Skip to main content
Chemistry LibreTexts

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

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

General Reaction

1.jpg

 

Example 1:
2.jpg

Mechanism

1) Nucleophilic attack by the hydride

 3.jpg

2) Leaving group removal

4.jpg

3) Nucleopilic attack by the hydride anion

5.jpg

4) The alkoxide is protonated

6.jpg

Contributors

Prof. Steven Farmer (Sonoma State University)