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Chemistry 161 (350) 1 Chem261 MODULE 1: The Basics: Bonding and Molecular Structure The Structural Theory of Organic Chemistry - isomers: the important of structural formulas - the tetrahedral shape of methane - ionic bonds - covalent bonds Writing Lewis Structures Exceptions to the Octet Rule Formal Charge Summary of Formal Charges Resonance Summary of Rules for Resonance Quantum Mechanics Atomic Orbitals and Electron Configuration Molecular Orbitals The Structure Of Methane And Ethane: sp3 Hybridization The structure of Methane The Structure of Ethane The Structure of Ethene (Ethylene): sp2 Hybridization Restricted Rotation and the Double Bond Cis-Trans Isomerism The Structure of Ethyne (Acetylene): Sp Hybridization Bond Lengths of Ethylene, Ethene, and Ethane A Summary of Important Concepts that Come From Quantum Mechanics Molecular Geometry: The Valence Shell Electron Pair Repulsion Model - methane - ammonia - water - boron trifluoride - beryllium hydride - carbon dioxide How to interpret and Write Structural Formulas for cyclic and acyclic molecules - dash structural formulas - condensed structural formulas - bond-line formulas - three-dimensional formulas Text Sections: 1.2-1.17 Chapter1 Homework: 1.3, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.13, 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, 1.33, 1.34, 1.35, 1.36, 1.37, 1.38, 1.39, 1.40, 1.41, 1.42, 1.43, 1.44, 1.45, 150 MODULE 2:Families of Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared (IR) Spectroscopy Hydrocarbons - alkanes - alkenes - alkynes - benzene: A representative Aromatic hydrocarbon Polar Covalent Bonds Polar and Nonpolar Molecules Dipole Moments in Alkenes Functional Groups - alkyl groups and the symbol R - phenyl and benzyl groups 2 - alkyl halides or haloalkanes - alcohols - ethers - amines - aldehydes and ketones - carboxylic acids - esters - amides - nitriles Summary of Important Families of Organic Compounds Physical Properties and Molecular Structures - ion-ion forces - dipole –dipole forces - hydrogen bonds - van der walls forces - solubilities - guidelines for water solubility Infrared Spectroscopy: An Instrumental Method for Detecting Functional groups - hydrocarbons - alcohols and phenols - carboxylic acids and esters - aldehydes, ketones - amines - amides - nitriles How to gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency Text Sections: 2.1-2.17, 4.17 Chapter 2 Homework: 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2. 9, 2.10, 2.12, 2.13, 2.16, 2.17, 2.18, 2.19, 2.20, 2.21, 2.22, 2.23, 2.24, 2.25, 2.26, 2.27, 2.28, 2.29, 2.30, 2.31, 2.32, 2.33, 2.34, 2.35, 2.36, 2.37, 2.38, 2.39, 2.40, 2.41, 2.42, 2.45, 2.46, 2.47, 2.48, 2.49, 2.50, 2.51, 2.52, 2.53, 2.54, 2.55, 2.56, 2.57 MODULE 3: An Introduction to Organic Reactions: Acids and Bases Reactions and their Mechanisms Homolysis and Heterolysis of Covalent Bonds Acid-Base Reactions - the Bronsted-Lowry Defination of acids and Bases - the lewis Definition of Acids and Bases - opposite charge attract Heterolysis of Bonds to Carbon: Carbocations and Carbanions Electrophiles and Nucleophiles The Use of Curved Arrows in Illustrating Reactions The strength of 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 Water Solubility as the Result of Salt Formation The Relationships between Structure and Acidity - the effect of hybridization - inductive effects The Acidity of Carboxylic Acids - an explanation based on resonance effects - an explanation based on inductive effects - inductive effects of other groups - the effect of solvent on acidity 3 Organic Compounds as Bases A Mechanism for an Organic Reaction Acids and Bases in Nonaqueous Solutions Acids – Bases Reactions and the Synthesis of Deuterium and tritium-Labeled Compounds Text Sections: 3.1-3.8, 3.11-3.16. Chapter3 Homework: 3.1, 3.2, 3.3, 3.5, 3.7, 3.8, 3.9, 3.10, 3.14, 3.15, 3.16,3.18, 3.18, 3.20, 3.21, 3.22, 3.23, 3.24, 3.25, 3.26, 3.27, 3.29, 3.31, 3.32, 3.33, 3.34, 3.35,3.37, 3.43, 3.44 MODULE4: Nomenclature and Conformations of Alkanes and Cycoalkanes Introduction to alkanes and Cycloalkane Shape of Alkanes IUPAC Nomenclature of Alkanes, Alkyl Halide, and Alcohols - 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 Nomenclature of Cycloalkanes - monocyclic compounds - bicyclic compounds Nomenclature of Alkenes and Cycloalkenes Nomenclature of 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 How to Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency Text Sections: 4.1-4.17. Chapter 4 Home work: 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, 4.25, 4.26, 4.27, 4.28, 4.29, 4.31, 4.32, 4.33, 4.34, 4.35, 4.36, 4.37, 4.39, 4.40, 4.41, 4.42, 4.43, 4.45, 4.48 MODULE5: Stereochemistry: Chiral Molecules Isomerism: Constitutional Isomers and Stereoisomers Enantiomers and Chiral Molecules A Single Chirality Center Causes a Molecule to be Chiral How to test for Chirality: Planes of symmetry 4 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 The Origin of optical Activity Racemic forms Racemic forms and Enantiomeric Excess The Synthesis of Chiral Molecules - racemic forms Moclecules with 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 - Pasteur’s method for separating enantiomers - Current method for resolution of enantiomers Compounds with Stereogenic Center other than Carbon Text Sections: 5.1- 5.4, 5.6-5.10, 5-12 –5-17. Chapter 5 Homework: 5.2, 5.4, 5.5, 5.6, 5.8, 5.9, 5.10, 5.11, 5.12, 5.13, 5.14, 5.16, 5.17, 5.18, 5.19, 5.20, 5.21, 5.22, 5.23, 5.24, 5.25, 5.26, 5.27, 5.285.33, 5.34, 5.35, 5.36, 5.37, 5.38, 5.39(not q), 55.41, 5.42, 5.44, 5.45, 5.46 MODULE 6.Ionic Reactions: Nucleophilic Substitution and Elimination Reactions of Alkyl Halides Organic Halides Physical Properties of Organic Halides Nucleophilic Substitution Reactions - nucleophiles - leaving groups Kinetic 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 the SN2 Reaction Transition State Theory: Free – Energy Diagrams The Stereochemistry of SN2 Reactions The Reaction of tert-Butyl chloride with hydroxide Ion: An SN1 Reaction Multistep Reactions and the Rate-Determining Step A Mechanism for the SN1 Reaction Carbocations - the structure of carbocations - the relative stabilities of carbocations The Stereochemistry of SN1 Reactions - reactions that involved Racemization, solvolysis Factors Affecting the Rates 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 on SN2 reactions: Polar protic and aprotic solvents - solvent effects on SN1 reactions: The ionizing ability of the solvent - the nature of leaving group - the unreactivity of vinylic and phenyl halides 5 - The Hammond-Leffler Postulate Summary: SN1 versus SN2 Organic Synthesis: Functional Group Transformations Using SN2 Reactions Elimination Reactions of Alkyl Halides - dehydrohalogenation - bases used in dehydrohalogenation - mechanism of dehydrohalogenations The E2 Reaction The E1 Reaction How to determine Whether Substitution or Elimination is Favored - SN2 versus E2 - tertiary halide: SN1 versus E1 - overall summary Text Sections: 6.1- 6.6, 6.8-6-19. Chapter 6 Homework: 6.1, 6.26.3, 6.5,6.6, 6.7, 6.8, 6.9, 6.10, 6.12, 6.136.14, 6.15, 6.16, 6.18, 6.19 (a, b, only) ,6.20, 6.21, 6.22, 6.23, 6.26, 6.27, 6.29, 6.30, 6.31, 6.33, 6.34, 6.37, 6.38, 6.41, 6.46, 6.47. MODULE7. Alkenes and Alkynes: Properties and Synthesis, Elimination Reactions of Alkyl Halides Introduction The (E) – (Z) System for Designating Alkene Diastereomers Relative Stabilities of Alkenes - heat of reaction - overall relative stabilities of alkenes Cycloalkenes Synthesis of Alkenes via Elimination Reactions Dehydrohalogenation of Alkyl Halides How to Favor an E2 Mechanism - Zaitsev’s rule: Formation
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