Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
2nd Edition
ISBN: 9780393655551
Author: KARTY, Joel
Publisher: W. W. Norton & Company
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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 Solutions

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)

Ch. 10 - Prob. 10.1PCh. 10 - Prob. 10.2PCh. 10 - Prob. 10.3PCh. 10 - Prob. 10.4PCh. 10 - Prob. 10.5PCh. 10 - Prob. 10.6PCh. 10 - Prob. 10.7PCh. 10 - Prob. 10.8PCh. 10 - Prob. 10.9PCh. 10 - Prob. 10.10P
Ch. 10 - Prob. 10.11PCh. 10 - Prob. 10.12PCh. 10 - Prob. 10.13PCh. 10 - Prob. 10.14PCh. 10 - Prob. 10.15PCh. 10 - Prob. 10.16PCh. 10 - Prob. 10.17PCh. 10 - Prob. 10.18PCh. 10 - Prob. 10.19PCh. 10 - Prob. 10.20PCh. 10 - Prob. 10.21PCh. 10 - Prob. 10.22PCh. 10 - Prob. 10.23PCh. 10 - Prob. 10.24PCh. 10 - Prob. 10.25PCh. 10 - Prob. 10.26PCh. 10 - Prob. 10.27PCh. 10 - Prob. 10.28PCh. 10 - Prob. 10.29PCh. 10 - Prob. 10.30PCh. 10 - Prob. 10.31PCh. 10 - Prob. 10.32PCh. 10 - Prob. 10.33PCh. 10 - Prob. 10.34PCh. 10 - Prob. 10.35PCh. 10 - Prob. 10.36PCh. 10 - Prob. 10.37PCh. 10 - Prob. 10.38PCh. 10 - Prob. 10.39PCh. 10 - Prob. 10.40PCh. 10 - Prob. 10.41PCh. 10 - Prob. 10.42PCh. 10 - Prob. 10.43PCh. 10 - Prob. 10.44PCh. 10 - Prob. 10.45PCh. 10 - Prob. 10.46PCh. 10 - Prob. 10.47PCh. 10 - Prob. 10.48PCh. 10 - Prob. 10.49PCh. 10 - Prob. 10.50PCh. 10 - Prob. 10.51PCh. 10 - Prob. 10.52PCh. 10 - Prob. 10.53PCh. 10 - Prob. 10.54PCh. 10 - Prob. 10.55PCh. 10 - Prob. 10.56PCh. 10 - Prob. 10.57PCh. 10 - Prob. 10.58PCh. 10 - Prob. 10.59PCh. 10 - Prob. 10.60PCh. 10 - Prob. 10.61PCh. 10 - Prob. 10.62PCh. 10 - Prob. 10.63PCh. 10 - Prob. 10.64PCh. 10 - Prob. 10.65PCh. 10 - Prob. 10.66PCh. 10 - Prob. 10.67PCh. 10 - Prob. 10.68PCh. 10 - Prob. 10.69PCh. 10 - Prob. 10.70PCh. 10 - Prob. 10.71PCh. 10 - Prob. 10.72PCh. 10 - Prob. 10.73PCh. 10 - Prob. 10.74PCh. 10 - Prob. 10.1YTCh. 10 - Prob. 10.2YTCh. 10 - Prob. 10.3YTCh. 10 - Prob. 10.4YTCh. 10 - Prob. 10.5YTCh. 10 - Prob. 10.6YTCh. 10 - Prob. 10.7YTCh. 10 - Prob. 10.8YTCh. 10 - Prob. 10.9YTCh. 10 - Prob. 10.10YTCh. 10 - Prob. 10.11YTCh. 10 - Prob. 10.12YTCh. 10 - Prob. 10.13YTCh. 10 - Prob. 10.14YTCh. 10 - Prob. 10.15YTCh. 10 - Prob. 10.16YTCh. 10 - Prob. 10.17YTCh. 10 - Prob. 10.18YTCh. 10 - Prob. 10.19YT
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