AlkynesandDienes第八章炔烃和二烯烃OrganicChemistryA(1)ByProf.LiYan-MeiTsinghuaUniversityPartIPartIAlkynesAlkynesContentContentContent8.1Structure,isomerization&nomenclature8.2Physicalproperties&spectrumdata8.3Chemicalreactions8.4Preparation(Learnonyourown)8.5Resource&application(Learnonyourown)8.1.1StructureofAlkynes8.1.2Isomerization(Learnonyourown)8.1.3Nomenclature8.1Structure,isomerization&nomenclature8.1.1StructureofAlkynesFormationofatriplebond既含双键，又含三键的结构选主链：含有双键和叁键的最长链编号：使双键、叁键具有最低的编号如果位号有选择，则优先照顾双键书写：先烯后炔CHCH33CH=CHCCH=CHC≡≡CH3-CH3-戊烯戊烯-1--1-炔炔CHCH33CHCH≡≡CCH=CHCCH=CH221-1-戊烯戊烯-3--3-炔炔HCHC≡≡CCHCCH22CH=CHCH=CH221-1-戊烯戊烯-4--4-炔炔8.1.2Isomerization(Learnonyourown)8.1.3Nomenclature8.2.Physicalproperties&spectrumdata8.2.1Physicalproperties8.2.2spectrumdata8.2.1Physicalproperties1、炔烃分子短小、细长，在液态及固态中彼此很靠近，分子间作用力强。熔点、沸点和密度较大短小短小键长键长:C-C0.154nm:C-C0.154nmC=C0.134nmC=C0.134nmCC≡≡C0.120nmC0.120nm细长细长CC≡≡CC直线型直线型2、炔烃分子极性比烯烃略强尽管电子云偏移大，但键长较短尽管电子云偏移大，但键长较短spsp33spspspsp33spsp228.2.2Spectrumdata11H-NMRH-NMR1313C-NMRC-NMRIRIR≡≡CC－－H1.7H1.7ppmppm≡≡CC－－H100-70H100-70ppmppm≡≡CC－－Hstretching3310-3300cmHstretching3310-3300cm-1-1CC≡≡Cstretching2260-2100cmCstretching2260-2100cm-1-1≡≡CC－－Hbending700-600cmHbending700-600cm-1-18.3Chemicalreactions8.3.1Acidity8.3.2ElectrophilicAddition8.3.3FreeRadicalAddition8.3.4NucleophilicAddition8.3.5Reduction8.3.6Oxidation8.3.7PolymerizationCCHR富含电子、弱的π键亲电加成加氢还原被氧化聚合具有酸性被亲核－加成8.3.1AcidityCC22HH66CC22HH44NHNH33CC22HH22CC22HH55OHHOHH22OOpKapKa5044342515.915.745044342515.915.74共轭碱炔化物含碳酸FormationofFormationofAlkynidesAlkynides炔化物的生成炔化物的生成动力之一：生成更弱的酸格氏试剂格氏试剂烷烷基基锂锂用途：作为亲核试剂用途：作为亲核试剂动力之二：生成沉淀白红干燥时，受热及撞击易发生爆炸，生成金...
