Nitration of bromobenzene

1) Electron density

Electrostatic potential map of bromobenzene: red marks the regions with the highest electron density and blue the poorest ones

The case is very similar to that of chlorobenzene.

2) Relative reaction rate

Bromobenzene reacts 11 times slower than benzene. The case is very similar to that of chlorobenzene. Br is slightly less deactivating than Cl.

3) Substitution direction

Like Cl, bromine is an ortho-para director and the explanation is exactly the same.

Ortho substitution

Resonance forms of the benzenonium ion in the ortho nitration of bromobenzene

Para substitution

Resonance forms of the benzenonium ion in the para nitration of bromobenzene

Meta substitution

Resonance forms of the benzenonium ion in the meta nitration of bromobenzene

The energy diagrams of bromo- and chlorobenzene are very much alike.

Energy diagram of the nitration of bromobenzene compared with that of benzene: ortho, meta and para pathways

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