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Hydride reduction (with LiAlH4 or NaBH4) of each of the following ketones has been
Chapter 17, Problem 17.28(choose chapter or problem)
Hydride reduction (with \(LiAlH_{4}\) or \(NaBH_{4})\) of each of the following has been reported in the chemical literature and gives a mixture of two diastereomeric alcohols in each case. Give the structure of both alcohol products for each ketone.
(a) (S)-3-phenyl-2-butanone
(b) 4-tert-butyl cyclohexanone
(c)
(d)
Questions & Answers
QUESTION:
Hydride reduction (with \(LiAlH_{4}\) or \(NaBH_{4})\) of each of the following has been reported in the chemical literature and gives a mixture of two diastereomeric alcohols in each case. Give the structure of both alcohol products for each ketone.
(a) (S)-3-phenyl-2-butanone
(b) 4-tert-butyl cyclohexanone
(c)
(d)
Step 1 of 5
The hydride reduction of ketones illustrates a synthetic route for the preparation of secondary alcohols. The diastereomeric products are obtained as a carbonyl is a planar structure; thus, a hydride attack on carbonyl carbon is possible from both sides.