DAT Achiever Ochem Question

[fit2]

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Soooo...I understand why their answer is correct but wouldn't theoretically all answers be correct?
Thinking about the Hammond postulate, isn't radical chlorination very non specific (unlike bromination) therefore yield primary, secondary and tertiary products?
I suppose my question is will the tertiary product be formed in abundance or will all products be formed in roughly equal amounts?

Thanks for the help!!

 

[DentalNucleicAcid]

There's a little bit more of the more substituted product than the less substituted product even in radical chlorination. The amounts aren't all equal, but they're not too far off from eachother. I think the more sub'd product is a little higher than 50% and the less sub'd product is a little less than 50% in chlorination if I remember correctly from my notes. So yeah the more sub'd product would qualify as being more abundant

 

[kimball]

It really does come down to the stability of the radical I think, with the more substituted alkyl(3>2>1) being more favored for both of them still, I think that's what this problem is looking for is that even though chlorination is less selective, it still has a degree of selectivity favoring the more stable intermediate.


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[WheatLom]

This is a stability question, we know the Chlorine will be added, just where. Remember 3>allylic>2>1>methyl for radicals!!!

If my understanding is complete (someone correct me if I am wrong), you could take it to a deeper level and say that this reaction is more thermodynamically favored, but slower since it would be slightly harder to access that tertiary hydrogen over a primary. The primary would be more kinetically favored when less energy is available. Usually this is seen with additions to dienes, but I would like to think it translates to all of organic chemistry as it is a basic principle.

 

[fit2]

Thanks for the responses! It makes sense