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Question

Consider the following reactions:

I.Me3CClOHMe3COHII.F3CCH|MeClOHF3CCH|MeOHIII.Me3CCl90%D2O+10%ether−−−−−−−−−−−Me3CODIV.Me3CCl90%H2O+10%ether−−−−−−−−−−−Me3COH

Which of the following statements are correct?


A

Reaction (I) is faster than (II).

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B

Reaction (II) is faster than (I).

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C

Reaction (III) is faster than (IV).

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D

Reaction (IV) is faster than (III).

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Solution

The correct options are
B

Reaction (II) is faster than (I).


D

Reaction (IV) is faster than (III).


i. In (II), carbocation is destabilised by stronger -I effect of three F atoms, and thus solvolysis of (II) is slower than that of (I).

ii. D -bonds are not as stabilising as H-bonds. So reaction (IV) is faster than (III).


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