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Q. $ C_6H_5 - CH = CHCHO \xrightarrow{X} C_6H_5CH = CHCH_2OH$ In the above sequence $X$ can be:

ManipalManipal 2005Alcohols Phenols and Ethers

Solution:

$ NaB{{H}_{4}} $ and $ LiAl{{H}_{4}} $ attacks only carbonyl group and reduce it into alcohol group. They do not attack on double bond.
$\underset{\text{Cinnamic aldehyde}}{C_6H_5 - CH = CHCHO} \xrightarrow{NaBH_4} $
$\underset{\text{Cinnamic alcohol}}{C_6H_5 - CH = CH . CH_2OH}$