Course Notes

Subject Description
Advanced Organic Chemistry bonding, organic reactions, reactivity
Computational Chemistry tutorials on how to use Gaussian
NMR Spectroscopy 1D and 2D methods, coupling constants, stereochemistry, pulse sequences
Experimental Organic Chemistry lab procedures for advanced undergraduates

Advanced Organic Chemistry

These course notes are a reinterpretation of the Chem 206 course notes created by Professor David A. Evans. If you would like to use them, please contact me. I can provide the corresponding ChemDraw files on request.

  • Energy and Reactivity
    free energy surface, Hammond postulate, Curtin–Hammett principle, Mayr scales, reactivity-selectivity

  • Bonding
    multielectron atoms, LCAO method, natural bond orbitals, resonance, anomeric effect, Bent’s rule

  • Pericyclic Reactions
    π-bonding, aromaticity, Dewar–Zimmerman, electrocyclizations, cycloadditions, sigmatropic shifts

  • Acyclic Conformational Analysis
    gauche and syn-pentane interactions, olefins, allylic strain, Thorpe–Ingold

  • Acyclic Stereocontrol
    hydroboration, directed reactions, epoxidation, Burgi–Dunitz, Cram chelate, Felkin–Anh–Eisenstein

  • Aldol Reaction
    Zimmerman–Traxler, enolate and aldehyde facial selectivity, double stereodifferentiating reactions

  • Aldol Reactions Cheat Sheet
    the key diastereoselective reactions and their transition structures

  • Small Ring Conformational Analysis
    types of strain, A values, Furst-Plattner, fused systems, oxocarbenium ions

  • Conformational Analysis of Macrocycles
    medium and large rings, peripheral attack, transannular reactions; courtesy of Dr. Joe Wzorek

  • Computational Chemistry I
    potential energy surface, optimization, basis sets, single point energies, accuracy

  • Computational Chemistry II
    computed KIEs, Singleton method, distinguishing between mechanisms, solvation

  • Nucleophilic Substitution
    endocyclic restriction, Baldwin’s rules, ion pairing, SN1 vs SN2

  • Acidity
    measurement, gas vs. solution phase, hybridization, induction vs. resonance, solvation effects

  • Organolithium Aggregates
    aggregates, enthalpy vs. entropy, HMPA and TMEDA, continuous variation, kinetics, optimizing reactions

  • Tetrahedral Intermediates
    ester and acetal hydrolysis, linear free energy, direct observation, Weinreb amides

  • Hydrogen Bonding
    donor-acceptor vs. electrostatic views, optimal geometry, charge and resonance asssistance, cooperativity

  • π-π Stacking and Cation-π Interactions
    optimal geometries, electrostatics and dispersion, Hunter–Sanders/Houk–Wheeler models, catalysis

  • N-Heterocyclic Carbenes
    bonding, Wanzlick equilibrium, benzoin reaction, Stetter reaction, asymmetric catalysis

  • First-Order Kinetics
    rate laws, approach to equilibrium, two-step system, Michaelis–Menten system, “1+rate” laws

  • Applications of Kinetics
    Halpern–Landis hydrogenation, reaction progress kinetic analysis, same vs. different excess

  • Rate Laws
    elementary reactions, differential vs. integral methods, two-step system, catalytic rate laws

  • Linear Free Energy Relationships
    Hammett equation, curvature, alternative references, Taft/Charton/Sterimol parameters, 2D LFERs

  • Kinetic Isotope Effects
    zero-point energy, hybridization, geometry, Hammond postulate, tunnelling, heavy atom effects

  • Competitive KIEs
    absolute rates vs. competition, inter- vs. intramolecular KIEs, competition equations

  • Rates and Temperature
    Arrehnius vs. Eyring, data analysis, interpretation of enthalpy and entropy

Computational Chemistry

This is a series of tutorials designed to cover the basics of performing routine calculations in Gaussian. The instructions are tailored for the Odyssey Cluster at Harvard University, but will mostly work for Gaussian in general.

NMR Spectroscopy

These course notes were previously used to teach Chem 117 at Harvard University.

Experimental Organic Chemistry

These lab experiments have been used in the past for Chem 135 at Harvard University. If you would like to use them, please contact me. I thank Dr. Andreas Roetheli for helping me to develop these laboratory procedures.