Freshman Organic Chemistry I

Course Number
CHEM 125a
About the Course

This is the first semester in a two-semester introductory course focused on current theories of structure and mechanism in organic chemistry, their historical development, and their basis in experimental observation. The course is open to freshmen with excellent preparation in chemistry and physics, and it aims to develop both taste for original science and intellectual skills necessary for creative research.

Course Structure

This Yale College course, taught on campus three times per week for 50 minutes, was recorded for Open Yale Courses in Fall 2008.

Course Materials
Download all course pages [zip - 10MB]

Syllabus

Professor
J. Michael McBride, Richard M. Colgate Professor Emeritus of Chemistry
Description

This is the first semester in a two-semester introductory course focused on current theories of structure and mechanism in organic chemistry, their historical development, and their basis in experimental observation. The course is open to freshmen with excellent preparation in chemistry and physics, and it aims to develop both taste for original science and intellectual skills necessary for creative research.

Texts

Reading assignments, problem sets, PowerPoint presentations, and other resources for this course can be accessed from Professor McBride’s on-campus course website, which was developed for his Fall 2008 students. Please see Resources section for each individual lecture.

Requirements

The course grade is based on a 650-point system: 100 points for each of the three hour-long midterm examinations, 300 points for the three-hour final examination, and 50 points for participation in the course Wiki. In borderline cases, faithfulness in completing and submitting problem sets will be considered.

Grading

Midterm Examination 1: 100 points
Midterm Examination 2: 100 points
Midterm Examination 3: 100 points
Course Wiki: 50 points
Final Examination: 300 points

Sessions

Lecture 1 How Do You Know?
Lecture 2 Force Laws, Lewis Structures and Resonance
Lecture 3 Double Minima, Earnshaw's Theorem and Plum-Puddings
Lecture 4 Coping with Smallness and Scanning Probe Microscopy
Lecture 5 X-Ray Diffraction
Lecture 6 Seeing Bonds by Electron Difference Density
Lecture 7 Quantum Mechanical Kinetic Energy
Lecture 8 One-Dimensional Wave Functions
Lecture 9 Chladni Figures and One-Electron Atoms
Lecture 10 Reality and the Orbital Approximation
Exam 1 Midterm Exam 1
Lecture 11 Orbital Correction and Plum-Pudding Molecules
Lecture 12 Overlap and Atom-Pair Bonds
Lecture 13 Overlap and Energy-Match
Lecture 14 Checking Hybridization Theory with XH3
Lecture 15 Chemical Reactivity: SOMO, HOMO, and LUMO
Lecture 16 Recognizing Functional Groups
Lecture 17 Reaction Analogies and Carbonyl Reactivity
Lecture 18 Amide, Carboxylic Acid and Alkyl Lithium
Lecture 19 Oxygen and the Chemical Revolution (Beginning to 1789)
Exam 2 Midterm Exam 2
Lecture 20 Rise of the Atomic Theory (1790-1805)
Lecture 21 Berzelius to Liebig and Wöhler (1805-1832)
Lecture 22 Radical and Type Theories (1832-1850)
Lecture 23 Valence Theory and Constitutional Structure (1858)
Lecture 24 Determining Chemical Structure by Isomer Counting (1869)
Lecture 25 Models in 3D Space (1869-1877); Optical Isomers
Lecture 26 Van't Hoff's Tetrahedral Carbon and Chirality
Lecture 27 Communicating Molecular Structure in Diagrams and Words
Lecture 28 Stereochemical Nomenclature; Racemization and Resolution
Lecture 29 Preparing Single Enantiomers and the Mechanism of Optical Rotation
Exam 3 Midterm Exam 3
Lecture 30 Esomeprazole as an Example of Drug Testing and Usage
Lecture 31 Preparing Single Enantiomers and Conformational Energy
Lecture 32 Stereotopicity and Baeyer Strain Theory
Lecture 33 Conformational Energy and Molecular Mechanics
Lecture 34 Sharpless Oxidation Catalysts and the Conformation of Cycloalkanes
Lecture 35 Understanding Molecular Structure and Energy through Standard Bonds
Lecture 36 Bond Energies, the Boltzmann Factor and Entropy
Lecture 37 Potential Energy Surfaces, Transition State Theory and Reaction Mechanism
Exam 4 Final Exam