trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter11: Ethers, Epoxides, And Sulfides
Section: Chapter Questions
Problem 11.41P: Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in...
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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 
A.Write the equation for the reaction between trans-2-chloro-1-cyclohexanol and the base to yield the cyclohexene oxide 
B.Why doesn’t the cis isomer yield the oxide? 
C.Write the mechanism for each of the two reactions. 

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