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 ▸

What is the geometry of a ClF3 molecule? (AQA Unit 1 2015 1d)


How does the reactivity of group 2 elements change down the group, and what is the cause of this trend?


State the reagents and conditions for the formation of an aldehyde, starting from a primary-alcohol.


Why does the nucleophilic addition of a cyanide ion to an aldehyde form a racemic mixture?