Answered: Draw a plausible mechanism for the…

Draw a plausible mechanism for the reaction shown below. Determine the reactant and provide explanations for each step in the mechanism. 1. 1, 3-butadiene, heat ? 2. Hg(OAC)2, H2O 3. NABH4 4. PCC

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

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.27P

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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

Draw a plausible mechanism for the reaction shown below. Determine the reactant and provide explanations
for each step in the mechanism.
1. 1, 3-butadiene, heat
? 2. Hg(OAC)2, H2O
3. NABH4
4. PCC

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