Organic Chemistry I PHS 2025 Fall 2013 Section 1 Lecture Topics Homework: I. a. b. c. d. Organic Chemistry: Introduction to Organic Chemistry Chapter 1- Structure & Bonding: 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12. Chapter 2-Polar Covalent Bonds: Acids & Bases: 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 2.10, 2.11, 2.12. Chapter 3-Organic Compounds: Alkanes and Their Stereochemistry: 3.1, 3.2, 3.3, 3.4, 3.6, 3.7. Chapter 4-The Nucleus: A Chemist View: 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9. Lecture Topics: Chapter 1-Structure & Bonding Atomic Structure: The Nucleus Define: Isotope Atomic Structure: Orbital Define: Orbital Electron Shell Node Know: Shape of s-orbital Shape of p-orbital Shape of d-orbital How many orbitals in the s-sublevel How many orbitals in the p-sublevel How many orbitals in the d-sublevel Atomic Structure: Electron Configuration Define: Ground-State Electron Configuration Know: How to write the electron configuration using the aufbau principle, Pauli Exclusion Principle, & Hund’s Rule Development of Chemical Bonding Theory Define: Valence Electrons Covalent Bonds Electron Dot Structure Line-Bond Structure Know: How to draw electron dot structures How to draw line-bond structure Describing the Chemical Bonds: Valence Bond Theory Define: Valence Bond Sigma () Bond Bond Length sp3 Hybrid Orbital & Structure of Methane Define: sp3 Hybrid Bond Angle Describe: sp3 hybrid orbitals in Methane sp3 Hybrid Orbital & Structure of Ethane Define: Single Bond Describe: sp3 hybrid orbitals in Ethane sp2 Hybrid Orbital & Structure of Ethylene Define: Double Bond sp2 hybrid orbital pi () bond Describe: sp2 hybrid orbital structure of ethylene Know: How to draw electron dot structure of ethylene How to draw the line-bond structure of ethylene Compare and contrast & bonds sp Hybrid Orbital & Structure of Acetylene Define: Triple Bond sp hybrid orbital Describe: sp hybrid orbital structure of acetylene Know: How to draw electron dot structure of acetylene How to draw the line-bond structure of acetylene Compare and contrast & bonds in triple and double bonds How the relationships of bond strength & bond length in methane, ethane, ethylene, & acetylene Hybridization of Nitrogen, Oxygen, Phosphorous, & Sulfur Know: Bond angles & hybridization of bonds connected to nitrogen, oxygen, phosphorous, & sulfur. Describing Chemical Bonds: Molecular Orbital Theory Define: Molecular Orbital Theory Bonding MO Antibonding MO Drawing Chemical Structure Define: Condensed Structure Skeletal Structure Know: Rules for drawing skeletal structure How to interpret a line-bond structure Chapter 2-Polar Covalent Bonds: Acids & Bases Polar Covalent Bonds: Electronegativity Define: Polar Covalent Bonds Electronegativity Inductive Effect Know: What is the implication of electronegativity on the polar covalent bond and the inductive effect Polar Covalent Bond: Dipole Moment Define: Dipole Moment Know: What is the implication of the dipole moment Formal Charge Define: Formal Charge Know: How to determine the formal charge for each atom Resonance Define: Resonance Form Resonance Hybrid Rules for Resonance Forms Know: Different Resonance Forms Drawing Resonance Forms Know: How to Draw Resonance Forms How to Draw Resonance Forms for Amine How to Draw Resonance Forms for Radical Acids & Bases: The Bronsted-Lowry Definition Define: Bronsted-Lowry Acid Bronsted-Lowry Base Conjugate Acid Conjugate Base Acid & Base Strength Define: Acidity Constant (Ka) Know: Based on Ka and pKa, determine the strength of acids Predicting Acid-Base Reaction from pKa values Know: How to predict acid strength from pKa How to calculate Ka & pKa Organic Acids & Organic Bases Define: Organic Acids Organic Bases Know: How to form organic acids How to form organic bases Acids & Bases: Lewis Definition Define: Lewis Acid Lewis Base Know: How to use curved arrows to show electron flow Noncovalent Interactions Between Molecules Define: Noncovalent Interactions Hydrogen Bonds Dispersive Forces Dipole Know: What are the implications of noncovalent interactions Chapter 3-Organic Compounds: Alkanes and Their Stereochemistry Functional Groups Define: Functional Groups Know: Functional Groups-Names & Structures Alkanes & Alkane Isomers Define: Alkanes Hydrocarbon Saturated Straight-Chain Alkane Branched-Chain Alkane Isomer Constitutional Isomer Know: Prefix names of hydrocarbons How to draw the line-bond structure of hydrocarbons Alkyl Groups Define: Alkyl Group Primary Secondary Tertiary Quaternary Naming Alkanes Define: Substituents Know: How to name organic molecules How to name alkanes Convert chemical name into line-bond structure Properties of Alkanes Know: Trends of Boiling Point & Melting Point of Alkanes Conformation of Ethane Define: Stereochemistry Conformation Conformers Newman Projection Staggered Eclipsed Torsional Strain Know: Potential Energy of Staggered vs Eclipsed Conformations Conformation of other Alkanes Define: Anti Conformation Gauche Conformation Steric Strain Know: The potential energy implications of the anti vs gauche conformation How to draw Newman Projections Chapter 4-Organic Compounds: Cycloalkanes & Their Stereochemistry Naming Cycloalkanes Define: Cycloalkane Alicyclic (Aliphatic Cyclic) Know: How to name cycloalkanes Cis-Trans Isomerism in Cycloalkanes Define: Cis-isomer Trans-isomer Stereoisomers Stereochemistry Know: Difference between constitutional isomers vs stereoisomers Stability of Cycloalkanes: Ring Strain Define: Angle Strain Torsional Strain Steric Strain Conformation of Cycloalkanes Know: Conformation of Cyclopropane Conformation of Cyclobutane Conformation of Cyclopentane Conformation of Cyclohexane Define: Chair Conformation Boat Conformation Know: Draw Cyclohexane in the Chair Conformation Draw Cyclohexane in the Boat Conformation Implication of chair vs boat conformation Axial & Equatorial Bonds in Cyclohexane Define: Axial Bond Equatorial Bond Know: How to draw chair conformation of substituted cyclohexane Conformation of Monosubstituted Cyclohexane Define: 1,3 diaxial interaction Know: Implication of diaxial steric strain Conformation of Disubstituted Cyclohexane Define: Conformational Analysis Know: Implication of cis- vs trans- conformation of dialkyl cyclohexane How to determine the most stable conformation of dialkyl cyclohexane Conformation of Polycyclic Molecules Define: Polycyclic Bicycloalkane Know: Implication of cis- vs trans- decalin