18 acid derivatives

Page 55

Mechanism: Reduction ­ Esters by LiAlH4 

Reduction occurs in three steps plus workup: • Steps 1 and 2 reduce the ester to an aldehyde. O R C OR' +

H

(1)

O R C OR'

(2)

O R C

H

A tetrahedral carbonyl addition intermediate

+

OR'

H

• Step 3: Work­up gives a 1° alcohol derived from the carbonyl group. O R C H

+ H

(3)

O R C H H

OH (4) R C H H A 1° alcohol

18­57


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