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5.43 a) 2-Methylhexane b) 2-Methylhexane c) 1,1-Dichlorocyclopentane d) 5-Methyl-1-heptyne e) 4,4-Dimethylcyclohexene f) 2-Cyclopentenol g) N,N-Dimethyl-3-pentanamine h) Ethoxycyclohexane 5.44 a) Hexane has a higher boiling point than pentane because it has a larger molecular weight. b) The primary amine on the left has a higher boiling point than the isomeric tertiary amine on the right because the primary amine can form hydrogen bonds. c) The alcohol (right structure) has a higher boiling point than the isomeric ether (left structure) because the alcohol can form hydrogen bonds. 5.45 a) Cyclopentane has a higher melting point than pentane because its symmetrical shape allows it to pack better into the crystal lattice. b) Propylamine has a higher melting point than butane because it is more polar and can form hydrogen bonds. 5.46 a) 1-Pentanol has a higher water solubility than hexane because it is more polar and can form hydrogen bonds. b) 2-Butanol has a higher water solubility than 1-pentanol because it has a smaller nonpolar alkyl group. Review of Mastery Goals After completing this chapter, you should be able to: Provide the systematic (IUPAC) name for an alkane. (Problems 5.1, 5.3, 5.24, and 5.26) Draw the structure of an alkane whose name is provided. (Problems 5.2, 5.6, and 5.25) Name a complex group. (Problems 5.4, 5.5, and 5.30) Name a cycloalkane, an alkene, an alkyne, an alkyl halide, an alcohol, an ether, or an amine. (Problems 5.10, 5.12, 5.14, 5.16, 5.18, 5.20, 5.21, 5.22, 5.24, 5.29, 5.30, 5.33, 5.34, and 5.43) 77