Acid Chloride Reactions: Reduction of Acid Chlorides using LiAlH4 to form Alcohols

Acid chlorides react with lithium aluminium hydride (LiAlH4) in acidic environments (H3O+) to form alcohols:

The reaction mechanism is depicted below:

In the first step, a hydride from LiAlH4 attacks the carbonyl carbon, breaking the carbonyl bond, sending the pi electrons up to the oxygen atom.

In the second step, the free electrons on the negatively charged oxygen come back down, reforming the carbonyl bond thereby kicking the chloride atom off the molecule.

In the third step, another LiAlH4 hydride attacks the carbonyl carbon, sending the pi electrons up to the oxygen atom (again).

In the forth and final step, an acid molecule (represented by H3O+) is attacked by the free electrons on the negatively charged oxygen atom, forming the alcohol product.

Practice this reaction using our Reaction Solver!