Skip to main content
Chemistry LibreTexts

Conversion of carboxylic acids to alcohols using LiAlH4

Carboxylic acids can be converted to 1o alcohols using Lithium aluminum hydride (LiAlH4). Note that NaBH4 is not strong enough to convert carboxylic acids or esters to alcohols. An aldehyde is produced as an intermediate during this reaction, but it cannot be isolated because it is more reactive than the original carboxylic acid. 

General reaction

1.jpg

2.jpg

Example

3.jpg

 

Possible Mechanism

1) Deprotonation

4.jpg

2)  Nucleopilic attack by the hydride anion

5.jpg

3)  Leaving group removal

6.jpg

4) Nucleopilic attack by the hydride anion

7.jpg

5) The alkoxide is protonated

 

8.jpg

Contributors

Prof. Steven Farmer (Sonoma State University)