Index:
Acidity
Alkanes
Aromaticity
- Aromaticity (PowerPoint)
- Aromaticity (PDF; better for smart phones)
- Aromaticity, the Da Vinci Code and the Golden Section (PowerPoint)
- Aromaticity, the Da Vinci Code and the Golden Section (PDF; better for smart phones)
- π-Molecular Orbitals of Benzene (JSmol) (all six MO's; version 1)
- π-Molecular Orbitals of Benzene (JSmol) (all six MO's; one at a time, version 2)
Carbohydrates
Conformation
- A Values
- Methane
- Ethane
- Propane
- Butane
- 2-Butene
- Rotational Barrier Plot of C2-C5 Acyclic Alkanes
- Rotational Barriers of Simple Alkanes (PowerPoint)
- Rotational Barriers of Simple Alkanes (PDF; better for smart phones)
- Baeyer and Cycloalkanes (PowerPoint)
- Baeyer and Cycloalkanes (PDF; better for smart phones)
- Cyclopropane
- Cyclobutane
- Cyclopentane
- Cyclohexane
- Strain in Cycloalkanes
- Diamond Lattice (JSmol)
- Hexamethylenetetramine
- Drawing cyclohexane (PowerPoint)
- Drawing cyclohexane (PDF; better for smart phones)
- Methylcyclohexane: equatorial vs. axial
- trans-1,4-Dimethylcyclohexane
- cis-1,4-Dimethylcyclohexane
- trans-1,3-Dimethylcyclohexane
- cis-1,3-Dimethylcyclohexane
- trans-1,2-Dimethylcyclohexane
- cis-1,2-Dimethylcyclohexane
- cis-1,4-(1-Bromo-4-isopropylcyclohexane)
- trans- and cis- Decalin
- Carbohydrate Configurations (PowerPoint)
- Carbohydrate Configurations (PDF; better for smart phones)
Degrees of Unsaturation
Dipoles/Electrostatic Potential Maps
History of Organic Chemistry
- Here at Yale
- The Composition and Structure of Ether
- The Etherin Theory
- The History of Ether (Powerpoint)
- The History of Ether (PDF; better for smart phones)
- A Brief History of Organic Chemistry (PowerPoint)
- A Brief History of Organic Chemistry (PDF; better for smart phones)
- The Evolution of Formulas and Structure in Organic Chemistry During the 19th Century (PowerPoint)
- The Evolution of Formulas and Structure in Organic Chemistry During the 19th Century (PDF; better for smart phones)
- Kekule's 19 Formulas of Acetic Acid (1867)
- Van't Hoff: The Arrangement of Atoms in Space
- Emil Fischer and the Structure of Glucose
- Rosanoff's Classification of Aldoses
- Gay-Lussac's Method for Determining Vapor Density
- Silliman's Commentary in Elements of Chemistry on Wohler's Urea (1831)
- Nobel Laureates in Chemistry
- Adolf von Baeyer
- Jons Jacob Berzelius
- Michael Faraday -(Christmas Lectures)
- Emil Fischer
- August Wilhelm Hofmann
- August Kekule
- Antoine Lavoisier
- Justus Liebig
- Louis Pasteur
- William Henry Perkin
- Jacobus van't Hoff's Molecular Models
- Friedrich
Wohler
- On the Web
- General Information
- Classic Papers and Other Items of
Interest
- Memoir on the Nature of the Principle which Combines with Metals during their Calcination and which Increases their Weight-Lavoisier-(1778)
- Essay on the Cause of Chemical Proportions, and on Some Circumstances Relating to Them.-Berzelius
- The Synthesis of Artificial Urea-Wohler (1828)
- On the Present State of Organic Chemistry (Radical Theory)-Dumas and Liebig (1837)
- Early Type Theory-On the Constitution of Acetic and Trichloroacetic Acid-Dumas (1839)
- Sketch of a Course on Chemical Philosophy-Cannizzaro-(1858)
- van't Hoff and the Tetrahedral Carbon (1874)
- Classic Papers I
- Classic Papers II
- Russell Marker and the Pill
- General Information
Hybridization
Mechanisms
- On the Halogenation of Alkenes
- On the Epoxidation of Alkenes
- From acetic acid to cholesterol
- Hydroboration
- Dimethyl Sulfoxide Oxidations
- Osazone Formation
- Oxymercuration (PowerPoint)
- Oxymercuration (PDF; better for smart phones)
- Ozonolysis
- Pericyclic Reactions
- Sharpless Asymmetric Epoxidation
- Sharpless Asymmetric Dihydroxylation
- Varrentrapp and the Zipper Reaction
- Wolff-Kishner Type Reactions
Old Exams
[Chem220a: F '04, Wade 5th ed.; Chem220a/Chem221b: '05, Wade 6th ed.; Chem225b: S '06, Vollhardt, 4th ed.; S '08, F '09, F '10, Wade 6th ed.; Chem220: F ' 11, Loudon, 5th ed.; S '13, Wade 8th ed.]
First term:
- Fall '04, Chem220a (HTML) x1 x2 x3 x4 final
- Fall '04, Chem220a (PDF) x1 x2 x3 x4 final
- Fall '05, Chem220a (HTML) x1 x2 x3 x4 final
- Fall '05, Chem220a (PDF) x1 x2 x3 x4 final
- Spring '06, Chem 225b (HTML) x1 x2 x3 x4 final
- Spring '06, Chem 225b (PDF) x1 x2 x3 x4 final
- Spring '08 Chem 225b (HTML) x1 x2 x3 final
- Spring '08 Chem 225b (PDF) x1 x2 x3 final
- Fall '09, Chem220a (HTML) x1 x2 x3 final
- Fall '09, Chem220a (PDF) x1 x2 x3 final
- Fall '10 Chem220 (HTML) x1 x2 x3 final
- Fall '10 Chem220 (PDF) x1 x2 x3 final
- Fall '11 Chem220 (HTML) x1 x2 x3 final; answer keys: x1 x2 x3 final
- Spring '13 Chem220 (HTML) x1 x2 x3 final; answer keys: x3 final
Old Problem Sets
[ '05, Wade 6th ed.; F '09, F '10, Wade 6th ed.; F '11, Loudon 5th ed; S '13, Wade 8th ed.]
First term:
- Fall '09 Chem220 (HTML) PS1 PS2 PS3 PS4 PS5 PS6 PS7 PS8 PS9 PS10
- Fall '10 Chem220 (HTML) PS1 PS2 PS3 PS4 PS5 PS6 PS7 PS8 PS9 PS10
- Fall '11 Chem220 (HTML) PS1 PS2 PS3 PS4 PS5 PS6 PS7 PS8 PS9 PS10
- Spring '13 Chem220 (HTML) PS1 PS2 PS3 PS4 PS5 PS6 PS7 PS8 PS9 PS10
- Spring '13 Chem220: Solutions (HTML) PS1 PS2 PS3 PS4 PS5 PS6 PS7 PS8 PS9 PS10
-
Second term:
-
On the
Lighter Side of Organic Chemistry
- Aromaticity, the Da Vinci Code and the Golden Section (PowerPoint)
- Aromaticity, the Da Vinci Code and the Golden Section (PDF; better for smart phones)
- Good Will Hunting
- High Tech vs. Low Tech
- How Not to get A's in Organic Chemistry
- How to Get an A- in Organic Chemistry
- Don't Party Too Much Before an Organic Chemistry Exam
- I
Hate Organic
- Left-Handed Bias
- Molecular Models in 1870
- More on the Lighter Side Yale Only
- On Being Prepared for the ORGO Final
- Professor Liebowitz's Duck
- Things They Don't Teach You in High School
- Wohler and Urea
- No-Cal
Sugar
Orbitals
- Aromaticity (PowerPoint)
- Aromaticity (PDF; better for smart phones)
- Sigma Bonds from p-Orbitals: Fluorine
- sp Hybrid Orbital
- sp2 Hybrid Orbital
- sp3 Hybrid Orbital
- π-Molecular Orbitals of Benzene (JSmol) (all six MO's; version 1)
- π-Molecular Orbitals of Benzene (JSmol) (all six MO's; one at a time, version 2)
- Molecular Orbitals of Acetylene
- Molecular Orbitals of Acetylene (JSmol) (all twelve MO's; version 1)
- Molecular Orbitals of Acetylene (JSmol) (all twelve MO's; one at a time, version 2)
- π-Molecular Orbitals of 1,3-Butadiene-I (JSmol)
- π-Molecular Orbitals of 1,3-Butadiene-II (JSmol)
- π-Molecular Orbitals of 1,3,5-Hexatriene-I (JSmol)
- π-Molecular Orbitals of 1,3,5-Hexatriene-II (JSmol)
- π-Molecular Orbitals of 1,3,5,7-Octatetraene-I (JSmol)
- π-Molecular Orbitals of 1,3,5,7-Octatetraene-II (JSmol)
- Molecular Orbitals of Ethane
- Molecular Orbitals of Ethylene
- π-Molecular Orbitals of Ethylene-I (JSmol) New
- π-Molecular Orbitals of Ethylene-II (JSmol) New
- Molecular Orbitals of Ethylene (JSmol) (all fourteen MO's; version 1)
- Molecular Orbitals of Ethylene (JSmol) (all fourteen MO's; one at a time, version 2)
- Molecular Orbitals of Formaldehyde (JSmol) (all twelve MO's; version 1)
- Molecular Orbitals of Formaldehyde (JSmol) (all twelve MO's; one at a time, version 2)
- Molecular Orbitals of Hydrogen (JSmol)
- Molecular Orbitals of Methane
- Pericyclic Reactions
- Pericyclic Reactions (PowerPoint)
- Pericyclic Reactions (PDF; better for smart phones)
- More on MO's Pericyclic and Electrocyclic Reactions (PowerPoint)
- More on MO's Pericyclic and Electrocyclic Reactions (PDF; better for smart phones)
- The Orbitron: Atomic and Molecular Orbitals
Organic Reactions Go Online (ORGO)
Oxidation Levels
Periodic Table of the Elements
pKa
Radicals
Redox Reactions
Resources on the Web
- Spectroscopy/Spectrometry
- Solving NMR Spectral Problems (UCLA)
- Solving NMR Spectral Problems (Notre Dame)
- More NMR Spectral Problems
- More on NMR Spectroscopy (Wake Forest)
- The Basics of NMR (UCalgary)
- NMR Spectroscopy (Michigan State)
- Karplus Equation
- Introduction to Infrared Spectroscopy (Michigan State)
- Visible and Ultraviolet Spectroscopy (Michigan State)
- What is Mass Spectrometry?
- Molecular Modeling
- Nomenclature
- Potpourri
- General Interest
Stereochemistry
- Introduction
- Exercises 1 2 3 4 5 6 7 8 9 10
- Cahn-Ingold-Prelog (CIP): Rules and Examples
- Chirotopicity and Stereogenicity
- R/S Configuration Primer
- R/S Configurations of 2,6-Disubstituted Adamantanes
- Cahn-Ingold-Prelog (CIP) Rules - 1982
- Cahn-Ingold-Prelog (CIP) Rules - 2013
- E/Z-Configuration
- R/S-E/Z Configuration Exercises
- The Inositols
- The Metaldehydes
- Axial Chirality Primer
- Axial Chirality Exercises
- Planar Chirality
- R/S-Spiro Compounds
- R/S-Spiro Exercises
- Assigning r/s-Configurations to Achiral Compounds
- More on Rings and Digraphs
- Facial, Enantiotopic and Diastereotopic Descriptors
- Chirality of Shells (Powerpoint)
- Chirality of Shells (PDF; better for smart phones)
- On Stereochemistry and Chirality (Powerpoint)
- On Stereochemistry and Chirality (PDF; better for smart phones)
- SN2 vs. E2 (Powerpoint)
- SN2 vs. E2 (PDF; better for smart phones)
- Optical Rotation Calculations
- Carbohydrate Configurations (PowerPoint)
- Carbohydrate Configurations (PDF; better for smart phones)
- Stereochemical Terminology - 2006 Yale Only
- On the Meaning of Meso - 2008 Yale Only
- Cahn-Ingold-Prelog Rules - 1966 Yale Only
- C-I-P Rules Revision - 1982 Yale Only
- C-I-P Rules Revision - 2013
- Stereoisomerism and Local Chirality - Mislow/Siegel - 1984 Yale Only
- Molecular Structure and Chirality - 1987 Yale Only
Thermochemistry
- Average Bond Energies (Heats of Atomization)
- Heats of Combustion, Heats of Formation, and Bond Dissociation Energies (Powerpoint)
- Heats of Combustion, Heats of Formation, and Bond Dissociation Energies (PDF; better for smart phones)
- Hess's Law of Constant Heat Summation
- Reaction Coordinates/Eact (PowerPoint)
- Reaction Coordinates/Eact (PDF; better for smart phones)
- Strain in Cycloalkanes
- Table of Bond Dissociation Energies (Wade)
- Table of Bond Dissociation Energies (Loudon)
- Table of Heats of Formation
- Group Additivity Values - Acyclic Aliphatic Alkanes
- Thermal Properties of n-Alkanes: ΔHo
- Geminal Repulsion and C-H Bond Energy Yale Only
- Heats of Formation of Alkenes and Their Heats of Hydrogenation
- Homodesmotic Reactions
Web of Reactions