Chapter 8 - Instructor Supplemental Solutions to Problems...

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Instructor Supplemental Solutions to Problems © 2010 Roberts and Company Publishers Chapter 8 Introduction to Alkyl Halides, Alcohols, Ethers, Thiols, and Sulfides Solutions to In-Text Problems 8.1 (b) Hexyl iodide is a primary alkyl halide. (c) Cyclopentyl bromide is a secondary alkyl halide. 8.2 (b) (d) 8.3 (b) ( Z )-3-Chloro-2-pentene (d) Chloroform (HCCl 3 ) is the traditional name for trichloromethane. (f) 1,3-Dibromocyclobutane 8.4 (b) (d) (f) 8.5 (b) 1-Butanol (d) 2-Chloro-5-methyl-2-cyclopentenol. The 2-refers to the position of the double bond; the position of the —OH group is assumed to be the 1-position because it is the principal group. It would not be incorrect to add the 1 to the name: 2-chloro-5-methyl-2-cyclopenten-1-ol. (f) 2,5-Cyclohexadienol (h) 2-Methyl-2-propanethiol 8.6 (b) (d) (f) (h) 8.7 (b) 2-Ethoxyethanol (or 2-ethoxy-1-ethanol) (d) 1-(Isobutylthio)-2-methylpropane
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INSTRUCTOR SUPPLEMENTAL SOLUTIONS TO PROBLEMS • CHAPTER 8 2 8.8 (b) The structure of 2-butoxyethanol is HO—CH 2 CH 2 —OCH 2 CH 2 CH 2 CH 3 . 8.12 Because of the molecular geometry of trans- 1,2-dichloroethylene, the C—Cl bonds are oriented in opposite directions, as are the C—H bonds. Consequently, their bond dipoles cancel, and the molecular dipole moment of trans- 1,2-dichloroethylene is zero. (The cancellation of the C—Cl bond dipoles is shown in the diagram below; the much weaker C—H bond dipoles also cancel for the same reason.) The corresponding bond dipoles of cis- 1,2- dichloroethylene do not cancel; consequently it has a significant dipole moment. The interaction of the molecular dipole moments of cis- 1,2-dichloroethylene molecules provides a cohesive force in the liquid state that is not present in the trans stereoisomer. (See text p. 334.) Because such cohesive forces enhance boiling point, cis -1,2- dichloroethylene has the higher boiling point of 60.3°. 8.13 (b) A chlorine contributes about the same molecular mass (35 units) as an ethyl group (29 units), and alkyl chlorides have about the same boiling points as alkanes of the same molecular mass. Hence, chloromethane has about the same boiling point as propane, which has a lower boiling point than the five-carbon alkene 1- pentene. The alcohol has the highest boiling point because it has about the same molecular mass as 1-pentene, but can donate and accept hydrogen bonds. Consequently, it has the highest boiling point of all. The order of increasing boiling points is, therefore, chloromethane (–42°) < 1-pentene (30°) < 1-butanol (118°). 8.14 (b) Hydrogen fluoride is an excellent hydrogen-bond donor, and the fluorine is an excellent hydrogen-bond acceptor. (d) N -methylacetamide can serve as both a hydrogen-bond donor and a hydrogen-bond acceptor. (f)
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Chapter 8 - Instructor Supplemental Solutions to Problems...

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