Rank the Following in Order of Increasing Nucleophilicity, Putting the Least

question 48

Multiple Choice

Rank the following in order of increasing nucleophilicity, putting the least nucleophilic first. $$\begin{array} { c c c c } \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { O } ^ { - } & \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm {~S} ^ { - } & \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { OH } & \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { SH } \\\text { I } & \text { II } & \text { III } & \text { IV }\end{array}$$

• A) II < IV < I < III
• B) IV < III < II < I
• C) III < IV < I < II
• D) II < I < IV < III

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