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有机化学第17章化合物PPT课件下载(共42页)文字介绍:17杂环化合物（HeterocyclicCompounds）基本内容和重点要求杂环化合物的分类和命名；杂环化合物的结构和芳香性；杂环化合物的化学性质；生物碱重点要求掌握芳香性；五元、六元杂环化合物的化学性质，杂环化合物的亲电取代反应的活性及规律；酸碱性规律。17杂环化合物17.1杂环化合物的分类和命名17.2几个重要环系的结构与性质17.3生物碱17.1杂环化合物的分类和命名杂环化合物是指组成环的原子中含有除碳以外的原子(杂原子——常见的是N、O、S等)的环状化合物。杂环化合物的成环规律和碳环一样，最稳定和最常见的也是五元环和六元环。有的环只有一个杂原子，有的环含有多个或多种杂原子。杂环化合物一般按环的大小分成五元环和六元环两大类。根据有无芳香性，可将杂环化合物分为非芳香性杂环和芳香性杂环。非芳香性杂环化合物具有与相应脂肪族化合物相类似的性质。例如：杂环化合物不包括极易开环的含杂原子的环状化合物。NHO,,,OOOOOO单杂环稠杂环五元杂环六元杂环碳环母核碳环母核重要的杂环ONSNNNNNHON杂环化合物一般采用音译法命名，根据化合物的英文读音，选用同音汉字，并以“口”字旁表示杂环化合物。OSNHNß»à«àç·ÔßÁ¿©ßÁà¤FuranthiophenepyrrolepyridineNSNàßøàçßòpuinolinethiazoleNNNHßäßòßÅßáimidazoleindole环上有取代基的杂环化合物，命名时以杂环为母体，从杂原子开始将环上的原子编号。当环上含有两个或两个以上相同杂原子时，应使杂原子所在位次的数字最小。当环上的杂原子不同时，按O、S、N的次序编号。OCHONNCH3HSNCH31234512345123452£ß»à«¼×È©4£¼×»ùßäßò5£¼×»ùàçßòOCH3CH3NCH3¦Á¦Á\'¦Â¦Â\'¦Á¦Â¦Ã¦Á,£-¶þ¼×»ùß»à«¦Ã££¼×»ùßÁà¤£¬¦Á\'17.2几种重要环系的结构与性质17.2.1呋喃、噻吩、吡咯和吡啶的结构17.2.2呋喃、噻吩和吡咯和吡啶的性质呋喃()：OO:2s2p24杂化轨道p轨道p轨道s轨道p轨道sp2sp2O杂化轨道sp2噻吩()具有与呋喃相似的结构。S17.2.1呋喃、噻吩、吡咯和吡啶的结构sp2杂化轨道psp2轨道p轨道s轨道Np轨道HN:2s2p2317.2.1呋喃、噻吩、吡咯和吡啶的结构吡咯()：N-H呋喃、噻吩和吡咯组成环的五个原子都位于同一平面上，四个碳原子和一个杂原子都为sp2杂化状态，彼此以σ键相连接；每个碳原子还有一个电子在p轨道上，杂原子的未共用电子对也是在p轨道上，这五个p轨道垂直于环所在的平面并相互重叠形成环闭共轭体系。这个共轭体系是由五个原子上的六个p电子组成的，其p电子数符合休克尔4n＋2规则。因此具有芳香性。总结：呋喃、噻吩和吡咯的原子轨道示意图：OSNHOSNH................................苯>噻吩>吡咯>呋喃芳香性大小：http://www.029nk.com/http://www.029nk.com/fkyz/http://www.029nk.com/byby/http://www.029nk.com/fkzl/http://www.029nk.com/gjjb/http://www.029nk.com/jhsy/http://www.029nk.com/fkzx/http://www.029nk.com/gjjb/gjml/http://www.029nk.com/fkyz/ydy/http://www.029nk.com/fkzl/zgjl/http://www.029nk.com/byby/byjc/http://www.029nk.com/fkzx/cvmxf/http://www.029nk.com/jhsy/rljs/http://www.029nk.com/fkyz/bdyc/http://www.029nk.com/byby/nxby/http://www.029nk.com/fkzx/yczx/http://www.029nk.com/jhsy/wtrl/http://www.029nk.com/jhsy/yaoliu/http://www.029nk.com/gjjb/gjxr/http://www.029nk.com/fkyz/fjy/http://www.029nk.com/fkzl/lcnz/http://www.029nk.com/byby/byzl/http://www.029nk.com/jhsy/gwy/http://www.029nk.com/byby/lcxby/http://www.029nk.com/fkzx/ydjs/http://www.029nk.com/jhsy/jyzs/http://www.029nk.com/gjjb/gjfd/http://www.029nk.com/fkyz/pqy/http://www.029nk.com/fkzl/ydnz/http://www.029nk.com/byby/byyy/http://www.029nk.com/fkzx/yjbt/http://www.029nk.com/gjjb/gjy/http://www.029nk.com/fkyz/ndy/http://www.029nk.com/fkzx/ydzx/http://www.029nk.com/byby/gjxby/http://www.029nk.com/fkzx/ydzz/http://www.029nk.com/jhsy/zyjc/http://www.xasg120.com/http://www.xasg120.com/fkzl/http://www.xasg120.com/fkzl/lc/http://www.xasg120.com/fkzl/wy/http://www.xasg120.com/fkzl/yd/http://www.xasg120.com/fkzl/zgjl/http://www.xasg120.com/fuke/http://www.xasg120.com/fuke/fujianyan/http://www.xasg120.com/fuke/gjy/http://www.xasg120.com/fuke/ndy/http://www.xasg120.com/fuke/pqy/http://www.xasg120.com/fuke/ydy/http://www.xasg120.com/fuke/zigongneimoyan/http://www.xasg120.com/gongjing/http://www.xasg120.com/gongjing/feida/http://www.xasg120.com/gongjing/gongjingai/http://www.xasg120.com/gongjing/milan/http://www.xasg120.com/gongjing/xirou/http://www.xasg120.com/gongjing/yanzheng/http://www.xasg120.com/gundong_1.htmlhttp://www.xasg120.com/jbzs/http://www.xasg120.com/jhsy/http://www.xasg120.com/jhsy/gwy/http://www.xasg120.com/jhsy/jiancha/http://www.xasg120.com/jhsy/shanghuanquhuan/http://www.xasg120.com/jhsy/wtrl/http://www.xasg120.com/jhsy/wutongyinchan/http://www.xasg120.com/jhsy/yaoliu/http://www.xasg120.com/jryuyue/http://www.xasg120.com/weichuangfuke/http://www.xasg120.com/yyhj/http://www.xasg120.com/zhengxing/cnmxf/http://www.xasg120.com/zhengxing/xyczx/http://www.xasg120.com/zhengxing/ydjss/http://www.xasg120.com/zhengxing/ydzx/呋喃、噻吩和吡咯的结构吡啶中氮原子采取不等性sp2杂化：结果是：Nsp2psp2pNN..未共用电子对占据sp2杂化轨道，与环共平面，不能参与环系的共轭p轨道与环平面垂直，相互重叠形成六个原子在内的闭合共轭体系N........吡啶的结构吡啶和吡咯的结构比较吡啶和吡咯的结构比较孤对电子在sp2杂化轨道上孤对电子在p轨道上17.2.2呋喃、噻吩和吡咯和吡啶的性质呋喃是无色液体，沸点32℃，具有类似氯仿的气味，微溶于水，易溶于乙醇、乙醚等有机溶剂。呋喃能使盐酸浸过的松木片显绿色,此现象可检验呋喃的存在。噻吩与苯共存于煤焦油中，噻吩是无色而有特殊气味的液体，沸点84℃。噻吩和靛红(吲哚满二酮)在硫酸作用下呈蓝色，此现象可检验噻吩的存在。吡咯存在于煤焦油和骨焦油中，是无色液体,沸点131℃，有弱的苯胺的气味。其蒸气遇盐酸浸湿的松木片则呈红色，可检验吡咯的存在。(1)环上的亲电取代反应(2)对氧化剂、酸及碱的稳定性(3)还原反应(4)吡咯和吡啶的酸碱性17.2.2呋喃、噻吩和吡咯和吡啶的性质(1)亲电取代反应呋喃、噻吩和吡咯环中的杂原子上的未共用电子对参与了环的共轭体系，使环上的电子云密度增加，故它们都比苯容易发生亲电取代反应，取代通常发生在α位上。磺化硝化卤代呋喃、噻吩和吡咯的卤代反应都比苯容易。卤代OOBrBr2BrH++¶þ‡fÍé0¡æSBr2SBrCH3COOHBrH++ÊÒÎÂNHNIIIIHI2NaOHNaIOH2++4+444+呋喃、吡咯必须用吡啶的三氧化硫加合物作为磺化剂，噻吩可直接用硫酸磺化。ONSO3OSO3HNSO3NHNSO3HHSSSO3HH2SO430¡æ磺化吡啶与硝基苯相似，亲电取代比苯困难，并且主要发生在β位上，反应条件要求较高。N+Br2以上C。300NBrNN+H2SO4C。350SO3HNNC。NO2+混酸30024h吡啶磺酸溴代吡啶硝基吡啶（产率很低）6％，约例：亲电取代反应活性同上。http://www.029nk.com/http://www.029nk.com/fkyz/http://www.029nk.com/byby/http://www.029nk.com/fkzl/http://www.029nk.com/gjjb/http://www.029nk.com/jhsy/http://www.029nk.com/fkzx/http://www.029nk.com/gjjb/gjml/http://www.029nk.com/fkyz/ydy/http://www.029nk.com/fkzl/zgjl/http://www.029nk.com/byby/byjc/http://www.029nk.com/fkzx/cvmxf/http://www.029nk.com/jhsy/rljs/http://www.029nk.com/fkyz/bdyc/http://www.029nk.com/byby/nxby/http://www.029nk.com/fkzx/yczx/http://www.029nk.com/jhsy/wtrl/http://www.029nk.com/jhsy/yaoliu/http://www.029nk.com/gjjb/gjxr/http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们主要存在于植物中，具有很强的生理作用。生物碱的结构一般都是比较复杂的多环化合物。生物碱是人们研究得最早和最多的一类中草药有效成份。17.4.1生物碱的物理性质　　生物碱一般为无色或白色结晶形固体，少数是有颜色的液体，难溶于水，易溶于乙醇、乙醚、氯仿和苯等有机溶剂。生物碱大多都有旋光性，自然界中存在的一般都是左旋体。左旋体和右旋体的生理作用往往差别很大。许多试剂能与生物碱作用，生成不溶性的沉淀或产生颜色反应，这些试剂称为生物碱试剂。可用这些试剂来检验生物碱的存在。沉淀试剂：丹宁、苦味酸、磷钼酸等。颜色反应试剂：硫酸、硝酸、甲醛、氨水等。

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