Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
Question
Book Icon
Chapter 24, Problem 4PP
Interpretation Introduction

Interpretation:

The Strecker synthesis of DL-phenylalanine is to be outlined, and by preparing the starting aldehyde using acrolein and methanethiol, Strecker synthesis of DL-methanethiol is to be outlined.

Concept introduction:

舧 Amino acids are organic compounds containing amine (NH2) and carboxyl (COOH) functional group along with a side chain (R group) specific to each amino acid.

舧 Strecker synthesis involves treating an aldehyde with ammonia and hydrogen cyanide to give an aminonitrile, which can be hydrolyzed to an αa-amino acid.

The general reaction is as:

Organic Chemistry, Chapter 24, Problem 4PP

舧 The Strecker synthesis involves formation of imine from phenyl acetaldehyde and ammonia, which on addition of hydrogen cyanide produces α amino nitrile, and further undergoes hydrolysis to yield DL-phenylalanine.

舧 Acrolein and methanethiol on treating with a base gives 3(methylthio)propanal, which when subjected to Strecker synthesis forms imine from 3(methylthio)propanal and ammonia, which on addition of hydrogen cyanide produces α amino nitrile, and further undergoes hydrolysis in the second step to yield DL-Methionine.

Blurred answer
Students have asked these similar questions
The reaction of ninhydrin with an -amino acid occurs in several steps (a) The first step is loss of water to give a triketone. Show the mechanism of the reaction and the structure of the triketone.(b) The second step is formation of an imine by reaction of the amino acid with the triketone. Show its structure. (c) The third step is a decarboxylation. Show the structure of the product and the mechanism of the decarboxylation reaction. (d) The fourth step is hydrolysis of an imine to yield an amine and an aldehyde. Show the structures of both products. (e) The final step is formation of the purple anion. Show the mechanism of the reaction
Synthesize octadecyl stearate using linoleic acid (18:2) (Given, stearic acid: 18:0) as the only starting material.
26. (i) Why is the ester formation of alcohols and acid chlorides done in a weakly basic solution like pyrmidine? (ii) Why is this setup not viable for alcohols and carboxylic acids to form esters? pyrimidine deprotonates the alcohol; the alkoxide ion forms pyrimidine deprotonates the alcohol; the carboxylate ion forms pyrimidine deprotonates the tetrahedral intermediate; the alkoxide ion forms pyrimidine deprotonates the tetrahedral intermediate; the carboxylate ion forms
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning