李艳梅有机化学课件第六章.pptx

Chapter 6Alkyl halides第六章 卤代烷Organic Chemistry A (1)By Prof. Li Yan-MeiTsinghua UniversityContent 6.1 Classification, nomenclature and isomers 6.2 Physical property Spectrum data 6.3 Chemical properties 6.4 Mechanism of nucleophilic substitution 6.5 Elimination reaction vs nucleophilic substitution 6.6 Preparation (learn on your own) 6.7 Important alkyl halides (learn on your own)6.1 Classification, nomenclature and isomers 6.1.1 Classification 6.1.2 Nomenclature 6.1.3 Isomers (learn on your own) 6.1.1 Classificationn = 1Aromatic alkyl halidepolyhaloalkaneSaturated alkyl haliden 1Unsaturated alkyl halideX = Fprimary halo alkaneX = ClSecondary halo alkaneX = BrTertiary halo alkaneX = I6.1.2 NomenclatureOrdinary namingn-butyl chlorideiso-butyl fluorideIUPAC nomenclature(R)-3-甲基-1-溴戊烷(R)-1-bromo-3-methylpentaneRS(2R, 3S)-3-甲基-2-溴己烷why not cis?(1S, 3R)-1-甲基-3-氯环己烷RS(1R,3S)-1-chloro-3-methylcyclohexaneRS(1S,3R)-1-chloro-3-methylcyclohexane6.1.3 Isomers (learn on your own)碳架异构卤原子位置异构 6.2 Physical property Spectrum data 6.2.1 Physical properties6.2.2 spectrum data 1 1H-NMR 2 13C-NMR 3 IR 1H-NMRXCHCHCH2222.16-4.41.25-1.551.03-1.08 13C-NMR?-碳、?-碳化学位移向低场方向移动10.0 UltraCCClFIBrCC IR750 ~ 700 cm-1(m)1350 ~ 1100 cm-1(s)610 ~ 485 cm-1(m)700 ~ 500 cm-1(s)6.3 Chemical properties 6.3.1 Structure and inductive effect 6.3.2 Nucleophilic substitution 6.3.3 Elimination 6.3.4 Reaction with metals 6.3.5 Reduction6.3.1 Structure and inductive effect结构与诱导效应1, Structure of alkyl halides卤代烷的结构C-F 139pmC-H 110pmC-Cl 176pmC-Br 194pm Both the carbon and the halo atom are sp3 hybridized.C-I 214pm2, Dipole moment偶极矩μ = q × dD(debye)barycentre of positive chargeCompoundμ/dCH3F1.82CH3Cl1.94CH3Br1.79CH3I1.64+ qd- qbarycentre of negative charge3, Inductive effect诱导效应含义δδδ +δδ +δ+δ-CH3CH2CH2Cl与C－H键相比HPolar covalent bond2.2LiBeBCNOF1.01.52.04.1NaMgAlSiPSCl2.8δδδ +δδ +δ+δ-CH3CH2CH2Cl诱导效应：分子中，由于电负性不同的取代基的影响，使整个分子中成键电子云按取代基团的电负性所决定的方向而偏移的效应。 “ I ” ?电子的偏移δδδ +