chapter8

chapter8 - 8-8-1Organic Organic H BrownWilliam H...

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Unformatted text preview: 8-8-1Organic Organic ChemistryChemistryWilliam H. BrownWilliam H. BrownChristopher S. FooteChristopher S. FooteBrent L. IversonBrent L. Iverson8-8-2HaloalkanesChapter 8Chapter 88-8-3StructureStructure◆Haloalkane (alkyl halide):Haloalkane (alkyl halide):a compound containing a halogen covalently bonded to an sp3hybridized carbon; given the symbol RX◆Haloalkene (vinylic halide):Haloalkene (vinylic halide):a compound containing a halogen bonded to an sp2hybridized carbon◆Haloarene (aryl halide):Haloarene (aryl halide):a compound containing a halogen bonded to a benzene ring; given the symbol ArX•(we do not study vinylic or aryl halides in this chapter)8-8-4NomenclatureNomenclature•number the parent chain to give the substituent encountered first the lowest number, whether it is halogen or an alkyl group•indicate halogen substituents by the prefixes fluoro-, chloro-, bromo-, and iodo-, and list them in alphabetical order with other substituents•locate each halogen on the parent chain by giving it a number preceding the name of the halogen•in haloalkenes, number the parent chain to give carbon atoms of the double bond the lower set of numbers8-8-5NomenclatureNomenclature•examples◆Common names:Common names:name the alkyl group followed by the name of the halideBr2-Bromo-4-methyl-pentane123454-Bromo-cyclohexene123456trans-2-Chloro-cyclohexanolBrClOHBrClCl2-Bromobutane(sec-Butyl bromideCnhloroethene(Vinyl chloride)3-Chloropropene(Allyl chloride)8-8-6NomenclatureNomenclature•several polyhaloalkanes are common solvents and are generally referred to by their common or trivial names•hydrocarbons in which all hydrogens are replaced by halogens are commonly named as perhaloalkanes or perhaloalkenesCHCl3CH2Cl2CCl2=CHClCH3CCl3 Dichloromethane(Methylene chloride) Trichloromethane (Chloroform)Trichloroethyne (Trichlor)1,1,1-Trichloroethane (Methyl chloroform) PerchloroethylenePerfluoropropanePerchloroethaneC CClClClClClClF C C CFFFFFFFClC CClClCl8-8-7Dipole MomentsDipole Moments◆Dipole moment of RX depends on:•the sizes of the partial charges •the distance between them •the polarizability of the unshared electrons on halogenCH3ClCH3FCH3BrCH3IHalomethaneElectronegativityof HalogenCarbon-HalogenBond Length (pm)Dipole Moment(debyes; D)4.03.02.82.51391781932141.851.871.811.628-8-8van der Waals Forcesvan der Waals Forces◆Haloalkanes are associated in the liquid state by van der Waals forces◆van der Waals forces:van der Waals forces:a group intermolecular attractive forces including •dipole-dipole forces•dipole-induced dipole forces•induced dipole-induced dipole (dispersion) forces◆van der Waals forces pull molecules together•as molecules are brought closer and closer, van der Waals attractive forces are overcome by repulsive forces between electron clouds of adjacent atoms or molecules8-8-9van der Waals Forcesvan der Waals Forces•the energy minimum is where the attractive forces are...
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chapter8 - 8-8-1Organic Organic H BrownWilliam H...

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