CH₂ + Ch HCI prevents CH3 from acting as a leaving group HCI ensures that only one H of the CH3 is substituted by lowering the pH CH₂CI HCI can accelerate the reaction as it forms by catalyzing keto-enol tautomerism HCI can slow the reaction by enabling the formation of an enolate + HCI

CH₂ + Ch HCI prevents CH3 from acting as a leaving group HCI ensures that only one H of the CH3 is substituted by lowering the pH CH₂CI HCI can accelerate the reaction as it forms by catalyzing keto-enol tautomerism HCI can slow the reaction by enabling the formation of an enolate + HCI

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

Chapter6: Reactions Of Alkenes

Section: Chapter Questions

Problem 6.34P: Treating 4-penten-1-ol with bromine in water forms a cyclic bromoether. Account for the formation of...

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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

HCI is a byproduct of this reaction. Which statements
are true?
CH₂
. Cl₂
HCI prevents CH3 from acting as a leaving group
HCI ensures that only one H of the CH3 is
substituted by lowering the pH
CH₂CI
HCI can accelerate the reaction as it forms by
catalyzing keto-enol tautomerism
HCI can slow the reaction by enabling the
formation of an enolate
+ HCI

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