有机化学英文教案.doc

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1、有机化学课程讲义（适用于化学教育、应用化学、化学工程专业）温梅姣 编写教 化学与资源环境学院二一年七月ContentsChapter 1 Introduction11.1 The development of Organic Chemistry as a science11.2 The importance of Organic Chemistry11.3 How to study Organic Chemistry21.4 Covalent Bonding & Shapes of Molecules31.5 Polar and Nonpolar Molecules51.6 Resonance

2、61.7 Molecular Orbital Theory81.8 Hybrid Orbitals9Chapter 2 Alkane and cycloalkane132.1 Alkane132.2 Nomenclature of Cycloalkanes172.3 Conformations182.4 Oxidation of Alkanes242.5 Chlorination and Bromination of Alkanes25Chapter 3 Alkene29 3.1 Structure and nomenclature29 3.2 Reaction Mechanism323.3

3、Reaction of Alkene35Chapter 4 Alkyne and Diene47 4.1 Structure and Nomenclature of Alkynes474.2 Physical Properties of Unsaturated Hydrocarbons484.3 addition reaction of alkyne484.5 An Introduction to Multistep Synthesis544.6 Preparation Of Alkyne544.7 Properties and nomenclature of Dienes554.8 Reac

4、tion of dienes57Chapeter 5 Stereochemistry605.1 Isomers605.2 Isomers with One Asymmetric Carbon615.3 Isomers with More than One Asymmetric Carbon645.4 resolution of a racemic mixture655.5 Stereochemistry of Reactions: Regioselective, Stereoselective, and Stereospecific Reactions66Chapter 6 Aromatic

5、hydrocarbons706.1 The structure of benzene706.2 Substitued derivatives of benzene and their nonmenclature726.3 polycyclic aromatic hydrocarbons746.4 Criteria for Aromaticity746.5 Electrophilic aromatic substitution reaction756.6 Reactions of Substituted Benzenes806.7 Reactions of Substituents on Ben

6、zene86Chapter 7 Alkyl Halides89 7.1 Nomenclature of Alkyl Halides897. 2 Classes of Alkyl Halides897. 3 Bonding in Alkyl Halides897.4 Physical properties of alkyl halides907.5 Substitution Reactions of Alkyl Halides917.6 Elimination Reactions of Alkyl Halides100Chapter 8 Alcohols and ethers108 8.1 No

7、menclature of Alcohols1088.2 Bonding in Alkyl Halides1088.3 Physical properties of alcohols1098.4 Acidity and Basicity of alcohols1108.5 Substitution Reactions of Alcohols1118.6 Elimination Reactions of Alcohols s1148.7 Substitution Reactions of Ethers1168.8 Reactions of Epoxides117Chapter 9 Infrare

8、d Spectroscopy and NMR Spectroscopy1209.1 Infrared Spectroscopy1209.2 Nuclear Magnetic Resonance127Chapter 10 Aldehydes and Ketones13910.1 Nomenclature13910.2 Structure and bonding: The carbonyl group14010.3 Physical Properties14110.4 Sources of Aldehydes and Ketones14110.5 Nucleophilic Addition1421

9、0.6 Oxidation of aldehydes14710.7 Enols and Enolates150Chapter 11 Carboxylic Acids15711.1 Nomenclature of Carboxylic Acids15711.2 Structure and bonding15711.3 Physical properties s15811.4 Acidity of Carboxylic Acids15811.5 Salts of Carboxylic acids15911.6 Substituents and Acid Strength16011.7 Ioniza

10、tion of Substituted Benzoic acids16111.8 Souces of Carboxylic Acids16211.9 Reactions of Carboxylic Acids162Chapter 12 Carboxylic Acid Derivatives16612.1 Nomenclature of all carboxylic acid derivatives16612.2 The structures of carboxylic acid derivatives16712.3 Nucleophilic Substitution in Acyl Chlor

11、ides16812.4 Nucleophilic Substitution in Carboxylic acid anhydrides16912.5 Nucleophilic Substitution in Esters17012.6 Reaction of Amides17212.7 Nitriles17412.8 Ester enolates175Chapter 13 Amines18213.1 Amines Nomenclature18213.2 Structure and Bonding18313.3 Physical Properties18413.4 Basicity of Ami

12、nes18513.5 Tetraalkyl Ammonium Salts as phase-transfer catalyst18513.6 Preparation of Amines18613.7 Reactions of Amines188Chapter 1 Introduction1.1 The development of Organic Chemistry as a science The history of Organic Chemistry：(1) The Swedish chemist Torbern Bergman was the first person to expre

13、ss this difference between Organic and Inorganic substance in 1770. (2) In 1807, Jns Jakob Berzelius gave names to the two kinds of materials. Compounds derived from living organisms were believed to contain an unmeasurable vital forcethe essence of life. These he called inorganic. Compounds derived

14、 from minerals-those lacking that vital force-were “inorganic”.(3) In 1816, Michel Chevreul found that soap, prepared by the reaction of alkali with animal fat, could be separated into several pure organic compounds, which he termed fatty acid. For the first time, one organic substance (fat) was con

15、verted into others (fatty acids plus glycerin) without the intervention of an outside vital force.（4）In 1828 when Friedrich Whler produced urea-a compound known to be excreted by mammals -by heating ammonium cyanate, an inorganic mineral. For the first time, an “organic” compound had been obtained f

16、rom something other than a living organism and certainly without the aid of any kind of vital force. Clearly，chemists needed a new definition for “organic compounds.”1.2 The importance of Organic Chemistry1.2.1 What is Organic Chemistry?Organic chemistry is the study of carbon compounds. Thus Organi

17、c compounds are now defined as compounds that contain carbon.What makes carbon so special? Why are there so many carbon-containing compounds? The answer lies in carbons position in the periodic table. Carbon is in the center of the second row of elements. The atoms to the left of carbon have a tende

18、ncy to give up electrons, whereas the atoms to the right have a tendency to accept electrons.Because carbon is in the middle, it neither readily gives up nor readily accepts electrons. Instead, it shares electrons. Carbon can share electrons with several different kinds of atoms, and it can also sha

19、re electrons with other carbon atoms. Consequently, carbon is able to form millions of stable compounds with a wide range of chemical properties simply by sharing electrons.1.2.2 The distribution of Organic compounds:(1)All of the molecules that make life possibleproteins, enzymes, vitamins, lipids,

20、 carbohydrates, and nucleic acidscontain carbon, so the chemical reactions that take place in living systems, including our own bodies, are organic reactions.(2)Most of the compounds found in naturethose we rely on for food, medicine, clothing (cotton, wool, silk), and energy (natural gas, petroleum

21、)are organic as well.(3)Important organic compounds are not, however, limited to the ones we find in nature. Chemists have learned to synthesize millions of organic compounds never found in nature, including synthetic fabrics, plastics, synthetic rubber, medicines, and even things like photographic

22、film and Super glue. Many of these synthetic compounds prevent shortages of naturally occurring products.1.3 How to study Organic ChemistryOrganic chemistry is a study of the relationship between the structure of molecules and their reaction.If you expect to learn organic chemistry well, you must dr

23、aw and redraw the structures of compounds and write out equations as you are studying.To study effectively, you should read the assignments before attending lectures. Spend most of you study time working out the problems. Work all of the problems, no matter how simple they seem, in writing and in fu

24、ll detail.In addition, the study guide contains concept maps, which are summaries of important ideas presented in outline form.1.4 Covalent Bonding & Shapes of Molecules1.4.1 Schematic View of an AtomA small dense nucleus, diameter 10-14 10-15m, which contains positively charged protons and most of

25、the mass of the atom.An extranuclear space, diameter 10-10 m, which contains negatively charged electrons.1.4.2 Electron Configuration of AtomsElectrons are confined to regions of space called principle energy levels (shells) . Each shell can hold 2n2 electrons (n = 1,2,3,4.) Electron Configuration

26、of AtomsShells are divided into subshells called orbitals, which are designated by the letters s, p, d, f,.s (one per shell) p (set of three per shell 2 and higher) d (set of five per shell 3 and higher) .Aufbau Principle: Orbitals fill in order of increasing energy from lowest energy to highest ene

27、rgy.Pauli Exclusion Principle: Only two electrons can occupy an orbital and their spins must be paired.Hunds Rule: When orbitals of equal energy are available but there are not enough electrons to fill all of them, one electron is added to each orbital before a second electron is added to any one of

28、 them.1.4.3 Lewis Dot StructuresGilbert N. LewisValence shell: the outermost occupied electron shell of an atomValence electrons: electrons in the valence shell of an atom; these electrons are used to form chemical bonds and in chemical reactionsLewis dot structure: the symbol of an element represen

29、ts the nucleus and all inner shell electronsdots represent valence electronsLewis Dot Structures for Elements 1-181.4.4 Lewis Model of BondingAtoms bond together so that each atom acquires an electron configuration the same as that of the noble gas nearest it in atomic numberan atom that gains elect

30、rons becomes an anionan atom that loses electrons becomes a cationthe attraction of anions and cations leads to the formation of ionic solidsan atom may share electrons with one or more atoms to complete its valence shell; a chemical bond formed by sharing electrons is called a covalent bondbonds ma

31、y be partially ionic or partially covalent; these bonds are called polar covalent bonds1.4.5 Formation of IonsA rough guideline: ions will form if the difference in electronegativity between interacting atoms is 1.9 or greaterexample: sodium (EN 0.9) and fluorine (EN 4.0)we use a single-headed (barb

32、ed) curved arrow to show the transfer of one electron from Na to Fin forming Na+F-, the single 3s electron from Na is transferred to the partially filled valence shell of F1.5 Polar and Nonpolar MoleculesTo determine if a molecule is polar, we need to determine if the molecule has polar bondsthe arr

33、angement of these bonds in spaceMolecular dipole moment (m): the vector sum of the individual bond dipole moments in a moleculereported in debyes (D)these molecules have polar bonds, but each has a zero dipole momentthese molecules have polar bonds and are polar moleculesformaldehyde has polar bonds

34、 and is a polar molecule1.6 ResonanceFor many molecules and ions, no single Lewis structure provides a truly accurate representationLinus Pauling - 1930smany molecules and ions are best described by writing two or more Lewis structuresindividual Lewis structures are called contributing structurescon

35、nect individual contributing structures by double-headed (resonance) arrowsthe molecule or ion is a hybrid of the various contributing structuresExamples: equivalent contributing structuresCurved arrow: a symbol used to show the redistribution of valence electronsIn using curved arrows, there are on

36、ly two allowed types of electron redistribution:from a bond to an adjacent atomfrom an atom to an adjacent bondElectron pushing is a survival skill in organic chemistrylearn it well!All contributing structures must1. have the same number of valence electrons2. obey the rules of covalent bondingno mo

37、re than 2 electrons in the valence shell of H no more than 8 electrons in the valence shell of a 2nd period element3rd period elements, such as P and S, may have up to 12 electrons in their valence shells3. differ only in distribution of valence electrons; the position of all nuclei must be the same

38、4. have the same number of paired and unpaired electronsfilled valence shellsstructures in which all atoms have filled valence shells contribute more than those with one or more unfilled valence shellsstructures that carry a negative charge on the more electronegative atom contribute more than those

39、 with the negative charge on the less electronegative atom1.7 Molecular Orbital TheorySigma 1s bonding and antibonding MOsMO energy diagram for H2: (a) ground state and (b) lowest excited statepi bonding and antibonding MOs1.8 Hybrid OrbitalsHybridization of orbitals (L. Pauling)the combination of t

40、wo or more atomic orbitals forms a new set of atomic orbitals, called hybrid orbitalsWe deal with three types of hybrid orbitalssp3 (one s orbital + three p orbitals)sp2 (one s orbital + two p orbitals)sp (one s orbital + one p orbital)Overlap of hybrid orbitals can form two types of bonds depending

41、 on the geometry of overlaps bonds are formed by “direct” overlapp bonds are formed by “parallel” overlapeach sp3 hybrid orbital has two lobes of unequal sizethe sign of the wave function is positive in one lobe, negative in the other, and zero at the nucleusthe four sp3 hybrid orbitals are directed toward the corners of a regular tetrahedron at angles of 109.5orbital overlap pictures of methane, ammonia, and watersp2 Hybrid Orbitalsthe axes of the three sp2 hybrid orbitals lie in a plane and are directed toward the corners of an equilateral trianglethe unhybridized 2p orbital lies perpendic