Benzene reacts with Chlorine gas in the presence of iron trichloride to yield hexachlorobenzene. However, when it reacts with fluorine gas, it forms a quinoid product (I would actually draw it for them - no need to know the name). Why the difference?

Fluorine is much more reactive than chlorine, even destroying the aromaticity. This is at the expense of the very strong C-F bonds (good orbital size and energy overlap) that are formed. C-Cl bonds are weaker so even when benzene is "burnt" in chlorine, the aromatic ring stays intact.

RB

Related Chemistry A Level answers

All answers ▸

Explain the relative resistance to bromination of benzene compared to phenol and compared to cyclohexene.


Determine whether a tertiary halogenoalkane will undergo a SN1 or SN2 reaction. Explain your choice.


Why does ethanoyl chloride have a lower boiling point that pentanoyl chloride?


How do I do redox calculations?