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benzyl chloride can undergo both sn1 and sn2 reaction with high rate.explain

benzyl chloride can undergo both sn1 and sn2 reaction with high rate.explain

Grade:12th pass

2 Answers

Arun
25750 Points
4 years ago

Benzyl halides react via SN1 and SN2 with equal probability..unless the reaction conditions are altered..

SN1: the benzyl carbocation formed in the rate determing step of the reaction is stable as the positive charge generated is spread over the ring.

SN2: recall the intermediate of the mechanism. The transition state involves a trigonal planar state where the leaving group and the nucleophile occupy the opposite lobe of the unhybridised p orbital lobe of the central C atom. In case of benzyl halides the ring es being planar to this p orbital can conjugate easily by delocalising the pi es..stabilising the transition state..and hence reaction occuring with equal probability via this pathway..

Vikas TU
14149 Points
4 years ago
SN1 reaction depends on carbocation stability. And benzylic and allylic carbocations are very stable carbocations due to resonance.
Beacause their carbocations are stabilised by resonance . It’s easy for the nuclwophile to attack the carbocation and form products.
Benzyl and allyl carbonations are stable due to resonance hence benzylic and allylic halides undergo SN1 reaction.

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