Question

In the reaction

$C{H}_{3}C{H}_{2}CH=C{H}_2\underset{2.NaB{D}_4}{\overset{1.Hg(OAc{)}_2,H_{2}O}{\to }}$
the product obtained is:

• A. CH${}_3$CH${}_2$CHOHCH${}_2$D
• B. CH${}_3$CH${}_2$CHDCH${}_2$OH
• C. CH${}_3$CH${}_2$CD(OH)CH${}_3$
• D. CH${}_3$CH${}_2$CD${}_2$CH${}_2$OH

Answer 1

Answer: (A)

CH${}_3$CH${}_2$CHOHCH${}_2$D

In the given reaction, the product obtained is CH${}_3$CH${}_2$CHOHCH${}_2$D. This is an oxymercuration demercuration reaction by using labelled sodium borohydride. A molecule of HOD is added across C=C bond. -OH group is attached to secondary carbon atom.