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 ▸

Why is methylamine a stronger base than aminobenzene?


If we burn 3 moles of carbon in air (as per the equation), what mass (in grams) of carbon dioxide will be produced? What volume will this gas occupy at standard temperature and pressure?


What is the oxidation number of Mn in K2MnO4?


Write a balanced equation for the oxidation of Iron from the 2+ oxidation state to the 3+ oxidation state using the manganate ion.