Detailed Course Content

Transcription

1 Detailed Course Content Chapter 1: Carbon Compounds and Chemical Bonds The Structural Theory of Organic Chemistry 4 Chemical Bonds: The Octet Rule 6 Lewis Structures 8 Formal Charge 11 Resonance 14 Quantum Mechanics 19 Atomic Orbitals 20 Molecular Orbitals 22 The Structure of Methane and Ethane: sp 3 Hybridization 25 The Structure of Ethene (Ethylene): sp 2 Hybridization 29 The Structure of Ethyne (Acetylene): sp Hybridization 34 A Summary of Concepts from Quantum Mechanics 36 Molecular Geometry: The Valence Shell Electron Pair Repulsion Model 38 Representation of Structural Formulas 41 Chapter 2: Compounds: Functional Groups, Intermolecular Forces, and Infrared (IR) Spectroscopy Carbon Carbon Covalent Bonds 53 Hydrocarbons: Alkanes, Alkenes, Alkynes, and Aromatic Compounds 53 Polar Covalent Bonds 56 Polar and Nonpolar Molecules 59 Functional Groups 61 Alkyl Halides or Haloalkanes 63 Alcohols 63 Ethers 65 Amines 66 Aldehydes and Ketones 67 Carboxylic Acids, Esters, and Amides 68 Nitriles 69 Summary of Important Families of Organic Compounds 70 Physical Properties and Molecular Structure 70 Summary of Attractive Electric Forces 78 Infrared Spectroscopy: An Instrumental Method for Detecting Functional Groups 79 (Only detail of summary notes and lab experience of IR) 1

2 Chapter 3: An Introduction to Organic Reactions: Acids and Bases Reactions and their Mechanisms 95 Acid Base Reactions 97 Heterolysis of Bonds to Carbon: Carbocations and Carbanions 101 The Use of Curved Arrows in Illustrating Reactions 102 The Strength of Acids and Bases: K a and p K a 104 Predicting the Outcome of Acid Base Reactions 107 The Relationship between Structure and Acidity Energy Changes The Relationship between Equilibrium Constant and?g o 114 The Acidity of Carboxylic Acids 115 The Effect of the Solvent on Acidity 120 Organic Compounds as Bases 121 A Mechanism for an Organic Reaction 122 Acids and Bases in Non-aqueous Solutions 124 Chapter 4: Alkanes: Nomenclature, Conformational Analysis and an Introduction to Synthesis Introduction to Alkanes and Cycloalkanes 135 Shapes of Alkanes 137 IUPAC Nomenclature of Alkanes, Alkyl Halides, and Alcohols 139 Nomenclature of Cycloalkanes 147 Omit naming of bicyclic compounds Nomenclature of Alkenes and Cycloalkenes 150 Nomenclature of Alkynes 152 Physical Properties of Alkanes and Cycloalkanes 152 Sigma Bonds and Bond Rotation 154 Conformational Analysis of Butane 157 The relative Stabilities of Cycloalkanes: Ring Strain 159 The Origin of Ring Strain in Cyclopropane and Cyclobutane: Angle Strain and Torsional Strain 162 Conformation of Cyclohexane 163 Substituted Cyclohexanes: Axial and Equatorial Hydrogen Atoms 167 Disubstituted Cycloalkanes: Cis Trans Isomerism 171 Bicyclic and Polycyclic Alkanes 175 The following Sections were omitted and important aspects covered under reactions of individual functional groups Chemical Reactions of Alkanes 177 Synthesis of Alkanes and Cycloalkanes 178 2

3 Chapter 5: Stereochemistry: Chiral Molecules The Biological Significance of Chirality 194 Isomerism: Constitutional Isomers and Stereoisomers 195 Enantiomers and Chiral Molecules 196 Historical Origin of Stereochemistry 201 Tests for Chirality: Planes of Symmetry 202 Nomenclature of Enantiomers: The R,S System 203 Properties of Enantiomers: Optical Activity 208 The Origin of Optical Activity 212 The Synthesis of Chiral Molecules 215 Molecules with more than one Stereogenic Center 219 (limited to 2 stereogenic centers) Fischer Projection Formulas 223 Stereoisomerism of Cyclic Compounds 224 (Omit section 5.15) Separation of Enantiomers: Resolution 230 Chapter 6: Ionic Reactions Nucleophilic Substitution and Elimination Reactions of Alkyl Halides Nucleophilic Substitution Reactions 241 Nucleophiles 241 Leaving Groups 242 Kinetics of a Nucleophilic Substitution Reaction: An S N 2 Reaction 243 A Mechanism for the S N 2 Reaction 244 Transition State Theory: Free-Energy Diagrams 245 The Stereochemistry of S N 2 Reactions 249 The Reaction of tert-butyl Chloride with Hydroxide Ion: An S N 1 Reaction 251 A Mechanism for the S N 1 Reaction 252 Carbocations 254 The Stereochemistry of S N 1 Reactions 256 Factors Affecting the Rates of S N 1 and S N 2 Reactions 258 Organic Synthesis: Functional Group Transformations Using S N 2 Reactions 267 Elimination Reactions of Alkyl Halides 271 The E2 Reaction 273 The E1 Reaction 274 Substitution versus Elimination 275 3

4 Chapter 7: Alkenes and Alkynes I: Properties and Synthesis. Elimination Reactions of Alkyl Halides The (E) (Z) System for Designating Alkene Diastereomers 288 Relative Stabilities of Alkenes 290 Cycloalkenes 292 Synthesis of Alkenes via Elimination Reactions 292 Dehydrohalogenation of Alkyl Halides 293 Acid-catalyzed Dehydration of Alcohols 298 Carbocation Stability and the Occurrence of Molecular Rearrangements 303 Synthesis of Alkynes by Elimination Reactions 307 The Acidity of Terminal Alkynes 308 Replacement of the Acetylenic Hydrogen Atom of Terminal Alkynes 309 Hydrogenation of Alkenes 310 Hydrogenation: The Function of the Catalyst 312 Hydrogenation of Alkynes 315 Syn and anti addition of hydrogen students responsible for sections 7.13 and 7.14s Structural Information from Molecular Formulas and the Degree of Unsaturation 317 Chapter 8: Alkenes and Alkynes II: Addition Reactions Introduction: Addition to Alkenes 329 Addition to Hydrogen Halides to Alkenes: Markovnikov s Rule 331 Stereochemistry of the Ionic Addition to an Alkene 336 Addition of Sulfuric Acid to Alkenes 337 Addition of Water to Alkenes: Acid-Catalyzed Hydration 338 Oxymercuration 8.6 omitted Alcohols from Alkenes through Hydroboration-Oxidation: Anti-Markovnikov Syn Hydration 343 Hydroboration: Synthesis of Alkylboranes 343 Oxidation and Hydrolysis of Alkylboranes 346 Summary of Alkene Hydration Methods 348 Protonolysis of Alkylboranes 348 Addition of Bromine and Chlorine to Alkenes 349 Stereochemistry of the Addition of Halogens to Alkenes 351 Halohydrin Formation 354 Oxidations of Alkenes: Syn 1,2-Dihydroxylation 359 Oxidative Cleavage of Alkenes 362 Addition of Bromine and Chlorine to Alkynes 365 Addition of Hydrogen Halides to Alkynes 366 Oxidative Cleavage of Alkynes 367 Synthetic Strategies Revisited 367 4

5 Chapter 10: Radical Reactions Homolytic Bond Dissociation Energies 450 The Reaction of Alkanes with Halogens 454 Chlorination of Methane: Mechanism of Reaction 456 Chlorination of Methane: Energy Changes 459 Radical Addition to Alkenes: The Anti-Markovnikov Addition of Hydrogen Bromide 472 Radical Polymerization of Alkenes: Chain-Growth Polymers 474 Chapter 11: Alcohols and Ethers Structure and Nomenclature 493 Physical Properties of Alcohol and Ethers 495 Important Alcohols and Ethers 497 Synthesis of Alcohols from Alkenes 499 Reactions of Alcohols 501 Alcohol as Acid 502 Conversion of alcohol into Alkyl Halides 503 Alkyl Halides from the Reaction of Alcohols with Hydrogen Halides 503 Alkyl Halides from the Reaction of alcohols with PBr 3 or SOCl Tosylates, Mesylates, and Triflates: Leaving Group Derivatives of Alcohols 507 Synthesis of Ethers 510 Reactions of Ethers 515 Epoxides 516 Reactions of Epoxides 519 Anti 1,2- Dihydroxylation of Alkenes via Epoxides 523 Summary of Reactions of Alkenes, Alcohols, and Ethers 529 5