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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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.
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
Propose a synthesis please explain

Chapter 24 Solutions

Organic Chemistry (9th Edition)

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