Chlorination of toluene in the presence of sublight produces_________________?
Correct answer: A. Benzyl chloride
- A. Benzyl chloride
- B. o - chlorotoluene
- C. p - chlorotoluene
- D. benzoic acid
Explanation
In sunlight, chlorine forms radicals that substitute a hydrogen atom at the benzylic position of toluene, producing benzyl chloride, C6H5CH2Cl. The benzylic radical is resonance-stabilised, making side-chain chlorination favoured. The likely mistake is o-chlorotoluene, which is formed by ring substitution under electrophilic chlorination conditions with a Lewis acid catalyst, not by sunlight.
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About Free Radical Substitution
Free radical substitution explains how alkanes react with halogens under ultraviolet light or heat through initiation, propagation and termination steps. The mechanism involves homolytic bond fission and radical intermediates, while product formation depends on the relative stability of radicals and differs from ionic substitution.
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