Arrange the following compounds in the decreasing order of hetrolytic bond dissociation energy of
bond.

Question

Arrange the following compounds in the decreasing order of hetrolytic bond dissociation energy of bond.

TestHub · Accepted Answer

Hetrolytic cleavage of bond in each of the given compounds results in the formation of benzyl carbocation which is stabilised by resonance. The methoxy group at meta position in compound (III) destabilises the benzyl carbocation by −I effect whereas methoxy group at ortho and para positions destabilises by −I effect and stabilises by +R effect. The stabilisation is stronger at the para position due to weak −I effect. Greater the stability of carbocation, lower is the bond dissociation energy of

bond.

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