Chapter 5
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isomer
nonidentical molecules that have the same formula
constitutional isomer
same molecular formula but a different order of connectivity of atoms
stereoisomers
same molecular formula and constitution but a different spatial arrangement
regioselectivity
determines the position within a molecule a reaction occurs, guiding which region or direction is favored
stereoselectivity
focuses on the spatial arrangement of atoms, leading to the preferential formation of one stereoisomer over others
regioselectivity is about ________ a reaction happens on a molecules, while stereoselectivity is about ___________ atoms are arranged in the resulting product
“where”, “how”
geometric isomers
cis and trans
chiral atoms
bonded to 4 DIFFERENT groups of atoms
enantiomers
non-superimposable mirror images (all stereo centers switch)
diastereomers
stereoisomers, but NOT mirror images (cis and trans) (at least one (but not all) stereo centers switch)
Cohn-Ingold-Prelog Rules
• identify chiral atom (4 different groups) • assign priority by atomic number • tie = take a step out • rotate so that priority 4 is in the back • determine R vs S
R configuration
clockwise
S configuration
counterclockwise
2^n
• equation to determine the maximum number of stereoisomers • n=chiral centers