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Chapter 23: Q23-4P (page 759)

Aldol condensation of 3-methyl cyclohexanone leads to a mixture of two enone products, not counting double-bond isomers. Draw them.

Short Answer

Expert verified

ENONE contains 饾泜 鈥� 饾泝 unsaturated carbonyl compound having alkene which is conjugated to ketone in the same compound.

Step by step solution

01

Reaction with base(NaOH):

02

After heating the above product, we get the major and minor products:

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Most popular questions from this chapter

What products would result after hydrolysis from the reaction of the enamineprepared from cyclopentanone and pyrrolidine with the following饾泜-饾泝-unsaturated acceptors?

(a)H2C=CHCO2Et

(b)H2C=CHCHO

(c)CH3CH=CHCOCH3

As shown in Figures 23-4, the Claisen reaction is reversible. That is, a饾泝-keto ester can be cleaved by base into two fragments. Using curved arrows to indicate electron flow, show the mechanism by which this cleavage occurs.

How might you synthesize each of the following compounds using an aldol reaction? Show the structure of the starting aldehyde(s) or ketone(s) you would use in each case.

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.

What product would you expect from the following reaction?
See all solutions

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