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Map: Organic Chemistry (Carey)

  • Page ID
    22647
  • 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?

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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

    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