Lecture + Chapter 10 Notes

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Thavarajah/ Woolley/ Nitz

CHM138H1 Jasmyn Lee Chapter 10: The Chemistry of the Alkyl Halides 10.1 Names and Properties of Alkyl Halides Structure of Alkyl Halides  Alkyl Halide – a compound containing a halogen atom covalently bonded to an sp hybridized carbon atom Nomenclature  Halogen substituents are indicated by the prefixes fluoro-, chloro-, bromo-, and iodo- and listed in alphabetical order with other substituents Properties of Alkyl Halides  Halogens increase in size going down the periodic table – lengths of corresponding C-H bonds increase accordingly  C-X bond strengths decrease going down the periodic table  C-X bond is polar; C δ+, X δ- o Results in dipole moment for all halomethanes o Implies that the alkyl halide C-X carbon atom should behave as an electrophile in polar reactions 10.2 Preparing Alkyl Halides from Alkanes: Radical Halogenation 10.3 Preparing Alkyl Halides from Alkenes: Allylic Bromination 10.4 Stability of the Allyl Radical: Resonance Revisited 10.5 Preparing Alkyl Halides from Alcohol (and Alkene) Preparation of Alkyl Halides 1) Reaction of Alkenes with HX or X2 2) From Alcohols  R-OH  R-X  Works best with 3° alcohols  A common approach for primary and secondary alcohols I. SOCl2 CHM138H1
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