Alkenes, Reactions.ppt

CH3CH=CH2 + Br2 + H2O + NaCl ? CH3CHCH2 + CH3CHCH2 + CH3CHCH2 Br Br OH Br Cl Br Some evidence suggests that the intermediate is not a normal carbocation but a “halonium” ion: | | — C — C — Br ? The addition of X2 to an alkene is an anti-addition. Addition of halogens + water (halohydrin formation): | | | | — C = C — + X2, H2O ? — C — C — + HX | | OH X X2 = Br2, Cl2 Br2 = electrophile CH3CH=CH2 + Br2(aq.) ? CH3CHCH2 + HBr OH Br Dimerization: CH3 CH3 CH3 CH3C=CH2 + H2SO4, 80oC ? CH3C-CH=CCH3 CH3 + CH3 CH3 CH3C-CH2C=CH2 CH3 carbocation as electrophile Alkylation: CH3 CH3 CH3C=CH2 + CH3CHCH3 + HF, 0oC ? CH3 CH3 CH3C-CH2CHCH3 CH3 2,2,4-trimethylpentane ( “isooctane” ) Used to increase gasoline yield from petroleum and to improve fuel performance. intermolecular hydride (H:-) transfer Internal combustion engine (four-stroke). Also called an Otto engine. 1. Intake stroke: air/fuel mixture is drawn into the cylinder. 2. Compression stroke: air/fuel mixture