Wade06a - Chapter 6 Alkyl Halides: Nucleophilic...

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Unformatted text preview: Chapter 6 Alkyl Halides: Nucleophilic Substitution and Elimination Organic Chemistry , 5 th Edition L. G. Wade, Jr. Chapter 6 2 Classes of Halides Alkyl: Halogen, X, is directly bonded to sp 3 carbon. Vinyl: X is bonded to sp 2 carbon of alkene. Aryl: X is bonded to sp 2 carbon on benzene ring. Examples: C H H H C H H Br alkyl halide C C H H H Cl vinyl halide I aryl halide => Chapter 6 3 Polarity and Reactivity Halogens are more electronegative than C. Carbon-halogen bond is polar, so carbon has partial positive charge. Carbon can be attacked by a nucleophile. Halogen can leave with the electron pair. => C H H H Br + - Chapter 6 4 Classes of Alkyl Halides Methyl halides: only one C, CH 3 X Primary: C to which X is bonded has only one C-C bond. Secondary: C to which X is bonded has two C-C bonds. Tertiary: C to which X is bonded has three C-C bonds. => Chapter 6 5 Classify These: CH 3 CH CH 3 Cl CH 3 CH 2 F (CH 3 ) 3 CBr CH 3 I => Chapter 6 6 Dihalides Geminal dihalide: two halogen atoms are bonded to the same carbon Vicinal dihalide: two halogen atoms are bonded to adjacent carbons. C H H H C H Br Br geminal dihalide C H H Br C H H Br vicinal dihalide => Chapter 6 7 IUPAC Nomenclature Name as haloalkane. Choose the longest carbon chain, even if the halogen is not bonded to any of those Cs. Use lowest possible numbers for position. CH 3 CH CH 2 CH 3 Cl CH 3 (CH 2 ) 2 CH(CH 2 ) 2 CH 3 CH 2 CH 2 Br 2-chlorobutane 4-(2-bromoethyl)heptane => Chapter 6 8 Systematic Common Names Name as alkyl halide. Useful only for small alkyl groups. Name these: CH 3 CH CH 2 CH 3 Cl (CH 3 ) 3 CBr CH 3 CH CH 3 CH 2 F => Sec-butyl chloride T-butyl Bromide iso-butyl fluoride Chapter 6 9 Trivial Names CH 2 X 2 called methylene halide. CHX 3 is a haloform. CX 4 is carbon tetrahalide. Examples: CH 2 Cl 2 is methylene chloride CHCl 3 is chloroform CCl 4 is carbon tetrachloride. => Chapter 6 10 Uses of Alkyl Halides Solvents - degreasers and dry cleaning fluid Reagents for synthesis of other compounds Anesthetic: Halothane (trade name) is CF 3 CHClBr CHCl 3 used originally (toxic and carcinogenic) Freons, chlorofluorocarbons or CFCs Freon 12, CF 2 Cl 2 , now replaced with Freon 22, CHClF 2 , not as harmful to ozone layer. Pesticides - DDT banned in U.S....
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Wade06a - Chapter 6 Alkyl Halides: Nucleophilic...

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