Organic Chemistry: Stereochemistry Flashcards
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How many stereoisomers are possible for a molecule with 3 stereocenters and no internal symmetry?
Answer: 8
The maximum number of stereoisomers is 2^n, so 2^3 = 8.
Two compounds are enantiomers. Which property differs between them?
Answer: Direction of plane-polarized light rotation
Enantiomers rotate plane-polarized light in equal but opposite directions while sharing all other physical properties.
A meso compound is best described as:
Answer: Achiral despite having stereocenters
A meso compound contains stereocenters but has an internal plane of symmetry, making it achiral.
What is the relationship between (2R,3R) and (2S,3R) of the same molecule?
Answer: Diastereomers
They differ at one stereocenter but not all, so they are diastereomers.
In assigning R/S, which atom gets highest priority?
Answer: Highest atomic number
CIP rules rank substituents by atomic number, highest first.
A racemic mixture has what observed optical rotation?
Answer: Zero
Equal amounts of two enantiomers cancel each other's rotation, giving zero.
Geometric (cis/trans) isomerism requires:
Answer: Restricted rotation such as a double bond or ring
Cis/trans isomerism arises when rotation is restricted, as in alkenes or rings.