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JEE Main · 2024 · 09 Apr 2024 · Shift 2 · Hydrocarbons

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Number of compounds from the following which cannot undergo Friedel-Crafts reactions is :
toluene, nitrobenzene, xylene, cumene, aniline, chlorobenzene, m-nitroaniline, m-dinitrobenzene

Answer: 4

Solution

Friedel–Crafts reactions fail on strongly deactivated rings and on aromatic amines (which complex with the Lewis-acid catalyst, AlCl).

Among toluene, nitrobenzene, xylene, cumene, aniline, chlorobenzene, m-nitroaniline and m-dinitrobenzene, the ones that fail are: nitrobenzene, aniline, m-nitroaniline, and m-dinitrobenzene (all deactivated by –NO and/or poison the catalyst via the –NH group).

Toluene, xylene, cumene and chlorobenzene (mildly deactivating/activating, no catalyst-poisoning group) do undergo Friedel–Crafts reactions.

Number that cannot react: 4.
Structure Nitrobenzene
Nitrobenzene
Structure Aniline
Aniline
Structure m-nitroaniline
m-nitroaniline
Structure m-dinitrobenzene
m-dinitrobenzene

JEE Main · 2024 · 09 Apr 2024 · Shift 2 · Integer answer

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