20.3 Stereoisomers Isomers: molecules with the same molecular formula, but different structural formulas.

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Presentation transcript:

20.3 Stereoisomers Isomers: molecules with the same molecular formula, but different structural formulas.

1.) Structural isomers have a different order of bonding: C 4 H 10

2.) Stereoisomers have the same bonding, but differ in their arrangement in space. Two categories i. Conformational isomers interconvert by rotation about a sigma (single) bond.

ii. Configurational isomers can only be interconverted by the breaking of bonds. Two classifications a.Cis-trans and E/Z b.Optical isomerism

Cis-trans isomers: Isomers that differ in their arrangement about restricted bond rotation. cis- Latin for "on this side” trans- Latin for "across" cis-2-butene (cis-but-2-ene) trans-2-butene (trans-but-2-ene)

cis-1,3-dichlorocyclobutane trans-1,3-dichlorocyclobutane

E/Z isomers: Isomers based on the Cahn-Ingold- Prelog (CIP) rules which assign priority around a double bond based on the atomic numbers of attached atoms.

Here the chlorines have a higher priority (atomic #) than H Both chlorines on the same side (together): Z Chlorines on opposite sides: E E and Z come from German words: E from entgegen (opposite) Z from zusammen (together)

cis-1-,2-dichloroethene trans-1-,2-dichloroethene [ Z ]-1-,2-dichloroethene or [ E ]-1-,2-dichloroethene or

[ Z ]-1-bromo-2-chloro-1-iodoethene However, when all atoms around the double are different, only the E/Z system will work… Here Cl and I have the highest priority (atomic #) on their respective carbons. [ E ]-1-bromo-2-chloro-1-iodoethene

Optical isomers: Isomers that have two possible arrangements of four different atoms or groups bonded to the same carbon atom. This will always occur whenever a carbon is bonded to four different atoms and/or groups. This property is called chirality (from the Latin chiro, meaning "hand").

Optical isomers will rotate polarized light: D-form: clockwise rotation [from the Latin dextro (right)] L-form: counterclockwise rotation [from the Latin levo (left)]

Optical isomers are called enantiomers (from the Latin enantio, meaning “opposite”). A racemic mixture contains equal amounts of two enantiomers and is optically inactive - i.e., each cancels the effect of the other. Enantiomers have identical physical and chemical properties, but may have different physiological effects. For example: The artificial sweetener aspartame is an optical isomer, one of its enantiomers tastes sweet, the other bitter.

Note: Diastereomers are not mirror images of each other. Aspartame is an example of a diastereomer, a stereoisomer that has two or more chiral carbons. Aspartame has two. Can you find them?