Originally posted by TheKing
so which one is correct? the carbon free radical not being electronegative enough or that its just not in syllabus.
Firstly, this is definitely not in the syllabus.
Secondly, I have some doubts about the mechanism MaryTylerMoore is describing.
Originally posted by MaryTylerMoore
I believe the CF3 becomes CF3O and when around O3, it can form CF3O2 and O2.
This is (IMO) highly unlikely - you are suggesting the formation of a peroxo radical via deoxygenation of ozone, which is not likely to occur. The major reaction of peroxo radicals tends to be loss of oxygen, and given the weakness of the oxygen-oxygen single bond, I have serious doubts that such a bond would form with ozone supplying the extra oxygen atom, as it would be thermodynamically unfavourable. It is much more likely that a peroxo radical would form by direct reaction of the CF<sub>3</sub> radical with O<sub>2</sub>
This can then again react with ozone forming CF3O and two O2's. This cycle repeats, but this isn't part of the syllabus.
Possible, but unlikely - peroxo radicals usually react with NO.
The most likely degradation pathway for CF<sub>3</sub> is:
CF<sub>3</sub> + O<sub>2</sub> ---> CF<sub>3</sub>O<sub>2</sub>
CF<sub>3</sub>O<sub>2</sub> + NO ---> CF<sub>3</sub>O + NO<sub>2</sub>
The CF<sub>3</sub>O radical will decompose via at least two possible paths:
Path 1:
CF<sub>3</sub>O + NO ---> F<sub>2</sub>CO + FNO
F<sub>2</sub>CO + H<sub>2</sub>O ---> CO<sub>2</sub> + 2HF
Path 2:
CF<sub>3</sub>O + H<sub>2</sub>O ---> CF<sub>3</sub>OH + OH
CF<sub>3</sub>O + RH ---> CF<sub>3</sub>OH + R
CF<sub>3</sub>OH + H<sub>2</sub>O ---> CO<sub>2</sub> + 3HF
This answer is based partly on my studies of Atmospheric Photochemistry (3rd year Uni subject) and partly on a paper "Mechanism and Rate of the Reactions of Fluorinated Oxygen-Containing Organic Radicals with Molecular Oxygen in the Gas Phase".