JEE Main Chemistry question

Which of the following is the best (strongest) nucleophile in a typical Sɴ2 substitution?

(A)CH₃C(=O)O⁻ (acetate)
(B)CH₃O⁻ (methoxide)
(C)CN⁻Correct
(D)p-CH₃C₆H₄SO₃⁻ (tosylate)

Answer: (C)

Solution

Cyanide, CN⁻, is a small, linear, highly polarisable ion whose negative charge is not delocalised away from the attacking atom, making it an excellent nucleophile in Sɴ2 reactions. Acetate's negative charge is resonance-delocalised over two oxygens, weakening its nucleophilicity; tosylate

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Question ID VK-139798