Organic Chemistry: Stereochemistry Flashcards
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E/Z nomenclature is used instead of cis/trans when:
Answer: Each double-bond carbon has different priority substituents
E/Z is required when substituents differ and cis/trans becomes ambiguous, using CIP priorities.
In the Z configuration, the two higher-priority groups are:
Answer: On the same side
Z (zusammen) means the higher-priority groups are on the same side of the double bond.
An inversion of configuration at a stereocenter during SN2 produces:
Answer: The opposite R/S designation (typically)
SN2 proceeds with backside attack, inverting the stereocenter and usually flipping R/S.
Which reaction mechanism typically gives a racemic product from a chiral starting material?
Answer: SN1 via a planar carbocation
SN1 forms a planar carbocation that can be attacked from either face, giving racemization.
Conformational isomers differ by:
Answer: Rotation about single bonds
Conformers interconvert by rotation about single (sigma) bonds without breaking any bonds.
The most stable conformation of cyclohexane places large substituents in the:
Answer: Equatorial position
Bulky groups prefer the equatorial position to minimize 1,3-diaxial strain.
A carbon attached to four different groups is called a:
Answer: Stereocenter (chiral center)
A carbon bonded to four distinct groups is a stereocenter, the basis of chirality.