On the treatment of the following compound with a strong acid, the most susceptible site for bond cleavage is:
A
O2−C3
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B
O5−C6
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C
C4−O5
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D
C1−O2
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Solution
The correct option is BO5−C6 On the treatment of the given compound with a strong acid, the most susceptible site for bond cleavage is O5−C6. 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)