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CITATION

Bloch, Daniel. Organic Chemistry Demystified. McGraw-Hill Professional, 2006.

Organic Chemistry Demystified

Authors: Daniel Bloch

Published:  March 2006

eISBN: 9780071487108 0071487107 | ISBN: 9780071459204
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  • Contents
  • Preface
  • Acknowledgments
  • Chapter 1 Structure and Bonding
  • Atomic Structure
  • Atomic Number and Atomic Mass (Weight)
  • Electron Energy Levels
  • The Octet Rule
  • Valences
  • Lewis Structures
  • Orbital Shapes
  • Quantum Mechanics
  • Bond Formation
  • Valence Bond Theory
  • Molecular Orbitals
  • Bonding and Antibonding MOs
  • Bonding and 3-D Molecular Shape
  • Curved Arrows
  • Electronegativity and Bond Polarity
  • Dipole Moments
  • Formal Charges
  • Resonance Structures
  • Intermolecular Forces
  • Quiz
  • Chapter 2 Families and Functional Groups
  • Chapter 3 Acids and Bases
  • Introduction
  • Arrhenius Definition
  • Brønsted-Lowry Definition
  • Conjugate Acids and Bases
  • Equilibrium Reactions
  • Weak Hydrocarbon Acids
  • Lewis Acids and Bases
  • Quiz
  • Chapter 4 Alkanes and Cycloalkanes
  • Introduction
  • Sources of Alkanes
  • Acyclic and Cyclic Alkanes
  • Nomenclature
  • Formulas
  • Structures
  • Constitutional Isomers
  • Cycloalkanes
  • Alkyl Groups
  • Nomenclature—Naming Compounds by the IUPAC System
  • Physical Properties
  • Chemical Properties
  • Conformations of Alkanes
  • Conformations of Cylcoalkanes
  • Quiz
  • Chapter 5 Stereochemistry
  • Isomers
  • Chiral Compounds
  • Stereocenters
  • Chirality Centers
  • Enantiomers
  • Racemic Mixtures
  • The R/S System
  • When the Lowest Priority Group Is not in the Back
  • Molecules with Multiple Asymmetric Centers
  • Enantiomers
  • Diastereomers
  • Meso Compounds
  • Fisher Projections
  • Rotating Fisher Projections/Structures
  • Cyclic Stereoisomers
  • Naming Cyclic Stereoisomers
  • Prochiral Carbons (Wanabees)
  • Quiz
  • Chapter 6 Structure and Properties of Alkenes
  • Introduction
  • Structure
  • Naming Alkenes
  • Common Names
  • Cis and Trans Isomers
  • The E/Z (Easy) System
  • Degrees of Unsaturation
  • Stability of Alkenes
  • Physical Properties of Alkenes
  • Chemical Properties
  • The Curved Arrow
  • Quiz
  • Chapter 7 Reaction Mechanisms
  • Introduction
  • Thermodynamics
  • Kinetics
  • Carbocations
  • Stereochemistry
  • The Hammond Postulate
  • Regiochemical Reactions
  • The Markovnikov Rule
  • Stereochemistry
  • Rearrangement Reactions of Carbocations
  • Quiz
  • Chapter 8 Reactions of Alkenes
  • Reaction with Hydrogen Halides in Inert Solvents
  • Reaction with Hydrogen Halides in Protic Solvents
  • Oxymercuration-Demercuration Reactions
  • Hydroboration-Reduction
  • Halogenation in Inert Solvents
  • Stereochemistry Halogenation
  • Halogenation in Reactive Solvents
  • Radical Bromination
  • Formation of Diols
  • Double Bond Cleavage
  • Hydrogenation
  • Epoxides
  • Cyclopropanes
  • Quiz
  • Chapter 9 Alkynes
  • Introduction
  • Structure
  • Nomenclature
  • Physical Properties
  • Chemical Properties
  • Reactions with Brønsted-Lowry Acids
  • Reactions with HBr and Peroxides
  • Reaction with Halogens
  • Hydration Reactions
  • Hydroboration-Oxidation Reactions
  • Hydrogenation/Reduction Reactions
  • Oxidation Reactions
  • Acidity of Alkynes
  • Alkylation Reactions
  • Preparation of Alkynes
  • Quiz
  • Chapter 10 Characterization
  • Introduction
  • Chromatography
  • Spectroscopy
  • UV Spectroscopy
  • Nuclear Magnetic Resonance Spectroscopy
  • Nuclear Properties
  • NMR Spectrometers
  • [sup(1)]H NMR Spectroscopy
  • [sup(13)]C NMR Spectroscopy
  • Mass Spectrometry
  • Quiz
  • Chapter 11 Organohalides
  • Introduction
  • Nomenclature
  • Properties
  • Preparation of Halides
  • Radical Halogenation
  • Isomeric Products
  • Allylic Halogenation
  • Reactions of Organohalides
  • Quiz
  • Chapter 12 Nucleophilic Substitution and Elimination Reactions
  • Introduction
  • Properties of Nucleophiles
  • Properties of Bases
  • Properties of Substrates/Electrophiles
  • Properties of Leaving Groups
  • Properties of Solvents
  • Second-Order Nucleophilic Substitution (S[sub(N)]2) Reactions
  • First-Order Nucleophilic Substitution (S[sub(N)]1) Reactions
  • Summary of S[sub(N)]1 and S[sub(N)]2 Reactions
  • Second-Order Elimination (E2) Reactions
  • First-Order Elimination (E1) Reactions
  • Summary of E1 and E2 Reactions
  • Competition between Substitution and Elimination Reactions
  • Quiz
  • Chapter 13 Alcohols
  • Introduction
  • Properties of Alcohols
  • Nomenclature
  • Acidity and Basicity of Alcohols
  • Reactions with Active Metals
  • Preparation of Alcohols
  • Organometallic Compounds
  • Preparation of Alcohols Using Organometallic Reagents
  • Reactions of Alcohols
  • Conversion of Alcohols to Alkyl Halides
  • Dehydration Reactions
  • Quiz
  • Chapter 14 Ethers
  • Introduction
  • Nomenclature
  • Properties
  • Preparation of Ethers
  • Reactions of Ethers
  • Three-Membered Ether Rings
  • Quiz
  • Chapter 15 Sulfur Compounds
  • Nomenclature
  • Properties
  • Reactions of Sulfur Compounds
  • Quiz
  • Chapter 16 Conjugated Systems
  • Introduction
  • Stability of Dienes
  • Electrophilic Addition to Conjugated Dienes
  • Allylic Cations, Radicals, and Anions
  • Diels-Alder Reactions
  • Quiz
  • Chapter 17 Aromatic Compounds
  • Introduction
  • Reactivity of Aromatic Compounds
  • Nomenclature
  • Kekulé Structures
  • Stability of Benzene
  • The Resonance Model
  • Molecular Orbital Description of Aromaticity
  • Properties of Aromatic, Nonaromatic, and Antiaromatic Compounds
  • Hückel's Rule
  • Heterocyclic Compounds
  • Aromatic Ions
  • Polycyclic Aromatic Compounds
  • Quiz
  • Chapter 18 Reactions of Benzene and other Aromatic Compounds
  • Introduction
  • Electrophilic Aromatic Substitution
  • Nucleophilic Aromatic Substitution
  • More Derivatives of Benzene
  • Multiple Substitution Reactions
  • Electrophilic Substitution in Disubstituted Benzenes
  • Quiz
  • Chapter 19 Aldehydes and Ketones
  • Introduction
  • Nomenclature
  • Physical Properties
  • Chemical Properties
  • Preparation of Aldehydes and Ketones
  • Hydration of Alkynes
  • Reduction of Acid Chlorides
  • Reactions of Aldehydes and Ketones with Nucleophiles
  • Wittig Reactions
  • Oxidation and Reduction Reactions
  • Quiz
  • Chapter 20 Carboxylic Acids
  • Introduction
  • Nomenclature
  • Three-Dimensional Structure
  • Molecular Orbital (MO) Description
  • Physical Properties
  • Acidity of Carboxylic Acids
  • Preparation of Carboxylic Acids
  • Derivatives of Carboxylic Acids
  • Quiz
  • Chapter 21 Derivatives of Carboxylic Acids
  • Introduction
  • Carboxylic Acid Halides
  • Carboxylic Acid Anhydrides
  • Carboxylic Esters
  • Amides
  • Cyclic Amides
  • Imides
  • Nitriles
  • Quiz
  • Chapter 22 Alpha-Substitution Reactions in Carbonyl Compounds
  • Introduction
  • Enol and Enolate Anions
  • Alpha Monohalogenation of Aldehydes and Ketones
  • α, β Unsaturated Ketones
  • α-Bromination of Carboxylic Acids
  • Acidity of α-Hydrogen Atoms
  • Malonic Ester Synthesis
  • Acetoacetic Ester Synthesis
  • Additional Condensation Reactions
  • Quiz
  • Chapter 23 Carbonyl Condensation Reactions
  • Introduction
  • Aldol Reactions
  • Dehydration of Aldol Compounds
  • Mixed or Crossed Aldol Reactions
  • Intramolecular Aldol Reactions
  • Claisen Condensation Reactions
  • α-Substitution Reactions
  • Quiz
  • Final Exam
  • Quiz and Exam Solutions
  • Appendix A / Periodic Table of the Elements
  • Bibliography
  • Index