Deck 5: Stereoisomerism

Question 1

Is the following alkene cis, trans, or neither?

Answer 1

cis

Question 2

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

Answer 2

trans

Question 3

Is the following alkene cis, trans, or neither?

Answer 3

neither

Question 4

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

Question 5

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

Question 6

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

Question 7

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

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 following alkene 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

Draw all the isomers with molecular formula C₄H₆.

Question 13

What is the relationship between the following two compounds?

A) Constitutional isomers
B) Stereoisomers
C) Identical
D) Not isomers; different compounds entirely.

Question 14

What is the relationship between the following two compounds?

A) Constitutional isomers
B) Stereoisomers
C) Identical
D) Not isomers; different compounds entirely.

Question 15

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

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

What is the relationship between the following two compounds?

A) Constitutional isomers
B) Stereoisomers
C) Identical
D) Not isomers; different compounds entirely.

Question 18

Draw all the isomers with molecular formula C₄H₈.

Question 19

What is the relationship between the following two compounds?

A) Constitutional isomers
B) Stereoisomers
C) Identical
D) Not isomers; different compounds entirely.

Question 20

Is the following alkene cis, trans, or neither?

Question 21

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 22

Draw the enantiomer of the following compound.

Question 23

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

Question 24

Identify the relationship between the following two structures.

A) Enantiomers
B) Identical
C) Neither

Question 25

Identify the relationship between the following two structures.

A) Enantiomers
B) Identical
C) Neither

Question 26

Draw the enantiomer of the following compound.

Question 27

Identify the relationship between the following two structures.

A) Enantiomers
B) Identical
C) Neither

Question 28

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

Question 29

Draw the enantiomer of the following compound.

Question 30

Identify the relationship between the following two structures.

A) Enantiomers
B) Identical
C) Neither

Question 31

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

Question 32

Draw the enantiomer of the following compound.

Question 33

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

Question 34

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

Question 35

Identify the relationship between the following two structures.

A) Enantiomers
B) Identical
C) Neither

Question 36

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

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

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 40

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

Question 41

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 42

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

A)
B)
C)
D)

Question 43

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 44

Provide an IUPAC name of the following compound.

Question 45

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 46

Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.

A) -CH₃
B) -CN
C) -CH₂OH
D) -Br

Question 47

What is the specific rotation of pure (S)-carvone if a sample of (R)-carvone of 85% ee has a specific rotation of −54?

Question 48

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 49

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 50

Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.

A) -F
B) -H
C) -OH
D) -SH

Question 51

What is the specific rotation of pure (S)-carvone if a sample of (R)-carvone of 85% ee has a specific rotation of −54?

A) −61
B) 64
C) 0
D) 61

Question 52

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 53

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

A)
B)
C)
D)

Question 54

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 55

Rank the following from highest to lowest priority according to the Cahn-Ingold-Prelog system.

A) -CH₂CH₃
B) -CHCH₂
C) -CCH
D) -CH₃

Question 56

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

Question 57

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

Question 58

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 59

Provide an IUPAC name of the following compound.

Question 60

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

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 61

What is the relationship of the following two structures?

A) Enantiomers
B) Diastereomers
C) Constitutional isomers
D) Identical

Question 62

Draw the enantiomer of the following compound.

Question 63

Draw a diastereomer of the following compound.

Question 64

Draw all the stereoisomers of the following compound.

Question 65

Draw a diastereomer of the following compound.

Question 66

Draw all the stereoisomers of the following compound.

Question 67

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%

Question 68

Draw the enantiomer of the following compound.

Question 69

Draw a diastereomer of the following compound.

Question 70

Draw the enantiomer of the following compound.

Question 71

Which of the following choices is a diastereomer of the first structure shown.

A)
B)
C)
D)

Question 72

What is the relationship of the following two structures?

A) Enantiomers
B) Diastereomers
C) Constitutional isomers
D) Identical

Question 73

Which of the following choices is a diastereomer of the first structure shown.

A)
B)
C)
D)

Question 74

Which of the following choices is a diastereomer of the first structure shown.

A)
B)
C)
D)

Question 75

What is the relationship of the following two structures?

A) Enantiomers
B) Diastereomers
C) Constitutional isomers
D) Identical

Question 76

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?

Question 77

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 78

What is the relationship of the following two structures?

A) Enantiomers
B) Diastereomers
C) Constitutional isomers
D) Identical

Question 79

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 80

What is the relationship of the following two structures?

A) Enantiomers
B) Diastereomers
C) Constitutional isomers
D) Identical