Freshman Organic Chemistry II

About the Course

This is a continuation of Freshman Organic Chemistry I (CHEM 125a), the introductory course on current theories of structure and mechanism in organic chemistry for students with excellent preparation in chemistry and physics. This semester treats simple and complex reaction mechanisms, spectroscopy, organic synthesis, and some molecules of nature.

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Course Structure

This Yale College course, taught on campus three times per week for 50 minutes, was recorded for Open Yale Courses in Spring 2011.

Course Materials

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About Professor J. Michael McBride

J. Michael McBride is the Richard M. Colgate Professor of Chemistry at Yale University. After undergraduate work at the College of Wooster and Harvard College, Professor McBride earned a PhD in physical organic chemistry at Harvard University. He joined the Yale Chemistry faculty in 1966, where he studies crystal growth and reactions in organic solids. His awards include the Prelog Medal, the Nobel Laureate Signature Award in Graduate Education, and the Catalyst Award of the Chemical Manufacturers Association for undergraduate education.

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Syllabus

Professor

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

Description

This is a continuation of Freshman Organic Chemistry I (CHEM 125a), the introductory course on current theories of structure and mechanism in organic chemistry for students with excellent preparation in chemistry and physics. This semester treats simple and complex reaction mechanisms, spectroscopy, organic synthesis, and some molecules of nature.

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 Spring 2011 students: https://webspace.yale.edu/chem125

Optional Text: Organic Chemistry, 4th edition, Maitland Jones, Jr. and Steven A. Fleming, W. W. Norton & Company, New York, 2010.

Requirements

Problem sets, three midterm examinations, final examination

Grading

Midterm Examination 1: 100 points
Midterm Examination 2: 100 points
Midterm Examination 3: 100 points
Final Examination: 300 points

Sessions

Lecture 1 Mechanism: How Energies and Kinetic Order Influence Reaction Rates
Lecture 2 Peculiar Rate Laws, Bond Dissociation Energies, and Relative Reactivities
Lecture 3 Rate and Selectivity in Radical-Chain Reactions
Lecture 4 Electronegativity, Bond Strength, Electrostatics, and Non-Bonded Interactions
Lecture 5 Solvation, H-Bonding, and Ionophores
Lecture 6 Brønsted Acidity and the Generality of Nucleophilic Substitution
Lecture 7 Nucleophilic Substitution Tools - Stereochemistry, Rate Law, Substrate, Nucleophile, Leaving Group
Lecture 8 Solvent, Leaving Group, Bridgehead Substitution, and Pentavalent Carbon
Lecture 9 Pentavalent Carbon? E2, SN1, E1
Lecture 10 Cation Intermediates – Alkenes: Formation, Addition, and Stability
Lecture 11 Carbocations and the Mechanism of Electrophilic Addition to Alkenes and Alkynes
Lecture 12 Nucleophilic Participation During Electrophilic Addition to Alkenes: Halogen, Carbene, and Borane
Lecture 13 Addition to Form Three-Membered Rings: Carbenoids and Epoxidation
Lecture 14 Epoxide Opening, Dipolar Cycloaddition, and Ozonolysis
Lecture 15 Metals and Catalysis in Alkene Oxidation, Hydrogenation, Metathesis, and Polymerization
Lecture 16 Isoprenoids, Rubber, and Tuning Polymer Properties
Lecture 17 Alkynes; Conjugation in Allylic Intermediates and Dienes
Lecture 18 Linear and Cyclic Conjugation Theory; 4n+2 Aromaticity
Lecture 19 Aromatic Transition States: Cycloaddition and Electrocyclic Reactions
Lecture 20 Electronic and Vibrational Spectroscopy
Lecture 21 Functional Groups and Fingerprints in IR Spectroscopy; Precession of Magnetic Nuclei
Lecture 22 Medical MRI and Chemical NMR
Lecture 23 Diamagnetic Anisotropy and Spin-Spin Splitting
Lecture 24 Higher-Order Effects, Dynamics, and the NMR Time Scale
Lecture 25 C-13 and 2D NMR – Electrophilic Aromatic Substitution
Lecture 26 Aromatic Substitution in Synthesis: Friedel-Crafts and Moses Gomberg
Lecture 27 Triphenylmethyl and an Introduction to Carbonyl Chemistry
Lecture 28 Mechanism and Equilibrium of Carbonyl Reactions
Lecture 29 Imines and Enamines; Oxidation and Reduction
Lecture 30 Oxidation States and Mechanisms
Lecture 31 Periodate Cleavage, Retrosynthesis, and Green Chemistry
Lecture 32 Measuring Bond Energies: Guest Lecture by Prof. G. Barney Ellison
Lecture 33 Green Chemistry; Acids and Acid Derivatives
Lecture 34 Acids and Acid Derivatives
Lecture 35 Acyl Insertions and α-Reactivity
Lecture 36 α-Reactivity and Condensation Reactions
Lecture 37 Proving the Configuration of Glucose and Synthesizing Two Unnatural Products
Lecture 38 Review: Synthesis of Cortisone

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Course Books and Other Related Titles

Yale University Press offers a 10% discount on the books used in CHEM 125b that it publishes, as well as on other related titles. A portion of the proceeds from your purchases will be donated for the ongoing support and development of the Open Yale Courses program.

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