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Q.

Pick out  from  following compounds which have a greater tendency to undergo SN1 reaction

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a

IV

b

III

c

I

answer is B, C.

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Detailed Solution

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I is vinyl halide ,vinyl halides can't under go SN1  reaction, because C-X  bond in vinyl halides gets partial double bond character, hence breaking of C-X bond is highly difficult;

Moreover the carbocation formed is highly unstable, so vinyl halides can't give SN1 reaction.

IV is bridged halo compound, bridge head halogen can't be replaced either by  SN1  or SN2.  

The carbocation formed at bridge head position is highly unstable because the attainment of planarity at bridge head position is not possible, it can't undergo SN1 reaction.

II is 30-alkyl halide and III is benzyl halide having a EDG group at para position. They are highly reactive with respect to SN1 ,as they form stable carbocations.

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Pick out  from  following compounds which have a greater tendency to undergo SN1 reaction