Acid Chloride Reactions: Carboxylic Acid formation Using Water

Acid chlorides react with water (H2O) to form carboxylic acids:

The reaction mechanism is depicted below:

In the first step, the lone pair electrons on the oxygen atom attack the carbonyl-carbon, breaking the double bond and sending those electrons to the oxygen atom.

In the second step, the free electrons from the negatively charged oxygen re-form the double bond, forcing the chloride bond to be removed.

In the third step, a nearby water molecule removes the proton, completing the reaction.

Pyridine (pyr) is used in this reaction as a base to counteract the HCl that is generated as a byproduct of this reaction.

Practice this reaction using our Reaction Solver!