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Conversion of carboxylic acids to carboxylates using base

Description: When treated with base, carboxylic acids form carboxylate salts.

Notes: Although this example shows the reaction of an amine with a carboxylic acid, this is also a  notably the result when a Grignard reagent is added to a carboxylic acid.


Notes: The third example shows the reaction of a carboxylic acid with a Grignard reagent. Instead of adding to the carbonyl, the Grignard deprotonates the carboxylic acid, forming a salt (and CH4 in this case).

Mechanism: The reaction proceeds through removal of a proton from O-H by a base (Step 1, arrows A and B).