JEE MainChemistryCompounds Containing NitrogenNumerical+4 / −1
Number of compounds from the following which cannot undergo Friedel-Crafts reactions is: toluene, nitrobenzene, xylene, cumene, aniline, chlorobenzene, -nitroaniline, -dinitrobenzene
Numerical answer
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Correct answer: 4
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Recall the condition for Friedel–Crafts reaction
Friedel–Crafts alkylation/acylation proceeds on aromatic rings that are sufficiently reactive toward electrophilic substitution.
Rings do not undergo Friedel–Crafts reactions when:
- they are strongly deactivated by electron-withdrawing groups such as ,
- or the substituent forms a complex with the Lewis acid catalyst (like ), as in aniline due to the lone pair on .
-
Check each compound one by one
(i) Toluene
- Substituent:
- This is an activating group.
- Hence, undergoes Friedel–Crafts reaction.
(ii) Nitrobenzene
- Substituent:
- Strongly deactivating group.
- Hence, does not undergo Friedel–Crafts reaction.
(iii) Xylene
- Two methyl groups, both activating.
- Hence, undergoes Friedel–Crafts reaction.
(iv) Cumene
- Isopropyl group is alkyl, hence activating.
- Hence, undergoes Friedel–Crafts reaction.
(v) Aniline
- Substituent:
- Though is activating in ordinary electrophilic substitution, in Friedel–Crafts conditions it forms a salt/complex with , making the ring unreactive.
- Hence, does not undergo Friedel–Crafts reaction.
(vi) Chlorobenzene
- Halogens are deactivating, but not so strongly as to completely prevent Friedel–Crafts reaction in the standard JEE classification.
- Chlorobenzene can undergo Friedel–Crafts reaction (though less reactive than benzene).
- Hence, undergoes Friedel–Crafts reaction.
(vii) -Nitroaniline
- Contains both and .
- strongly deactivates the ring, and also complexes with .
- Hence, does not undergo Friedel–Crafts reaction.
(viii) -Dinitrobenzene
- Contains two strongly deactivating groups.
- Very strongly deactivated ring.
- Hence, does not undergo Friedel–Crafts reaction.
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Count the compounds that cannot undergo Friedel–Crafts reaction
These are:
- Nitrobenzene
- Aniline
- -Nitroaniline
- -Dinitrobenzene
Total number
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Final answer
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