# Free-Radical chlorination: Find all unique mono-chlorinated products

I'm having trouble with this problem. I suspect that there is a typo, as the methylcyclohexene described in the wording does not match the methylcyclopentene shown in the image(someone please confirm if my suspicion is correct or if I made a mistake in interpreting nomenclature, I am very new to Organic Chemistry). If it does appear to be a typo, I would like help in solving for the methylcyclopentene(the molecule described by the image).

I'm not quite sure how to tackle this problem, as this is actually the first time I've had to mono-chlorinate something with a double bond. I'm confused about how stereochemistry factors in, since there's no symmetry in the molecule, and the double bond onto one carbon suggests a sp2 triplanar configuration where there is only one H position that a radical chlorine can take. This problem isn't like anything I've seen so far, so I would appreciate any help from some veteran organic chemists.

• Well of course it's incorrect. Also you need to remember that it's two step - first alkenyl radical then halogenide – Mithoron Sep 4 '16 at 0:55
• @Mithoron halogenide is the German word for halide – DHMO Sep 4 '16 at 1:00
• Nice first question! – DHMO Sep 4 '16 at 1:33
• Hint for the stereochemistry part of the question: as soon as you have any cyclic $\mathrm{sp^3}$ carbon with two different substituents attached, stereochemistry comes into play. – Jan Sep 4 '16 at 21:53
• Can someone check these for me: 1. At the end of the methyl group, there is only one monochlorinated product because every hydrogen in the CH3 is identical to each other? 2. The cyclic carbon that is double bonded and is attached to the methyl group cannot be chlorinated 3. The cyclic carbon that is double bonded and is not attached to the methyl group can be chlorinated, but because of its sp2 configuration, there is only 1 chlorinated product – Garner Deng Sep 13 '16 at 23:03