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Question
Arrange the following set of compounds in the order of their decreasing relative reactivity with an electrophile. Give reason.
Solution
The methoxy group (-OCH3) is electron releasing group. It increases the electron density in benzene nucleus due to resonance effect (+R-effect). Hence, it makes anisole more reactive than benzene towards the electrophile.
In case of alkyl halides, the electron density increases at ortho and para positions due to +R effect. However, the halogen atom also withdraws electrons from the ring because of its -I effect. Since the -I effect is stronger than the +R effect, the halogens are moderately deactivating. Thus, overall electron density on benzene ring decreases, which makes further substitution difficult. -NO2 group is electron-withdrawing group. It decreases the electron density in benzene nucleus due to its strong -R-effect and strong -I-effect. Hence, it makes nitrobenzene less reactive. Therefore, overall reactivity of these three compounds towards electrophiles decreases in the following order:
Anisole > Chlorobenzene > Nitrobenzene
In phenol, benzene ring has alternate single and double bonds while cyclohexanol is alicyclic compound.
Cyclohexanol
Phenol
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