Molecular Models For Organic Lectures

A feature of modern organic chemistry is that quantitative models can often provide considerable insight into the selectivity and reactivity of many organic reactions. This collection was prepared by Henry Rzepa and provides a set of such models, deriving from problem sets issued to students over the years, and of examples discussed in lectures.
  1. Racemization of isobornyl chloride via carbocations: a non-classical look at a classic mechanism. (Henry Rzepa, 2007)
  2. The mechanism for CO insertion into an alkyl borane (Don Craig problem sheet, 2007)
  3. Two problems in Stereoelectronic effects: The Anomeric effect and the Tiffeneau-Demjanov Reaction (Alan Spivey problem sheet, 2006)
  4. The sulfonylation of naphthalene (2005)
  5. The asymmetric Strecker reaction: A new light on the mechanism (Organic Synoptic problems II, 2005).
  6. Is Co(acac)3 aromatic? (2005)
  7. The synthesis of a Mobius annulene and the Eschenmoser fragmentation (Organic problems, 2005).
  8. Pseudorotation in Trigonal bipyramidal, square pyramidal and pentagonal bipyramidal systems (2005).
  9. A molecular orbital illustration of the directing effects of electron withdrawing and donating groups in benzene (2005)
  10. Felkin-Anh and acyloxyborane transition states (2004, based on Problem sheet 2 by Alan Armstrong)
  11. Zimmerman-Traxler Transition states (2004, based on Problem sheet 1 by Don Craig)
  12. From Double to Hextuple bonds (2004)
  13. Bio-mimetic Pericyclic reactions: Stereochemistry of cycloaddition reactions (2004)
  14. 3D Models for Stereoelectronic and Steric effects (2003).
  15. 3D Models for Caryophyllene (2003).
  16. Normal vibrational modes for methylbutenyne (2003).
  17. Cyclohexane models showing eclipsing/staggered interactions (2003)
  18. Synthesis of the diterpenoid core of natural products such as tetrodecamycin. Taken from problem sheet 4, 2003.
  19. Electrophilic substitution in Furan, pyrrole and thiophene and benzo derivatives (2002).
  20. S vs O solvolysis rates: An example of neighbouring group effects. Taken from problem sheet 5, 2002.
  21. 3D Models of the Molecular Orbitals of simple molecules, including the series CH3X, X=F...At.
  22. Mechanisms of reactions involving Histrinicotoxin and dicyclopentacyclo-octenyl ring systems. Taken from Problem sheet 4, 2001.
  23. Models for Sigmatropic Rearrangements. Taken from Problem sheet 4, 2000.
  24. Counting electrons in Reaction Mechanisms. Adapted from the Pericyclic Lecture Course, 1999.
  25. Enol Borinates in Stereospecific C-C bond formation. Taken from Set 1 organic problems, 1999.
  26. Diels Alder Intermediates in Xestoquinone Synthesis. Taken from Set 6 organic problems, 1998.
  27. Diels Alder Cycloaddition using a cavity-based template. Taken from the Pericyclic Lecture Course, 1998.
  28. Carbonium Ion rearrangements. Adapted from the Organic Modelling lecture course, 1998.
  29. Non-classical Norbornyl and Bromonium ions. Adapted from the Organic Modelling lecture course, 1998.

To view these models, you are advised to install a 3D chemistry model viewer on your computer. This can be most easily done by installing a plug-in to your browser such as Chime or Chem3D Net.

Copyright H. S. Rzepa, 1994-2007.