Question

An organic compound $\left(\mathrm{A}\right)$ (molecular formula ${\mathrm{C}}_6{\mathrm{H}}_{12}{\mathrm{O}}_2$) was hydrolysed with $\mathrm{dilute}{\mathrm{H}}_2{\mathrm{SO}}_4$ to give a $\mathrm{carboxylic}\mathrm{acid}\left(\mathrm{B}\right)\mathrm{and}\mathrm{alcohol}\left(\mathrm{C}\right).‘\mathrm{C}’$ gives white turbidity immediately when treated with $\mathrm{anhydrous}{\mathrm{ZnCl}}_2\mathrm{and}\mathrm{conc}.\mathrm{HCl}.$ The organic compound $\left(\mathrm{A}\right)$is:

• A.

  

• B.

  

• C.

  

• D.

  

Answer 1

The correct option is D

The correct option is D.

Explanation for correct option :

Compound A should be an ester because whenever a carboxylic acid reacts with an alcohol in the presence of acidic medium $\mathrm{dilute}{\mathrm{H}}_2{\mathrm{SO}}_4$esterification reaction takes place. Options B and C are not esters so they can't be the correct option.

$\mathrm{Anhydrous}{\mathrm{ZnCl}}_2\mathrm{and}\mathrm{conc}.\mathrm{HCl}$ are Lucas reagents for Lucas test. Lucas test is done to identify whether the alcohol is $1°,2°\mathrm{or}3°$. The extent of turbidity depends on the degree of alcohol.

So, the alcohol should be a $3°$alcohol. Option A can't be the correct option since it's a $1°$ alcohol.

Since Option D is an ester and a $3°$ alcohol, it's a correct option.

The scheme of reaction of structure in option D is as follows:

Hence, The organic compound $\left(\mathrm{A}\right)$is the given structure in option D.

Explanation for incorrect options :

The given structures in B and C are not esters so they are incorrect options.

The given structure in option A is $1°$ alcohol so it's also an incorrect option.

Therefore, A, B and C are incorrect options.