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The complete mechanism that leads to the three alkenes produced by N-ethylhexan-3-amine under Hofmann elimination conditions is to be drawn, and the major product is to be predicted. Concept introduction: Hofmann elimination is an E2 elimination of an amine group along with a β hydrogen to produce an alkene. Unlike most elimination reactions that preferentially form the most substituted alkenes, Hofmann elimination preferentially forms the least substituted alkene. When two different types of β hydrogens are present, the one from the less substituted carbon is removed preferentially. The leaving group in Hofmann elimination is a bulky tertiary amine group NR 3 . An E2 reaction is a single-step concerted reaction. It requires that the two groups that are eliminated must be anti to each other. The most stable conformer has the β hydrogen in anti position on the less substituted carbon. This gives a least substituted alkene as the major product.

The complete mechanism that leads to the three alkenes produced by N-ethylhexan-3-amine under Hofmann elimination conditions is to be drawn, and the major product is to be predicted. Concept introduction: Hofmann elimination is an E2 elimination of an amine group along with a β hydrogen to produce an alkene. Unlike most elimination reactions that preferentially form the most substituted alkenes, Hofmann elimination preferentially forms the least substituted alkene. When two different types of β hydrogens are present, the one from the less substituted carbon is removed preferentially. The leaving group in Hofmann elimination is a bulky tertiary amine group NR 3 . An E2 reaction is a single-step concerted reaction. It requires that the two groups that are eliminated must be anti to each other. The most stable conformer has the β hydrogen in anti position on the less substituted carbon. This gives a least substituted alkene as the major product.

Solution Summary: The author describes the mechanism that leads to the three alkenes produced by N-ethylhexan-3-amine under Hofmann elimination conditions.

EBK GET READY FOR ORGANIC CHEMISTRY

EBK GET READY FOR ORGANIC CHEMISTRY

2nd Edition

ISBN: 9780321830555

Author: KARTY

Publisher: VST

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Question

Chapter 10, Problem 10.64P

Interpretation Introduction

Interpretation:

The complete mechanism that leads to the three alkenes produced by N-ethylhexan-3-amine under Hofmann elimination conditions is to be drawn, and the major product is to be predicted.

Concept introduction:

Hofmann elimination is an E2 elimination of an amine group along with a β hydrogen to produce an alkene. Unlike most elimination reactions that preferentially form the most substituted alkenes, Hofmann elimination preferentially forms the least substituted alkene.

When two different types of β hydrogens are present, the one from the less substituted carbon is removed preferentially. The leaving group in Hofmann elimination is a bulky tertiary amine group NR3. An E2 reaction is a single-step concerted reaction. It requires that the two groups that are eliminated must be anti to each other. The most stable conformer has the β hydrogen in anti position on the less substituted carbon. This gives a least substituted alkene as the major product.

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Chapter 10, Problem 10.63P

Chapter 10, Problem 10.65P

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Chapter 10 Solutions

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Ch. 10 - Prob. 10.1P Ch. 10 - Prob. 10.2P Ch. 10 - Prob. 10.3P Ch. 10 - Prob. 10.4P Ch. 10 - Prob. 10.5P Ch. 10 - Prob. 10.6P Ch. 10 - Prob. 10.7P Ch. 10 - Prob. 10.8P Ch. 10 - Prob. 10.9P Ch. 10 - Prob. 10.10P

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