Problem
The products formed in the reaction
$$\ce{CH2=CHOCH2CH3 + HI ->}$$
are
(a) $\ce{CH2=CHI}$ and $\ce{CH3CH2I}$
(b) $\ce{CH2=CHI}$ and $\ce{CH3CH2OH}$
(c) $\ce{CH3CHO}$ and $\ce{CH3CH2I}$
(d) $\ce{CH3CH(I)OCH2CH3}$
Answer
(c) $\ce{CH3CHO}$ and $\ce{CH3CH2I}$
Question
Does ether cleavage occur or electrophilic addition of $\ce{HI}$ to the double bond take place or both? I'm equally inclined towards both (c) and (d).