6.卤代烷（课件）- 《有机化学》同步教学（清华大学版）

Chapter 6 Alkyl halides 第六章 卤代烷 Content 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) 6.1.1 Classification 6.1.2 Nomenclature 6.1.3 Isomers (learn on your own) 6.1 Classification, nomenclature and isomers 6.1.1 Classification Unsaturated alkyl halide Saturated alkyl halide Aromatic alkyl halide n = 1 n > 1 polyhaloalkane Tertiary halo alkane Secondary halo alkane primary halo alkane X = F X = Cl X = Br X = I 6.1.2 Nomenclature Ordinary naming n-butyl chloride iso-butyl fluoride IUPAC nomenclature (R)-1-bromo-3-methylpentane (R)-3-甲基-1-溴戊烷 (2R, 3S)-3-甲基-2-溴己烷 R S (1R,3S)-1-chloro-3-methylcyclohexane (1S, 3R)-1-甲基-3-氯环己烷 R S S R why not cis? (1S,3R)-1-chloro-3-methylcyclohexane 6.1.3 Isomers (learn on your own) 碳架异构 卤原子位置异构 6.2.1 Physical properties 6.2.2 spectrum data 1 1H-NMR 2 13C-NMR 3 IR 6.2 Physical property & Spectrum data 1H-NMR X C H 2 C H 2 C H 2 2 . 1 6 - 4 . 4 1 . 2 5 - 1 . 5 5 1 . 0 3 - 1 . 0 8 13C-NMR 10.0 Ultra -碳、-碳化学位移向低场方向移动 IR C F C Br C Cl C I 1350 ~ 1100 cm-1(s) 750 ~ 700 cm-1(m) 700 ~ 500 cm-1(s) 610 ~ 485 cm-1(m) 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 Reduction 6.3 Chemical properties 1, Structure of alkyl halides 卤代烷的结构 C-F 139pm C-Cl 176pm C-Br 194pm C-I 214pm C-H 110pm Both the carbon and the halo atom are sp3 hybridized. 6.3.1 Structure and inductive effect 结构与诱导效应 2, Dipole moment 偶极矩 barycentre of positive charge barycentre of negative charge + q - q d μ = q × d D(debye) Compound μ/d CH3F 1.82 CH3Cl 1.94 CH3Br 1.79 CH3I 1.64 3, Inductive effect 诱导效应 CH3 CH2 CH2 Cl δ+ δδ + δδδ + δ- Polar covalent bond H 2.2 L