NBS Reaction

Aug 26, 2022, 16:45 IST

About NBS Reaction

The side chain halogenation of alkyl benzene takes place in the presence of light or high temperature. Side chain bromination is many times carried out by using the reagent N-bromosuccinimide (NBS) in the presence of light.

An alkyl benzene with side chain other than methyl may lead to the formation of more than one products.

Product (I) is the only product obtained, and formation of such product can be attributed to mechanism governing this reaction. Side chain halogenation has a similar mechanism as that of alkanes. It involves the formation of free radical intermediates. Now if we observe the free radicals formed by attack of Bromine free radical on Ethyl benzene, we will find that product (I) involves formation of Benzyl free radical and (II) involves formation of Primary free radical.

The benzyl free radical is more stable than primary free radical because its bond dissociation energy is 19 kcal/mole less than that of primary free radical.

Order of stability of free-radicals. Benzyl > Allyl > 3° > 2° > 1° (from bond dissociation energy data. 

Find Mechanism of NBS Reaction

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