Question

In the fischer esterification of lauric acid, why is the majority of ethanol boiled off prior...

In the fischer esterification of lauric acid, why is the majority of ethanol boiled off prior to extraction?

Please explain.

Homework Answers

Answer #1
  • The esters and water have significantly higher boiling points than the ethanol, which makes it impossible to remove those compounds from the equilibrium by simple distillation.
  • A larger excess of ethanol (a five-fold molar excess) usually causes problems in the phase separation later on. Thus it would have to be distilled off before the workup.
  • Water is one of the products in the Fischer esterification. Thus, any water in the system due to wet reagents, wet glassware, etc. will reduce the yield of the ester because the equilibrium will be shifted to the left side.

RCOOH +  R'OH    <====>    RCOOR' +  H2O

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