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Acidity of Alcohols and Phenols

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Question

Write the mechanism involved in the esterification of a carboxylic acid with alcohol.

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Solution

The mechanism involved in the esterification of a carboxylic acid with alcohol is shown below.

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Q. A carboxylic acid ester is prepared commonly by reacting a carboxylic acid with excess of an alcohol in the presence of a small quantity of a strong acid such as

c o n c . H_{2} S O_{4}

as a catalyst. The reaction is reversible and generally the equilibrium constant for the esterification is close to

1

. As it is a reversible reaction, different methods are used to increase the yield of ester. It is established that the mechanism of esterification under such conditions involves initial protonation of the acid followed by the attack of the alcohol as a nucleophile.
The correct statement(s) is/are__________.

Q. Explain the mechanism of esterification. Write the reactions involved in dehydration of

1^{o}

2^{o}

3^{o}

Q. Assertion :M Reason: During esterification, removed water molecule contains H of alcohol and OH of carboxylic acid.

Q. Esterification ( shown below ) is a reaction converting a carboxylic acid to its ester. It involves only the carbonyl carbon. Esterification of

(-) -

lactic acid with menthol yields

(+) -

methyl lactate. Assuming that there are no side reactions, what is true about this reaction ?

Q. STATEMENT-1: Phenols cannot be converted to esters by direct reaction with carboxylic acids whereas alcohols can.

STATEMENT-2: This is because esterification reaction is exothermic for alcohols but slightly endothermic for phenols.

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Acidity of Alcohols and Phenols

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