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
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