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MolSynapse / Question bank / Organic Reaction Mechanisms I: Nucleophiles and Carbonyl Addition / Nucleophilic acyl substitution of carboxylic acid derivatives

JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o1218

In the acid-catalysed Fischer esterification of acetic acid with ethanol, which statements are correct?

Aremoving water as it forms increases the yield of ester
Bprotonation of the carbonyl oxygen makes the carbon more electrophilic
Cwater leaves from a protonated tetrahedral intermediate
Dthe alkoxy oxygen of the ester is the oxygen of the acid's C-OH

Answer: A, B, C

The acid first protonates

C = O

, ethanol adds, proton transfer converts one OH to

OH X_{2} X^{+}

and water leaves. Le Chatelier's principle makes removal of water useful. The alkoxy oxygen of the ester comes from ethanol, not from the acid; the lost water takes the OH of the acid.

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