Question

Tertiary alcohols $(3{}^{\circ })$ having at least four carbon atoms upon drastic oxidation yield carboxylic acid with

• A. one carbon atom less
• B. two carbon atoms less
• C. three carbon atoms less
• D. All the above three options are correct

Answer 1

Answer: (B)

A $3{}^{\circ }$ alcohol is very difficult to oxidised because they dont have carbon bearing $-H$ and $-OH$ both the groups. However, when treated under drastic conditions, cleavage of $C-C$ bond takes place. They form mixture of ketone and carboxylic acid contains two carbon atom lesser than the starting alcohol. $\underset{t-butylalcohol}{C{H}_3-\underset{C{H}_3}{\stackrel{C{H}_3}{\underset{|}{\stackrel{|}{C}}}}-OH}\underset{(Strongcondition)}{\overset{4[O]}{\to }}\underset{\begin{array}{c}acetone\\ (onecarbonatomless)\end{array}}{C{H}_3-\stackrel{C{H}_3}{\stackrel{|}{C}}=O}$ $\underset{(strongcondition)}{\overset{4[O]}{\to }}\underset{twocarbonatomsless}{C{H}_{3}COOH}+C{O}_2+H_{2}O$