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Question

Which of the following holds true with regard to the order of stability?

A
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B
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C
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D
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Solution

The correct option is D
(a) Acetate ion (carboxylate ion) is more stable than phenoxide ion since the negative charge in acetate resides on more electronegative O atoms in both its resonating structures whereas in phenoxide ion, it resides on one more electronegative O and less electronegative C atoms in its resonating structures.

(b) Both cations are resonating structures of each other. First one is more stable as it is 2o and have more hyperonjugation.

(c) Cyclobutylmethylium cation is less stable due to ring strain so it rearranges to give cyclopentylium cation.

(d) Due to σ-bond resonance or dancing resonance, cyclopropylmethyl cation is more stable than cyclobutyl cation.

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