Question

An organic compound [$\mathrm{A}$], molecular formula ${\mathrm{C}}_{10}{\mathrm{H}}_{20}{\mathrm{O}}_2$ was hydrolyzed with dilute sulphuric acid to give a carboxylic acid [$\mathrm{B}$] and alcohol [$\mathrm{C}$]. Oxidation of [$\mathrm{C}$] with ${\mathrm{CrO}}_3-{\mathrm{H}}_2{\mathrm{SO}}_4$ produced [$\mathrm{B}$]. Which of the following structures are not possible for [$\mathrm{A}$]?

• A.

  

• B.

  

• C.

  

• D.

  

Answer 1

The correct option is B

Explanation for the correct option:

B)

Explanation for the incorrect options:

A)

C)

D)

Hence option B is correct. In all other options, compound C on oxidation produces compound B.