Benzene and Alkyl Benzene - Result Question 51

51. Arrange the following in increasing order of reactivity towards sulphonation with fuming sulphuric acid.

Benzene, toluene, methoxy benzene, chlorobenzene.

$(1988,1 M)$

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Solution:

Both $-\mathrm{CH}_3$ and $-\mathrm{OCH}_3$ are activating groups but chloro is deactivating group in electrophilic aromatic substitution reaction.

Also $-\mathrm{OCH}_3$ activate more than $-\mathrm{CH}_3$ due to resonance effect by the former group. Therefore, the overall order of reactivity is:

Chlorobenzene $<$ benzene $<$ toluene $<$ methoxy benzene