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Among the following compounds the one that is most reactive towards electrophilic nitration is:
A
Benzene
B
Benzoic acid
C
Nitrobenzene
D
Toluene
Detailed Solution
Electrophilic nitration is faster when the ring is electron rich.
In toluene the $-CH_3$ group releases electrons (+I effect and hyperconjugation); it is ortho-para directing and activates the ring.
$-COOH$ and $-NO_2$ are electron-withdrawing and deactivate the ring.
Reactivity: toluene > benzene > benzoic acid > nitrobenzene
In toluene the $-CH_3$ group releases electrons (+I effect and hyperconjugation); it is ortho-para directing and activates the ring.
$-COOH$ and $-NO_2$ are electron-withdrawing and deactivate the ring.
Reactivity: toluene > benzene > benzoic acid > nitrobenzene