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Question

The decreasing basic character of the following is:
I. PhO II. CH3S III. OH IV. MeO

A
I > II > III > IV
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B
III > IV > II > I
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C
IV > III > II > I
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D
I > II > IV > III
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Solution

The correct option is B III > IV > II > I
Convert conjugate base into acid by adding H, find the acidic character and then reverse the order after removing H ions that would be the order for basic character.

PhO is most stable because the negative charge on oxygen is stabilised by resonance. In between CH3S and MeO size od S is greater than O. So, CH3S is more stable than MeO. OH is the least stable among all.

Acidity : PhOH>CH3SH>MeOH>H2O

Basicity: PhO<CH3S<MeO<OH
(Hence the answer is b.)

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