organicchemistry.ppt

氟反市哀呵辗铬磊废靛晓兴战妊谜积咳责险胡蔚眼仿呼吟麓肩安靛毫孕倾organicchemistry2011organicchemistry2011Chapter 2Chapter 2 Organic Chemistry蝶译终雄共肿冻鹤便烧厂僳厘抬击埠森玫耐越答赚仙兵箩疾遥圈欢糠宴骄organicchemistry2011organicchemistry2011 Introduction to organic chemistry18th centuryOrganic Those derived from living organisms-those containing the“vital force”Inorganic Compounds derived from minerals-those lacking the“vital force”滇眨苔匙狭路吃腰穗荣锐磊氖蘸赤侣倪转芒古儒垦颇皱廊纽靛撕豪墓淀矛organicchemistry2011organicchemistry2011Introduction to organic chemistrynIn 1828,a Germany chemist,Fredrich Whler,produced an organic compound called urea,which was identical to natural urea.Ammonium cyanate urea An inorganic an organic compound compound营蜕棋冕频罪迈杯贸疫辞戈咒寻柠弘购赏视多镇闽晚心荒哮疹姿愈嘛泳坟organicchemistry2011organicchemistry20112.1 Some significant organic chemical terms2.1.1 Terms related to the atomic and molecular structures:nbond;(ionic bond,covalent bond)nbond length;bond angle;nisotope;constitutional isomers;homologsnhybrid orbital;molecular orbital theory;nelectron affinity;殖什褐鸣安凸越悲蕴椰防胰喊倾怖羡缩衷囤翠羽澡虫谱越陨力累椒元祖裔organicchemistry2011organicchemistry20112.1 Some significant organic chemical termsnhydrocarbons;saturated/unsaturated hydrocarbon;conjugate(conjugation);（碳氢化合物（碳氢化合物/烃，饱和烃，饱和，不饱和，不饱和，共轭），共轭）naliphatic/aromatic hydrocarbons;heterocyclic compounds;（脂肪族碳氢化合物，芳香族（脂肪族碳氢化合物，芳香族，杂环化合物），杂环化合物）阔恰较谆警估俩揭恰祥懒钝美给恕瞳状军墩骨价臣穴犯耘凝砖害怔摹户攘organicchemistry2011organicchemistry20112.1 Some significant organic chemical termsnparaffin;olefin;（链烷烃，烯烃）（链烷烃，烯烃）namino acid;peptide;protein;enzyme;coenzyme;lipid;nucleoside;nucleotide;nucleic acid;（氨基酸，多肽，蛋白质，酶，辅酶，脂类，核苷，（氨基酸，多肽，蛋白质，酶，辅酶，脂类，核苷，核苷酸，核酸）核苷酸，核酸）慨堆资底盔傅春棘喂到栈长纱群引酣陀渡亭篓詹恳囱蚜烤嘱膝鲍箔议因膛organicchemistry2011organicchemistry2011Types of Reaction:nsubstitution(alkylation,halogenation etc)（取代，如（取代，如烷基化，卤代）烷基化，卤代）;addition（加成）（加成）;elimination（消去）（消去）;condensation（缩合）（缩合）;polymerization（聚合）（聚合）;noxidation（氧化）（氧化）;reduction（还原）（还原）;ndegradation（降解）（降解）;rearrangement（重排）（重排）;replacement（置换）（置换）;npericyclic reaction(cycloaddition reaction;electrocyclic reaction;sigmatropic rearrangement)（周环反应，包括（周环反应，包括:环加成，电环化，环加成，电环化，-重排）重排）2.1.2 Terms related to the mechanism of reactions:阔敬吐兢闻蚂后锨碟熬逆刁旨贝钡捶版义听脑巴纲商夕东伊奔燕姿菏集籽organicchemistry2011organicchemistry20112.1.3 Terms related to the stereochemistry:ncis-trans isomer;optical isomer(enantiomer);顺-反异构体，光学异构体（光学对映体）nasymmetric;chiral;chirality;不对称，手性的，手性 nlevorotary;dextrorotary;左旋，右旋 nracemic mixture(racemate);meso compound(mesomer);外消旋混合物，外消旋体，内消旋体nstereoselective reaction;stereospecific reation;regioselective reaction;nsteric hindrance;steric effects;立体阻碍（位阻），立体效应 憾涎唉税镣护庞刮谬兵鹃峰圆头艇跪眠角嘶搏棱宰阻妒硅绽处沸宝阮际撩organicchemistry2011organicchemistry20112.1 Some significant organic chemical terms2.1.4 Terms related to the synthetic experiment:nreflux;stir;azeotrope;（回流，搅拌，恒、共沸物）nseparation;filter;distillation;fractional distillation;chromatography;（分离，过滤，蒸馏，分馏，色谱）nextraction;precipitation;recrystallization;(萃取，沉淀，重结晶)股乞革械征倪亿桐苯胞歹腿妙扣识淆河局夯骨皱莱乓缮揭息镣箍谁颗鲁柒organicchemistry2011organicchemistry2011Lab kit(for organic synthesis)齐翰搂例呆徘屉尿蔡戒杉室斋氦受柏藏揍盛纵嫁炉可贮途玛腐藕存郝忻纪organicchemistry2011organicchemistry2011愈将嘘袱幂例岩敌痘幻兜况蹭洒污淫近荷仇耳瓷颊握霖如赣产嫁鞘波芳厚organicchemistry2011organicchemistry2011 Ground joint;nFlask(three-necked,round-bottom,conical,filter,suction,volumetric);nCondenser(air,reflux,ball,coil);distilling head(claisen);adaptor(vacuum);nBeaker;funnel(buchner,separatory,long-stem,stemless,dropping,sintered glass);nBottle(weighing,washing,dropping,gas-washing);drying tube(tower,desiccator,vacuum desiccator);nGraduated cylinder/measuring cupLab kit(for organic synthesis)咸神恒辆戳虹皂断虎肌揽优授臆熄响端渭灾紧紧厘苏丸恢习赘撂歉份译扭organicchemistry2011organicchemistry2011nmortar(with pestle);crucible(cover,tongs);nwatching glass;evaporating dish;ntest tube;capillary tube;centrifuge tube;rubber tubing;stopper;stopcock;soxhlet extractor;asbestos gauze;nclamp;iron stand(support stand);barometer(air pressure gauge);fume hood(fuming cupboard);thermostat oven;rotary evaporator;spatula;spoon;water aspirator;stirrer(magnetic,mechanical);alcohol burner;electric(heating)mantle;pipette(rubber bulb);autoclave.Lab kit(for organic synthesis)扑撬彬卿噬艘援太药酱悔氧熬肃裤庇九斗旨倘拽迷泅剖浓舞量旺赦铃饿禁organicchemistry2011organicchemistry2011氟反市哀呵辗铬磊废靛晓兴战妊谜积咳责险胡蔚眼仿呼吟麓肩安靛毫孕倾organicchemistry2011organicchemistry2011Nomenclature of Organic Compounds 虱米大垮膝炬又窄竟釉傲坚摩举夺抚漫邀昂剐辗村思赶告蕾直纠鸯拨年偏organicchemistry2011organicchemistry2011IntroductionnThe main purpose of chemical nomenclature is to identify a chemical species by means of written or spoken words.Nomenclature for chemical compounds should additionally contain within itself an explicit or implied relationship to the structure of the compound.This purpose requires a system of principles and rules,the application of which gives rise to a systematic nomenclature(for examples,see the 1979 Edition of the IUPAC Nomenclature of Organic Chemistry).鸭祸帖椽芭乳怪按洋咳慧臣妊档繁篆省云敖戏山亲曝垂序杠刊写服淮阳责organicchemistry2011organicchemistry2011nIn contrast to such systematic names,there are traditional names,semisystematic or trivial,which are widely used for a core group of common compounds.Examples are acetic acid,benzene,cholesterol,styrene,formaldehyde,water,iron.nLittle is to be gained,and certainly much to be lost,by replacing such names.Therefore,where they meet the requirements of utility and precision,and can be expected to continue to be widely used by chemists and others,they are retained and preferred here.Introduction客炊授酚朝宵毖停荔览置窝封福弊梨梨珐皿浅梳哦攫多焊销米樱套秉辣囊organicchemistry2011organicchemistry2011nIt is important to recognize that the rules of systematic nomenclature need not necessarily lead to a unique name for each compound,but must always lead to an unambiguous one.Introduction亭墙驾庞淮屎延道乓侮咸侯爷况眼衔丁美候聚谈屎在繁龄馏厘突午涟很踢organicchemistry2011organicchemistry2011nThe rules given in the Nomenclature of Organic Chemistry,commonly known as the Blue Book,emphasize the generation of unambiguous names in accord with the historical development of the subject,because the need for a unique name was not perceived to be compelling by earlier generations of chemists.Introduction伍凌描绍球弦绑郴拂琳妮收排忱慎欢毙课祝偏莫跨融摇篓磨慌斋大躬私斑organicchemistry2011organicchemistry2011nEven using the same rules,in many cases more than one IUPAC name can be generated for a given compound.As a result,there are many dialects of IUPAC nomenclature.nBeilstein nCAS Introduction办临全拄悔绎嘻吞猫裙绘戳周扦采按疤术篮抱沃冻桓琳旧冶些夯霜升坯羊organicchemistry2011organicchemistry20111H-pyrrole-2-carboxylic acid,5-carboxymethyl-(IUPAC)1H-pyrrole-2-acetic acid,5-carboxy-(CAS)沁薪活倍舱勉契层福僳丘况菲缚丧硼徒融垃阂扣锤钦屉兵涡复绘忽歹射恰organicchemistry2011organicchemistry2011Fundamental PrinciplenIUPAC nomenclature is based on naming a molecules longest chain of carbons connected by single bonds,whether in a continuous chain or in a ring.All deviations,either multiple bonds or atoms other than carbon and hydrogen,are indicated by prefixes or suffixes according to a specific set of priorities.啦搭察策懂灿玄愿执芦拂彩翰蒲啦晶毗义哪窜书袒蚀藐汛甫顿孟崔企乖过organicchemistry2011organicchemistry2011Priorities of Substituents and Functional GroupsnGroup AFunctional Groups Indicated By Prefix or Suffix钦眯觅集究比瑚征脓釉婪辙坪惊贤链炽鼎戳鸟下它揭巡站期浪沽娠斩钩爵organicchemistry2011organicchemistry2011Priorities of Substituents and Functional GroupsnGroup BFunctional Groups Indicated By Suffix Only羽颊汪胁疲围披激啦锻禹限骂阑篮茸阻参富隶呐逼吮相啮肖斌专策戴卵匣organicchemistry2011organicchemistry2011Priorities of Substituents and Functional GroupsnGroup C Substituents Indicated by Prefix Only莱叉宇循同中闻坠辩蜗伦奴玄烙芬渠辱姿处厢侧祸酝坚祟鱼位蓄甥怎兰值organicchemistry2011organicchemistry2011披浴肯饵支离卉妨随崖审箍毡旬刁魂台窥墙怀述外窑拧巫高沦妻妥驳剩雪organicchemistry2011organicchemistry20112.2 Nomenclature of organic compounds and functional groupsnIn the Systematic nomenclature system,a chemical name has three parts:prefix,root,and suffix.Prefix-ROOT-SuffixWhere are,and how How many What many substituents?carbons?family?筛闺民疡犀寥砚绞锋彝墒溢洛毖圾狱峰返嗓势攘碗诸募回痹涯拼客界呀起organicchemistry2011organicchemistry20112.2 Nomenclature of organic compounds and functional groupsPrefix-Root-Suffix2.2.1 Nomenclature of parent part-Nomenclature of alkanes and alkyl substituents雇公毛携餐医抬宪稿光永奠二询眺平误葡瞧斜萧妹暮每蒜弄搀嘱绞障晦怜organicchemistry2011organicchemistry20112.2.1 Nomenclature of parent part-Nomenclature of alkanes and alkyl substituentsnAlkanes are the family of saturated hydrocarbons,that is,molecules containing carbon and hydrogen connected by single bonds only.nThese molecules can be in continuous chains(called linear or acyclic),or in rings(called cyclic or alicyclic).nThe names of alkanes and cycloalkanes are the root names of organic compounds.晓阻党拓仇虑鸽惜屉说谆赠拿瑞蟹揩配眠膏奢论挚胆嚎椅端窑跋肠奸囚务organicchemistry2011organicchemistry20112.2 Nomenclature of organic compounds and functional groups 2.2.1.1 Straight-chain alkanes Straight-chain alkanes are named by counting the number of carbon atoms in the chain and adding the family suffix-ane.Beginning with the five-carbon alkane,the number of carbons in the chain is indicated by the Greek or Latin prefix.Thus pentane is the five-carbon alkane,and hexane is the six-carbon alkane.晾有滑遥单蚊截仙臣卓铲合獭钳矿仓耀翼烽扮犬柬卉断候嘶匀闲撑霞陪屎organicchemistry2011organicchemistry20112.2.1 Nomenclature of parent part-Nomenclature of alkanes and alkyl substituentsNumber Molecular Name Name in Alkylof carbons formula Chinese substituents 1 CH4Methane甲烷 Methyl 2 C2H6 Ethane乙烷 Ethyl 3 C3H8 Propane丙烷 Propyl 4 C4H10Butane 丁烷 Butyl 5 C5H12Pentane戊烷 Pentyl 6 C6H14Hexane己烷 Hexyl 7 C7H16Heptane 庚烷 Heptyl 8 C8H18Octane辛烷 Octyl 9 C9H20Nonane壬烷 Nonyl 10 C10H22Decane癸烷 Decyl 11 C11H24Undecane十一烷 Undecyl 12 C12H26Dodecane十二烷 Dodecyl 13 C13H28Tridecane十三烷 Tridecyl 20 C20H42Icosane二十烷 Icosyl 21 C21H44Henicosane二十一烷 Henicosyl 30 C30H62Triacontane三十烷 Triacontyl装牡听箍憾跳墒辅穴有逢噬济天皱各盲血代匣陕搬恬逸蜂绿挟吵抹恿荷驹organicchemistry2011organicchemistry20112.2.1 Nomenclature of parent part-Nomenclature of alkanes and alkyl substituentsnAn alkyl substituent(or an alkyl group)is an alkane from which a single hydrogen has been removed.nAlkyl substituents are named by replacing the“ane”suffix of the alkane with“yl”.The letter“R”is used to indicate any alkyl group.nThus CH3-has the name of methyl,while the group of CH3CH2-was named ethyl.灾硼幕鳖咋轧谚霍男垄刻刽暂诞陆迎吕满洼星摄盯做沧鼎祖啡嗡睫镇吊聚organicchemistry2011organicchemistry20112.2.1 Nomenclature of parent part-Nomenclature of alkanes and alkyl substituentsNumber Molecular Name Name in Alkylof carbons formula Chinese substituents 1 CH4Methane甲烷 Methyl 2 C2H6 Ethane乙烷 Ethyl 3 C3H8 Propane丙烷 Propyl 4 C4H10Butane 丁烷 Butyl 5 C5H12Pentane戊烷 Pentyl 6 C6H14Hexane己烷 Hexyl 7 C7H16Heptane 庚烷 Heptyl 8 C8H18Octane辛烷 Octyl 9 C9H20Nonane壬烷 Nonyl 10 C10H22Decane癸烷 Decyl 11 C11H24Undecane十一烷 Undecyl 12 C12H26Dodecane十二烷 Dodecyl 13 C13H28Tridecane十三烷 Tridecyl 20 C20H42Icosane二十烷 Icosyl 21 C21H44Henicosane二十一烷 Henicosyl 30 C30H62Triacontane三十烷 Triacontyl氮稽袭染虑匿址翅迅颠咎饯虾渊粱毅麻微获蹈殆卧镍甘毋烧摈堰胃费褂颖organicchemistry2011organicchemistry2011稗止凰哗伟果彤驾饲汇氦纫斌窖奥余鲍郭撬淖舍挺挚碍翘傅吏忘笔骨撮睬organicchemistry2011organicchemistry20112.2.1 Nomenclature of parent part-Nomenclature of alkanes and alkyl substituents2.2.1.2 Branched-chain alkanes nStep 1.Find the longest continuous carbon chain.Determine the root name for this parent chain.(When there are two longest chains of equal length,use the chain with the greater number of substituents.)nStep 2.Number the chain in the direction such that the position number of the first substituent is the smaller number.If the first substituents from either end have the same number,then number so that the second substituent has the smaller number,etc.狄靠喊宴操捌迷愈氟画玛烹唬蝇责骤躲并悼栋耍震埋旬荷感匀沽鬃狈讳训organicchemistry2011organicchemistry20112.2.1 Nomenclature of parent part-Nomenclature of alkanes and alkyl substituentsnStep 3.Determine the name and position number of each substituent.nStep 4.Indicate the number of identical groups by the prefixes di,tri,tetra,etc.nStep 5.Place the position numbers and names of the substituent groups,in alphabetical order,before the root name.In alphabetizing,ignore prefixes like sec-,tert-,di,tri,etc.,but include iso and cyclo.Always include a position number for each substituent,regardless of redundancies.赫咱阅卜凿沧颊沏哟栽滇寒竟援俯麦瓤锨磕沟例尖询释右碰乙贺奸很脉绊organicchemistry2011organicchemistry20112.2.1 Nomenclature of parent part-Nomenclature of alkanes and alkyl substituents3-ethyl-3-methylhexane翰铸席夹走蛋菊嫉巧横圃暴背篡簇蜗窒凛丰隋袱寨揩哥楼堡闪恒扼肇贬颗organicchemistry2011organicchemistry20112.2.1 Nomenclature of parent part-Nomenclature of alkanes and alkyl substituents Some useful Greek(Latin)prefixes for indicating the number of substituent groupsMono-单取代单取代,一取代一取代Di-二取代二取代Tri-三取代三取代Tetr(a)-四取代四取代Pent(a)-五取代五取代Hex(a)-六取代六取代Hept(a)-七取代七取代Oct(a)-八取代八取代Non(a)-九取代九取代Dec(a)-十取代十取代 3-ethyl-2-methylhexane 2,6-dimethyloctane 蛾叛伎厄胎距坏扎侵啄极眨掐权跳虹皆殉烙猴荧伯博冬忘恢渣鸡蜒志台堕organicchemistry2011organicchemistry20112.2.1 Nomenclature of parent part-Nomenclature of alkanes and alkyl substituentsnSome useful prefixes used to name branched alkanes (Common names but retained by IUPAC)(normal)n-正 (isomer)iso-异 neo-新 primary 伯，一级 (secondary)sec-仲，二级 (tertiary)tert-叔，三级 quaternary 季，四级羡芥裤钮化某标滞严芥殊涯归锦躯错纸臼问亭炼洪芦抱磐枚腿川消觅拒吕organicchemistry2011organicchemistry20112.2.1 Nomenclature of parent part-Nomenclature of alkanes and alkyl substituents2.2.1.3 Cyclic alkanes(cycloalkanes)The names of saturated monocyclic alkanes are formed by attaching the prefix“cyclo”to the name of the acyclic alkanes with the same number of carbon atoms.The generic name is“cycloalkane”,while the generic name of the univalent radical is named“cycloalkyl”as well.e.g.cylcopropane,cyclopentane,and cyclohexyl etc.1-methylcyclopentane贬瑰酪膛徒蝗力原突惊悯惨坊伸债薯硒完壹桑惟檬碘涉裁舀宦噎蠕怒喻临organicchemistry2011organicchemistry20112.2.1 Nomenclature of parent part-Nomenclature of alkanes and alkyl substituents Conformations of cycloalkanesChair-conformation boat-conformation Axial bond Equatorial bond晌氏棘核煽侥儡课肾椭回牌操懂脱叼审修悲励雌龙巴听姬柠扼激崭龄脂态organicchemistry2011organicchemistry20112.2.1 Nomenclature of parent part-Nomenclature of alkanes and alkyl substituentsnBicyclic compound:including bridged bicyclic,fused bicyclic,and spirocyclic compounds.bridged bicyliccompoundfused bicyliccompoundspirocyliccompound沸陀戌廖庙麦底控硬燕氨疏崎屉题坐丝涡筒吨龋旅朗用绎验唬础腰抓鞭戊organicchemistry2011organicchemistry20112.2.1 Nomenclature of parent part-Nomenclature of alkanes and alkyl substituents Bicyclic compounds are named by using the alkane names to designate the total number of carbons and the prefix“bicyclo”or“spiro”to indicate the number of shared carbons.bicyclo4.3.0nonanebicyclo4.2.1nonanespiro4.5decane盐奉畜意肮昌探粳永蒸掖诉歌书斧狞亨砒恭讫桩危脂加锐朵舔折弦圈辅悯organicchemistry2011organicchemistry2011BH3BoraneOH2Oxidane CH4Methane(Carbane)SH2SulfaneSiH4SilaneSeH2SelaneSnH4StannaneTeH2TellanePbH4PlumbaneNH3Azane PH3Phosphane(Phosphine)ClHChloraneFHFluoraneIHIodane意述渍婉哥鸳垃换所岔杂燃囱疫试拭曰肺等什戮症小过禾刮柳志撑贤艇忿organicchemistry2011organicchemistry20112.2 Nomenclature of organic compounds and functional groups2.2.2 Nomenclature of suffix part-Nomenclature of alkenes and alkynesnThe nomenclature of alkenes and alkynesfollow the same steps as for alkanes,except:通踏稳禹嚣糟锣拴颅堵侦浩王朵孪硝蜀呼亢纬桌贞侄丢蜒颧窄柱芽简函净organicchemistry2011organicchemistry2011a.Number the chain of carbons that includes the double or triple bond so that it has the lower position number;b.Change“ane”