AlkylHalides - Alkyl Halides R-X (X = F, Cl, Br, I)...

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Alkyl Halides R-X (X = F, Cl, Br, I) Classification of alkyl halides according to the class of the carbon that the halogen is attached to. RCH 2 -X R 2 CH-X R 3 C-X 1 o 2 o 3 o
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Nomenclature: common names : “alkyl halide” (fluoride, chloride, bromide, iodide) IUPAC names : use rules for alkanes halogen = halo (fluoro, chloro, bromo, iodo) Cl CH 3 CH 2 CH 2 CH 2 -Br CH 3 CHCH 3 n -butyl bromide isopropyl chloride 1-bromobutane 2-chloropropane 1 o 2 o
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CH 3 CH 3 CH 3 CHCH 2 CHCH 3 CH 3 CCH 3 Br I 2-bromo-4-methylpentane tert -butyl iodide 2-iodo-2-methylpropane 2 o 3 o CH 3 Cl-CHCH 2 CH 3 sec -butyl chloride 2-chlorobutane 2 o
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Physical properties: polar + no hydrogen bonding => moderate boiling/melting points water insoluble Uses: pesticides, refrigerants (freons), solvents, synthetic intermediates. CH 3 Br CClF 3 CCl 4
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Synthesis of alkyl halides: 1. From alcohols a) HX b) PX 3 1. Halogenation of certain hydrocarbons 3. ( later) 4. (later) 5. Halide exchange for iodide
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1. From alcohols. #1 synthesis! a) With HX R-OH + HX R-X + H 2 O i) HX = HCl, HBr, HI ii) may be acid catalyzed (H + ) iii) ROH: 3 o > 2 o > CH 3 > 1 o o
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CH 3 CH 2 CH 2 CH 2 -OH + NaBr, H 2 SO 4 , heat CH 3 CH 2 CH 2 CH 2 -Br n -butyl alcohol (HBr) n -butyl bromide 1-butanol 1-bromobutane CH 3 CH 3 CH 3 CCH 3 + HCl CH 3 CCH 3 OH Cl tert -butyl alcohol tert -butyl chloride 2-methyl-2-propanol 2-chloro-2-methylpropane CH 3 -OH + HI, H + ,heat CH 3 -I methyl alcohol methyl iodide methanol iodomethane
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from alcohols: b) PX 3 i) PX 3 = PCl 3 , PBr 3 , P + I 2 ii) ROH: CH 3 > 1 o > 2 o iii) no rearragements CH 3 CH 2 -OH + P, I 2 CH 3 CH 2 -I ethyl alcohol ethyl iodide ethanol iodoethane CH 3 CH 3 CH 3 CHCH 2 -OH + PBr 3 CH 3 CHCH 2 -Br isobutyl alcohol isobutyl bromide
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Halogenation of certain hydrocarbons . R-H + X 2 , Δ or hν R-X + HX (requires Δ or hν; Cl 2 > Br 2 (I 2 NR); 3 o >2 o >1 o ) o yields mixtures ! In syntheses, limited to those hydrocarbons that yield only one monohalogenated product . CH
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AlkylHalides - Alkyl Halides R-X (X = F, Cl, Br, I)...

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