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Question

Which of the following order is correct for the decreasing reactivity of ring monobromination of the following compounds?

A
I > II > III > IV
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B
II > III > IV > I
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C
I > III > II > IV
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D
III > I > II > IV
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Solution

The correct option is C I > III > II > IV
Ring monobromination is electrophilic aromatic substitution reaction. Higher is the electron density on aromatic ring. Higher will be the reactivity towards ring monobromination alkyl substituents increases the electron density by +I effect. Hence, the reactivity of toluene (I) is maximum and then benzene.

Substitutents such as COOH group and NO2 group are electron withdrawing groups, hence, they decrease the electron density of the ring.
nitrobenzene has lower reactivity towards ring monobromination as compared to benzoic acid as NO2 group is strong withdrawing group than COOH.
Hence, the correct order for the decreasing reactivity of ring monobromination is I (toluene) > III (benzene) > II (benzoic acid) > IV (nitrobenzene)

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