Flag Organic Chemistry> benzyl chloride can undergo both sn1 and ...
question mark

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

Dulal Pathak , 6 Years ago
Grade 12th pass
anser 2 Answers
Arun

Last Activity: 6 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

Last Activity: 6 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.
star
LIVE ONLINE CLASSES

Prepraring for the competition made easy just by live online class.

tv

Full Live Access

material

Study Material

removal

Live Doubts Solving

assignment

Daily Class Assignments