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 dipoles on the following covalent bonds: Cl-Cl, H-Cl


At what temperature does the reaction become feasible? When ΔH = 492.7 kJmol^-1 and ΔS = 542.6 JK^-1mol^-1.


What is the difference in kinetics between a 0th, 1st and 2nd order reaction?


How does the reducing ability of halide ions vary?