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Chapter 20: Q15P b. (page 1062)

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 32°C)

(c) ethyl phenylacetate

Short Answer

Expert verified

When formic acid is treated with a methanol solvent in the presence of a strong acid catalyst, methyl formate is formed along with water. Methyl formate can be removed by distillation.

Synthesis of methyl formate

Step by step solution

01

Synthesis of methyl formate

When formic acid is treated with a methanol solvent in the presence of a strong acid catalyst, methyl formate is formed along with water. Methyl formate can be removed by distillation.

Synthesis of methyl formate

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Most popular questions from this chapter

Question:

  1. Why do most long-chain fatty acids show a large peak in the mass spectrum at m/z 60?
  2. Use equations to explain the prominent peaks at m/z 74 and m/z 87 in the mass spectrum of 2-methylpentanoic acid.
  3. Why doesn’t the mass spectrum of 2-methylpentanoic acid show a large peak at m/z 60?

Predict the major products formed when the following amines undergo exhaustive methylation, treatment with Ag2O, and heating.

  1. Hexan-2-amine
  2. 2-methylpiperidine
  3. N-ethylpiperidine

5.

6.

Question:

  1. The Key Mechanism for Fischer esterification omitted some important resonance forms of the intermediates shown in brackets. Complete the mechanism by drawing all the resonance forms of these two intermediates.
  2. Propose a mechanism for the acid-catalyzed reaction of acetic acid with ethanol to give ethyl acetate.
  3. The Principle of Microscopic Reversibility states that a forward reaction and a reverse reaction taking place under the same conditions (as in equilibrium) must follow the same reaction pathway in microscopic detail. The reverse of the Fischer esterification is the acid-catalyzed hydrolysis of an ester. Propose a mechanism for the acid-catalyzed hydrolysis of ethyl benzoate, PhCOOCH2CH3.

Which of the following compounds are chiral? Draw each compound in its most symmetric conformation, star any asymmetric carbon atoms, and draw any mirror planes. Label any meso compounds. You may use Fischer projections if you prefer.

(a) meso-2,3-dibromo-2,3-dichlorobutane

(b) -2,3-dibromo-2,3-dichlorobutane

(c) (2R,3S)-2-bromo-3-chlorobutane

(d) (2R,3S)-2,3-dibromobutane

(e) (R,R)-2,3-dibromobutane

(f)

(g)

(h)

Question: Propose a mechanism for conversion of the dianion to the ketone under mildly acidic conditions.
See all solutions

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