Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 8, Problem 63P
Interpretation Introduction

Interpretation: The stereoisomer of 1, 2, 3, 4, 5, 6-hexachlorocyclohexane that reacts 7000 times more slowly than any of the other isomer in an E2 elimination is to be drawn and the reason for the same is to be stated.

Concept introduction: The one-step bimolecular elimination reaction that favors the removal of a proton by a base from carbon adjacent to the leaving group that results in the formation of a carbocation is termed as E2 elimination reaction. The formation of a double bond takes place simultaneously through the carbocation to form an alkene as the desired product. In case of E2 elimination, the anti-periplanar geometry should exist between the halogen and the proton that is being abstracted.

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3-bromo-1-pentene and 1-bromo-2-pentene undergo SN1 reaction at almost the same rate, but one is a secondary halide while the other is a primary halide. Explain your answer.  Then,    decide which the following compounds will react faster in an E2 reaction; trans-1-bromo-2-isopropylcyclohexane or cis-1-bromo-2-isopropylcyclohexane. and Explain your answer.
Consider an E2 reaction between (2-bromoethyl)cyclohexane and base potassium tert-butoxide. Describe the rate of elimination when each of the following changes occurred: (i) The base is changed to sodium hydroxide. (ii) The halogen atom of alkyl halide is replaced by chlorine.
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Organic Chemistry (6th Edition)

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