Physical organic chemistry
Undergraduate · Chemistry
Syllabus focus
Standard syllabus · Theoretical / proof-based
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Topics typically covered
Standard syllabus
Structure and bonding in organic chemistry
- Resonance, inductive, and hyperconjugative effects
- Aromaticity: Hückel's rule and antiaromaticity
- Steric effects: A-values, Thorpe–Ingold effect
- Torsional strain and conformational analysis
- Bond dissociation energies and radical stability
- Carbocation stability and rearrangements
- Carbanion structure and pKa correlations
- Carbene and nitrene intermediates (introduction)
- Biradicals and triplet vs singlet states
- Hammett equation and substituent constants (intro)
Reaction mechanisms and kinetics
- Reaction coordinates and transition states
- Hammond postulate and Curtin–Hammett principle
- Kinetic vs thermodynamic control
- Rate laws and mechanism determination
- Steady-state and pre-equilibrium approximations
- Isotope effects: primary and secondary kinetic isotope effects
- Linear free-energy relationships
- Marcus theory for electron transfer (overview)
- Solvent effects on reaction rates
- Catalysis: acid-base, nucleophilic, and organocatalysis
Reactive intermediates
- Carbocations: generation, trapping, and spectroscopy
- Carbanions: formation, aggregation, and reactivity
- Free radicals: initiation, propagation, termination
- Radical clocks and radical probe experiments
- Carbenes: singlet vs triplet, insertion reactions
- Nitrenes and oxenes (overview)
- Arenium ions in electrophilic aromatic substitution
- Benzyne and aryne intermediates
- Zwitterions and dipolar intermediates
- Matrix isolation spectroscopy of intermediates (intro)
Stereochemistry and pericyclic reactions
- Conformational effects on reactivity
- Stereoelectronic effects: anomeric, gauche, β-silicon effect
- Neighboring group participation
- Asymmetric induction: Cram's rule, Felkin–Anh model
- Pericyclic reactions: electrocyclic, cycloaddition, sigmatropic
- Woodward–Hoffmann rules and frontier molecular orbitals
- Diels–Alder reaction: regio- and stereoselectivity
- Claisen and Cope rearrangements
- Photochemical pericyclic reactions (overview)
- Molecular orbital analysis of reaction selectivity
Theoretical / proof-based
Quantitative structure–reactivity
- Brønsted catalysis law and pKa correlations
- Hammett plots: ρ values and reaction mechanisms
- Yukawa–Tsuno equation (where covered)
- Taft steric parameters (Es)
- Marcus cross-relation for electron transfer
- More O'Ferrall–Jencks diagrams for mechanisms
- Potential energy surface diagrams
- Computational characterization of transition states
- Activation parameters from Eyring plots
- Rigorous kinetic analysis of complex mechanisms
Advanced mechanistic analysis
- Probing mechanisms with isotopic labeling
- Stereochemical probes for concerted vs stepwise pathways
- Kinetic isotope effect theory and interpretation
- Heavy atom isotope effects
- Hammett–type correlations for aliphatic systems (σ* scales)
- Solvent isotope effects
- Laser flash photolysis for short-lived intermediates
- CIDNP and EPR detection of radical intermediates
- Cryogenic trapping and spectroscopic identification
- Designing experiments to distinguish competing mechanisms
Notes
Topics reflect common physical organic chemistry syllabi at US colleges and universities. Typically for upper-level chemistry majors. Strong organic chemistry and physical chemistry background expected.