Aldehydes Ketones Question 11
Question: If 3-hexanone is reacted with $ NaBH_4 $ followed by hydrolysis with $ D_2O $ , the product will be
Options:
A) $ CH_3CH_2CH(OH)CH_2CH_2CH_3 $
B) $ CH_3CH_2CD( OH )CH_2CH_2CH_3 $
C) $ CH_3CH_2CH( OD )CH_2CH_2CH_3 $
D) $ CH_3CH_2CD( OD )CH_2CH_2CH_3 $
Show Answer
Answer:
Correct Answer: C
Solution:
[c] Remember that during reduction with $ NaBH_4 $ , a hydride ion is transferred by $ NaBH_4 $ to carbonyl carbon and a proton (or deutron) is transferred from the solvent (in the second step) to carbonyl oxygen. $ \underset{3-Hexanone}{\mathop{C_2H_5-\overset{O}{\mathop{\overset{||}{\mathop{C}}}}-C_3H_7}}\xrightarrow{NaBH_4}C_2H_5-\overset{{O^{-}}}{\mathop{\overset{|}{\mathop{C}}}}H-C_3H_7 $
$ \xrightarrow[(-O{D^{-}})]{D_2O}\underset{{}}{\mathop{C_2H_5-\overset{OD}{\mathop{\overset{|}{\mathop{C}}H}}-C_3H_7}} $
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