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Tài liệu Bài giảng organic chemistry chapter5

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ORGANIC CHEMISTRY Dr Nam T. S. Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 38647256 ext. 5681 Email: [email protected] 1 Chapter 5: ALKENES An sp2 hybridized carbon 2 NOMENCLATURE OF ALKENES The IUPAC name of an alkene is obtained by replacing the “ane” ending of the corresponding alkane with “ene” • Ethylene is an acceptable synonym for ethene in the IUPAC system • Propylene, isobutylene and other common names ending in “ylene” are NOT acceptable IUPAC names 3 Determine the parent hydrocarbon – the longest continuous carbon chain containing the C=C 4 Note: Alkenes can have geometric isomers 5 PREPARATION OF ALKENES Dehydrations of alcohols Acid isomerization 6 isomerization 7 Eliminations of alkyl halides Base 8 Alkyne hydrogenations Pd/CaCO3 + Pb(OAc)2 / quinoline 9 REACTIONS OF ALKENES Additions of hydrogen halides (AE) More stable Markovnikov’s rule 10 Carbocation rearrangement More stable 11 More stable 12 Stereochemistry Racemic mixture 13 Already has 1 asymmetric carbon 14 2 asymmetric carbons are created 15 Additions of hydrogen bromide (AR) Electrophilic addition (AE) Radical addition (AR) – only for HBr 16 Reaction mechanism: 17 Additions of halogens 18 Major addition product – NOT a dihalide 19 Stereochemistry 20
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