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Chapter 22: Q72P-a (page 1205)

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

Short Answer

Expert verified

It鈥檚 a method in which substituted derivative of acetic acid is formation occur from dimethyl malonate in the presence of sodium ethoxide followed by alkylation or acylation then hydrolysis followed by decarboxylation to form derivate of acetic acid as a product.

Step by step solution

01

Step-by-Step Solution Step1: Malonic ester synthesis

It鈥檚 a method in which substituted derivative of acetic acid is formation occur from dimethyl malonate in the presence of sodium ethoxide followed by alkylation or acylation then hydrolysis followed by decarboxylation to form derivate of acetic acid as a product.

02

Reaction followed by alkylation

Ethoxide is used as a base to form enolate ion which on further reaction with the alkyl halide the alkylation occur means the by removal of halide ion 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-oxideCO2 . Decarboxylation occurs by providing heat in the reaction.

04

Mechanism

  1. Acidic hydrogen protonated
  2. Formation of the enolate ion
  3. Alkylation
  4. Decarboxylation
  5. Derivative of acetic acid formed

Mechanism

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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 octane-2,7-dione might cyclize to a cycloheptenone. Explain why ring closure to the cycloheptenone is not favored.

Show how the following ketones might be synthesized by using the acetoacetic ester synthesis.

Phenylacetone can form two different enols.

  1. Show the structures of these enols.
  2. Predict which enol will be present in the larger concentration at equilibrium.

Propose a mechanism for the conjugate addition of a nucleophile (Nuc:-) to acrylonitrile (H2C=CHCN) and to nitroethylene. Use resonance forms to show how the cyano and nitro groups activate the double bond toward conjugate addition.
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