chapter8

chapter8 - 8-8-1Organic Organic ChemistryChemistryWilliam...

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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 88-8-3StructureStructureHaloalkane (alkyl halide):Haloalkane (alkyl halide):a compound containing a halogen covalently bonded to an sp3hybridized carbon; given the symbol RXHaloalkene (vinylic halide):Haloalkene (vinylic halide):a compound containing a halogen bonded to an sp2hybridized carbonHaloarene (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)8-8-4NomenclatureNomenclaturenumber the parent chain to give the substituent encountered first the lowest number, whether it is halogen or an alkyl groupindicate halogen substituents by the prefixes fluoro-, chloro-, bromo-, and iodo-, and list them in alphabetical order with other substituentslocate each halogen on the parent chain by giving it a number preceding the name of the halogenin haloalkenes, number the parent chain to give carbon atoms of the double bond the lower set of numbers8-8-5NomenclatureNomenclatureexamplesCommon 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)8-8-6NomenclatureNomenclatureseveral polyhaloalkanes are common solvents and are generally referred to by their common or trivial nameshydrocarbons 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 MomentsDipole 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 ForcesHaloalkanes are associated in the liquid state by van der Waals forcesvan der Waals forces:van der Waals forces:a group intermolecular attractive forces including dipole-dipole forcesdipole-induced dipole forcesinduced dipole-induced dipole (dispersion) forcesvan der Waals forces pull molecules togetheras 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 Forcesthe energy minimum is where the attractive forces are...
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chapter8 - 8-8-1Organic Organic ChemistryChemistryWilliam...

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