When performing the nitration of methyl benzoate, methyl m‐nitrobenzoate was formed. It is possible to introduce a second nitro group to form the dinitrated product. This was largely avoided because:
a. the nitronium ion is not a strong enough electrophile.
b. steric hindrance would not allow a second bulky NO2 to react with the ring.
c. the reaction is carefully timed so that no dinitration is possible.
d. the nitration mixture that was used is weak and therefore highly selective.
e. the first NO2 group introduced has a strong deactivating effect so that the addition of a second group is more difficult.
Answer: e. the first NO2 group introduced has a strong deactivating effect so that the addition of a second group is more difficult.