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Which of the following compounds will undergo bromination most rapidly using Br2, FeBr3?

A) p-methylacetanilide
B) bromobenzene
C) acetanilide
D) benzenesulfonic acid
E) dibromobenzene

User OpenSauce
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Final answer:

Acetanilide will undergo bromination most rapidly using Br2, FeBr3 due to the electron-donating effect of its acetylamine group, which activates the benzene ring and increases its reactivity towards electrophiles.(Option c)

Step-by-step explanation:

Among these options, acetanilide will undergo bromination most rapidly. Acetanilide has an amino group (-NHCOCH3) which is an activating group for the benzene ring. This group is electron-donating through resonance, which increases the electron density on the ring and makes it more reactive towards electrophilic attack.

When comparing substituents on the aromatic ring, electron-donating groups like the acetylamine in acetanilide make the benzene ring more reactive to electrophiles like bromine, while electron-withdrawing groups and steric hindrance slow down the reaction. The other compounds either have electron-withdrawing groups, steric hindrance, or are already extensively substituted, which lessens their reaction speed under these conditions.

User Sophiane
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