3D structures - configuration vs. conformation
various conventions for showing 3D
Newman projections, Fischer projections, dash/wedge, sawhorse, etc.
types of isomerism (Figure 2.2)
molecular symmetry
symmetry elements - inversion (point), rotation (axis), reflection (plane)
point groups
chirality
asymmetric - no symmetry element
dissymmetric - has a symmetry element but is chiral (e.g., allenes)
atropisomers - dissymmetric due to hindered rotation (e.g., biphenyls)
designation of configuration - (R) and (S) - priority rules
applications to dissymmetric, atropisomers, helical molecules
symbolism for uncertain stereochemistry (p 83)
designation of relative cis & trans (e.g., for 1,4-substituted cyclohexanes)
special terminology
(E) & (Z) - double bonds
syn & anti - heteroatom double bonds, some other uses
endo & exo - bicyclics
a & b - steroids, carbohydrates
D & L - carbohydrates
anomers - carbohydrates
epimers - for multiple chiral centers
erythro & threo - for two chiral centers
meso
stereoselective / stereospecific
regioselective
tacticity - polymer stereochemistry
optical activity
specific rotation
molecular rotation
optical purity
enantiomeric excess
ORD, CD
designation of substituent relationships
homotopic / heterotopic / enantiotopic / diastereotopic (Figure 2.31)
magnetic equivalence (NMR)
prochiral
re & si faces of sp2 centers