Question

An organic compound ‘$\mathrm{A}$’ (${\mathrm{C}}_9{\mathrm{H}}_{10}\mathrm{O}$) when treated with conc. $\mathrm{HI}$ undergoes cleavage to yield compounds ‘$\mathrm{B}$’ and ‘$\mathrm{C}$’. ‘$\mathrm{B}$’ gives a yellow precipitate with ${\mathrm{AgNO}}_3$ whereas ‘$\mathrm{C}$’ tautomerizes to ‘$\mathrm{D}$’. ‘$\mathrm{D}$’ gives a positive iodoform test. ‘$\mathrm{A}$’ could be:

• A.

  

• B.

  

• C.

  

• D.

  

Answer 1

The correct option is A

The above question can be contextualize as

1. The formed ‘$\mathrm{B}$’ compound under the action of conc. $\mathrm{HI}$ gives yellow colour shows precipitate of $\mathrm{AgI}$
2. The compound ‘$\mathrm{D}$’ gives positive iodoform test which shows the presence of $-{\mathrm{CH}}_3$ group.
3. Iodoform test is a laboratory method used to detect carbonyl compounds contain $-\mathrm{R}-\mathrm{CO}-{\mathrm{CH}}_3$ group and alcohol containing $-\mathrm{R}-\mathrm{CH}\left(\mathrm{OH}\right)-{\mathrm{CH}}_3$. The test can be explained in below diagram:
4. 
5. The compound ‘$\mathrm{A}$’ would be ((vinyloxy)methyl)benzene.
6. The whole setup of reaction can be explained in detail diagram below:

Therefore, the above points and reaction diagram clearly explains the identity of ‘$\mathrm{A}$’.