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Chapter 22: Q68P-F (page 1204)

Question:Show how you would use an aldol, Claisen, or another type of condensation to make each compound

f.

Short Answer

Expert verified

Answer

Two methods to obtain product:

Step by step solution

01

Enamine acylation

In this, acylation of the enamine occurs to form the di-carbonyl product.Enamine occurs s nucleophile forming iminium ion followed by acylation of the carbon of carbonyl group followed by hydrolysis to form di-carbonyl compound as shown:

02

 Claisen condensation followed by aldol self-condensation

The nucleophilic acyl substitution reaction of carbonyl forming the enolate ion with ether group followed by the removal of -OEt group, which further leads to removing 鈥揙H (aldol self-condensation) shown to form the di-carbonyl product.

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Most popular questions from this chapter

Predict the major products of the following reactions.

a)

Question: Predict the products of the following reactions

e.

Write equations showing the expected products of the following enamine alkylation and acylation reactions. Then give the final products expected after hydrolysis of the iminium salts.

(a) pyrrolidine enamine of pentan-3-one + allyl chloride

(b) pyrrolidine enamine of acetophenone + butanoyl chloride

(c) piperidine enamine of cyclopentanone + methyl iodide

(d) piperidine enamine of cyclopentanone + methyl vinyl ketone

Question:Show how you would use an aldol, Claisen, or another type of condensation to make each compound

e.

The following compounds can be synthesized by aldol condensations, followed by further reactions. (In each case, work backward from the target molecule to an aldol product, and show what compounds are needed for the condensation.)
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