JEE MAIN - Chemistry (2018 - 15th April Evening Slot - No. 8)

On treatment of the following compound with a strong acid, the most susceptible site for bond cleavage is :
JEE Main 2018 (Online) 15th April Evening Slot Chemistry - Basics of Organic Chemistry Question 221 English
Cl $$-$$ O2
O2 $$-$$ C3
C4 $$-$$ O5
O5 $$-$$ C6

Explanation

Here the lone pair of electrons on O2 is involved in resonace with C = C.
So,   O2 will not be protonated.

The lone pair electrons of O5 is not involved in resonance with any C = C. So, O5 can be protonated.

When we use strong acid like HCl then chloride ion will attack least substituted C atom (C6).
JEE Main 2018 (Online) 15th April Evening Slot Chemistry - Basics of Organic Chemistry Question 221 English Explanation

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