That is not a reaction that will be covered on this site.

I’m going to be annoying and answer your first question with a question.

1) What is the IUPAC name of the chlorinated cyclohexane I drew?

2) What would be the IUPAC name of the product where the chlorine is attached to the top?

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[Writing articles where people have to scroll down, I try to minimize the vertical space each image occupies. So that gives you some ideas of my motivation for writing it that particular way]

With the reaction with Br, the starting material is not the same as in the first example. It is cyclohexane with a methyl group attached. The Br is *selective* for the carbon which is attached to the fewest carbons (i.e. the carbon attached to the methyl group).

Thanks for your comment – I had no idea this might trip people up.

Bottom line – in the Cl example, it would still be correct for Cl to attach to any carbon around the ring because they all give 1-chlorocyclohexane. Bromine would also give only 1-bromocyclohexane

With methylcyclohexane, the correct answer is to show Br attaching preferentially to the carbon bearing the methyl group to give 1-bromo-1-methylcyclohexane since Br is highly selective for tertiary C-H. If we drew Br on any other carbon it would be wrong.

Absolutely! Doesn’t get covered very often, but the reaction of C-H bonds with molecular oxygen to give C-OOH primarily occurs with tertiary C-H bonds, C-H bonds adjacent to oxygen (e.g. ethers) and benzylic and allylic C-H bonds.

This is why saturated fats (e.g. margarine) are much less likely to spoil when left out in air than unsaturated fats (e.g. butter)…

Could autooxidation also be considered a reaction of alkanes? I recently came across a problem in my textbook in which methylcyclohexane was converted to methylcyclohexene via auto-oxidation followed by reduction and treatment with an acid.