Wednesday, December 31, 2008

Organic Lecture 4: Enantionmers, Diasteriomers, Optical Activity


We are going to continue with isomerism.

Enantiomers: non-superimposable mirror images. They can only occur when chiral centers are present. NOTE: two molecules that are enantiomers will always have opposite absolute configurations (one has R, the other will have S, and vice versa).

Optical Activity: a compound that rotates the plane of polarized light is said to be optically active.

**A pair of enantiomers will rotate plane-polarized light with equal magnitude, but in opposite directions

If it rotates clockwise it is said to be dextrorotarory (d), also denoted (+)

If it rotates counterclockwise it is said to be levorotatory (l), also denoted (-)

Specific rotation: the magnitude of rotation of plane-polarized light for any compound

**Racemic mixtures are not optically active

One last EXTREMELY IMPORTANT NOTE: (+) and (-) say nothing about whether the absolute configuration is R or S. Therefore, there is no correlation between the sign of rotation and the absolute configuration.

Diastereomers: stereoisomers that are not enantiomers; they are non-superimposable, non-mirror images. Take a look at the picture for a better understanding.

No comments:

Post a Comment