Organic Chemistry · College

Organic Chemistry: Stereochemistry and Reaction Mechanisms

Stereochemistry concepts (R/S, E/Z, chirality) and reaction mechanism steps taught in a college organic chemistry sequence.

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What is a chiral center?
An atom (usually carbon) bonded to four different groups
How many stereoisomers does a molecule with one chiral center have?
Two (one pair of enantiomers)
Define enantiomers
Non-superimposable mirror images that rotate plane-polarized light in opposite directions
Define diastereomers
Stereoisomers that are not mirror images of each other
What does R/S nomenclature describe?
The three-dimensional spatial orientation around a chiral center
What is the first step in assigning R or S configuration?
Rank the four groups by atomic number using Cahn-Ingold-Prelog rules
After ranking groups 1-2-3, which direction means R configuration?
Clockwise (when group 4 points away)
After ranking groups 1-2-3, which direction means S configuration?
Counterclockwise (when group 4 points away)
Define a meso compound
A molecule with multiple chiral centers that is achiral due to an internal plane of symmetry
In a Fischer projection, what do horizontal bonds represent?
Bonds projecting forward toward the viewer (wedge bonds)
In a Fischer projection, what do vertical bonds represent?
Bonds pointing backward away from the viewer (hash bonds)
What is the E/Z nomenclature used for?
Describing the geometry (cis/trans) around a double bond
In E/Z nomenclature, what does E stand for?
Entgegen (German for opposite); the two highest-priority groups are on opposite sides of the double bond
In E/Z nomenclature, what does Z stand for?
Zusammen (German for together); the two highest-priority groups are on the same side of the double bond
What are the Cahn-Ingold-Prelog rules?
Priority rules for assigning 1-4 to groups in R/S and E/Z nomenclature based on atomic number

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