Question

What would be the product formed upon treatment of (Z)-$3$-methyl-$3$-hexene with $B_2{H}_6$ followed by treatment with $H_2{O}_2,{}^{-}OH$?

• A. $3$-methyl-$3$-hexanol
• B. $3$-methyl-$2$-hexanol
• C. $4$-methyl-$3$-hexanol
• D. $3$-methyl-$4$-hexanol

Answer 1

Answer: (C)

$4$-methyl-$3$-hexanol

Treatment of (Z)-3-methyl-3-hexene with $B_2{H}_6$ followed by treatment with $H_2{O}_2/O{H}^{-}$ will give 4-methyl-3-hexanol.

It is an example of hydroboration oxidation reaction. Net reaction is addition of a molecule of water to $C=C$ double bond. $-OH$ group is added to less substituted $C$ atom.