Chirality Practice Problems (Answer Key)
Carey, 8th Edition, Chapter 7
1. Determine if each of the following molecules are chiral. Mark all chiral centers.
2. Identify and label all carbon chiral centers as R or S for the following compounds.
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Chirality Practice Problems (Answer Key)
Carey, 8th Edition, Chapter 7
3. Determine the R or S configuration for each of these compounds. Note that they are all
Fischer Projections.
4. Classify each of the following pairs of molecules as enantiomers, diastereomers, or
identical. Label any molecules that are meso. Keep in mind the “most powerful
definitions” for each of these stereoisomers.
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Chirality Practice Problems (Answer Key)
Carey, 8th Edition, Chapter 7
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Chirality Practice Problems (Answer Key)
Carey, 8th Edition, Chapter 7
5. Draw the structure of each molecule. Be careful that your creature possesses the correct
stereochemistry.
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Chirality Practice Problems (Answer Key)
Carey, 8th Edition, Chapter 7
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Chirality Practice Problems (Answer Key)
Carey, 8th Edition, Chapter 7
6. Complete the following reactions by supplying the missing information, be that
product(s), reagent(s), or reactant(s). For each reaction, identify any chiral centers that
were created and assign R or S. Also, state whether the product mixture is optically active
– if it is not, give a reason why. NOTE: only one product has been drawn for each
reaction, but other stereoisomers may exist for a given reaction.
Though one stereoisomer has been drawn, note that an equal amount of the enantiomer would
also be produced. That is, the product solution would be racemic, so it would not be optically
active. The giveaway is that our starting molecule had no chiral centers and no unique spatial
restrictions.
Because the tert-butanol is so large, the ring is fixed in this configuration (think of chairs). As
such, the ending solution should be optically active. Note that we started with a (presumably)
pure starting material with specific stereochemistry (optically active).
A stereoisomer would also be produced, creating a racemic mixture. Optically-inactive product
solution.
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Chirality Practice Problems (Answer Key)
Carey, 8th Edition, Chapter 7
The first reaction eliminates the alcohol to form a double bond towards the downward
hydrogen; doing so destroys the chiral center (with hydrogen). Hence, the second reaction will
generate a racemic mixture of the final product. Optically-inactive product mixture.
Recall that this is a syn-addition reaction. If the deuterium were to approach the double bond
from the top, they would encounter steric hindrance from the overshadowing methyl groups
on the bridge. It is far easier for the deuterium to add across the double bond when they come
from the bottom of the molecule. Overall, the reaction will be very selective towards a
downward stereochemistry for the deuterium, generating an optically active solution.
Possibly helpful “equations”:
(Optically inactive reactant) + (optically inactive reagent) = (optically inactive product)
(Optically active reactant) + (optically inactive reagent) = (possible optically active product,
depending on the type of reaction)
(Optically inactive reactant) + (optically active reagent) = (possible optically active product)
(Optically active reactant) + (optically active reagent) = (optically active product)
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