Question 1

A solution containing 0.08 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4°.What is the specific rotation of the S enantiomer?

Accepted Answer

A)  +50°
B)  -40°
C)  +40°
D)  -50°E) A) and D)
F) B) and C)

Question 2

How many stereoisomers are possible for a molecule with formula CH3CHBrCH(OH) CH3?

Accepted Answer

A)  1
B)  2
C)  3
D)  4E) A) and D)
F) A) and B)

Question 3

Which of the following molecules are chiral? I.cis-1,3-Dibromocyclohexane
II) 1-Bromo-1-methylcyclohexane
III) trans-1-Bromo-3-methylcyclohexane
IV) cis-1-Bromo-3-methylcyclohexane

Accepted Answer

A)  I,II
B)  II,III
C)  I,IV
D)  III,IVE) None of the above
F) B) and D)

Question 4

Which of the following compounds are chiral?

Accepted Answer

A)  I and II
B)  II and III
C)  III and IV
D)  I and IVE) None of the above
F) C) and D)

Question 5

How many stereogenic centers are present in menthol?

Accepted Answer

A)  1
B)  2
C)  3
D)  4E) A) and B)
F) A) and C)

Question 6

How many stereogenic centers are present in the following compound?

Accepted Answer

A)  1
B)  2
C)  3
D)  4E) B) and D)
F) A) and B)

Question 7

What is the relationship between the following compounds?

Accepted Answer

A)  Constitutional isomers
B)  Diastereomers
C)  Enantiomers
D)  IdenticalE) B) and C)
F) C) and D)

Question 8

Which of the following statements about meso compounds is not true?

Accepted Answer

A)  A meso compound generally has a plane of symmetry.
B)  A meso compound and its mirror image are identical.
C)  A meso compound is achiral.
D)  A meso compound is chiral.E) B) and D)
F) None of the above

Question 9

A reaction mixture is three parts of one enantiomer and one part of the other.What is the percent ee of this mixture?

Accepted Answer

A)  75
B)  40
C)  65
D)  50E) None of the above
F) A) and C)

Question 10

How many stereogenic centers are present in ephedrine,a bronchodilator and decongestant?

Accepted Answer

A)  0
B)  1
C)  2
D)  3E) All of the above
F) B) and C)

Question 11

What is the relationship between the following compounds?

Accepted Answer

A)  Constitutional isomers
B)  Diastereomers
C)  Enantiomers
D)  IdenticalE) B) and C)
F) A) and B)

Question 12

A solution containing 0.4 g/mL of a pure S enantiomer is a 1 dm polarimeter rotates plane polarized light by +5.6°.What is the rotation of a solution containing 0.8 g/mL of the S enantiomer in the same polarimeter?

Accepted Answer

A)  +5.6°
B)  +11.2°
C)  +2.8°
D)  +1.4°E) B) and C)
F) A) and B)

Question 13

How many stereogenic centers are present in gabapentin,used clinically to treat seizures and certain types of chronic pain?

Accepted Answer

A)  0
B)  1
C)  2
D)  3E) All of the above
F) A) and D)

Question 14

A natural product was isolated in the laboratory,and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of H2O.What is the specific rotation of this compound?

Accepted Answer

A)  -10°
B)  +100°
C)  +10°
D)  -100°E) None of the above
F) A) and D)

Question 15

Give the IUPAC name for the following compound:

Accepted Answer

A)  (1R,2R) -1,2-dimethylcyclopentane
B)  (1R,2S) -1,2-dimethylcyclopentane
C)  (1S,2R) -1,2-dimethylcyclopentane
D)  (1S,2S) -1,2-dimethylcyclopentaneE) None of the above
F) A) and B)

Question 16

What is the relationship between the following compounds?

Accepted Answer

A)  Constitutional isomers
B)  Diastereomers
C)  Enantiomers
D)  IdenticalE) A) and B)
F) A) and C)

Question 17

What is the relationship between the following compounds?

Accepted Answer

A)  Constitutional isomers
B)  Diastereomers
C)  Enantiomers
D)  IdenticalE) B) and D)
F) A) and C)

Question 18

Which of the following structures has the R configuration?

Accepted Answer

A)  Only I
B)  Only II
C)  Only I and II
D)  I,II,and IIIE) A) and D)
F) All of the above

Question 19

Which of the following molecules are chiral?

Accepted Answer

A)  II,III
B)  I,II
C)  I,IV
D)  III,IVE) None of the above
F) A) and B)

Question 20

How many stereogenic centers are present in the following molecule?

Accepted Answer

A)  1
B)  2
C)  4
D)  5E) None of the above
F) B) and C)

Exam 5: Stereochemistry

How many stereogenic centers are present in the following molecule?

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How many stereogenic centers are present in menthol?

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Give the IUPAC name for the following compound:

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Which of the following compounds are chiral?

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How many stereogenic centers are present in ephedrine,a bronchodilator and decongestant?

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What is the relationship between the following compounds?

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Which of the following structures has the R configuration?

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Which of the following molecules are chiral?

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What is the relationship between the following compounds?

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What is the relationship between the following compounds?

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Which of the following molecules are chiral? I.cis-1,3-Dibromocyclohexane II) 1-Bromo-1-methylcyclohexane III) trans-1-Bromo-3-methylcyclohexane IV) cis-1-Bromo-3-methylcyclohexane

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Which of the following statements about meso compounds is not true?

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How many stereoisomers are possible for a molecule with formula CH3CHBrCH(OH) CH3?

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What is the relationship between the following compounds?

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How many stereogenic centers are present in the following compound?

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A natural product was isolated in the laboratory,and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of H2O.What is the specific rotation of this compound?

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How many stereogenic centers are present in gabapentin,used clinically to treat seizures and certain types of chronic pain?

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A reaction mixture is three parts of one enantiomer and one part of the other.What is the percent ee of this mixture?

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A solution containing 0.08 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4°.What is the specific rotation of the S enantiomer?

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A solution containing 0.4 g/mL of a pure S enantiomer is a 1 dm polarimeter rotates plane polarized light by +5.6°.What is the rotation of a solution containing 0.8 g/mL of the S enantiomer in the same polarimeter?

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How many stereoisomers are possible for a molecule with formula CH₃CHBrCH(OH) CH₃?

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A natural product was isolated in the laboratory,and its observed rotation was +10° when measured in a 1 dm sample tube containing 1.0 g of compound in 10 mL of H₂O.What is the specific rotation of this compound?

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