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Question

On the treatment of the following compound with a strong acid, the most susceptible site for bond cleavage is:
870154_f7c6cac488f54b3a844e0ae2fe6bfd7e.png

A
O2C3
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B
O5C6
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C
C4O5
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D
C1O2
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Solution

The correct option is B O5C6
On the treatment of the given compound with a strong acid, the most susceptible site for bond cleavage is O5C6.
The lone pair of electrons on O2 is involved in resonance with C=C. Hence, O2 will not be protonated.
The lone pair of electrons on O5 is not involved in resonance with C=C. Hence, O5 will be protonated. Chloride ion will then attack least substituted C atom (C6)
808650_870154_ans_6f686e3fa9984d33ac226a36ae04fa48.PNG

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