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. Why doesn’t the cis isomer yield the oxide?
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. Why doesn’t the cis isomer yield the oxide?
Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter17: Aldehydes And Ketones
Section: Chapter Questions
Problem 17.60P: 17-60 1-Propanol can be prepared by the reduction of an aldehyde, but it cannot be prepared by the...
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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.
Why doesn’t the cis isomer yield the oxide?
Expert Solution
Step 1
In Transforms, substituents are placed on different sides, and in Cis forms, substituents are placed on the same sides.
Step 2
- Base abstracts the hydrogen of –OH from trans forms and alkoxide is formed which as a nucleophile attacks the carbon that has Cl attached. There is less repulsion and hence, the SN2 reaction takes place.
- In cis form, both groups are on the same side and this brings the steric hindrance and hence alkoxide cannot attack the carbon. So, the elimination reaction occurs in cis form.
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