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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o1045

Toward $CH X_{3} I$ in methanol, in which of the following pairs is the first species the stronger nucleophile?

A $CH X_{3} S X^{-}$ than $CH X_{3} O X^{-}$
B $I X^{-}$ than $F X^{-}$
C $CH X_{3} O X^{-}$ than $CH X_{3} OH$
D $(CH X_{3}) X_{3} C - O X^{-}$ than $CH X_{3} O X^{-}$

Answer: A, B, C

In methanol, large polarisable and weakly hydrogen-bonded sulfur is more nucleophilic than oxygen (A), and

I X^{-}

beats the strongly hydrogen-bonded

F X^{-}

(B). The anion

CH X_{3} O X^{-}

is far more nucleophilic than neutral methanol (C). Tert-butoxide is bulkier, so it is a poorer nucleophile than methoxide toward

CH X_{3} I

(D false).

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