These slides are from the fourth edition of the textbook and may differ slightly from the current one.
Chapter 1
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Chemical Bonding
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Sections 1.1-1.6: html
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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
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1.7 STRUCTURAL FORMULAS OF ORGANIC MOLECULES
1.8 CONSTITUTIONAL ISOMERS
1.9 RESONANCE
Sections 1.10-1.11: html
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1.10 THE SHAPES OF SOME SIMPLE MOLECULES
1.11 MOLECULAR DIPOLE MOMENTS
Sections 1.12-1.14: html
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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
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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
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Copyright 2000 by Francis A. Carey. All rights reserved.
Sections 2.1-2.7: html
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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
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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
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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
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Sections 3.1-3.3: html
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3.1 CONFORMATIONAL ANALYSIS OF ETHANE
3.2 CONFORMATIONAL ANALYSIS OF BUTANE
3.3 CONFORMATIONS OF HIGHER ALKANES
Sections 3.4-3.8: html
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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
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3.9 SMALL RINGS: CYCLOPROPANE AND CYCLOBUTANE
3.10 CYCLOPENTANE
3.11 MEDIUM AND LARGE RINGS
Sections 3.12-3.13: html
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3.12 DISUBSTITUTED CYCLOALKANES. STEREOISOMERS
3.13 CONFORMATIONAL ANALYSIS OF DISUBSTITUTED CYCLOHEXANES
Sections 3.14-3.15: html
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3.14 POLYCYCLIC RING SYSTEMS
3.15 HETEROCYCLIC COMPOUNDS
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Alcohols and Alkyl Halides
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Sections 4.1-4.3: html
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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
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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
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4.6 ACIDS AND BASES: GENERAL PRINCIPLES
4.7 ACID-BASE REACTIONS: A MECHANISM FOR PROTON TRANSFER
Sections 4.8-4.14: html
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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
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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
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Sections 5.1-5.4: html
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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
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5.5 PHYSICAL PROPERTIES OF ALKENES
5.6 RELATIVE STABILITIES OF ALKENES
5.7 CYCLOALKENES
Sections 5.8-5.13: html
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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
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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
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Sections 6.1-6.3: html
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6.1 HYDROGENATION OF ALKENES
6.2 HEATS OF HYDROGENATION
6.3 STEREOCHEMISTRY OF ALKENE HYDROGENATION
Sections 6.4-6.7: html
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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
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6.8 FREE-RADICAL ADDITION OF HYDROGEN BROMIDE TO ALKENES
6.9 ADDITION OF SULFURIC ACID TO ALKENES
Sections 6.10-6.13: html
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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
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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
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6.18 EPOXIDATION OF ALKENES
6.19 OZONOLYSIS OF ALKENES
Section 6.20: html / PowerPoint
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6.20 INTRODUCTION TO ORGANIC CHEMICAL SYNTHESIS
Sections 6.21: html / PowerPoint
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6.21 REACTIONS OF ALKENES WITH ALKENES: POLYMERIZATION
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Stereochemistry
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Sections 7.1-7.3: html
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7.1 MOLECULAR CHIRALITY: ENANTIOMERS
7.2 THE STEREOGENIC CENTER
7.3 SYMMETRY IN ACHIRAL STRUCTURES
Sections 7.4-7.5: html
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7.4 PROPERTIES OF CHIRAL MOLECULES: OPTICAL ACTIVITY
7.5 ABSOLUTE AND RELATIVE CONFIGURATION
Sections 7.6-7.8: html
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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
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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
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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
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Sections 8.1-8.2: html
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8.1 FUNCTIONAL GROUP TRANSFORMATION BY NUCLEOPHILIC SUBSTITUTION
8.2 RELATIVE REACTIVITY OF HALIDE LEAVING GROUPS
Sections 8.3-8.6: html
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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
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8.7 NUCLEOPHILES AND NUCLEOPHILICITY
Sections 8.8-8.12: html
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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
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8.13 SUBSTITUTION AND ELIMINATION AS COMPETING REACTIONS
Sections 8.14-8.15: html
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8.14 SULFONATE ESTERS AS SUBSTRATES IN NUCLEOPHILIC SUBSTITUTION
8.15 LOOKING BACK: REACTIONS OF ALCOHOLS WITH HYDROGEN HALIDES
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Alkynes
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Sections 9.1-9.4: html
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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
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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
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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
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Copyright 2000 by Francis A. Carey. All rights reserved.
Sections 10.1-10.4: html
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10.1 THE ALLYL GROUP
10.2 ALLYLIC CARBOCATIONS
10.3 ALLYLIC FREE RADICALS
10.4 ALLYLIC HALOGENATION
Sections 10.5-10.8: html
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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
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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
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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
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Copyright 2000 by Francis A. Carey. All rights reserved.
Sections 11.1-11.6: html
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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
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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
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11.10 REACTIONS OF ARENES: A PREVIEW
11.11 THE BIRCH REDUCTION
Sections 11.12-11.14: html
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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
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11.15 PREPARATION OF ALKENYLBENZENES
11.16 ADDITION REACTIONS OF ALKENYLBENZENES
11.17 POLYMERIZATION OF STYRENE
Sections 11.18-11.22: html
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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
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Copyright 2000 by Francis A. Carey. All rights reserved.
Sections 12.1-12.8: html
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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
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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
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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
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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
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Copyright 2000 by Francis A. Carey. All rights reserved.
Sections 13.1-13.5: html
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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
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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
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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
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13.19 INFRARED SPECTROSCOPY
Section 13.20: html / PowerPoint
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13.20 ULTRAVIOLET-VISIBLE (UV-VIS) SPECTROSCOPY
Section 13.21: html / PowerPoint
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13.21 MASS SPECTROMETRY
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Organometallic Compounds
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Copyright 2000 by Francis A. Carey. All rights reserved.
Sections 14.1-14.5: html
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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
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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
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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
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Alcohols, Diols, and Thiols
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Copyright 2000 by Francis A. Carey. All rights reserved.
Sections 15.1-15.5: html
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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
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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
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15.13 PREPARATION OF THIOLS
15.14 PROPERTIES OF THIOLS
15.15 SPECTROSCOPIC ANALYSIS OF ALCOHOLS
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Chapter 16
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Ethers, Epoxides, and Sulfides
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Copyright 2000 by Francis A. Carey. All rights reserved.
Sections 16.1-16.3: html
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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
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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
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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
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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
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Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group
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Copyright 2000 by Francis A. Carey. All rights reserved.
Sections 17.1-17.4: html
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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
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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
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17.8 ACETAL FORMATION
17.9 ACETALS AS PROTECTING GROUPS
Sections 17.10-17.11: html
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17.10 REACTION WITH PRIMARY AMINES: IMINES
17.11 REACTION WITH SECONDARY AMINES: ENAMINES
Sections 17.12-17.13: html
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17.12 THE WITTIG REACTION
17.13 PLANNING AN ALKENE SYNTHESIS VIA THE WITTIG REACTION
Sections 17.14-17.16: html
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17.14 STEREOSELECTIVE ADDITION TO CARBONYL GROUPS
17.15 OXIDATION OF ALDEHYDES
17.16 BAEYER-VILLIGER OXIDATION OF KETONES
Section 17.17: html / PowerPoint
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17.17 SPECTROSCOPIC ANALYSIS OF ALDEHYDES AND KETONES
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Chapter 18
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Enols and Enolates
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Copyright 2000 by Francis A. Carey. All rights reserved.
Sections 18.1-18.5: html
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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
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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
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18.9 THE ALDOL CONDENSATION
18.10 MIXED ALDOL CONDENSATIONS
Sections 18.11-18.15: html
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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
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Carboxylic Acids
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Copyright 2000 by Francis A. Carey. All rights reserved.
Sections 19.1-19.5: html
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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
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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
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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
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Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution
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Copyright 2000 by Francis A. Carey. All rights reserved.
Sections 20.1-20.2: html
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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
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20.17 THE HOFMANN REARRANGEMENT
Sections 20.18-20.20: html
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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
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Ester Enolates
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Copyright 2000 by Francis A. Carey. All rights reserved.
Sections 21.1-21.5: html
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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
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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
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Amines
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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
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Aryl Halides
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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
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23.8 THE ELIMINATION-ADDITION MECHANISM OF NUCLEOPHILIC AROMATIC SUBSTITUTION:
BENZYNE
23.9 DIELS-ALDER REACTIONS OF BENZYNE
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Chapter 24
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Phenols
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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
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Carbohydrates
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Copyright 2000 by Francis A. Carey. All rights reserved.
Sections 25.1-25.4: html
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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
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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
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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
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Lipids
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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
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Amino Acids, Peptides, and Proteins. Nucleic Acids
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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
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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
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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
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