REACTIVITY A ND E LECTRON-‐PUSHING A RROWS
organic c hemistry
reaction t ypes
Substitution: substituting one group for another group.
Elimination: eliminating two groups to form a pi bond.
Addition: adding two groups to remove a pi bond
stereochemistry o f r eactions
You need to use wedges and dashes: (1) around a stereocenter, or (2) when there are
cis/trans relationships around a ring.
Otherwise, you don’t need wedges and dashes.
When you attack an atom that is tetrahedral, you get one product.
When you attack an atom that is trigonal planar, you get two stereoisomer products, if
possible.
the r ule f or d etermining h ybridization
number of hybridized orbitals = number of attached atoms + number of lone pairs
2
Radicals are sp
hybridized.
molecular g eometry
3
An atom that is sp
hybridized with no lone pairs is tetrahedral.
2
An atom that is sp
hybridized with no lone pairs is trigonal planar.
single-‐swap r ule
If you make a single swap, while maintaining the same bond orientation, at a
stereocenter, you invert the configuration at that stereocenter.
3