Deck 5: Stereoisomerism

Question 1

Locate the chirality center(s) in the following compound.

Answer 1

Question 2

What is the relationship between the following two compounds?

A) constitutional isomers
B) stereoisomers
C) identical
D) not isomers; different compounds entirely

Answer 2

constitutional isomers

Question 3

Shown below is the structure of Singulair (montelukast), a medication used to manage athsma. Is the alkene of montelukast cis, trans, or neither?

Answer 3

trans

Question 4

Shown below is the structure of the drug nicotine. Locate the chirality center(s) in the following compound.

Question 5

Is the following alkene cis, trans, or neither?

Question 6

What is the relationship between the following two compounds?

A) constitutional isomers
B) stereoisomers
C) identical
D) not isomers; different compounds entirely

Question 7

Shown below is the structure of Crestor (rosuvastatin), a medication used to reduce cholesterol. Is the highlighted alkene of rosuvastatin cis, trans, or neither?

Question 8

Locate the chirality center(s) in the following compound.

Question 9

Is the following alkene cis, trans, or neither?

Question 10

Is the alkene on the left in the molecule below cis, trans, or neither?

Question 11

What is the relationship between the following two compounds?

A) constitutional isomers
B) stereoisomers
C) identical
D) not isomers; different compounds entirely

Question 12

Is the following alkene cis, trans, or neither?

Question 13

Is the following alkene cis, trans, or neither?

Question 14

Draw all the isomers with molecular formula C₄H₈.

Question 15

What is the relationship between the following two compounds?

A) constitutional isomers
B) stereoisomers
C) identical
D) not isomers; different compounds entirely

Question 16

What is the relationship between the following two compounds?

A) constitutional isomers
B) stereoisomers
C) identical
D) not isomers; different compounds entirely

Question 17

Draw all the isomers with molecular formula C₄H₆.

Question 18

What is the relationship between the following two compounds?

A) constitutional isomers
B) stereoisomers
C) identical
D) not isomers; different compounds entirely

Question 19

Is the following alkene cis, trans, or neither?

Question 20

Locate the chirality center(s) in the following compound.

Question 21

Identify the relationship between the following two structures.

A) enantiomers
B) identical
C) neither

Question 22

Draw the enantiomer of the following compound.

Question 23

Locate the chirality center(s) in the following compound.

Question 24

Draw the enantiomer of the following compound.

Question 25

Assign the absolute configuration of the chirality center as R or S.

Question 26

Identify the relationship between the following two structures.

A) enantiomers
B) identical
C) neither

Question 27

Drawn below is the structure of Plavix (clopidogrel), a medication used to manage blood clots. Assign the absolute configuration of the chirality center as R or S.

Question 28

Draw the enantiomer of the following compound.

Question 29

Assign the absolute configuration of the chirality center as R or S.

Question 30

Assign the absolute configuration of the chirality center as R or S.

Question 31

Identify the relationship between the following two structures.

A) enantiomers
B) identical
C) neither

Question 32

Assign the absolute configuration of the chirality center as R or S.

Question 33

Assign the absolute configuration of the chirality center as R or S.

Question 34

Drawn below is the structure of Crestor (rosuvastatin), a medication used to reduce cholesterol. Assign the absolute configurations of the two chirality centers as R or S.

Question 35

Draw the enantiomer of the following compound.

Question 36

Identify the relationship between the following two structures.

A) enantiomers
B) identical
C) neither

Question 37

Drawn below is the structure of Singulair (montelukast), a medication used to manage athsma. Assign the absolute configuration of the chirality center as R or S.

Question 38

Draw the enantiomer of the following compound.

Question 39

Identify the relationship between the following two structures.

A) enantiomers
B) identical
C) neither

Question 40

Assign the absolute configuration of the chirality center as R or S.

Question 41

Which of the following is the correct IUPAC name of the following structure? SHAPE \* MERGEFORMAT

A) (S)-3-ethyl-2-methylhexane
B) (R)-3-ethyl-2-methylhexane
C) (S)-3-ethyl-2-methylpentane
D) (R)-3-ethyl-2-methylpentane

Question 42

What is the % ee of a sample of carvone that exhibits a specific rotation of −40, given that the specific rotation of (R)-carvone is −61?

Question 43

What is the specific rotation of pure (S)-carvone if a sample of (R)-carvone of 85% ee has a specific rotation of −52?

A) −61
B) 64
C) 0
D) 61

Question 44

Which of the following is the correct structure for the compound (S)-3-methylheptane.

A) I
B) II
C) III
D) IV

Question 45

Redraw the structure below as a wedge-dash structure and label any/all stereocenters with their absolute configuration.

Question 46

If a sample of carvone gives a specific rotation of −60 and the specific rotation of (R)-carvone is −61, does the unknown sample primarily have the R or S absolute configuration?

Question 47

Draw the structure of the compound (R)-4-ethyloctane.

Question 48

What is the % ee of a sample of carvone that exhibits a specific rotation of −20, given that the specific rotation of (R)-carvone is −61?

Question 49

Redraw the structure below as a wedge-dash structure and label all stereocenters with their absolute configuration.

Question 50

Provide an IUPAC name of the following compound.

Question 51

If a sample of carvone gives a specific rotation of 0 and the specific rotation of pure (R)-carvone is −61, what is the configuration of the unknown sample?

Question 52

Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.
I. -F II. -H III. -OH IV. -SH

Question 53

Which of the following is the correct IUPAC name of the following structure?

A) (S)-2-ethylhexane
B) (S)-3-methylheptane
C) (R)-2-ethylhexane
D) (R)-3-methylheptane

Question 54

Which of the following is the correct structure for the compound (R)-2-pentanol?

A) I
B) II
C) III
D) IV

Question 55

Draw the structure of the compound (S)-3-methylheptane.

Question 56

Drawn below is the structure of Cymbalta (duloxetine), a medication used to manage depression. Assign the absolute configuration of the chirality center as R or S.

Question 57

Provide an IUPAC name of the following compound.

Question 58

Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.
I. -CH₃ II. -CN III. -CH₂OH IV. -Br

Question 59

Identify the relationship between these two structures.

A) diastereomers
B) enantiomers
C) the same compound
D) different compounds

Question 60

Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.
I. -CH₂CH₃ II. -CHCH₂ III. -CCH IV. -CH₃

Question 61

What is the percentage of the S enantiomer in a sample of carvone that has a specific rotation of 10, given that the specific rotation of (R)-carvone is −61?

A) 42
B) 84
C) 16
D) 58

Question 62

What is the specific rotation of a sample of carvone that is an equal mixture of the R and S enantiomers? (R)- carvone has a specific rotation of −61.

A) −61
B) 64
C) 0
D) 61

Question 63

What is the percentage of the S enantiomer in a sample of carvone that has a specific rotation of 30, given that the specific rotation of (R)-carvone is −61?

A) 25.5%
B) 51%
C) 49%
D) 74.5%

Question 64

What is the relationship of the following two structures?

A) enantiomers
B) diastereomers
C) constitutional isomers
D) identical

Question 65

Draw a diastereomer of the following compound.

Question 66

Draw a diastereomer of the following compound.

Question 67

What is the relationship of the following two structures?

A) enantiomers
B) diastereomers
C) constitutional isomers
D) identical

Question 68

Draw the enantiomer of the following compound.

Question 69

What is the relationship of the following two structures?

A) enantiomers
B) diastereomers
C) constitutional isomers
D) identical

Question 70

Draw all the stereoisomers of the following compound.

Question 71

The structure of Crestor (rosuvastatin), a medication used to reduce cholesterol, is shown below. If the specific rotation for this compound is known to be +100, what would be the specific rotation for the stereoisomer shown at the right?

A) +100
B) -100
C) 0
D) Impossible to predict

Question 72

What is the relationship of the following two structures?

A) enantiomers
B) diastereomers
C) constitutional isomers
D) identical

Question 73

What is the relationship of the following two structures?

A) enantiomers
B) diastereomers
C) constitutional isomers
D) identical

Question 74

What is the percentage of the R enantiomer in a sample of limonene that has a specific rotation of −38, given that the specific rotation of (S)-limonene is −116?

Question 75

What is the percentage of the R enantiomer in a sample of carvone that has a specific rotation of 30, given that the specific rotation of (R)-carvone is −61?

A) 26%
B) 51%
C) 49%
D) 75%

Question 76

Draw the enantiomer of the following compound.

Question 77

Draw the enantiomer of the following compound.

Question 78

What is the percentage of the R enantiomer in a sample of carvone that has a specific rotation of 10, given that the specific rotation of (R)-carvone is −61?

A) 42
B) 84
C) 16
D) 58

Question 79

Draw a diastereomer of the following compound.

Question 80

What is the percentage of the R enantiomer in a sample of carvone that has a specific rotation of −20, given that the specific rotation of (R)-carvone is −61?

A) 20%
B) 66.5%
C) 33.5%
D) 61%