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Chapter 23: Q55E (page 783)

The aldol reaction is catalyzed by acid as well as the base. What is the reactive nucleophile in the acid-catalyzed aldol reaction? Propose a mechanism.

Short Answer

Expert verified

The reactive nucleophile in the acid-catalyzed aldol reaction is the enol and electrophile is a protonated carbonyl group.

Step by step solution

01

Formation of Enol:

02

Addition of enol to the protonated carbonyl group:

03

loss of +H ion from the carbonyl oxygen:

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Most popular questions from this chapter

What product would you obtain from a base-catalyzed Michael reaction of 2,4-pentanedione with each of the following ฮฑ-ฮฒ unsaturated acceptors?

(a) 2-Cyclohexenone

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(c) Ethyl 2-butenoate.

The following reaction involves an intramolecular Michael reaction followed by an intramolecular aldol reaction. Write both steps, and show their mechanisms.

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