Answered: 4. One of the products that results…

4. One of the products that results when 1-bromo-2,2-dimethylcyclopentane is heated in ethanol is shown below. CH3 CH3 Propose a mechanism by which it is formed. Name the mechanism. (ii)

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 26MP: Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium...

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

4. One of the products that results when 1-bromo-2,2-dimethylcyclopentane is
heated in ethanol is shown below.
CH3
-CH3
(i)
(ii)
Propose a mechanism by which it is formed.
Name the mechanism.

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