Chemical Bonding |
| Sections 1.1-1.6: html / PowerPoint / PDF 1.1 ATOMS, ELECTRONS, AND ORBITALS 1.2 IONIC BONDS 1.3 COVALENT BONDS 1.4 DOUBLE BONDS AND TRIPLE BONDS 1.5 POLAR COVALENT BONDS AND ELECTRONEGATIVITY 1.6 FORMAL CHARGE Sections 1.7-1.9: html / PowerPoint / PDF 1.7 STRUCTURAL FORMULAS OF ORGANIC MOLECULES 1.8 CONSTITUTIONAL ISOMERS 1.9 RESONANCE Sections 1.10-1.11: html / PowerPoint / PDF 1.10 THE SHAPES OF SOME SIMPLE MOLECULES 1.11 MOLECULAR DIPOLE MOMENTS Sections 1.12-1.14: html / PowerPoint / PDF 1.12 ELECTRON WAVES AND CHEMICAL BONDS 1.13 BONDING IN H2: THE VALENCE BOND MODEL 1.14 BONDING IN H2: THE MOLECULAR ORBITAL MODEL Sections 1.15-1.19: html / PowerPoint / PDF 1.15 BONDING IN METHANE AND ORBITAL HYBRIDIZATION 1.16 sp3 HYBRIDIZATION AND BONDING IN ETHANE 1.17 sp2 HYBRIDIZATION AND BONDING IN ETHYLENE 1.18 sp HYBRIDIZATION AND BONDING IN ACETYLENE 1.19 WHICH THEORY OF CHEMICAL BONDING IS BEST? |
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Alkanes |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 2.1-2.7: html / PowerPoint / PDF 2.1 CLASSES OF HYDROCARBONS 2.2 REACTIVE SITES IN HYDROCARBONS 2.3 THE KEY FUNCTIONAL GROUPS 2.4 INTRODUCTION TO ALKANES: METHANE, ETHANE, AND PROPANE 2.5 ISOMERIC ALKANES: THE BUTANES 2.6 HIGHER n-ALKANES 2.7 THE C5H12 ISOMERS Sections 2.8-2.12: html / PowerPoint / PDF 2.8 IUPAC NOMENCLATURE OF UNBRANCHED ALKANES 2.9 APPLYING THE IUPAC RULES: THE NAMES OF THE C6H14 ISOMERS. 2.10 ALKYL GROUPS 2.11 IUPAC NAMES OF HIGHLY BRANCHED ALKANES 2.12 CYCLOALKANE NOMENCLATURE Sections 2.13-2.16: html / PowerPoint / PDF 2.13 SOURCES OF ALKANES AND CYCLOALKANES 2.14 PHYSICAL PROPERTIES OF ALKANES AND CYCLOALKANES 2.15 CHEMICAL PROPERTIES. COMBUSTION OF ALKANES 2.16 OXIDATION-REDUCTION IN ORGANIC CHEMISTRY |
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Conformations of Alkanes and Cycloalkanes |
| Sections 3.1-3.3: html / PowerPoint / PDF 3.1 CONFORMATIONAL ANALYSIS OF ETHANE 3.2 CONFORMATIONAL ANALYSIS OF BUTANE 3.3 CONFORMATIONS OF HIGHER ALKANES Sections 3.4-3.8: html / PowerPoint / PDF 3.4 THE SHAPES OF CYCLOALKANES: PLANAR OR NONPLANAR? 3.5 CONFORMATIONS OF CYCLOHEXANE 3.6 AXIAL AND EQUATORIAL BONDS IN CYCLOHEXANE 3.7 CONFORMATIONAL INVERSION (RING FLIPPING) IN CYCLOHEXANE 3.8 CONFORMATIONAL ANALYSIS OF MONOSUBSTITUTED CYCLOHEXANES Sections 3.9-3.11: html / PowerPoint / PDF 3.9 SMALL RINGS: CYCLOPROPANE AND CYCLOBUTANE 3.10 CYCLOPENTANE 3.11 MEDIUM AND LARGE RINGS Sections 3.12-3.13: html / PowerPoint / PDF 3.12 DISUBSTITUTED CYCLOALKANES. STEREOISOMERS 3.13 CONFORMATIONAL ANALYSIS OF DISUBSTITUTED CYCLOHEXANES Sections 3.14-3.15: html / PowerPoint / PDF 3.14 POLYCYCLIC RING SYSTEMS 3.15 HETEROCYCLIC COMPOUNDS |
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Alcohols and Alkyl Halides |
| Sections 4.1-4.3: html / PowerPoint / PDF 4.1 IUPAC NOMENCLATURE OF ALKYL HALIDES 4.2 IUPAC NOMENCLATURE OF ALCOHOLS 4.3 CLASSES OF ALCOHOLS AND ALKYL HALIDES Sections 4.4-4.5: html / PowerPoint / PDF 4.4 BONDING IN ALCOHOLS AND ALKYL HALIDES 4.5 PHYSICAL PROPERTIES OF ALCOHOLS AND ALKYL HALIDES. INTERMOLECULAR FORCES Sections 4.6-4.7: html / PowerPoint / PDF 4.6 ACIDS AND BASES: GENERAL PRINCIPLES 4.7 ACID-BASE REACTIONS: A MECHANISM FOR PROTON TRANSFER Sections 4.8-4.14: html / PowerPoint / PDF 4.8 PREPARATION OF ALKYL HALIDES FROM ALCOHOLS AND HYDROGEN HALIDES 4.9 MECHANISM OF THE REACTION OF ALCOHOLS WITH HYDROGEN HALIDES 4.10 STRUCTURE, BONDING, AND STABILITY OF CARBOCATIONS 4.11 POTENTIAL ENERGY DIAGRAMS FOR MULTISTEP REACTIONS. THE SN1 MECHANISM 4.12 EFFECT OF ALCOHOL STRUCTURE ON REACTION RATE 4.13 REACTION OF PRIMARY ALCOHOLS WITH HYDROGEN HALIDES. THE SN2 MECHANISM 4.14 OTHER METHODS FOR CONVERTING ALCOHOLS TO ALKYL HALIDES Sections 4.15-4.19: html / PowerPoint / PDF 4.15 HALOGENATION OF ALKANES 4.16 CHLORINATION OF METHANE 4.17 STRUCTURE AND STABILITY OF FREE RADICALS 4.18 MECHANISM OF METHANE CHLORINATION 4.19 HALOGENATION OF HIGHER ALKANES |
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Structure and preparation of Alkenes. Elimination Reactions |
| Sections 5.1-5.4: html / PowerPoint / PDF 5.1 ALKENE NOMENCLATURE 5.2 STRUCTURE AND BONDING IN ALKENES 5.3 ISOMERISM IN ALKENES 5.4 NAMING STEREOISOMERIC ALKENES BY THE E-Z NOTATIONAL SYSTEM Sections 5.5-5.7: html / PowerPoint / PDF 5.5 PHYSICAL PROPERTIES OF ALKENES 5.6 RELATIVE STABILITIES OF ALKENES 5.7 CYCLOALKENES Sections 5.8-5.13: html / PowerPoint / PDF 5.8 PREPARATION OF ALKENES: ELIMINATION REACTIONS 5.9 DEHYDRATION OF ALCOHOLS 5.10 REGIOSELECTIVITY IN ALCOHOL DEHYDRATION: THE ZAITSEV RULE 5.11 STEREOSELECTIVITY IN ALCOHOL DEHYDRATION 5.12 THE MECHANISM OF ACID-CATALYZED DEHYDRATION OF ALCOHOLS 5.13 REARRANGEMENTS IN ALCOHOL DEHYDRATION Sections 5.14-5.17: html / PowerPoint / PDF 5.14 DEHYDROHALOGENATION OF ALKYL HALIDES 5.15 MECHANISM OF THE DEHYDROHALOGENATION OF ALKYL HALIDES: THE E2 MECHANISM 5.16 ANTI ELIMINATION IN E2 REACTIONS: STEREOELECTRONIC EFFECTS 5.17 A DIFFERENT MECHANISM FOR ALKYL HALIDE ELIMINATION: THE E1 MECHANISM |
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Reactions of Alkenes: Addition Reactions |
| Sections 6.1-6.3: html / PowerPoint / PDF 6.1 HYDROGENATION OF ALKENES 6.2 HEATS OF HYDROGENATION 6.3 STEREOCHEMISTRY OF ALKENE HYDROGENATION Sections 6.4-6.7: html / PowerPoint / PDF 6.4 ELECTROPHILIC ADDITION OF HYDROGEN HALIDES TO ALKENES 6.5 REGIOSELECTIVITY OF HYDROGEN HALIDE ADDITION: MARKOVNIKOV'S RULE 6.6 MECHANISTIC BASIS FOR MARKOVNIKOV'S RULE 6.7 CARBOCATION REARRANGEMENTS IN HYDROGEN HALIDE ADDITION TO ALKENES Sections 6.8-6.9: html / PowerPoint / PDF 6.8 FREE-RADICAL ADDITION OF HYDROGEN BROMIDE TO ALKENES 6.9 ADDITION OF SULFURIC ACID TO ALKENES Sections 6.10-6.13: html / PowerPoint / PDF 6.10 ACID-CATALYZED HYDRATION OF ALKENES 6.11 HYDROBORATION-OXIDATION OF ALKENES 6.12 STEREOCHEMISTRY OF HYDROBORATION-OXIDATION 6.13 MECHANISM OF HYDROBORATION-OXIDATION Sections 6.14-6.17: html / PowerPoint / PDF 6.14 ADDITION OF HALOGENS TO ALKENES 6.15 STEREOCHEMISTRY OF HALOGEN ADDITION 6.16 MECHANISM OF HALOGEN ADDITION TO ALKENES: HALONIUM IONS 6.17 CONVERSION OF ALKENES TO VICINAL HALOHYDRINS Sections 6.18-6.19: html / PowerPoint / PDF 6.18 EPOXIDATION OF ALKENES 6.19 OZONOLYSIS OF ALKENES Section 6.20: html / PowerPoint / PDF 6.20 INTRODUCTION TO ORGANIC CHEMICAL SYNTHESIS Sections 6.21: html / PowerPoint / PDF 6.21 REACTIONS OF ALKENES WITH ALKENES: POLYMERIZATION |
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Stereochemistry |
| Sections 7.1-7.3: html / PowerPoint / PDF 7.1 MOLECULAR CHIRALITY: ENANTIOMERS 7.2 THE STEREOGENIC CENTER 7.3 SYMMETRY IN ACHIRAL STRUCTURES Sections 7.4-7.5: html / PowerPoint / PDF 7.4 PROPERTIES OF CHIRAL MOLECULES: OPTICAL ACTIVITY 7.5 ABSOLUTE AND RELATIVE CONFIGURATION Sections 7.6-7.8: html / PowerPoint / PDF 7.6 THE CAHN-INGOLD-PRELOG RS NOTATIONAL SYSTEM 7.7 FISCHER PROJECTIONS 7.8 PHYSICAL PROPERTIES OF ENANTIOMERS Sections 7.9-7.12: html / PowerPoint / PDF 7.9 REACTIONS THAT CREATE A STEREOGENIC CENTER 7.10 CHIRAL MOLECULES WITH TWO STEREOGENIC CENTERS 7.11 ACHIRAL MOLECULES WITH TWO STEREOGENIC CENTERS 7.12 MOLECULES WITH MULTIPLE STEREOGENIC CENTERS Sections 7.13-7.16: html / PowerPoint / PDF 7.13 REACTIONS THAT PRODUCE DIASTEREOMERS 7.14 RESOLUTION OF ENANTIOMERS 7.15 STEREOREGULAR POLYMERS 7.16 STEREOGENIC CENTERS OTHER THAN CARBON |
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Nucleophilic Substitution |
| Sections 8.1-8.2: html / PowerPoint / PDF 8.1 FUNCTIONAL GROUP TRANSFORMATION BY NUCLEOPHILIC SUBSTITUTION 8.2 RELATIVE REACTIVITY OF HALIDE LEAVING GROUPS Sections 8.3-8.6: html / PowerPoint / PDF 8.3 THE SN2 MECHANISM OF NUCLEOPHILIC SUBSTITUTION 8.4 STEREOCHEMISTRY OF SN2 REACTIONS 8.5 HOW SN2 REACTIONS OCCUR 8.6 STERIC EFFECTS IN SN2 REACTIONS Section 8.7: html / PowerPoint / PDF 8.7 NUCLEOPHILES AND NUCLEOPHILICITY Sections 8.8-8.12: html / PowerPoint / PDF 8.8 THE SN1 MECHANISM OF NUCLEOPHILIC SUBSTITUTION 8.9 CARBOCATION STABILITY AND SN1 REACTION RATES 8.10 STEREOCHEMISTRY OF SN1 REACTIONS 8.11 CARBOCATION REARRANGEMENTS IN SN1 REACTIONS 8.12 EFFECT OF SOLVENT ON THE RATE OF NUCLEOPHILIC SUBSTITUTION Section 8.13: html / PowerPoint / PDF 8.13 SUBSTITUTION AND ELIMINATION AS COMPETING REACTIONS Sections 8.14-8.15: html / PowerPoint / PDF 8.14 SULFONATE ESTERS AS SUBSTRATES IN NUCLEOPHILIC SUBSTITUTION 8.15 LOOKING BACK: REACTIONS OF ALCOHOLS WITH HYDROGEN HALIDES |
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Alkynes |
| Sections 9.1-9.4: html / PowerPoint / PDF 9.1 SOURCES OF ALKYNES 9.2 NOMENCLATURE 9.3 PHYSICAL PROPERTIES OF ALKYNES 9.4 STRUCTURE AND BONDING IN ALKYNES: sp HYBRIDIZATION Sections 9.5-9.7: html / PowerPoint / PDF 9.5 ACIDITY OF ACETYLENE AND TERMINAL ALKYNES 9.6 PREPARATION OF ALKYNES BY ALKYLATION OF ACETYLENE AND TERMINAL ALKYNES 9.7 PREPARATION OF ALKYNES BY ELIMINATION REACTIONS Sections 9.8-9.14: html / PowerPoint / PDF 9.8 REACTIONS OF ALKYNES 9.9 HYDROGENATION OF ALKYNES 9.10 METAL-AMMONIA REDUCTION OF ALKYNES 9.11 ADDITION OF HYDROGEN HALIDES TO ALKYNES 9.12 HYDRATION OF ALKYNES 9.13 ADDITION OF HALOGENS TO ALKYNES 9.14 OZONOLYSIS OF ALKYNES |
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Conjugation in Alkadienes and Allylic Systems |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 10.1-10.4: html / PowerPoint / PDF 10.1 THE ALLYL GROUP 10.2 ALLYLIC CARBOCATIONS 10.3 ALLYLIC FREE RADICALS 10.4 ALLYLIC HALOGENATION Sections 10.5-10.8: html / PowerPoint / PDF 10.5 CLASSES OF DIENES 10.6 RELATIVE STABILITIES OF DIENES 10.7 BONDING IN CONJUGATED DIENES 10.8 BONDING IN ALLENES Sections 10.9-10.11: html / PowerPoint / PDF 10.9 PREPARATION OF DIENES 10.10 ADDITION OF HYDROGEN HALIDES TO CONJUGATED DIENES 10.11 HALOGEN ADDITION TO DIENES Sections 10.12-10.14: html / PowerPoint / PDF 10.12 THE DIELS-ALDER REACTION 10.13 THE PI MOLECULAR ORBITALS OF ETHYLENE AND 1,3-BUTADIENE 10.14 A PI MOLECULAR ORBITAL ANALYSIS OF THE DIELS-ALDER REACTION |
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Arenes and Aromaticity |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 11.1-11.6: html / PowerPoint / PDF 11.1 BENZENE 11.2 KEKULE AND THE STRUCTURE OF BENZENE 11.3 A RESONANCE PICTURE OF BONDING IN BENZENE 11.4 THE STABILITY OF BENZENE 11.5 AN ORBITAL HYBRIDIZATION VIEW OF BONDING IN BENZENE 11.6 THE PI MOLECULAR ORBITALS OF BENZENE Sections 11.7-11.9: html / PowerPoint / PDF 11.7 SUBSTITUTED DERIVATIVES OF BENZENE AND THEIR NOMENCLATURE 11.8 POLYCYCLIC AROMATIC HYDROCARBONS 11.9 PHYSICAL PROPERTIES OF ARENES Sections 11.10-11.11: html / PowerPoint / PDF 11.10 REACTIONS OF ARENES: A PREVIEW 11.11 THE BIRCH REDUCTION Sections 11.12-11.14: html / PowerPoint / PDF 11.12 FREE-RADICAL HALOGENATION OF ALKYLBENZENES 11.13 OXIDATION OF ALKYLBENZENES 11.14 NUCLEOPHILIC SUBSTITUTION IN BENZYLIC HALIDES Sections 11.15-11.17: html / PowerPoint / PDF 11.15 PREPARATION OF ALKENYLBENZENES 11.16 ADDITION REACTIONS OF ALKENYLBENZENES 11.17 POLYMERIZATION OF STYRENE Sections 11.18-11.22: html / PowerPoint / PDF 11.18 CYCLOBUTADIENE AND CYCLOOCTATETRAENE 11.19 HUCKEL'S RULE: ANNULENES 11.20 AROMATIC IONS 11.21 HETEROCYCLIC AROMATIC COMPOUNDS 11.22 HETEROCYCLIC AROMATIC COMPOUNDS AND HUCKEL'S RULE |
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Reactions of Arenes, Electrophilic Aromatic Substitution |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 12.1-12.8: html / PowerPoint / PDF 12.1 REPRESENTATIVE ELECTROPHILIC AROMATIC SUBSTITUTION REACTIONS OF BENZENE 12.2 MECHANISTIC PRINCIPLES OF ELECTROPHILIC AROMATIC SUBSTITUTION 12.3 NITRATION OF BENZENE 12.4 SULFONATION OF BENZENE 12.5 HALOGENATION OF BENZENE 12.6 FRIEDEL-CRAFTS ALKYLATION OF BENZENE 12.7 FRIEDEL-CRAFTS ACYLATION OF BENZENE 12.8 SYNTHESIS OF ALKYLBENZENES BY ACYLATION-REDUCTION Sections 12.9-12.11: html / PowerPoint / PDF 12.9 RATE AND REGIOSELECTIVITY IN ELECTROPHILIC AROMATIC SUBSTITUTION 12.10 RATE AND REGIOSELECTIVITY IN THE NITRATION OF TOLUENE 12.11 RATE AND REGIOSELECTIVITY IN THE NITRATION OF (TRIFLUOROMETHYL)BENZENE Sections 12.12-12.14: html / PowerPoint / PDF 12.12 SUBSTITUENT EFFECTS IN ELECTROPHILIC AROMATIC SUBSTITUTION: ACTIVATING SUBSTITUENTS 12.13 SUBSTITUENT EFFECTS IN ELECTROPHILIC AROMATIC SUBSTITUTION: STRONGLY DEACTIVATING SUBSTITUENTS 12.14 SUBSTITUENT EFFECTS IN ELECTROPHILIC AROMATIC SUBSTITUTION: HALOGENS Sections 12.15-12.18: html / PowerPoint / PDF 12.15 MULTIPLE SUBSTITUENT EFFECTS 12.16 REGIOSELECTIVE SYNTHESIS OF DISUBSTITUTED AROMATIC COMPOUNDS 12.17 SUBSTITUTION IN NAPHTHALENE 12.18 SUBSTITUTION IN HETEROCYCLIC AROMATIC COMPOUNDS |
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Spectroscopy |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 13.1-13.5: html / PowerPoint / PDF 13.1 PRINCIPLES OF SPECTROSCOPY: ELECTROMAGNETIC RADIATION 13.2 PRINCIPLES OF MOLECULAR SPECTROSCOPY: QUANTIZED ENERGY STATES 13.3 INTRODUCTION TO 1H NMR SPECTROSCOPY 13.4 NUCLEAR SHIELDING AND 1H CHEMICAL SHIFTS 13.5 EFFECTS OF MOLECULAR STRUCTURE ON 1H CHEMICAL SHIFTS Sections 13.6-13.13: html / PowerPoint / PDF 13.6 INTERPRETING PROTON NMR SPECTRA 13.7 SPIN-SPIN SPLITTING IN NMR SPECTROSCOPY 13.8 SPLITTING PATTERNS: THE ETHYL GROUP 13.9 SPLITTING PATTERNS: THE ISOPROPYL GROUP 13.10 SPLITTING PATTERNS: PAIRS OF DOUBLETS 13.11 COMPLEX SPLITTING PATTERNS 13.12 1H NMR SPECTRA OF ALCOHOLS 13.13 NMR AND CONFORMATIONS Sections 13.14-13.18: html / PowerPoint / PDF 13.14 13C NMR SPECTROSCOPY 13.15 13C CHEMICAL SHIFTS 13.16 13C NMR AND PEAK INTENSITIES 13.17 13C-1H COUPLING 13.18 USING DEPT TO COUNT THE HYDROGENS ATTACHED TO 13C Section 13.19: html / PowerPoint / PDF 13.19 INFRARED SPECTROSCOPY Section 13.20: html / PowerPoint / PDF 13.20 ULTRAVIOLET-VISIBLE (UV-VIS) SPECTROSCOPY Section 13.21: html / PowerPoint / PDF 13.21 MASS SPECTROMETRY |
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Organometallic Compounds |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 14.1-14.5: html / PowerPoint / PDF 14.1 ORGANOMETALLIC NOMENCLATURE 14.2 CARBON-METAL BONDS IN ORGANOMETALLIC COMPOUNDS 14.3 PREPARATION OF ORGANOLITHIUM COMPOUNDS 14.4 PREPARATION OF ORGANOMAGNESIUM COMPOUNDS: GRIGNARD REAGENTS 14.5 ORGANOLITHIUM AND ORGANOMAGNESIUM COMPOUNDS AS BRONSTED BASES Sections 14.6-14.10: html / PowerPoint / PDF 14.6 SYNTHESIS OF ALCOHOLS USING GRIGNARD REAGENTS 14.7 SYNTHESIS OF ALCOHOLS USING ORGANOLITHIUM REAGENTS 14.8 SYNTHESIS OF ACETYLENIC ALCOHOLS 14.9 RETROSYNTHETIC ANALYSIS 14.10 PREPARATION OF TERTIARY ALCOHOLS FROM ESTERS AND GRIGNARD REAGENTS Sections 14.11-14.15: html / PowerPoint / PDF 14.11 ALKANE SYNTHESIS USING ORGANOCOPPER REAGENTS 14.12 AN ORGANOZINC REAGENT FOR CYCLOPROPANE SYNTHESIS 14.13 CARBENES AND CARBENOIDS 14.14 TRANSITION-METAL ORGANOMETALLIC COMPOUNDS 14.15 ZIEGLER-NATTA CATALYSIS OF ALKENE POLYMERIZATION |
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Chapter 15 |
Alcohols, Diols, and Thiols |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 15.1-15.5: html / PowerPoint / PDF 15.1 SOURCES OF ALCOHOLS 15.2 PREPARATION OF ALCOHOLS BY REDUCTION OF ALDEHYDES AND KETONES 15.3 PREPARATION OF ALCOHOLS BY REDUCTION OF CARBOXYLIC ACIDS AND ESTERS 15.4 PREPARATION OF ALCOHOLS FROM EPOXIDES 15.5 PREPARATION OF DIOLS Sections 15.6-15.12: html / PowerPoint / PDF 15.6 REACTIONS OF ALCOHOLS: A REVIEW AND A PREVIEW 15.7 CONVERSION OF ALCOHOLS TO ETHERS 15.8 ESTERIFICATION 15.9 ESTERS OF INORGANIC ACIDS 15.10 OXIDATION OF ALCOHOLS 15.11 BIOLOGICAL OXIDATION OF ALCOHOLS 15.12 OXIDATIVE CLEAVAGE OF VICINAL DIOLS Sections 15.13-15.15: html / PowerPoint / PDF 15.13 PREPARATION OF THIOLS 15.14 PROPERTIES OF THIOLS 15.15 SPECTROSCOPIC ANALYSIS OF ALCOHOLS |
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Chapter 16 |
Ethers, Epoxides, and Sulfides |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 16.1-16.3: html / PowerPoint / PDF 16.1 NOMENCLATURE OF ETHERS, EPOXIDES, AND SULFIDES 16.2 STRUCTURE AND BONDING IN ETHERS AND EPOXIDES 16.3 PHYSICAL PROPERTIES OF ETHERS Sections 16.4-16.8: html / PowerPoint / PDF 16.4 CROWN ETHERS 16.5 PREPARATION OF ETHERS 16.6 THE WILLIAMSON ETHER SYNTHESIS 16.7 REACTIONS OF ETHERS: A REVIEW AND A PREVIEW 16.8 ACID-CATALYZED CLEAVAGE OF ETHERS Sections 16.9-16.13: html / PowerPoint / PDF 16.9 PREPARATION OF EPOXIDES: A REVIEW AND A PREVIEW 16.10 CONVERSION OF VICINAL HALOHYDRINS TO EPOXIDES 16.11 REACTONS OF EPOXIDES: A REVIEW AND A PREVIEW 16.12 NUCLEOPHILIC RING-OPENING REACTIONS OF EPOXIDES 16.13 ACID-CATALYZED RING-OPENING REACTIONS OF EPOXIDES Sections 16.14-16.18: html / PowerPoint / PDF 16.14 EPOXIDES IN BIOLOGICAL PROCESSES 16.15 PREPARATION OF SULFIDES 16.16 OXIDATION OF SULFIDES: SULFOXIDES AND SULFONES 16.17 ALKYLATION OF SULFIDES: SULFONIUM SALTS 16.18 SPECTROSCOPIC ANALYSIS OF ETHERS |
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Chapter 17 |
Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 17.1-17.4: html / PowerPoint / PDF 17.1 NOMENCLATURE 17.2 STRUCTURE AND BONDING: THE CARBONYL GROUP 17.3 PHYSICAL PROPERTIES 17.4 SOURCES OF ALDEHYDES AND KETONES Sections 17.5-17.7: html / PowerPoint / PDF 17.5 REACTIONS OF ALDEHYDES AND KETONES: A REVIEW AND A PREVIEW 17.6 PRINCIPLES OF NUCLEOPHILIC ADDITION: HYDRATION OF ALDEHYDES AND KETONES 17.7 CYANOHYDRIN FORMATION Sections 17.8-17.9: html / PowerPoint / PDF 17.8 ACETAL FORMATION 17.9 ACETALS AS PROTECTING GROUPS Sections 17.10-17.11: html / PowerPoint / PDF 17.10 REACTION WITH PRIMARY AMINES: IMINES 17.11 REACTION WITH SECONDARY AMINES: ENAMINES Sections 17.12-17.13: html / PowerPoint / PDF 17.12 THE WITTIG REACTION 17.13 PLANNING AN ALKENE SYNTHESIS VIA THE WITTIG REACTION Sections 17.14-17.16: html / PowerPoint / PDF 17.14 STEREOSELECTIVE ADDITION TO CARBONYL GROUPS 17.15 OXIDATION OF ALDEHYDES 17.16 BAEYER-VILLIGER OXIDATION OF KETONES Section 17.17: html / PowerPoint / PDF 17.17 SPECTROSCOPIC ANALYSIS OF ALDEHYDES AND KETONES |
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Chapter 18 |
Enols and Enolates |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 18.1-18.5: html / PowerPoint / PDF 18.1 THE alpha-CARBON ATOM AND ITS HYDROGENS 18.2 HALOGENATION OF ALDEHYDES AND KETONES 18.3 MECHANISM OF alpha-HALOGENATION OF ALDEHYDES AND KETONES 18.4 ENOLIZATION AND ENOL CONTENT 18.5 STABILIZED ENOLS Sections 18.6-18.8: html / PowerPoint / PDF 18.6 BASE-CATALYZED ENOLIZATION: ENOLATE ANIONS 18.7 THE HALOFORM REACTION 18.8 SOME CHEMICAL AND STEREOCHEMICAL CONSEQUENCES OF ENOLIZATION Sections 18.9-18.10: html / PowerPoint / PDF 18.9 THE ALDOL CONDENSATION 18.10 MIXED ALDOL CONDENSATIONS Sections 18.11-18.15: html / PowerPoint / PDF 18.11 EFFECTS OF CONJUGATION IN alpha,beta-UNSATURATED ALDEHYDES AND KETONES 18.12 CONJUGATE ADDITION TO alpha,beta-UNSATURATED CARBONYL COMPOUNDS 18.13 ADDITION OF CARBANIONS TO alpha,beta-UNSATURATED KETONES: THE MICHAEL REACTION 18.14 CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS TO alpha,beta-UNSATURATED CARBONYL COMPOUNDS 18.15 ALKYLATION OF ENOLATE ANIONS |
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Chapter 19 |
Carboxylic Acids |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 19.1-19.5: html / PowerPoint / PDF 19.1 CARBOXYLIC ACID NOMENCLATURE 19.2 STRUCTURE AND BONDING 19.3 PHYSICAL PROPERTIES 19.4 ACIDITY OF CARBOXYLIC ACIDS 19.5 SALTS OF CARBOXYLIC ACIDS Sections 19.6-19.12: html / PowerPoint / PDF 19.6 SUBSTITUENTS AND ACID STRENGTH 19.7 IONIZATION OF SUBSTITUTED BENZOIC ACIDS 19.8 DICARBOXYLIC ACIDS 19.9 CARBONIC ACID 19.10 SOURCES OF CARBOXYLIC ACIDS 19.11 SYNTHESIS OF CARBOXYLIC ACIDS BY THE CARBOXYLATION OF GRIGNARD REAGENTS 19.12 SYNTHESIS OF CARBOXYLIC ACIDS BY THE PREPARATION AND HYDROLYSIS OF NITRILES Sections 19.13-19.15: html / PowerPoint / PDF 19.13 REACTIONS OF CARBOXYLIC ACIDS: A REVIEW AND A PREVIEW 19.14 MECHANISM OF ACID-CATALYZED ESTERIFICATION 19.15 INTRAMOLECULAR ESTER FORMATION: LACTONES Sections 19.16-19.17: html / PowerPoint / PDF 19.16 alpha-HALOGENATION OF CARBOXYLIC ACIDS: THE HELL-VOLHARD-ZELINSKY REACTION 19.17 DECARBOXYLATION OF MALONIC ACID AND RELATED COMPOUNDS Section 19.18: html / PowerPoint / PDF 19.18 SPECTROSCOPIC ANALYSIS OF CARBOXYLIC ACIDS |
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Chapter 20 |
Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 20.1-20.2: html / PowerPoint / PDF 20.1 NOMENCLATURE OF CARBOXYLIC ACID DERIVATIVES 20.2 STRUCTURE OF CARBOXYLIC ACID DERIVATIVES Sections 20.3-20.5: html / PowerPoint / PDF 20.3 NUCLEOPHILIC SUBSTITUTION IN ACYL CHLORIDES 20.4 PREPARATION OF CARBOXYLIC ACID ANHYDRIDES 20.5 REACTIONS OF CARBOXYLIC ACID ANHYDRIDES Sections 20.6-20.12: html / PowerPoint / PDF 20.6 SOURCES OF ESTERS 20.7 PHYSICAL PROPERTIES OF ESTERS 20.8 REACTIONS OF ESTERS: A REVIEW AND A PREVIEW 20.9 ACID-CATALYZED ESTER HYDROLYSIS 20.10 ESTER HYDROLYSIS IN BASE: SAPONIFICATION 20.11 REACTION OF ESTERS WITH AMMONIA AND AMINES 20.12 THIOESTERS Sections 20.13-20.16: html / PowerPoint / PDF 20.13 PREPARATION OF AMIDES 20.14 LACTAMS 20.15 IMIDES 20.16 HYDROLYSIS OF AMIDES Section 20.17: html / PowerPoint / PDF 20.17 THE HOFMANN REARRANGEMENT Sections 20.18-20.20: html / PowerPoint / PDF 20.18 PREPARATION OF NITRILES 20.19 HYDROLYSIS OF NITRILES 20.20 ADDITION OF GRIGNARD REAGENTS TO NITRILES Section 20.21: html / PowerPoint / PDF 20.21 SPECTROSCOPIC ANALYSIS OF CARBOXYLIC ACID DERIVATIVES |
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Chapter 21 |
Ester Enolates |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 21.1-21.5: html / PowerPoint / PDF 21.1 THE CLAISEN CONDENSATION 21.2 INTRAMOLECULAR CLAISEN CONDENSATION: THE DIECKMANN REACTION 21.3 MIXED CLAISEN CONDENSATIONS 21.4 ACYLATION OF KETONES WITH ESTERS 21.5 KETONE SYNTHESIS VIA beta-KETO ESTERS Sections 21.6-21.7: html / PowerPoint / PDF 21.6 THE ACETOACETIC ESTER SYNTHESIS 21.7 THE MALONIC ESTER SYNTHESIS Sections 21.8-21.10: html / PowerPoint / PDF 21.8 BARBITURATES 21.9 MICHAEL ADDITIONS OF STABILIZED ANIONS 21.10 alpha-DEPROTONATION OF CARBONYL COMPOUNDS BY LITHIUM DIALKYLAMIDES |
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Chapter 22 |
Amines |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 22.1-22.3: html / PowerPoint / PDF 22.1 AMINE NOMENCLATURE 22.2 STRUCTURE AND BONDING 22.3 PHYSICAL PROPERTIES Sections 22.4-22.6: html / PowerPoint / PDF 22.4 MEASURES OF AMINE BASICITY 22.5 BASICITY OF AMINES 22.6 TETRAALKYLAMMONIUM SALTS AS PHASE-TRANSFER CATALYSTS Sections 22.7-22.11: html / PowerPoint / PDF 22.7 REACTIONS THAT LEAD TO AMINES: A REVIEW AND A PREVIEW 22.8 PREPARATION OF AMINES BY ALKYLATION OF AMMONIA 22.9 THE GABRIEL SYNTHESIS OF PRIMARY ALKYLAMINES 22.10 PREPARATION OF AMINES BY REDUCTION 22.11 REDUCTIVE AMINATION Sections 22.12-22.15: html / PowerPoint / PDF 22.12 REACTIONS OF AMINES: A REVIEW AND A PREVIEW 22.13 REACTIONS OF AMINES WITH ALKYL HALIDES 22.14 THE HOFMANN ELIMINATION 22.15 ELECTROPHILIC AROMATIC SUBSTITUTION IN ARYLAMINES Sections 22.16-22.19: html / PowerPoint / PDF 22.16 NITROSATION OF ALKYLAMINES 22.17 NITROSATION OF ARYLAMINES 22.18 SYNTHETIC TRANSFORMATIONS OF ARYL DIAZONIUM SALTS 22.19 AZO COUPLING Section 22.20: html / PowerPoint / PDF 22.20 SPECTROSCOPIC ANALYSIS OF AMINES |
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Chapter 23 |
Aryl Halides |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 23.1-23.7: html / PowerPoint / PDF 23.1 BONDING IN ARYL HALIDES 23.2 SOURCES OF ARYL HALIDES 23.3 PHYSICAL PROPERTIES OF ARYL HALIDES 23.4 REACTIONS OF ARYL HALIDES: A REVIEW AND A PREVIEW 23.5 NUCLEOPHILIC SUBSTITUTION IN NITRO-SUBSTITUTED ARYL HALIDES 23.6 THE ADDITION-ELIMINATION MECHANISM OF NUCLEOPHILIC AROMATIC SUBSTITUTION 23.7 RELATED NUCLEOPHILIC AROMATIC SUBSTITUTION REACTIONS Sections 23.8-23.9: html / PowerPoint / PDF 23.8 THE ELIMINATION-ADDITION MECHANISM OF NUCLEOPHILIC AROMATIC SUBSTITUTION: BENZYNE 23.9 DIELS-ALDER REACTIONS OF BENZYNE |
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Chapter 24 |
Phenols |
| Sections 24.1-24.3: html / PowerPoint / PDF 24.1 NOMENCLATURE 24.2 STRUCTURE AND BONDING 24.3 PHYSICAL PROPERTIES Sections 24.4-24.5: html / PowerPoint / PDF 24.4 ACIDITY OF PHENOLS 24.5 SUBSTITUENT EFFECTS ON THE ACIDITY OF PHENOLS Sections 24.6-24.10: html / PowerPoint / PDF 24.6 SOURCES OF PHENOLS 24.7 NATURALLY OCCURRING PHENOLS 24.8 REACTIONS OF PHENOLS. ELECTROPHILIC AROMATIC SUBSTITUTION 24.9 ACYLATION OF PHENOLS 24.10 CARBOXYLATION OF PHENOLS. ASPIRIN AND THE KOLBE-SCHMITT REACTION Sections 24.11-24.14: html / PowerPoint / PDF 24.11 PREPARATION OF ARYL ETHERS 24.12 CLEAVAGE OF ARYL ETHERS BY HYDROGEN HALIDES 24.13 CLAISEN REARRANGEMENT OF ALLYL ARYL ETHERS 24.14 OXIDATION OF PHENOLS. QUINONES Section 24.15: html / PowerPoint / PDF 24.15 SPECTROSCOPIC ANALYSIS OF PHENOLS |
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Chapter 25 |
Carbohydrates |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 25.1-25.4: html / PowerPoint / PDF 25.1 CLASSIFICATION OF CARBOHYDRATES 25.2 FISCHER PROJECTIONS AND D,L-NOTATION 25.3 THE ALDOTETROSES 25.4 ALDOPENTOSES AND ALDOHEXOSES Section 25.5: html / PowerPoint / PDF 25.5 A MNEMONIC FOR CARBOHYDRATE CONFIGURATIONS Sections 25.6-25.8: html / PowerPoint / PDF 25.6 CYCLIC FORMS OF CARBOHYDRATES: FURANOSE FORMS 25.7 CYCLIC FORMS OF CARBOHYDRATES: PYRANOSE FORMS 25.8 MUTAROTATION Sections 25.9-25.12: html / PowerPoint / PDF 25.9 KETOSES 25.10 DEOXY SUGARS 25.11 AMINO SUGARS 25.12 BRANCHED-CHAIN CARBOHYDRATES Sections 25.13-25.16: html / PowerPoint / PDF 25.13 GLYCOSIDES 25.14 DISACCHARIDES 25.15 POLYSACCHARIDES 25.16 CELL-SURFACE GLYCOPROTEINS Sections 25.17-25.23: html / PowerPoint / PDF 25.17 CARBOHYDRATE STRUCTURE DETERMINATION 25.18 REDUCTION OF CARBOHYDRATES 25.19 OXIDATION OF CARBOHYDRATES 25.20 CYANOHYDRIN FORMATION AND CARBOHYDRATE CHAIN EXTENSION 25.21 EPIMERIZATION, ISOMERIZATION, AND RETRO-ALDOL CLEAVAGE REACTIONS OF CARBOHYDRATES 25.22 ACYLATION AND ALKYLATION OF HYDROXYL GROUPS IN CARBOHYDRATES 25.23 PERIODIC ACID OXIDATION OF CARBOHYDRATES |
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Chapter 26 |
Lipids |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 26.1-26.6: html / PowerPoint / PDF 26.1 ACETYL COENZYME A 26.2 FATS, OILS, AND FATTY ACIDS 26.3 FATTY ACID BIOSYNTHESIS 26.4 PHOSPHOLIPIDS 26.5 WAXES 26.6 PROSTAGLANDINS Section 26.7-26.10: html / PowerPoint / PDF 26.7 TERPENES: THE ISOPRENE RULE 26.8 ISOPENTENYL PYROPHOSPHATE: THE BIOLOGICAL ISOPRENE UNIT 26.9 CARBON-CARBON BOND FORMATION IN TERPENE BIOSYNTHESIS 26.10 THE PATHWAY FROM ACETATE TO ISOPENTENYL PYROPHOSPHATE Sections 26.11-26.16: html / PowerPoint / PDF 26.11 STEROIDS: CHOLESTEROL 26.12 VITAMIN D 26.13 BILE ACIDS 26.14 CORTICOSTEROIDS 26.15 SEX HORMONES 26.16 CAROTENOIDS |
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Chapter 27 |
Amino Acids, Peptides, and Proteins. Nucleic Acids |
| Copyright 2000 by Francis A. Carey. All rights reserved. Sections 27.1-27.2: html / PowerPoint / PDF 27.1 CLASSIFICATION OF AMINO ACIDS 27.2 STEREOCHEMISTRY OF AMINO ACIDS Section 27.3: html / PowerPoint / PDF 27.3 ACID-BASE BEHAVIOR OF AMINO ACIDS Sections 27.4-27.6: html / PowerPoint / PDF 27.4 SYNTHESIS OF AMINO ACIDS 27.5 REACTIONS OF AMINO ACIDS 27.6 SOME BIOCHEMICAL REACTIONS OF AMINO ACIDS Section 27.7: html / PowerPoint / PDF 27.7 PEPTIDES Sections 27.8-27.13: html / PowerPoint / PDF 27.8 INTRODUCTION TO PEPTIDE STRUCTURE DETERMINATION 27.9 AMINO ACID ANALYSIS 27.10 PARTIAL HYDROLYSIS OF PEPTIDES 27.11 END GROUP ANALYSIS 27.12 INSULIN 27.13 THE EDMAN DEGRADATION AND AUTOMATED SEQUENCING OF PEPTIDES Sections 27.14-27.18: html / PowerPoint / PDF 27.14 THE STRATEGY OF PEPTIDE SYNTHESIS 27.15 AMINO GROUP PROTECTION 27.16 CARBOXYL GROUP PROTECTION 27.17 PEPTIDE BOND FORMATION 27.18 SOLID-PHASE PEPTIDE SYNTHESIS: THE MERRIFIELD METHOD Sections 27.19-27.22: html / PowerPoint / PDF 27.19 SECONDARY STRUCTURES OF PEPTIDES AND PROTEINS 27.20 TERTIARY STRUCTURES OF PEPTIDES AND PROTEINS 27.21 COENZYMES 27.22 PROTEIN QUATERNARY STRUCTURE: HEMOGLOBIN Sections 27.23-27.29: html / PowerPoint / PDF 27.23 PYRIMIDINES AND PURINES 27.24 NUCLEOSIDES 27.25 NUCLEOTIDES 27.26 NUCLEIC ACIDS 27.28 DNA-DIRECTED PROTEIN BIOSYNTHESIS 27.29 DNA SEQUENCING |