Q17P - Organic Chemistry (Mcmurry)

Question

What product would you expect from the reaction of butyrolactone with LiAlH4? With DIBAH?

 

Step-by-Step Solution

Answer

Product formed are:.

1. 1,4-Butanediol (with LiAlH₄)

2.4-Hydroxy butanal (DIBAL-H)

Step 1: Reduction with LiAlH 4

Esters are easily reduced to primary alcohols using LiAlH₄. In case of cyclic esters diols are formed.

 

Step 2: Reduction with DIBAL-H

Partial reduction take place in case of DIBAL-H, and reaction stops at formation of aldehydes.