For each alkane,
1. Draw all the possible mono-chlorinated derivatives.
2. Determine whether free-radical chlorination would be a good way to make any of these mono-chlorinated derivatives. (Will the reaction give mostly one major product?)
3. Which mono-brominated derivatives could you form in good yield by free-radical bromination?
(a) cyclo-pentane
(b) methyl-cyclo-pentane
(c) 2-methylpentane
(d) 2,2,3,3-tetramethylbutane