Acidity
Alkanes
Carbohydrates
Conformation
- A Values
- Methane
- Ethane
- Propane
- Butane
- 2-Butene
- Rotational Barrier Plot of C2-C5 Acyclic Alkanes
- Rotational Barriers of Simple Alkanes (PowerPoint)
- Baeyer and Cycloalkanes (PowerPoint)
- Cyclopropane
- Cyclobutane
- Cyclopentane
- Cyclohexane
- Strain in Cycloalkanes
- Diamond Lattice (Jmol)
- Hexamethylenetetramine
- Drawing cyclohexane (PowerPoint)
- 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)
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)
- A Brief History of Organic Chemistry (PowerPoint)
- The Evolution of Formulas and Structure in Organic Chemistry During the 19th Century (PowerPoint)
- 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
- nobel Laureates in ChemistryGay-Lussac Method for Determining Vapor Density
- Silliman's Commentary in Elements of Chemistry on Wohler's Urea (1831)
- Nobel Laureates in Chemistry
- 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)
- On the Artificial Production of Urea (F. Wöhler, 1828)
- Essay on the Cause of Chemical Proportions, and on Some Circumstances Relating to Them:...-Berzelius
- 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)
- Wöhler's S.C.H.Windler letter to Liebig on Dumas's Substitution Theory-(1840)
- Sketch of a Course on Chemical Philosophy-Cannizzaro-(1858)
- van't Hoff and the Tetrahedral Carbon (1874)
- Classic Papers I
- Classic Papers II
- General Information
Mechanisms
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.]
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
- For second term exams, see the archival version of Chem221b ('05) at http://classes.yale.edu/04-05/chem221b/studyaids.html#oldexams
Old Problem Sets
[F '04, Wade 5th ed.; '05, Wade 6th ed.; S '06, Vollhardt, 4th ed.; S '08, F '09, F '10, Wade 6th ed.; F '11, Loudon 5th ed.]
First term:
- Fall '04, Chem220a (HTML) PS1 PS2 PS3 PS4 PS5 PS6 PS7 PS8 PS9 PS10
- Fall '04, Chem220a (PDF) PS1 PS2 PS3 PS4 PS5 PS6 PS7 PS8 PS9 PS10
- Fall '05, Chem220a (HTML) PS1 PS2 PS3 PS4 PS5 PS6 PS7 PS8 PS9 PS10
- Fall '05, Chem220a (PDF) PS1 PS2 PS3 PS4 PS5 PS6 PS7 PS8 PS9 PS10
- Spring '06, Chem225b (HTML) PS1 PS2 PS3 PS4 PS5 PS6 PS7 PS8 PS9 PS10
- Spring '06, Chem225b (PDF) PS1 PS2 PS3 PS4 PS5 PS6 PS7 PS8 PS9 PS10
- Spring '08 Chem225b (HTML) PS1 PS2 PS3 PS4 PS5 PS6 PS7 PS8 PS9 PS10
- Spring '08 Chem225b (PDF) PS1 PS2 PS3 PS4 PS5 PS6 PS7 PS8 PS9 PS10
- Fall '09 Chem220 (HTML) PS1 PS2 PS3 PS4 PS5 PS6 PS7 PS8 PS9 PS10
- Fall '09 Chem220 (PDF) 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
-
Second term:
-
For older second term problem sets, see the archival version of Chem221b ('05) at http://classes.yale.edu/04-05/chem221b/studyaids.html#oldexams
On the
Lighter Side of Organic Chemistry
- Aromaticity, the Da Vinci Code and the Golden Section (PowerPoint)
- Baeyer and the Golden Section (PowerPoint)
- Good Will Hunting
- Good Will Hunting - "Have You Studied Organic Chemistry" (YouTube)
- 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)
- Sigma Bonds from p-Orbitals: Fluorine
- sp Hybrid Orbital
- sp2 Hybrid Orbital
- sp3 Hybrid Orbital
- π-Molecular Orbitals of Benzene (Jmol)
- Molecular Orbitals of Acetylene
- Molecular Orbitals of Acetylene (Jmol) (all twelve MO's)
- Molecular Orbitals of Ethane
- Molecular Orbitals of Ethane (Jmol)
- Molecular Orbitals of Ethylene
- Molecular Orbitals of Ethylene (Jmol)
- Molecular Orbitals of Ethylene (Jmol) (all fourteen MO's)
- Molecular Orbitals of Formaldehyde (Jmol)
- Molecular Orbitals of Hydrogen (Jmol)
- Molecular Orbitals of Methane
- Molecular Orbitals of Methyl Chloride (Jmol)
- Pericyclic Reactions
- Pericyclic Reactions (PowerPoint)
- A Quantum Primer: Introduction to Orbitals (PSU)
- 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
(If you know of other links that should be here, mail to: frederick.ziegler@yale.edu.)
- 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 (RIT)
- NMR Spectroscopy I (Michigan State)
- NMR Spectroscopy II (Michigan State)
- Karplus Equation
- Introduction to Infrared Spectroscopy
- Visible and Ultraviolet Spectroscopy
- What is Mass Spectrometry?
- Flashcards of Chemical Reactions
- IUPAC Rules of Nomenclature
- IUPAC Chemical Terminology
- On Edwin Abbott's Flatland ----> The Online Text
- Molecule of the Month
- The Plattner Story by H. G. Wells (1898)
- Classic Organic Reactions
- Virtual Molecular Model Kit (YouTube Tutorial)
- A Quantum Primer: Introduction to Orbitals (Penn State)
- The Orbitron: Atomic and Molecular Orbitals
Stereochemistry
- Introduction
- Exercises 1 2 3 4 5 6 7 8 9 10
- RS Convention
- Facial, Enantiotopic and Diastereotopic Descriptors
- Chirality of Shells (Powerpoint)
- More on Stereochemistry and Chirality (Powerpoint)
- Optical Rotation Calculations
- SN2/E2 (Powerpoint)
- 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
- 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)
- Hess's Law of Constant Heat Summation
- Reaction Coordinates/Eact (PowerPoint)
- Strain in Cycloalkanes
- Table of Bond Dissociation Energies (Wade)
- Table of Bond Dissociation Energies (Loudon)
- Table of Heats of Formation
- 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
Web of Reactions