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University Of PennsylvaniaCollege of General StudiesProfessor William A. Price, Ph.D.
CHEM 241-601Organic Chemistry, 9th EditionBy T.W. Graham Solomons
From the Bark of the Pacific Yew Tree
Introduction: Structure and BondingAtomic structureLewis StructuresResonanceStructural FormulasAcids and Bases
Nucleus is a Tiny Fraction of the Volume of an Atom
Orbitals are Probabilities
2s Orbital Has a Node
The p Orbital
px, py, pz
Electron Configurations
Lewis Dot Structure of Methane
Tetrahderal Geometry
Bonding Characteristics of Period 2 Elements
Saturated with Hydrogen
All Have the Same GeometryAll Have 4 Regions of Electron Density
A Saturated Hydrocarbon
Nitromethane
Nitromethane has 2 Formal Charges
Both Resonance Structures Contribute to the Actual Structure
Resonance RulesCannot break single (sigma) bondsOnly electrons move, not atoms3 possibilities:Lone pair of e- to adjacent bond positionForms p bond- p bond to adjacent atom- p bond to adjacent bond position
Curved Arrow Formalism Shows flow of electrons
Resonance Stabilization of IonsPos. charge is delocalized
Bonding Pattens for C, N, and O
Common Cationic, Neutral and Anionic Forms
Two Nonequivalent Resonance Structures in Formaldehyde
Resonance in Acetate Anion
Resonance in [CH2NH2]+
Propose Lewis StructuresH2CO2b) O3 c) N2O
d) NH3Oe) C2H3ClO f) C2H5NO
ProblemDraw [NO2]+ and [NO2]-. Which ion has a localized charge and which has a delocalized charge. Explain.
Drawing Structures
Octane Representations
Condensed Formulas
Line-Angle Structures are Often Used as a Short-hand
Line-Angle Structures
Line-Angle structure Superimposed on Lewis Structure
Double Bonds are Shown
For Cyclic Structures, Draw the Corresponding Polygon
Some Steroids
Adrogenic/Anabolic Steroids
Anabolic Steroids
Benzene can be drawn as one of two resonance structures
Some Line-Angle Structures