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.
- Racemization of isobornyl chloride via carbocations: a non-classical look at a classic mechanism. (Henry Rzepa, 2007)
- The mechanism for CO insertion into an alkyl borane (Don Craig problem sheet, 2007)
- Two problems in Stereoelectronic effects: The Anomeric effect
and the Tiffeneau-Demjanov Reaction (Alan Spivey problem sheet, 2006)
- The sulfonylation of naphthalene (2005)
- The asymmetric Strecker reaction: A new
light on the mechanism (Organic Synoptic problems II,
- Is Co(acac)3 aromatic?
- The synthesis of a Mobius annulene and
the Eschenmoser fragmentation (Organic problems,
- Pseudorotation in Trigonal bipyramidal,
square pyramidal and pentagonal bipyramidal systems
- A molecular orbital
illustration of the directing effects of electron withdrawing
and donating groups in benzene (2005)
- Felkin-Anh and acyloxyborane transition
states (2004, based on Problem sheet 2 by Alan
- Zimmerman-Traxler Transition states
(2004, based on Problem sheet 1 by Don Craig)
- From Double to Hextuple bonds
- Bio-mimetic Pericyclic reactions: Stereochemistry
of cycloaddition reactions (2004)
- 3D Models for Stereoelectronic and Steric
Models for Caryophyllene (2003).
vibrational modes for methylbutenyne (2003).
- Cyclohexane models showing
eclipsing/staggered interactions (2003)
of the diterpenoid core of natural products such as
tetrodecamycin. Taken from problem sheet 4, 2003.
- Electrophilic substitution in Furan,
pyrrole and thiophene and benzo derivatives (2002).
- S vs O
solvolysis rates: An example of neighbouring group
effects. Taken from problem sheet 5, 2002.
- 3D Models
of the Molecular Orbitals of simple molecules, including the
series CH3X, X=F...At.
of reactions involving Histrinicotoxin and
dicyclopentacyclo-octenyl ring systems. Taken from
Problem sheet 4, 2001.
- Models for
Sigmatropic Rearrangements. Taken from Problem sheet 4,
- Counting electrons in
Reaction Mechanisms. Adapted from the Pericyclic Lecture Course, 1999.
- Enol Borinates in Stereospecific C-C bond
formation. Taken from Set 1 organic problems, 1999.
- Diels Alder Intermediates in Xestoquinone
Synthesis. Taken from Set 6 organic problems,
- Diels Alder
Cycloaddition using a cavity-based template. Taken from
the Pericyclic Lecture
Ion rearrangements. Adapted from the Organic Modelling lecture course, 1998.
- 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
Copyright H. S. Rzepa, 1994-2007.