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The increasing order of nucleophilicity of the following nucleophiles is: (a) CH$_3$CO$_2^-$, (b) H$_2$O, (c) CH$_3$SO$_3^-$, (d) OH$^-$

1. (b) < (c) < (a) < (d)
2. (b) < (c) < (d) < (a)
3. (a) < (d) < (c) < (b)
4. (a) < (d) < (c) < (b)

Correct answer: (b) < (c) < (a) < (d)

Solution

Nucleophilicity generally increases with availability of the lone pair and decreases with resonance stabilization. H$_2$O is the weakest, CH$_3$SO$_3^-$ is strongly resonance-stabilized, CH$_3$CO$_2^-$ is less stabilized than mesylate, and OH$^-$ is the strongest nucleophile here.

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