Question 13 - 2020 (02 Sep Shift 2)

An organic compound ‘A’ ($\text{C}9\text{H}{10}\text{O}$) when treated with conc. HI undergoes cleavage to yield compounds ‘B’ and ‘C’. ‘B’ gives yellow precipitate with $\text{AgNO}_3$ whereas ‘C’ tautomerizes to ‘D’. ‘D’ gives positive iodoform test. ‘A’ could be:

(1) $\text{C}_6\text{H}_5-\text{O}-\text{CH}_2-\text{CH}=\text{CH}_2$

(2) $\text{C}_6\text{H}_5-\text{O}-\text{CH}=\text{CH}-\text{CH}_3$

(3) $\text{C}_6\text{H}_5-\text{CH}_2-\text{O}-\text{CH}=\text{CH}_2$

(4) $\text{H}_3\text{C}-\text{C}_6\text{H}_4-\text{O}-\text{CH}=\text{CH}_2$