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 solvent leveling? How can we distinguish between two strongly acidic solutions? (This is a challenging question and is included for interest only)


Explain why the first ionisation energy of Al is less than that of Mg?


A chemist has 3 beakers, each containing a pure sample of acetone (2-propanone), isopropanol (2-propanol) and propanal. Using chemical techniques, suggest how the chemist may be able to determine which beaker contains which sample. [4]


How do you deal with remembering all the knowledge required for organic chemistry questions?