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Solutions to Problems 59 X X X Two monohalogenation products: 2,3-dimethylbutane X X (c) As illustrated above, 2,3-dimethylbutane possesses only two distinct sites for halogenation: two indistinguishable tertiary hydrogens and twelve indistinguishable primary H's. In the case of X = Br, virtually the entire product will arise from bromination at a tertiary position. 46. (e) 47. (c) (1-Chloro-2-methyl-4-propyloctane) Yes, they actually ask questions like this. 48. (a) For chlorination, six secondary hydrogens outcompete the lone tertiary in (b). 49. (d)