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Question:

On the treatment of the following compound with a strong acid, the most susceptible site for bond cleavage is: C4−O5O5−C6C1−O2O2−C3

O5−C6

O2−C3

C4−O5

C1−O2

Solution:

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)