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In consideration of today’s classroom dynamics and the changes coming to the 2015 MCAT, this revision offers a completely new design with enhanced art throughout, reorganization of materials to reinforce fundamental skills and facilitate more efficient studying.
Brown This package in PDF format is Color-Coded Quran in Arabic Text with a corresponding English Text translation.
About the Translator: Talal Itani is an Electronics Engineer.
Part 1 An Introduction to the Study of Organic Chemistry 1 Remembering General Chemistry: Electronic Structure and Bonding 1.1 The Structure of an Atom 1.2 How the Electrons in an Atom Are Distributed 1.3 Ionic and Covalent Bonds 1.4 How the Structure of a Compound Is Represented 1.5 Atomic Orbitals 1.6 An Introduction to Molecular Orbital Theory 1.7 How Single Bonds Are Formed in Organic Compounds 1.8 How a Double Bond Is Formed: The Bonds in Ethene 1.9 How a Triple Bond Is Formed: The Bonds in Ethyne 1.10 The Bonds in the Methyl Cation, the Methyl Radical, and the Methyl Anion 1.11 The Bonds in Ammonia and In the Ammonium Ion 1.12 The Bonds in Water 1.13 The Bond in a Hydrogen Halide 1.14 Hybridization and Molecular Geometry 1.15 Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles 1.16 The Dipole Moments of Molecules 2 Acids and Bases: Central to Understanding Organic Chemistry 2.1 An Introduction to Acids and Bases 2.2 pka and p H 2.3 Organic Acids and Bases 2.4 How to Predict the Outcome of an Acid—Base Reaction 2.5 How to Determine the Position of Equilibrium 2.6 How the Structure of an Acid affects its p Ka Value 2.7 How Substituent’s affect the Strength of an Acid 2.8 An Introduction to Delocalized Electrons 2.9 A Summary of the Factors That Determine Acid Strength 2.10 How p H affects the Structure of an Organic Compound 2.11 Buffer Solutions 2.12 Lewis Acids and Bases Tutorial: Acids and Bases 3 An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure 3.1 How Alkyl Substituents Are Named 3.2 The Nomenclature of Alkanes 3.3 The Nomenclature of Cycloalkanes • Skeletal Structures 3.4 The Nomenclature of Alkyl Halides 3.5 The Nomenclature of Ethers 3.6 The Nomenclature of Alcohols 3.7 The Nomenclature of Amines 3.8 The Structures of Alkyl Halides, Alcohols, Ethers, and Amines 3.9 The Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines 3.10 Rotation Occurs about Carbon—Carbon single Bonds 3.11 Some Cycloalkanes Have Angle Strain 3.12 The Conformers of Cyclohexane 3.13 Conformers of Monosubstituted Cyclohexanes 3.14 Conformers of Disubstituted Cyclohexanes 3.15 Fused Cyclohexane Rings Part Two Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization Tutorial: Using Molecular Models 4 Isomers: The Arrangement of Atoms in Space 4.1 Cis—Trans Isomers Result from Restricted Rotation 4.2 A Chiral Object Has a Nonsuperimposable Mirror Image 4.3 An Asymmetric Center is a Cause of Chirality in a Molecule 4.4 Isomers with One Asymmetric Center 4.5 Asymmetric Centers and Stereocenters 4.6 How to Draw Enantiomers 4.7 Naming Enantiomers by the R, S System 4.8 Chiral Compounds Are Optically Active 4.9 How Specific Rotation Is Measured 4.10 Enantiomeric Excess 4.11 Compounds with More than One Asymmetric Center 4.12 Stereoisomers of Cyclic Compounds 4.13 Meso Compounds Have Asymmetric Centers but Are Optically Inactive 4.14 How to Name Isomers with More than One Asymmetric Center 4.15 How Enantiomers Can be Separated 4.16 Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers Tutorial: Interconverting Structural Representations 5 Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics 5.1 Molecular Formulas and the Degree of Unsaturation 5.2 The Nomenclature of Alkenes 5.3 The Structure of Alkenes 5.4 Naming Alkenes Using the E, Z System 5.5 How an Organic Compound Reacts Depends On Its Functional Group 5.6 How Alkenes React • Curved Arrows Show the Flow of Electrons 5.7 Thermodynamics and Kinetics 5.8 The Rate of a Chemical Reaction 5.9 The Difference between the Rate of a Reaction and the Rate Constant for a Reaction 5.10 A Reaction Coordinate Diagram Describes the Energy Changes that Take Place during a Reaction 5.11 Catalysis 5.12 Catalysis by Enzymes Tutorial: An Exercise in Drawing Curved Arrows: Pushing Electrons 6 The Reactions of Alkenes: The Stereochemistry of Addition Reactions 6.1 The Addition of a Hydrogen Halide to an Alkene 6.2 Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon 6.3 What Does the Structure of the Transition State Look Like?
6.4 Electrophilic Addition Reactions Are Regioselective 6.5 The Addition of Water to an Alkene 6.6 The Addition of an Alcohol to an Alkene 6.7 A Carbocation will rearrange if it can Form a More Stable Carbocation 6.8 Oxymercuration—Demercuration Is another Way to Add Water to an Alkene 6.9 The Addition of Borane to an Alkene: Hydroboration—Oxidation 6.10 The Addition of a Halogen to an Alkene 6.11 The Addition of a Peroxyacid to an Alkene 6.12 The Addition Of Ozone To An Alkene: Ozonolysis 6.13 The Addition of Hydrogen to an Alkene 6.14 The Relative Stabilities of Alkenes 6.15 Regioselective, Stereoselective, and Stereospecific Reactions 6.16 The Stereochemistry of Electrophilic Addition Reactions of Alkenes 6.17 The Stereochemistry of Enzyme-Catalyzed Reactions 6.18 Enantiomers Can Be Distinguished by Biological Molecules 6.19 Reactions and Synthesis 7 The Reactions of Alkynes: An Introduction to Multistep Synthesis 7.1 The Nomenclature of Alkynes 7.2 How to Name a Compound That Has More than One Functional Group 7.3 The Physical Properties of Unsaturated Hydrocarbons 7.4 The Structure of Alkynes 7.5 Alkynes Are Less Reactive than Alkenes 7.6 The Addition of Hydrogen Halides and the Addition of Halogens to an Alkyne 7.7 The Addition of Water to an Alkyne 7.8 The Addition of Borane to an Alkyne: Hydroboration—Oxidation 7.9 The Addition of Hydrogen to an Alkyne 7.10 A Hydrogen Bonded to an sp Carbon Is “Acidic” 7.11 Synthesis Using Acetylide Ions 7.12 Designing a Synthesis I: An Introduction to Multistep Synthesis 8 Delocalized Electrons and Their Effect on Stability, p Ka, and the Products of a Reaction 8.1 Delocalized Electrons Explain Benzene’s Structure 8.2 The Bonding in Benzene 8.3 Resonance Contributors and the Resonance Hybrid 8.4 How to Draw Resonance Contributors 8.5 The Predicted Stabilities of Resonance Contributors 8.6 Delocalization Energy Is the Additional Stability Delocalized Electrons Give to a Compound 8.7 Benzene is an Aromatic Compound 8.8 The Two Criteria for Aromaticity 8.9 Applying the Criteria for Aromaticity 8.10 Aromatic Heterocyclic Compounds 8.11 Antiaromaticity 8.12 A Molecular Orbital Description of Aromaticity and Antiaromaticity 8.13 More Examples that Show How Delocalized Electrons Affect Stability 8.14 A Molecular Orbital Description of Stability 8.15 How Delocalized Electrons Affect p Ka Values 8.16 Delocalized Electrons Can Affect the Product of a Reaction 8.17 Reactions of Dienes 8.18 Thermodynamic Versus Kinetic Control 8.19 The Diels—Alder Reaction Is a 1,4-Addition Reaction 8.20 Retrosynthetic Analysis of the Diels—Alder Reaction 8.21 Organizing What We Know About the Reactions of Organic Compounds Tutorial: Drawing Resonance Contributors Part Three Substitution and Elimination Reactions 9 Substitution Reactions of Alkyl Halides 9.1 The Mechanism for an SN2 Reaction 9.2 Factors That Affect SN2 Reactions 9.3 The Mechanism for an SN1 Reaction 9.4 Factors That Affect SN1 Reactions 9.5 Benzylic Halides, Allylic Halides, Vinylic Halides, and Aryl Halides 9.6 Competition between SN2 and SN1 Reactions 9.7 The Role of the Solvent in SN1 and SN2 Reactions 9.8 Intermolecular Versus Intramolecular Reactions 9.9 Methylating Agents Used by Chemists Versus Those Used by Cells 10 Elimination Reactions of Alkyl Halides • Competition between Substitution and Elimination 10.1 The E2 Reaction 10.2 An E2 Reaction Is Regioselective 10.3 The E1 Reaction 10.4 Benzylic and Allylic Halides 10.5 Competition between E2 and E1 Reactions 10.6 E2 and E1 Reactions Are Stereoselective 10.7 Elimination from Substituted Cyclohexanes 10.8 A Kinetic Isotope Effect Can Help Determine a Mechanism 10.9 Competition between Substitution and Elimination 10.10 Substitution and Elimination Reactions in Synthesis 10.11 Designing a Synthesis II: Approaching the Problem 11 Reactions of Alcohols, Ethers, Amines, Thiols, and Thioethers 11.1 Nucleophilic Substitution Reactions of Alcohols: Forming Alkyl Halides 11.2 Other Methods used to Convert Alcohols into Alkyl Halides 11.3 Converting an Alcohol into a Sulfonate Ester 11.4 Elimination Reactions of Alcohols: Dehydration 11.5 Oxidation of Alcohols 11.6 Nucleophilic Substitution Reactions of Ethers 11.7 Nucleophilic Substitution Reactions of Epoxides 11.8 Arene Oxides 11.9 Amines do not Undergo Substitution or Elimination Reactions 11.10 Quaternary Ammonium Hydroxides Undergo Elimination Reactions 11.11 Thiols, Sulfides, and Sulfonium Salts 11.12 Organizing What We Know About the Reactions of Organic Compounds 12 Organometallic Compounds 12.1 Organolithium and Organomagnesium Compounds 12.2 The Reaction of Organolithium Compounds And Gridnard Reagents With Electrophiles 12.3 Transmetallation 12.4 Coupling Reactions 12.5 Palladium-Catalyzed Coupling Reactions 12.6 Alkene Metathesis 13 Radicals • Reactions of Alkanes 13.1 Alkanes Are Unreactive Compounds 13.2 The Chlorination and Bromination of Alkanes 13.3 Radical Stability Depends On the Number of Alkyl Groups Attached To the Carbon with the Unpaired Electron 13.4 The Distribution of Products Depends On Probability and Reactivity 13.5 The Reactivity Selectivity Principle 13.6 Formation of Explosive Peroxides 13.7 The Addition of Radicals to an Alkene 13.8 The Stereochemistry of Radical Substitution and Radical Addition Reactions 13.9 Radical Substitution of Benzylic and Allylic Hydrogens 13.10 Designing a Synthesis III: More Practice with Multistep Synthesis 13.11 Radical Reactions Occur In Biological Systems 13.12 Radicals and Stratospheric Ozone Tutorial: Drawing Curved Arrows in Radical Systems Part Four Identification of Organic Compounds 14 Mass Spectrometry, Infrared Spectroscopy, and Ultraviolet/ Visible Spectroscopy 14.1 Mass Spectrometry 14.2 The Mass Spectrum • Fragmentation 14.3 Using the m/z of the Molecular Ion to Calculate the Molecular Formula 14.4 Isotopes in Mass Spectrometry 14.5 High-Resolution Mass Spectrometry Can Reveal Molecular Formulas 14.6 The Fragmentation Patterns of Functional Groups 14.7 Other Ionization Methods 14.8 Gas Chromatography–Mass Spectrometry 14.9 Spectroscopy and the Electromagnetic Spectrum 14.10 Infrared Spectroscopy 14.11 Characteristic Infrared Absorption Bands 14.12 The Intensity of Absorption Bands 14.13 The Position of Absorption Bands 14.14 The Position and Shape of an Absorption Band Is Affected By Electron Delocalization, Electron Donation and Withdrawal, and Hydrogen Bonding 14.15 The Absence of Absorption Bands 14.16 Some Vibrations Are Infrared Inactive 14.17 How to Interpret an Infrared Spectrum 14.18 Ultraviolet and Visible Spectroscopy 14.19 The Beer- Lambert Law 14.20 The Effect of Conjugation on λmax 14.21 The Visible Spectrum and Color 14.22 Some Uses of UV/ VIS Spectroscopy 15 NMR Spectroscopy 15.1 An Introduction to NMR Spectroscopy 15.2 Fourier Transform NMR 15.3 Shielding Causes Different Hydrogens to Show Signals at Different Frequencies 15.4 The Number of Signals in an 1H NMR Spectrum 15.5 The Chemical Shift Tells How Far the Signal Is from the Reference Signal 15.6 The Relative Positions of 1H NMR Signals 15.7 The Characteristic Values of Chemical Shifts 15.8 Diamagnetic Anisotropy 15.9 The Integration of NMR Signals Reveals the Relative Number of Protons Causing Each Signal 15.10 The Splitting of Signals Is Described by the N 1 Rule 15.11 What causes Splitting? She then received an NIH postdoctoral fellowship for study in the Department of Biochemistry at the University of Virginia Medical School and held a postdoctoral appointment in the Department of Pharmacology at Yale Medical School.
15.12 More Examples of 1H NMR Spectra 15.13 Coupling Constants Identify Coupled Protons 15.14 Splitting Diagrams Explain the Multiplicity of a Signal 15.15 Diastereotopic Hydrogens Are Not Chemically Equivalent 15.16 The Time Dependence of NMR Spectroscopy 15.17 Protons Bonded to Oxygen and Nitrogen 15.18 The Use of Deuterium in 1H NMR Spectroscopy 15.19 The Resolution of 1H NMR Spectra 15.20 13C NMR Spectroscopy 15.21 Dept 13C NMR Spectra 15.22 Two-Dimensional NMR Spectroscopy 15.23 NMR Used in Medicine Is Called Magnetic Resonance Imaging 15.24 X-Ray Crystallography Part 5 Carbonyl Compounds 16 Reactions of Carboxylic Acids and Carboxylic Derivatives 16.1 The Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives 16.2 The Structures of Carboxylic Acids and Carboxylic Acid Derivatives 16.3 The Physical Properties of Carbonyl Compounds 16.4 Fatty Acids Are Long-Chain Carboxylic Acids 16.5 How Carboxylic Acids and Carboxylic Acid Derivatives React 16.6 The Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives 16.7 The General Mechanism for Nucleophilic Addition- Elimination Reactions 16.8 The Reactions of Acyl Chlorides 16.9 The Reactions of Esters 16.10 Acid-Catalyzed Ester Hydrolysis and Transesterification 16.11 Hydroxide-Ion-Promoted Ester Hydrolysis 16.12 How the Mechanism for Nucleophilic Addition-Elimination Was Confirmed 16.13 Fats and Oils are Triglycerides 16.14 Reactions of Carboxylic Acids 16.15 Reactions of Amides 16.16 Acid- Catalyzed Amide Hydrolysis and Alcoholysis 16.17 Hydroxide-Ion Promoted Hydrolysis of Amides 16.18 The Hydrolysis of an Imide: A Way to Synthesize Primary Amines 16.19 Nitriles 16.20 Acid Anhydrides 16.21 Dicarboxylic Acids 16.22 How Chemists Activate Carboxylic Acids 16.23 How Cells Activate Carboxylic Acids 17 Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives • Reactions of α, β- Unsaturated Carbonyl Compounds 17.1 The Nomenclature of Aldehydes and Ketones 17.2 The Relative Reactivities of Carbonyl Compounds 17.3 How Aldehydes and Ketones React 17.4 The Reactions of Carbonyl Compounds with Gringard Reagents 17.5 The Reactions of Carbonyl Compounds with Acetylide Ions 17.6 The Reactions of Aldehydes and Ketones with Cyanide Ion 17.7 The Reactions of Carbonyl Compounds with Hydride Ion 17.8 More about Reduction Reactions 17.9 Chemoselective Reactions 17.10 The Reactions of Aldehydes and Ketones with Amines 17.11 The Reactions of Aldehydes and Ketones with Water 17.12 The Reactions of Aldehydes and Ketones with Alcohols 17.13 Protecting Groups 17.14 The Addition of Sulfur Nucleophiles 17.15 The Reactions of Aldehydes and Ketones with a Peroxyacid 17.16 The Wittig Reaction Forms an Alkene 17.17 Designing a Synthesis IV: Disconnections, Synthons, and Synthetic Equivalents 17.18 Nucleophilic Addition to α, β- Unsaturated Aldehydes and Ketones 17.19 Nucleophilic Addition to α, β- Unsaturated Carboxylic Acid Derivatives 18 Reactions at the α- Carbon of Carbonyl Compounds 18.1 The Acidity of an α-Hydrogen 18.2 Keto-Enol Tautomers 18.3 Keto-Enol Interconversion 18.4 Halogenation of the α-Carbon of Aldehydes and Ketones. Paula has been a member of the faculty at the University of California, Santa Barbara since 1972, where she has received the Associated Students Teacher of the Year Award, the Academic Senate Distinguished Teaching Award, two Mortar Board Professor of the Year Awards, and the UCSB Alumni Association Teaching Award.