ORGANIC CHEMISTRY (PETRO)

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Ngày đăng: 14/04/2018, 14:57

ORGANIC CHEMISTRY Dr Nam T S Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 8647256 ext 5681 Email: ptsnam@hcmut.edu.vn Chapter 5: ALKENES An sp2 hybridized carbon 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 Determine the parent hydrocarbon – the longest continuous carbon chain containing the C=C Note: Alkenes can have geometric isomers PREPARATION OF ALKENES Dehydrations of alcohols Acid isomerization isomerization Eliminations of alkyl halides Base Alkyne hydrogenations Pd/CaCO3 + Pb(OAc)2 / quinoline REACTIONS OF ALKENES Additions of hydrogen halides (AE) More stable 10 Additions of hydrogen – hydrogenation 26 Reaction mechanism: Syn addition 27 Stereochemistry 28 29 Alkene epoxidations – Anti hydroxylations 30 Stereochemistry 31 Reactions of epoxides 32 33 Stereochemistry Anti additions 34 Syn hydroxylations of alkenes 35 Reaction mechanism: Syn additions 36 Permanganate cleavage of alkenes 37 Ozonolysis of alkenes 38 In the presence of an oxidizing agent, the products will be ketones / carboxylic acids 39 Polymerizations 40 ... mechanism: 14 Stereochemistry Racemic mixture 15 Already has asymmetric carbon 16 asymmetric carbons are created 17 Additions of halogens 18 Major addition product – NOT a dihalide 19 Stereochemistry asymmetric... hydrogen – hydrogenation 26 Reaction mechanism: Syn addition 27 Stereochemistry 28 29 Alkene epoxidations – Anti hydroxylations 30 Stereochemistry 31
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