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Chapter 20: Problem (page 1038)

Q. 15 Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

  1. methyl salicylate
  2. methyl formate (bp 32oC )
  3. ethyl phenylacetate

Short Answer

Expert verified

Answer

(a)

Step by step solution

01

Step-by-Step SolutionStep 1: Fischer esterification

Fischer esterification is a type of organic reaction used for converting carboxylic acid into ester in the presence of an acid catalyst and excess alcohol. The ester formation is done along with water.

02

Synthesis of methyl salicylate

  1. When salicylate is treated with a methanol solvent in the presence of a strong acid catalyst, methyl salicylate is formed along with water. The water is removed by distillation.

Synthesis of methyl salicylate

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Most popular questions from this chapter

Phenols (pKaโ‰ˆ 10) are more acidic than other alcohols, so they are easily deprotonated by sodium hydroxide or potassium hydroxide. The anions of phenols (phenoxide ions) can be used in the Williamson ether synthesis, especially with very reactive alkylating reagents such as dimethyl sulfate. Using phenol, dimethyl sulfate, and other necessary reagents, show how you would synthesize methyl phenyl ether.

Question: Arrange each group of compounds in order of increasing acidity.

  1. phenol, ethanol, acetic acid
  2. p-toluenesulfonic acid, acetic acid, chloroacetic acid
  3. benzoic acid, o-nitrobenzoic acid, m-nitrobenzoic acid
  4. butyric acid, ฮฑ-bromobutyric acid, ฮฒ-bromobutyric acid

An unknown compound gives a mass spectrum with a weak molecular ion at m/z113 and a prominent ion at m/z68. Its NMR and IR spectra are shown here. Determine the structure, and show how it is consistent with the observed absorptions. Propose a favorable fragmentation to explain the prominent MS peak at m/z68.

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a) methyl salicylate

(b) methyl formate (bp 32ยฐC)

(c) ethyl phenylacetate

(a) Give the products expected when acetic formic anhydride reacts with

(i) aniline and

(ii) benzyl alcohol

(b) Propose mechanisms for these reactions.
See all solutions

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