Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
Question
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Chapter 24.5B, Problem 24.10P

(a)

Interpretation Introduction

To determine: The bromination of compound followed by amination to synthesize glycine.

Interpretation: The bromination of compound followed by amination to synthesize glycine is to be stated.

Concept introduction: The process of an introduction of bromine atom into a compound is known as bromination. Amino acids are carbon containing compounds that possess two functional groups named as amine (NH2) and carboxyl (COOH) and these are prepared by reductive amination of αketoacids by using transaminase enzyme and bromination of carboxylic acid groups followed by amination. Reductive amination comprises transformation of carbonyl group of keto acids to an imine intermediate, which leads to the formation of an amine. Transaminase enzymes are specifically used for speed up the transamination reactions.

(b)

Interpretation Introduction

To determine: The bromination of compound followed by amination to synthesize leucine.

Interpretation: The bromination of compound followed by amination to synthesize leucine is to be stated.

Concept introduction: The process of an introduction of bromine atom into a compound is known as bromination. Amino acids are carbon containing compounds that possess two functional groups named as amine (NH2) and carboxyl (COOH) and these are prepared by reductive amination of αketoacids by using transaminase enzyme and bromination of carboxylic acid groups followed by amination. Reductive amination comprises transformation of carbonyl group of keto acids to an imine intermediate, which leads to the formation of an amine. Transaminase enzymes are specifically used for speed up the transamination reactions.

(c)

Interpretation Introduction

To determine: The bromination of compound followed by amination to synthesize glutamic acid.

Interpretation: The bromination of compound followed by amination to synthesize glutamic acid is to be stated.

Concept introduction: The process of an introduction of bromine atom into a compound is known as bromination. Amino acids are carbon containing compounds that possess two functional groups named as amine (NH2) and carboxyl (COOH) and these are prepared by reductive amination of αketoacids by using transaminase enzyme and bromination of carboxylic acid groups followed by amination. Reductive amination comprises transformation of carbonyl group of keto acids to an imine intermediate, which leads to the formation of an amine. Transaminase enzymes are specifically used for speed up the transamination reactions.

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Students have asked these similar questions
Why do you wash the dichloromethane solution of your reductive amination product with sodium bicarbonate, rather than dilute aqueous HCl? a) Sodium bicarbonate is a good method of removing aldehydes from organic solvent.b) The amine product will be protonated by acid and remain in the aqueous layer as a salt.c) Sodium bicarbonate transfers the amine starting material into the aqueous layer.d) Sodium bicarbonate reacts with leftover NaBH(OAc)3 and removes it from the mixture.
Show how you would use bromination followed by amination to synthesize the followingamino acids.  leucine
Show how you would use an acid chloride as an intermediate to synthesize(a) N-phenylbenzamide (PhCONHPh) from benzoic acid and aniline

Chapter 24 Solutions

Organic Chemistry (9th Edition)

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