Reduction of ketones cannot be carried outwith which of the following
reagents ?

Ketones are reduced to secondary alcohols by sodium borohydride \( \left(\mathrm{N} a \mathrm{BH}_{4}\right) \) or lithium aluminum hydride \( \left(\mathrm{LiAl} \mathrm{H}_{4}\right) \)
as well as by catalytic hydrogenation.

\[
\left(R-\stackrel{i}{C}_{\frac{1}{R}}^{\frac{\pi}{1}}\right)_{4} A l^{-}+4 H^{+}(a q) \rightarrow R-\stackrel{1}{C}-O H+A l^{3+}(a q)
\]
Carbonyl carbon of ketones are reduced to \( -\mathrm{CH}_{2}- \) group in treatment with zinc amalgam and conc. \( \mathrm{HCl}(\mathrm{Clemmensen} \)
reduction) or with hydrazine followed by heating with sodium or \( \mathrm{KOH} \) in high boiling solvent such as ethylene glycol
(Wolff-Kishner reduction).

Clemmensen reduction

Wolff-Kishner reduction