Esters can be reduced to 1° alcohols using \(LiAlH_4\)

Esters can be converted to 1^o alcohols using LiAlH₄, while sodium borohydride (\(NaBH_4\)) is not a strong enough reducing agent to perform this reaction.

General Reaction

Example 1:

Mechanism

1) Nucleophilic attack by the hydride

2) Leaving group removal

3) Nucleopilic attack by the hydride anion

4) The alkoxide is protonated

Contributors

Prof. Steven Farmer (Sonoma State University)