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Chapter 22: Q.69-H (page 1204)

Question: Predict the products of the following reactions

h.

Short Answer

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Answer

Step by step solution

01

Claisen ester condensation

In this sodium ethoxide is used for condensation to avoid transesterification. Ethoxide is the base that protonates the acidic hydrogen to form 尾 keto ester.

02

Reaction followed by alkylation

Ethoxide is used as a base to form an enolate ion which forms keto ester on further reaction with the alkyl halide the alkylation occurs means the removal of halide ion in the alkyl group attached at the alpha position to the carbonyl.

03

Decarboxylation

It is the reaction that leads to the removal of the carbonyl group and releases carbon di-oxide (CO2) . Decarboxylation occurs by providing heat in the reaction

04

Mechanism

  1. Acidic hydrogen protonated
  2. Formation of the enolate ion
  3. Alkylation
  4. Decarboxylation

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Most popular questions from this chapter

The following compound results from base-catalyzed aldol cyclization of a 2-substituted cyclohexanone.

  1. Show the diketone that would cyclize to give this product.
  2. Propose a mechanism for the cyclization

Show how you would use the acetoacetic ester synthesis to make the following compounds

Propose a mechanism for the following reaction. Show the structure of the compound that results from hydrolysis and decarboxylation of the product.

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: Predict the products of the following reactions

e.
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