Question

I have a question for my homework that says to react the following compounds with one equivalent of NBS with CCl₄, and that they give only one major product. Then we have to explain why we gave our answers. I think this was just an accident that my professor left it out of the question, but wouldn't the reaction with NBS and CCl₄ also need heat or light and peroxides to work? I've done the questions as if they were included, and it would be nice if I could check my answers with whoever answers this question, too.

The first compound was 3,3-dimethylcyclohexene, and the answer I got was 6-bromo-3,3-dimethylcyclohexene (I'm actually not 100% sure I typed that out in the correct order, my IUPAC naming isn't very good, but I think you should be able to tell the structure from that still? Hopefully? Sorry!). This is because there aren't any allylic hydrogens available at the third carbon because of the two methyl groups.

The second compound was 4-tert-butyltoluene, and the answer I got was that you just added the bromine onto the methyl group that branches off of the first carbon. I'm not sure how to name a substituent group that is one methyl group with a halogen attached to it. 1-(bromomethyl)-4-tert-butylbenzene, I think? Either way, it's because of benzylic bromination on that methyl group; it can't happen at the other benzylic carbon because, once again, there aren't any available hydrogens there.

Sorry that this is so confusing, but I appreciate the help!

Answer 1

You have tried very well, I am impressed.

Here is your answers:

NBS and CCl₄ doesn't need heat or light and peroxides to work as NBS can easily form Br radical in nonpolar solvent.

1)I recomend you to read about IUPAC nomenclature from your text book.

2)

Tell me in the comment section if you have any doubt.