If 3 -hexanone is reacted with $\mathrm{NaBH}_{4}$ followed by hydrolysis with $\mathrm{D}_{2} \mathrm{O}$,…

If 3 -hexanone is reacted with $\mathrm{NaBH}_{4}$ followed by hydrolysis with $\mathrm{D}_{2} \mathrm{O}$, the product will be
  1. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$
  2. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CD}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$
  3. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}(\mathrm{OD}) \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$
  4. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CD}(\mathrm{OD}) \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$

Solution

Remember that during reduction with $\mathrm{NaBH}_{4}$, a hydride ion is transferred by $\mathrm{NaBH}_{4}$ to carbonyl carbon and a proton (or deutron) is transferred from the solvent (in the second step) to carbonyl oxygen.
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Asked in: JEE-TOPICTESTS-CHEMISTRY

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