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Question

Consider the reactions
(i) (CH3)2CHCH2BrC2H5OH−−−−(CH3)2CHCH2OC2H5+HBr
(ii) (CH3)2CHCH2BrC2H5O−−−−(CH3)2CHCH2OC2H5+Br
The mechanisms of reactions (i) and (ii) are respectively:

A
SN1 and SN2
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B
SN1 and SN1
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C
SN2 and SN2
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D
SN2 and SN1
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Solution

The correct option is B SN1 and SN2
C2H5OH being a weaker nucleopbile, when used as a solvent in case of hindered 1 halide, favours SN1 mechanism while C2H5O being a strong nucleophile in this reaction favours SN2 mechanism.

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