Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 24.5C, Problem 24.11P

(a)

Interpretation Introduction

To determine: The use of Strecker synthesis to make phenylalanine.

Interpretation: The use of Strecker synthesis to make phenylalanine is to be shown.

Concept introduction: Strecker synthesis is a two step procedure that is used to synthesize alpha amino acids from aldehydes using a metal cyanide, acid catalyst and water. In first step, condensation of ammonia takes place with aldehyde to form an imine. It is followed generally by hydrolysis to α-aminoacids.

(b)

Interpretation Introduction

To determine: A mechanism for each step in the synthesis in part (a).

Interpretation: A mechanism for each step in the synthesis in part (a) is to be proposed.

Concept introduction: Strecker synthesis is a two step procedure that is used to synthesize alpha amino acids from aldehydes using a metal cyanide, acid catalyst and water. In first step, condensation of ammonia takes place with aldehyde to form an imine. It is followed generally by hydrolysis to α-aminoacids.

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2. (a) Mark the alpha carbons with "a" and draw out the alpha hydrogens (if any are present). (b) If enolizable, draw a mechanism and the enolate product below. Use B: as a generic base. H₂N
a. Predict the structure of the hydrolysis product(s), including all organic compound(s) formed. b. Propose a plausible mechanism for the hydrolysis of enamine (Show enamine hydrolysis mechanism only), show all steps.
Propose a synthesis please explain

Chapter 24 Solutions

Organic Chemistry (9th Edition)

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