Answered: C=O =O Reduction of Benzil to…

C=O =O Reduction of Benzil to Hydrobenzoin NaBH4 ethanol, water -H H -OH -OH or H- -OH HOH meso-hydrobenzoin racemic-hydrobenzoin

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter15: Benzene And Aromaticity

Section15.SE: Something Extra

Problem 19AP: Draw structures corresponding to the following names: (a) 3-Methyl-1, 2-benzenediamine (b) 1, 3,...

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Question

Rationalize the selectivity observed in the benzil reduction. Draw the transition states of the nucleophilic attack leading to either meso or racemic products and indicate why one is more stable than the other.

C=O
C=O
Reduction of Benzil to Hydrobenzoin
NaBH4
ethanol, water
H- -OH
£ £
or
H- -OH
HO- -H
meso-hydrobenzoin racemic-hydrobenzoin
HOH
I

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