A compound among the following that does not undergo Friedel-Craft's reaction easily is:
Cumene
Xylene
Nitrobenzene
Toluene
Friedel-Crafts reaction is an electrophilic aromatic substitution reaction. For this reaction to occur easily, the benzene ring must be relatively electron-rich. In nitrobenzene, the nitro group () is a strongly deactivating group due to its strong electron-withdrawing nature ( and effects). It drastically reduces the overall electron density on the benzene ring, making further electrophilic substitution difficult . On the other hand, the alkyl groups in cumene, xylene, and toluene are electron-donating (activating) groups, which increase the electron density on the ring and facilitate electrophilic attack . Therefore, nitrobenzene does not undergo Friedel-Crafts reactions.
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