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Question

The major product of the given substitution reaction is
(CH3)2C=CH−CH2−BrH2O−−→

A
(CH3)2(Br)CCH=CH2
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B
(CH3)2C=CHCH2OH
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C
(CH3)2(OH)CCH=CH2
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D
None of the above
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Solution

The correct option is B (CH3)2C=CHCH2OH
Weak electrophile H2O is used in the given substitution reaction hence, it will favour SN1 mechanism.
Allyl system favour both SN1 and SN2 mechanism but due to formation of a stable carbocation, they undergo
SN1 reaction at a faster rate.

Major and minor products are determined by steric hindrance.
The attack of nucleophile is faster at the less-hindered end of the allylic system.
Major product also depends on the stability of the alkene compound formed.
Since, (c) is the more substituted alkene and has a less steric carbocation intermediate.
It is the major product.


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