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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

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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 β 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

A reaction involved in the metabolism of sugars is the splitting of fructose-1,6-diphosphate to give glyceraldehyde3-phosphate and dihydroxyacetone phosphate. In the living system, this retro-aldol is catalyzed by an enzyme called aldolase; however, it can also be catalyzed by a mild base. Propose a mechanism for the base-catalyzed reaction

Question:Show how you would use the Robinson annulation to synthesize the following compounds.

Propose mechanisms for the following reactions.

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.)

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.
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