On the treatment of the following compound with a strong acid, the most susceptible site for bond cleavage is:
On the treatment of the following compound with a strong acid, the most susceptible site for bond cleavage is:
$\mathrm{O} 2-\mathrm{C} 3$
O5-C6
$\mathrm{C} 4-\mathrm{O} 5$
$\mathrm{C} 1-\mathrm{O} 2$
Solution
The lone pair of electrons on $\mathrm{O} 2$ is involved in resonance with $\mathrm{C}=\mathrm{C}$. Hence $\mathrm{O} 2$ will not be protonated.
The lone pair of electrons on O5 is not involved in resonance with $\mathrm{C}=\mathrm{C}$. Hence, O5 will be protonated. Chloride ion will then attack least substituted $\mathrm{C}$ atom (C6)
