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Question

The decreasing order of relative nucleophilicity of the following nucleophiles in a protic solvent is
SH,AcO,PhO,OH,H2O

A
SH>OH>H2O>AcO>PhO
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B
SH>OH>PhO>AcO>H2O
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C
SH>PhO>OH>H2O>AcO
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D
OH>SH>PhO>AcO>H2O
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Solution

The correct option is B SH>OH>PhO>AcO>H2O
Nucleophilicity α negative charge ions

α 1delocalisation

Nucleophilicity of the negative charged ions are more than that of neutral compounds because they have more electron density therefore,

SH,OH,OPh,OAc>H2O

Nucleophilicity of the ions which have more size (along the group) will be more in case of protic solvents

SH>OH,OPh,OAc>H2O

More the delocalisation less is the nucleophilicity because of the less availability of electron density. As in OAc there is equivalent resonance hence it is weaker nucleophile than OPh.

SH>OH>OPh>OAc>H2O


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