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