Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
Question
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Chapter 8, Problem 8.16P
Interpretation Introduction

(a)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom adjacent to the carbocation is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

Interpretation Introduction

(b)

Interpretation:

The product with greater abundance in the given E1 reaction is to be predicted.

Concept introduction:

The E1 reaction proceeds with the formation of a carbocation intermediate by elimination of the leaving group in the first step. In the second step, the hydrogen atom, adjacent to the carbocation, is removed by the base to form a double bond. As the carbocation is planar, the elimination product would be a mixture of diastereomers when the double bonded carbon atoms are asymmetrically substituted. The stereochemistry of C=C bond is indicated by E/Z notation. E represents the trans double bond. When the same priority groups are on opposite side of the double bond, the representation E is used. Z represents the cis double bond. When the same priority groups are on the same side of the double bond., the representation Z is used. The isomer with the bulkier groups on opposite side of C=C bond is more stable due to less steric hindrance.

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Chapter 8 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

Ch. 8 - Prob. 8.11PCh. 8 - Prob. 8.12PCh. 8 - Prob. 8.13PCh. 8 - Prob. 8.14PCh. 8 - Prob. 8.15PCh. 8 - Prob. 8.16PCh. 8 - Prob. 8.17PCh. 8 - Prob. 8.18PCh. 8 - Prob. 8.19PCh. 8 - Prob. 8.20PCh. 8 - Prob. 8.21PCh. 8 - Prob. 8.22PCh. 8 - Prob. 8.23PCh. 8 - Prob. 8.24PCh. 8 - Prob. 8.25PCh. 8 - Prob. 8.26PCh. 8 - Prob. 8.27PCh. 8 - Prob. 8.28PCh. 8 - Prob. 8.29PCh. 8 - Prob. 8.30PCh. 8 - Prob. 8.31PCh. 8 - Prob. 8.32PCh. 8 - Prob. 8.33PCh. 8 - Prob. 8.34PCh. 8 - Prob. 8.35PCh. 8 - Prob. 8.36PCh. 8 - Prob. 8.37PCh. 8 - Prob. 8.38PCh. 8 - Prob. 8.39PCh. 8 - Prob. 8.40PCh. 8 - Prob. 8.41PCh. 8 - Prob. 8.42PCh. 8 - Prob. 8.43PCh. 8 - Prob. 8.44PCh. 8 - Prob. 8.45PCh. 8 - Prob. 8.46PCh. 8 - Prob. 8.47PCh. 8 - Prob. 8.48PCh. 8 - Prob. 8.49PCh. 8 - Prob. 8.50PCh. 8 - Prob. 8.51PCh. 8 - Prob. 8.52PCh. 8 - Prob. 8.53PCh. 8 - Prob. 8.54PCh. 8 - Prob. 8.55PCh. 8 - Prob. 8.56PCh. 8 - Prob. 8.57PCh. 8 - Prob. 8.58PCh. 8 - Prob. 8.59PCh. 8 - Prob. 8.60PCh. 8 - Prob. 8.61PCh. 8 - Prob. 8.62PCh. 8 - Prob. 8.63PCh. 8 - Prob. 8.64PCh. 8 - Prob. 8.65PCh. 8 - Prob. 8.66PCh. 8 - Prob. 8.67PCh. 8 - Prob. 8.68PCh. 8 - Prob. 8.69PCh. 8 - Prob. 8.70PCh. 8 - Prob. 8.71PCh. 8 - Prob. 8.72PCh. 8 - Prob. 8.73PCh. 8 - Prob. 8.74PCh. 8 - Prob. 8.75PCh. 8 - Prob. 8.76PCh. 8 - Prob. 8.1YTCh. 8 - Prob. 8.2YTCh. 8 - Prob. 8.3YTCh. 8 - Prob. 8.4YTCh. 8 - Prob. 8.5YTCh. 8 - Prob. 8.6YTCh. 8 - Prob. 8.7YTCh. 8 - Prob. 8.8YTCh. 8 - Prob. 8.9YTCh. 8 - Prob. 8.10YTCh. 8 - Prob. 8.11YTCh. 8 - Prob. 8.12YTCh. 8 - Prob. 8.13YTCh. 8 - Prob. 8.14YTCh. 8 - Prob. 8.15YTCh. 8 - Prob. 8.16YTCh. 8 - Prob. 8.17YTCh. 8 - Prob. 8.18YTCh. 8 - Prob. 8.19YT
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