Stereochemistry Flashcards
(10 cards)
Stereoisomers
isomers that have same formula and connectivity but differ in the position of the atoms in space. They possess one or more stereocenters
Stereocenter
a carbon atom bearing 4 different atoms or group of atoms
Chiral
any molecule that is nonsuperposable with its mirror image
Enantiomers
stereoisomers that are non superimposable mirror images
Properties:
have same chemical and physical properties in an achiral environment but they differ on the sign of rotation of plane polarized light
Opposite configuration at all chirality centers
Racemic mixture
a 1:1 (equimolar) mixture of two enantiomers
Optically Active
the ability of some compounds to rotate plane polarized light
Configuration of Stereocenters
Priority is based on the atomic number, i.e. H has lower priority than Cl. But methyl and ethyl both are attached to the stereocenter through carbon! In these cases, priority assignments proceed outward, to the next atoms. The Methyl carbon has 3 Hs attached while the Ethyl carbon has 2Hs and and a carbon (the terminal methyl group). Therefore, the latter gets higher priority.
Diastereomers
stereoisomers that are non-superimposable non-mirror images
Properties:
have different chemical and physical properties in any type of environment
opposite configurations at some chirality centers
E-Z system
(E)- : the higher priority groups are on the opposite side of the double bond
(Z)- : the higher priority groups are on the same side of the double bond
Confirmations
Different 3-D position for the same molecule