ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
4th Edition
ISBN: 9781119745105
Author: Klein
Publisher: WILEY
Question
Book Icon
Chapter 25.3, Problem 14PTS

(a)

Interpretation Introduction

Interpretation:

Reagents required for preparation of isoleucine, alanine and valine by using amidomalonate synthesis need to be identified.

Concept introduction:

Amidomalonate synthesis is a process in which an halide is converted to a aminoacid with two new carbon atoms (comes from amidomalonate).  By use of this method a new alkyl groups can be introduced.  A general scheme of this synthesis is shown below,

ORGANIC CHEMISTRY, Chapter 25.3, Problem 14PTS , additional homework tip  1

Steps involved in amidomalonater synthesis are,

  • Deprotonation of α carbon in amidomalonate
  • Alkylation of enolate
  • Hydrolysis of ester using aqueous acid
  • Decarboxylation at high temperature

To find: the reagents used for synthesis of isoleucine by amidomalonate synthesis.

(b)

Interpretation Introduction

Interpretation:

Reagents required for preparation of isoleucine, alanine and valine by using amidomalonate synthesis need to be identified.

Concept introduction:

Amidomalonate synthesis is a process in which an halide is converted to a aminoacid with two new carbon atoms (comes from amidomalonate).  By use of this method a new alkyl groups can be introduced.  A general scheme of this synthesis is shown below,

ORGANIC CHEMISTRY, Chapter 25.3, Problem 14PTS , additional homework tip  2

Steps involved in amidomalonater synthesis are,

  • Deprotonation of α carbon in amidomalonate
  • Alkylation of enolate
  • Hydrolysis of ester using aqueous acid
  • Decarboxylation at high temperature

To find: the reagents used for synthesis of alanine by amidomalonate synthesis.

(c)

Interpretation Introduction

Interpretation:

Reagents required for preparation of isoleucine, alanine and valine by using amidomalonate synthesis need to be identified.

Concept introduction:

Amidomalonate synthesis is a process in which an halide is converted to a aminoacid with two new carbon atoms (comes from amidomalonate).  By use of this method a new alkyl groups can be introduced.  A general scheme of this synthesis is shown below,

ORGANIC CHEMISTRY, Chapter 25.3, Problem 14PTS , additional homework tip  3

Steps involved in amidomalonater synthesis are,

  • Deprotonation of α carbon in amidomalonate
  • Alkylation of enolate
  • Hydrolysis of ester using aqueous acid
  • Decarboxylation at high temperature

To find: the reagents used for synthesis of valine by amidomalonate synthesis.

Blurred answer

Chapter 25 Solutions

ORGANIC CHEMISTRY

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