Question

Methyl benzoate reacts . . .
1.slower than methyl nitrobenzoate
2.faster than methyl nitrobenzoate
3.slower than nitrobenzene
4.at the same rate as methyl nitrobenzoate
5.there is no predictable relationship in reactivity

and

Benzene would react . . .

there is no predictable relationship in reactivity

at the same rate as methyl benzoate

slower than methyl nitrobenzoate

faster than methyl benzoate

slower than nitrobenzene

Answer 1

2.faster than methyl nitrobenzoate

OCH OCH NO Methyl m-nitrobenzoate The first nitration proceeds much faster than the second two because the first-NO, group to be added is added to the isolated toluene. The methyl group on the benzene ring is an activating group. It causes the benzene ring to be more electron rich and thus, have a high reactivity. -CH is an ortho-para activator. So, the first-NO, group adds to the toluene in the para-position in order to avoid steric crowding from the methyl group. The toluene has now been coaverted to para-nitrotoluene. The -NO: group that is now on the benzene ring is a deactivating group, and causes the benzene ring to be not nearly as reactive as it was before the first-NO group was added. Thus, the second and third nitrations occur much more slowly