ORGANIC CHEMISTRY, Chapter 25.3, Problem 17CC , additional homework tip  2

Steps involved in Strecker synthesis are,

  • Protonation of carbonyl
  • Nucleophilic attack of ammonia to form imine
  • Attack of cyanide to form α -aminonitrile
  • Hydrolysis to give α -aminoacid

To find: the reagents used for synthesis of histidine by Strecker synthesis.

(c)

Interpretation Introduction

Interpretation:

Reagents required for preparation of methionine, histidine, phenylalanine and leucine by using Strecker synthesis need to be identified.

Concept introduction:

Strecker synthesis is a process in which the aldehyde reacts with ammonium chloride and alkali cyanide to form α -aminonitrile.  The formed α -aminonitrile is undergoes hydrolysis to give the respective amino acids.  The general scheme can be shown as,

ORGANIC CHEMISTRY, Chapter 25.3, Problem 17CC , additional homework tip  3

Steps involved in Strecker synthesis are,

  • Protonation of carbonyl
  • Nucleophilic attack of ammonia to form imine
  • Attack of cyanide to form α -aminonitrile
  • Hydrolysis to give α -aminoacid

To find: the reagents used for synthesis of phenylalanine by Strecker synthesis.

d)

Interpretation Introduction

Interpretation:

Reagents required for preparation of methionine, histidine, phenylalanine and leucine by using Strecker synthesis need to be identified.

Concept introduction:

Strecker synthesis is a process in which the aldehyde reacts with ammonium chloride and alkali cyanide to form α -aminonitrile.  The formed α -aminonitrile is undergoes hydrolysis to give the respective amino acids.  The general scheme can be shown as,

ORGANIC CHEMISTRY, Chapter 25.3, Problem 17CC , additional homework tip  4

Steps involved in Strecker synthesis are,

  • Protonation of carbonyl
  • Nucleophilic attack of ammonia to form imine
  • Attack of cyanide to form α -aminonitrile
  • Hydrolysis to give α -aminoacid

To find: the reagents used for synthesis of leucine by Strecker synthesis.

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Chapter 25 Solutions

ORGANIC CHEMISTRY

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