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Question

Arrange the following compounds in decreasing order of reactivity for hydrolysis reaction.
I. PhCH2Br
II. Ph−Br|CH−CH2CH3
III.
IV.

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

The correct option is B IV > II > I > III
Hydrolysis will proceed by SN1 mechanism.
Rate of the SN1 reaction depends on the stability of carbocation formed. More stable carbocation will undergo SN1 reaction fastly.
Comparing (I) and (II)
Benzyl cation is generally stable but in (II) the carbocation is also stabilised by +I group of CH2CH3. This make (II) more stable than (I)
Comapring (III) and (IV)
III will be less reactive as it will involves the least stable, anti aromatic carbocation. IV will be most reactive as its carbocation is the most stable.
Thus, the decreasing order of reactivity for hydrolysis is,
IV > II > I > III

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