有机化学

章节摘录

插图：Atomic orbitals are grouped into different“shells”at difierent distances from the nucleus．Each shell is identified by a principal quantum number n,with n=1 for the lowest．energy shell closest to the nucleus．As n increases，the shells are farther from the nucleus，higher in energy，and can hold more electrons．Most of the common elements in organic compounds are found in the first two rows of the periodic table，indicating that their electrons are found in the first two electron shells．The first shell（n=1）can hold two electrons．and the second shell（n=2）can hold eight．The first electron shell contains just the l s orbital．All s orbitals are spherically symmetrical，meaning that they are nondirectional．The electron density iS only a function of the distance from the nucleus．The electron density of the l s orbital is graphed in Figure 1-2．Notice how the electron density is highest at the nucleus and falls off exponentially with increasing distance from the nucleus．The second electron shell consists of the 2s and 2p orbitals．The 2s orbital iS spherically symmetrical like the ls orbital，but its electron density is not a simple exponential function．The 2s orbital has a smaller amount of electron density close to the nucleus．  Most of the electron density is farther away，beyond a region of zero electron density called a node．Because most of the 2s electron density is farther from the nucleus than that of the ls，the 2s orbital is higher in energy． Figure 1-3 shows a graph ofthe 2s orbital．

前言

为了推动全国高校的双语教学工作，教育部、财政部在《关于实施高等学校本科教学质量与教学改革工程的意见》（教高[2007]1号）中强调教学质量工程要重视双语教学。在《关于启动2007年度双语教学示范课程建设项目的通知》中，提出要在2007年至2010年建设500门国家双语教学示范课程，并且在2007年正式启动高等学校双语教学示范课程建设项目，审定了全国首批百门双语教学示范课程建设项目。这为规范全国高等学校双语教学，提高双语教学水平提供了很好的契机。大连理工大学“有机化学及实验双语教学示范课程建设”项目是教育部首批百门双语教学示范课程建设项目之一。有机化学双语教学课程建设亟待进行的工作之一就是出版对国内教师和学生切实适用的有机化学双语教材。有机化学双语教学十余年的实践表明，改编英文原版有机化学教材是建设有机化学双语教学教材的有效途径，既可保持英文版教材的“原汁原味”，亦能适合中国国情。在教育部项目的支持下，我们将L G．Wade编著的Organic Chemistry（第六版）改编为有机化学双语教材，适合普通高等学校化学、化工专业70～100学时的有机化学双语教学课程使用。改编的有机化学双语教材具有以下特点：1．对英文原版教材只做章节顺序的调整和内容的删减，未增加新的英文内容，目的是使改编的双语教材保持英文版教材的“原汁原味”。2．本书突出双语教材特色，对部分有机化学专业词汇、术语及化合物名称给出中文注释，书后增加专业词汇中英文对照表（Vocabulary），方便学生自学和查阅。3．每章末增加中文概要（Summary in Chinese），有利于学生对教学重点的理解和掌握。4．为了使改编教材的章节编排遵循有机化学双语教学的特点，将有机化合物的命名部分从各章中抽出来，合并为新的一章，作为第3章“Brief Introduction and Nomenclature of Organic Compounds”。在双语教学中，有机化合物命名部分放在较前面的章节集中讲授，有利于学生自学和课堂理解教师英文授课内容。5．适当调整章节顺序，例如，将原版教材中第15章“Conjugated Systems，Orbital Symmetry，and Uhraviolet Spectroscopy”调换为第11章的内容，紧随烯烃（第9章）和炔烃（第10章）的章节之后，并将第15章中紫外光谱的内容抽出来与红外光谱合并作为第12章；将质谱与核磁共振谱合并作为第13章。调整后的双语教材的内容相对规整，符合国内的教学特点，方便教师双语教学使用。

内容概要

作者：(美国)韦德

书籍目录

chapter 1 introduction and renew

1-1 the origins of organic chemistry

1-2 principles of atomic structure

1-3 bond formation：the octet rule

1-4 lewis structures

1-5 multiple bonding

1-6 electronegativity and bond polarity

1-7 formal charges

1-8 ionic structures

1-9 resonance

1-10 structural formulas

1-11 molecular formulas and empirical formulas

1-12 arrhenius acids and bases

1-13 brensted．lowry acids and bases

1-14 lewis acids and bases

summary in chinese

study problems

chapter 2 structure and properties of organic molecules

2-1 wave properties of electrons in qrbitals

.2-2 molecular orbitals

2-3 pi bonding

2-4 hybridization and molecular shapes

2-5 drawing three-dimensional molecules

2-6 general rules of hybridization and geometry

2-7 bond rotation

2-8 isomerism

2-9 polarity of bonds and molecules

2-10 intermolecular forces

2-11 polarity effects on solubilities

summary in chinese

study problems

chapter 3 brief introduction and nomenclature of organic compounds

3-1 hydrocarbons

3-2 organic compounds containing oxygen

3-3 organic compounds containing nitrogen

3-4 nomenclature of a1kanes

3-5 nomenclature of alkenes

3-6 nomenclature of alkynes

3-7 nomenclature of cycloalkanes

3-8 nomenclature of benzene derivatives

3-9 nomenclature of alkyl halides

3-10 nomenclature of alcohols and thiols

3-11 nomenclature of ethers and sulfides

3-12 nomenclature of amines

3-13 nomenclature of ketones and aldehydes

3-14 nomenclature of carboxylic acids

3-15 structure and nomenclature of acid derivatives

summary in chinese

study problems

chapter 4 structure and stereochemistry of alkanes

4-1 physical properties of alkanes

4-2 uses and sources of alkanes

4-3 reactions of alkanes

4-4 structure and conformations of alkanes

4-5 cycloalkanes

4-6 cyclohexane conformations

4-7 conformations of monosubstituted cyclohexanes

4-8 conformations of disubstituted cyclohexanes

summary in chinese

study problems

chapter 5 the study of chemical reactions

5-1 introduction

5-2 chlorination of methane

5-3 the free-radical chain reaction

5-4 equilibrium constants and free energy

5-5 enthalpy and entropy

5-6 bond-dissociation enthalpies

5-7 enthalpy changes in chlorination

5-8 kinetics and the rate equation

5-9 activation energy and the temperature dependence of rates

5-10 transition states

5-11 rates of multistep reactions

5-12 temperature dependence of halogenation

5-13 selectivity in halogenation

5-14 the hammond postulate

5-15 radical inhibitors

5-16 reactive intermediates

summary tin chinese

study problems

chapter 6 stereochemistry

6-1 introduction

6-2 chirality

6-3（r）and（s）nomenclature of asymmetric carbon atoms

6-4 optical activity

6-5 racemic mixtures

6-6 enantiomeric excess and optical purity

6-7 chirality of conformationally mobile systems

6-8 chiral compounds without asymmetric atoms

6-9 fischer projections

6-10 diastereomers

6-11 stereochemistry of molecules with two or more asymmetric carbons

6-12 meso compounds

6-1 3 absolute and relative configuration

6-14 physical properties of diastereomers

6-1 5 resolution of enantiomers

summary in chinese

study problems

chapter 7 alkyl halides：nucleophilic substitution and elimination

7-1 introduction

7-2 common uses of alkyl halides

7-3 structure of alkyl halides

7-4 physical properties of alkyl halides

1-5 preparation of alkyl halides

7-6 reactions of alkyl halides：substitution and elimination

7-7 second-order nucleophilic substitution：the sn2 reaction

7-8 generality of the sn2 reaction

7-9 factors affecting sn2 reactions： strength of the nucleophile

7-10 reactivity of the substrate in sn2 reactions

7-11 stereochemistry of the sn2 reaction

7-12 first．order nucleophilic substitution：the snl reaction

7-13 stereochemistry of the snl reaction

7-14 rearrangements in sn 1 reactions

7-15 comparison of snl and sn2 reactions

7-16 first．order elimination：the e1 reaction

7-17 positional orientation of elimination：zaitsev's rule

7-18 second-order elimination：the e2 reaction

7-19 stereochemistry of the e2 reaction

7-20 comparison of e1 and e2 elimination mechanisms

summary in chinese

study problems

chapter 8 structure and synthesis of alkenes

8-1 introduction

8-2 the 0rbital description of the alkene double bond

8-3 elements of unsaturation

8-4 commercial importance of alkenes

8-5 stability of alkenes

8-6 physical properties of alkenes

8-7 alkene synthesis by elimination of alkyl halides

8-8 alkene synthesis by dehydration of alcohols

8-9 alkene synthesis by high-temperature industrial methods

summary in chinese

study problems

chapter 9 reactions of aikenes

9-1 reactivity of the carbon-carbon double bond

9-2 electrophilic addition to alkenes

9-3 addition of hydrogen halides to alkenes

9-4 addition of water：hydration of alkenes

9-5 hydration by oxymercuration-demercuration

9-6 alkoxymercuration-demercuration

9-7 hydroboration of alkenes

9-8 addition of halogens to alkenes

9-9 formation of halohydrins

9-10 catalytic hydrogenation of alkenes

9-11 addition of carbenes to alkenes

9-12 epoxidation of alkenes

9-13 acid-catalyzed opening of epoxides

9-14 syn hydroxylation of alkenes

9-15 oxidative cleavage of alkenes

9-16 polymerization of alkenes

summary in chinese

study problems

chapter 10 alkynes

10-1 introduction

10-2 physical properties of alkynes

10-3 commercial importance of alkynes

10-4 electronic structure of alkynes

10-5 acidity of alkynes：formation of acetylide ions

10-6 synthesis of alkynes from acetylides

10-7 synthesis of alkynes by elimination reactions

10-8 addition reactions of alkynes

10-9 oxidation of alkynes

summary in chinese

study problems

chapter 11 conjugated systems and orbital symmetry

11-1 introduction

11-2 stabilities of dienes

11-3 molecular orbitals of a conjugated system

11-4 allylic cations

11-5 1，2-and 1，4-addition to conjugated dienes

11-6 kinetic versus thermodynamic control in the addition of hbr to 1．3-butadiene

11-7 allylic radicals

11-8 molecular orbitals of the allylic system

11-9 electronic configurations of the allyl radical，cation，and anion

11-10 sn2 displacement reactions of allylic halides and tosylates

11-11 the diels-alder reaction

1-12 the diels-alder as an example of a pericyclic reaction

summary in chinese

study problems

chapter 12 infrared and ultraviolet spectros-copy

12-1 introduction

12-2 the electromagnetic spectrum

12-3 the infrared region

12-4 molecular vibrations

12-5 ir-active and ir．inactive vibrations

12-6 measurement of the ir spectrum

12-7 infrared spectroscopy of hydrocarbons

12-8 characteristic absorptions of alcohols and amines

12-9 characteristic absorptions of carbonyl compounds

12-10 characteristic absorptions of c-n bonds

12-11 simplified summary of ir stretching frequencies

12-12 reading and interpreting ir spectra

12-13 uhraviolet absorption spectroscopy

12-1 4 ultraviolet light and electronic transition

12-15 measurement of the uv-visible spectrum

12-16 interpreting uv-visible spectra

summary in chinese

study problems

chapter 13 nuclear magnetic resonance spectroscopy and mass spectrometry

13-1 introduction to nuclear magnetic resonance spectroscopy

13-2 theory of nuclear magnetic resonance

13-3 magnetic shielding by electrons

13-4 the nmr spectrometer

13-5 the chemical shift

13-6 the number of signals

13-7 areas of the peaks

13-8 spin-spin splitting

13-9 carbon-13 nmr spectroscopy

13-10 interpreting carbon nmr spectra

13-11 introduction to mass spectrometry

13-12 determination of the moleeular formula by mass spectrometry

13-13 fragmentation patterns in mass spectrometry

summary in chinese

study problems

chapter 14 structure and synthesis of alcohols

14-1 introduction

14-2 structure and classification of alcohols

14-3 physical properties of alcohols

14-4 commercially important alcohols

14-5 acidity of alcohols and phenols

14-6 organometallic reagents for alcohol synthesis

14-7 synthesis of alcohols：addition of organometallic reagents to carbonyl compounds

14-8 side reactions of organometallic reagents：reduction of alkyl halides

14-9 synthesis of 1°and 2°alcohols： reduction of the carbonyl group

14-10 thiols（mercaptans）

summary in chinese

study problems

chapter 15 reactions of alcohols

15-1 oxidation states of alcohols and related functional groups

15-2 oxidation of alcohols

15-3 additional methods for oxidizing alcohols

15-4 alcohols as nucleophiles and electro-philes：formation of tosylates

15-5 reduction of alcohols

15-6 reactions of alcohols with hydrohalic acids

15-7 reactions of alcohols with phosphorus halides

15-8 reactions of alcohols with thionyl chloride

15-9 dehydration reactions of alcohols

15-10 unique reactions of diols

15-11 esterification of alcohols

15-12 reactions of alkoxides

summary in chinese

study problems

chapter 16 ethers, epoxdes,and sulfdes

chapter 17 aromatic compiunds

chapter 18 eeactions of aromatic compounds

chapter 19 ketones and aldehydes

chapter 20 amines

chapter 21 carboxylic acids

chapter 22 carboxylic acid derivatives

chapter 23 condensations and alpha substitutions of carbonyl compounds

chapter 24 carbohydrates and nucleic acids

chapter 25 amino acids, peptides, and proteins

chapter 26 lipids

answers to selected problems

index

vocabulary

编辑推荐

《有机化学》(第6版)可作为化学、化工专业的有机化学双语教材，亦可作为其他相关专业的教学参考书，可使学生在学习有机化学基础知识的同时提高专业英语水平。

作者简介

《有机化学》(第6版)是L．G．Wade编写的Organic Chemistry(Sixth Edition)的改编版，是根据教育部关于高等学校本科教学质量工程要重视双语教学的文件精神，选择国外优秀英文原版有机化学教材，结合双语教学的实践经验改编而成的双语教材。全书共26章，涵盖内容与国内高等学校化学、化工类有机化学教材基本一致，包括有机化学概论、有机化合物命名、立体化学、结构表征、烃及卤代烃、含氧化合物、含氮化合物、天然有机化合物等内容。每章后有中文概要，书后附有索引和专业词汇中英文对照表。

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