ORGANIC CHEMISTRY-WILEYPLUS NEXTGEN
ORGANIC CHEMISTRY-WILEYPLUS NEXTGEN
4th Edition
ISBN: 9781119760924
Author: Klein
Publisher: WILEY
Question
Book Icon
Chapter 25, Problem 59PP

(a)

Interpretation Introduction

Interpretation:

The products formed in the given set of transformation need to be predicted.

Concept introduction:

α -bromination of carboxylic acid in presence of bromine and a catalytic amount of phosphorous tribromide to form α -bromocarboxylic acid is known as Hell-Volhard-Zelinsky reaction.  The formed α -bromocarboxylic acid when treated with ammonia gives α -aminocarboxylic acid as the product.

ORGANIC CHEMISTRY-WILEYPLUS NEXTGEN, Chapter 25, Problem 59PP , additional homework tip  1

(b)

Interpretation Introduction

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-WILEYPLUS NEXTGEN, Chapter 25, Problem 59PP , 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

(c)

Interpretation Introduction

Concept introduction:

Amidomalonate synthesis is a process in which a halide is converted to an amino acid 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-WILEYPLUS NEXTGEN, Chapter 25, Problem 59PP , 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

Blurred answer
Students have asked these similar questions
Don't used hand raiting and don't used Ai solution
Don't used Ai solution and don't used hand raiting
OA. For the structure shown, rank the bond lengths (labeled a, b and c) from shortest to longest. Place your answer in the box. Only the answer in the box will be graded. (2 points) H -CH3 THe b Н

Chapter 25 Solutions

ORGANIC CHEMISTRY-WILEYPLUS NEXTGEN

Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
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