ORGANIC CHEMISTRY  LL PRINT UPGRADE
ORGANIC CHEMISTRY LL PRINT UPGRADE
4th Edition
ISBN: 9781119810643
Author: Klein
Publisher: WILEY
Question
Book Icon
Chapter 25, Problem 57PP
Interpretation Introduction

Interpretation:

Why there is a difference in yield when alanine and valine is prepared via amidomalonate synthesis need to be explained.

Concept introduction:

Amidomalonate synthesis is a process in which a 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  LL PRINT UPGRADE, Chapter 25, Problem 57PP

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

Please remember that if the primary alkyl halide reactivity is more than secondary alkyl halide due to less steric hindrance.

Blurred answer

Chapter 25 Solutions

ORGANIC CHEMISTRY LL PRINT UPGRADE

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