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1 Chem261 MODULE 1: The Basics: Bonding and Molecular Structure Atomic Structure - Isotopes - Valence Electrons Chemical Bonds: The Octet Rule - Ionic bond - Covalent bond How to write Lewis Structures Formal Charges and How to Calculate Them Isomers: Different Compounds That Have the Same Molecular Formula How to write and Interpret Structural Formula - Dash Structural Formulas - Condensed Structural Formulas - Bond-Line Formulas - How to Draw Bond-Line Formulas - Three-Dimensional Formulas Resonance Theory - The Use of Curve Arrows - How to Write Resonance Structures - Rules For Writing Resonance Structures - How To Decide When One Resonance Structure Contribute More To The Hybrid Than Another Atomic Orbitals and Electron Configuration Molecular Orbitals The Structure of Methane and Ethane: sp3 Hybridization The Structure of Ethene (Ethylene): sp2 Hybridization - Restricted Rotation and the Double Bond - Cis-Trans Isomerism The Structure of Ethyne (Acetylene): sp Hybridization How to Predict Molecular Geometry: The Valence Shell Electron Pair Repulsion Model - Methane - Ammonia - Water - Boron Trifluoride - Beryllium Hydride - Carbon Dioxide Text Sections: 1.2-1.17 Homework: Chapter 1:1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20, 1. 21, 1.22, 1.23, 1.24, 1.25, 1.27, 1.28, 1.29, 1.30, 1.31, 1.32, 1.35, 1.36, 1.37, 1.38, 1.39, 1.40, 1.41, 1.43, 1.44, 1.45, 149, 1.50 MODULE 2: Families of Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared (IR) Spectroscopy Hydrocarbons: Representative Alkanes, Alkenes, Alkynes, and Aromatic Compounds - alkanes - alkenes - alkynes - benzene: A representative Aromatic hydrocarbon Polar Covalent Bonds Polar and Nonpolar Molecules Dipole Moments in Alkenes Functional Groups 2 - alkyl groups and the symbol R - phenyl and benzyl groups - alkyl halides or haloalkanes - alcohols and Phenols - ethers - amines - aldehydes and ketones - carboxylic acids esters amides - nitriles Summary of Important Families of Organic Compounds Physical Properties and Molecular Structures - Ionic Compounds: ion-ion forces Intermolecular Forces (Van der Waals Forces) - dipole –dipole forces - hydrogen bonds - Dispersion Forces Dipole-Dipole Forces Boiling Points Solubilities Guidelines for Water Solubility Summary of Attractive Electronic Forces Infrared Spectroscopy: An Instrumental Method for Detecting Functional Groups Interpreting IR Spectra Infrared Spectra of Hydrocarbons IR Spectra of Some Functional Groups Containing Heteroatoms How to Interpret an IR Spectrum without Any Knowledge of the Structure Applications of Basic Principles How to Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency Text Sections: 2.1-2.17, 4.17 Homework: Chapter 2: 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2. 9, 2.10, 2.12,2.15, 2.17, 2.18, 2.19, 2.20, 2.21, 2.22, 2.23, 2.24, 2.25, 2.26, 2.27, 2.29, 2.30, 2.31, 2.32, 2.33, 2.34, 2.35, 2.36, 2.37, 2.38, 2.39, 2.40, 2.43, 2.44, 2.45, 2.46, 2.47, 2.48, 2.50, 2.51, 2.52, 2.53, 2.54, 2.56 MODULE 3: An Introduction to Organic Reactions and Their Mechanism: Acids and Bases Acid-Base Reactions - the Bronsted-Lowry Definition of acids and Bases - the Lewis Definition of Acids and Bases - opposite charge attract How to Use Curved Arrows in Illustrating Reactions Lewis Acids and Bases Heterolysis of Bonds to Carbon - Carbocations - Carbanions - Electrophiles - Nucleophiles The Strength of Bronsted-Lowry Acids and Bases: Ka and pka - The Acidity Constant, Ka Acidity and pka - Predicting the Strength of Bases How to Predict the Outcome of Acid-Base Reactions Relationship between Structure and Acidity - The Effect of Hybridization 3 - Inductive Effect Acidity: Carboxylic Acids versus Alcohols - The effect of Delocalization - The Inductive Effect - Summary and a Comparison of Conjugate Acid-Base Strength - Inductive Effect of Other Groups - Strength of Phenols and Acids - Distinguishing and Separating Phenols from Alcohols and Carboxylic Acids The Effect of Solvents on Acidity Organic Compounds as Bases A mechanism for an Organic Reaction Acids and Bases in Non-aqueous Solution Acid and Bases and the Synthesis of Deuterium and Tritium-Labeled Compounds Text Sections: 3.1-3.7, 3.10-3.15. Homework: Chapter3: 3.1, 3.2, 3.3, 3.4, 3.6, 3.7, 3.8, 3.9, 3.13, 3.14, 3.16, 3.17, 3.18, 3.19, 3.20, 3.21, 3.22, 3.23, 3.24, 3.25, 3.26, 3.27, 3.29, 3.30, 3.32, 3.34, 3.35, 3.36, 3.38 MODULE4: Nomenclature and Conformations of Alkanes and Cycoalkanes Introduction to alkanes and Cycloalkane Shape of Alkanes How to name Alkanes, Alkyl Halides, and Alcohols: The IUPAC System - nomenclature of unbranched alkyl groups - nomenclature of branched-chain alkanes - nomenclature of branched alkyl groups - classification of hydrogen atoms - nomenclature of alkyl halides - nomenclature of alcohols How to Name Cycloalkanes - monocyclic compounds - bicyclic compounds How to Name Alkenes and Cycloalkenes How to Name Alkynes Physical Properties of Alkanes and Cycloalkanes Sigma Bonds and Bond Rotation Newman Projections and How to Draw Them How to do Conformational Analysis Conformational Analysis of Butane Stereoisomers and Conformational Stereoisomers The relative Stabilities of Cycloalkanes: Ring Strain -cyclopropane -cycobutane -cyclopentane Conformations of Cyclohexane: The chair and the boat Conformations of Higher Cycloalkanes Substituted Cyclohexanes: Axial and Equatorial Hydrogen Groups How to Draw Chair Conformational Structures A Conformational Analysis of Methylcyclohexane 1,3-Diaxial interactions of a tert-Butyl Group Disubstituted Cycloalkanes: Cis – trans Isomerism Cis –Trans isomerism and Conformational Structures of Cyclohexanes Bicyclic and Polycyclic Alkanes Chemical Reactions of Alkanes Synthesis of Alkanes and Cycloalkanes Hydrogenation of alkenes and alkynes 4 How to Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency Text Sections: 4.1-4.17. Homework: Chapter 4: 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 4.10, 4.11, 4.12, 4.15, 4.16, 4.17, 4.18, 4.19, 4.20, 4.21, 4.23, 4.24, 4.26, 4.27, 4.28, 4.29, 4.31, 4.33, 4.34, 4.35, 4.36, 4.37, 4.39, 4.40, 4.41, 4.42, 4.43, 4.46 MODULE5: Stereochemistry: Chiral Molecules Chirality and Stereochemistry Isomerism: Constitutional Isomers and Stereoisomers Enantiomers and Chiral Molecules Molecules having one Chirality Center are Chiral Tetrahedral versus Trigonal Stereogenic Center How to test for Chirality: Planes of symmetry Naming Enantiomers: The R, S –System How to Assign (R) and (S) Configurations Properties of Enantiomers: Optical Activity - specific rotation - Plane polarized light - The polarimeter Racemic forms - Racemic forms and Enantiomeric Excess The Synthesis of Chiral Molecules - racemic Mixtures Molecules with More than One Chirality Center - How to Draw Stereoisomers for Molecules having more than one Chirality Center - Meso compounds - How to name Compounds with more than one Chirality Center Fischer Projection Formulas How to Draw and Use Fischer Projections Stereoisomerism of Cyclic Compounds - Cyclohexane Derivatives Relating Configurations through Reactions in which No Bonds to the Stereogenic Carbon are broken Relative and Absolute Configurations Separation of Enantiomers: Resolution Text Sections: 5.1- 5.4, 5.6-5.10, 5-12 –5-17. Homework: Chapter 5: 5.4, 5.5, 5.6, 5.8, 5.9, 5.10, 5.11, 5.12, 5.13, 5.14, 5.18, 5.19, 5.21, 5.22, 5.23, 5.24, 5.26, 5.27, 5.28, 5.33, 5.34, 5.35, 5.39, 5.40(a-i), 55.42, 5.43, 5.45, 5.46, 5.47 MODULE6. Nucleophilic Substitutions: Properties and Substitution Reactions of Alkyl Halides and Alkyl Halides Nucleophilic Substitution Reactions Nucleophiles Leaving Groups Kinetics of a Nucleophilic Substitution Reaction: An SN2 Reaction - How do we Measure the Rate of This Reaction? - What is the Order of This Reaction? A Mechanism for SN2 Reaction The Stereochemistry of SN2 Reactions The Reaction of Tert-Butyl Chloride with Water A Mechanism for the SN1 Reaction Carbocations - The Structure of Carbocations - The Relative Stabilities of Carbocations The Stereochemistry of SN1 Reactions 5 - Reactions that Involve Racemization - Solvolysis Factor Affecting the Rate of SN1 and SN2 Reactions - The Effect of the Structure of the Substrate - The Effect of the Concentration and Strength of the Nucleophile - Solvent Effects in SN2 and SN1 Reactions - The Nature of the Leaving Group Organic Synthesis: Functional Group Transformations Using SN2 Reactions Text Sections: 6.1- 6.6, 6.8-6-14. Homework: Chapter 6: 6.1, 6.2, 6.3, 6.5, 6.7, 6.8, 6.9, 6.10, 6.12, 6.13,6.14, 6.15, 6.16, 6.18, 6.20, 6.21, 6.22, 6.27, 6.29, 6.30, 6.35, 6.40, 6.41 MODULE7. Alkenes and Alkynes: Properties and Synthesis. Elimination Reactions of Alkyl Halides Introduction PHYSICAL Properties of Alkenes and Alkynes The (E) – (Z) System for Designating Alkene Diastereomers How to Use the (E) –(Z) System Relative Stabilities of Alkenes - heat of reaction - overall relative stabilities of alkenes Cycloalkenes Synthesis of Alkenes: Elimination Reactions Dehydrohalogenation of Alkyl Halides - Bases Used in Dehydrohalogenation - Mechanism of Dehydrohalogenation The E2 Reaction - Zaitsev’s Rule: Formation of the more Substituted Alkene is Favored with a Small Bases - Formation of the Less Substituted Alkenes Using a Bulky Base - The Stereochemistry of E2 Reactions: The Orientation of Group in the Transition State How to Favor an E2 Mechanism Elimination and Substitution Reactions Compete with Each Other How to Determine Substitution or Elimination is Favored Elimination of Alcohols: Acid-Catalyzed Dehydration - Mechanism for Dehydration of Secondary and Tertiary Alcohols: An E1 Reaction - Carbocation Stability and Transition State Carbocation Stability and Occurrence of Molecular Rearrangements - Rearrangements During Dehydration of Secondary Alcohols - Rearrangement After Dehydration of a Primary Alcohol The Acidity of Terminal Alkynes Synthesis of Alkynes by Elimination Reactions Practical Considerations for Alkyne Synthesis by Double Dehyrohalogenation The Terminal Alkynes Can be converted to Nucleophiles for Carbon-Carbon Bond Formation General Principle of Structure and Reactivity Illustrated by the Alkylation of Alkynide Anion Text Sections: 7.1- 7-7, 7.9-7.10(a-b), 7.11-7.14 Homework: Chapter 7: 7.1, 7.2, 7.3, 7.4, 7.6, 7.7, 7.8, 7.10, 7. 11, 7.12, 7.13, 7.14, 7.15, 7.16, 7.17, 7.19, 7.22, 7.27, 7.28, 7.29, 7.30, 7.33, 7.34, 7.35, 7.36, 7.37, 7.38, 7.39, 7.43, 7.44, 7.44, 7.46, 7.47, 7.49, 7.50, 7.52, 7.53 T.W.GrahamSolomons , Craig B. Fryhle and Scott A. Snyder Organic Chemistry, 12th edition The End