MU Chemistry 210 WS97
Catalog of Things-to-Study

Geometrical Isomers (cis-trans, E/Z) of Alkenes
Ability to recognize and to name cis and trans isomers
Ability to recognize and to name E and Z isomers
Know the CIP rules for E/Z nomenclature
Ability to apply the sequence rule
Ability to provide examples for these kinds of geometrical isomers
Knowledge of how E/Z isomers interconvert
Knowledge of the magnitude of barriers to rotation about double bond

Configurational Isomers
Knowledge of the definition of terms
chirality, enantiomer, diastereoieomer, meso form, optical activity
Ability to recognize asymmetric centers
Ability to recognize and generate Fischer Projections
Ability to recognize and to name L and D isomers
Ability to recognize and to name R and S isomers
Ability to provide examples for enantiomers, meso-forms, and diastereoisomers
Knowledge as to differences/similarities in phyical and chemical properties of nonchiral molecules, enantiomers and diastereoisomers
Knowledge of how enantiomers can be separated (resolution)

Conformational, Geometrical and Configurational Isomers of Cycloalkanes
Focus on 3-, 4- and 6-membered cycloalkanes
Ability to draw chair and boat forms of cyclohexanes
Ability to recognize axial and equatorial positions
Ability to judge preferential conformations of simple cyclohexane derivatives
Ability to recognize and name cis-trans isomers of cycloalkanes
Ability to recognize and name chiral structures
Having an idea of the magnitude of the barrier to ring flips (conformational change) and cis-trans interconversions (involves sigma bond cleavage!)

Halogenation of Alkanes & Radical Chemistry
Homolysis and magnitudes of most important bond dissociation energies
Stabilization mechanisms (alkyl, vinyl, phenyl)
Chlorination of Methane
Forward and backwards! You should know this in your sleep.
Knowledge of selectivity issues
tertiary > secondary > primary > methyl
chlorination versus bromination
Knowledge of what potential energy diagrams are
What are the axes?
What are minima and transition states?
Where do the activation barriers show up?
Where do the reaction energies show up?
Knowledge of Hammond's Postulate
What are early and late transition states?
Ability to apply the HP to the selectivity differences in chlorination and bromination of alkanes.