When trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone. 1. Write the equation for the reaction between trans-2-chloro-1-cyclohexanol and the base to yield the cyclohexene oxide. 2. Why doesn't the cis isomer yield the oxide? 3. Write the mechanism for each of the two reactions

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter23: Addition To A Carbonyl
Section: Chapter Questions
Problem 20E
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When trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone.

1. Write the equation for the reaction between trans-2-chloro-1-cyclohexanol and the base to yield the cyclohexene oxide.

2. Why doesn't the cis isomer yield the oxide?

3. Write the mechanism for each of the two reactions

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