Alkylhalides第六章卤代烷OrganicChemistryA(1)ByProf.LiYan-MeiTsinghuaUniversityContentContentContent6.1Classification,nomenclatureandisomers6.2Physicalproperty&Spectrumdata6.3Chemicalproperties6.4Mechanismofnucleophilicsubstitution6.5Eliminationreactionvsnucleophilicsubstitution6.6Preparation(learnonyourown)6.7Importantalkylhalides(learnonyourown)6.1.1Classification6.1.2Nomenclature6.1.3Isomers(learnonyourown)6.1Classification,nomenclatureandisomers6.1.1ClassificationUnsaturatedalkylhalideSaturatedalkylhalideAromaticalkylhalideBrBrBrRXnBrn=1n>1polyhaloalkaneTertiaryhaloalkaneSecondaryhaloalkaneprimaryhaloalkaneX=FX=ClCXCH3BrX=BrX=IBrBr6.1.2NomenclatureOrdinarynamingCln-butylchlorideFiso-butylfluorideIUPACnomenclatureBr(R)-1-bromo-3-methylpentane(R)-3-甲基-1-溴戊烷(2R,3S)-3-甲基-2-溴己烷RSCl(1R,3S)-1-chloro-3-methylcyclohexane(1S,3R)-1-甲基-3-氯环己烷RSClHCH3HSRwhynotcis?ClCl(1S,3R)-1-chloro-3-methylcyclohexane6.1.3Isomers(learnonyourown)碳架异构卤原子位置异构6.2.1Physicalproperties6.2.2spectrumdata11H-NMR213C-NMR3IR6.2Physicalproperty&Spectrumdata1H-NMR1.061.813.47ClXCH2CH2CH22.16-4.41.25-1.551.03-1.0813C-NMRChemNMR13CEstimation11.226.646.9ClEstimationqualityisindicatedbycolor:good,medium,rough01020304050PPM10.0Ultra-碳、-碳化学位移向低场方向移动IRCFCBrCClCI1350~1100cm-1(s)750~700cm-1(m)700~500cm-1(s)610~485cm-1(m)6.3.1Structureandinductiveeffect6.3.2Nucleophilicsubstitution6.3.3Elimination6.3.4Reactionwithmetals6.3.5Reduction6.3Chemicalproperties1,Structureofalkylhalides卤代烷的结构C-F139pmC-Cl176pmC-Br194pmC-I214pmC-H110pmBoththecarbonandthehaloatomaresp3hybridized.6.3.1Structureandinductiveeffect结构与诱导效应2,Dipolemoment偶极矩barycentreofpositivechargebarycentreofnegativecharge+q-qdμ=q×dD(debye)Compoundμ/dCH3F1.82CH3Cl1.94CH3Br1.79CH3I1.643,Inductiveeffect诱导效应CH3CH2CH2Clδ+δδ+δδδ+δ-PolarcovalentbondH2.2Li1.0Na0.9Be1.5Mg1.2B2.0Al1.5C2.5Si1.7N3.1P2.1O3.5S2.4F4.1Cl2.8含义与C－H键相比诱导效应诱导效应：分子中，由于：分子中，由于电负性电负性不同的...
