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How many stereoisomers of 4-bromo-2-pentanol, CH3CH(OH) CH2CHBrCH3, exist?


A) 1
B) 2
C) 3
D) 4

E) None of the above
F) B) and C)

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Which of the following statements is true?


A) All mirror images are enantiomers
B) All molecules that have stereocenter centers are chiral
C) Isomers that are not superposable on their mirror images are enantiomers
D) Superposable structural isomers are enantiomers

E) None of the above
F) All of the above

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Complete the following diagram so that it represents (S)-2-butanol. Complete the following diagram so that it represents (S)-2-butanol.

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Which of the following is the definition of a meso compound?


A) A molecule with stereocenter centers which is chiral
B) A molecule with stereocenter centers which is not chiral
C) A diastereomer with no stereocenter centers
D) A chiral compound with more than one stereocenter center

E) A) and D)
F) C) and D)

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Which of the following structures represent the same stereoisomer? Which of the following structures represent the same stereoisomer? A) only 1 and 2 B) only 1 and 3 C) only 2 and 3 D) 1, 2 and 3


A) only 1 and 2
B) only 1 and 3
C) only 2 and 3
D) 1, 2 and 3

E) A) and B)
F) A) and C)

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Which of the following is a use of atropisomers?


A) Used for the kinetic resolution of tertiary alcohols
B) Used for the kinetic resolution of secondary alcohols
C) Used for the kinetic resolution of primary alcohols
D) Used as a hydrogen bond catalyst in a single component domino reaction

E) A) and D)
F) A) and B)

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Complete the following zig-zag structure so that it represents (2R,3S)-3-chlorobutan-2-ol. Complete the following zig-zag structure so that it represents (2R,3S)-3-chlorobutan-2-ol.

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Complete the following zig-zag structure so that it represents (2R,3S)-2,3-butanediol. Complete the following zig-zag structure so that it represents (2R,3S)-2,3-butanediol.

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How many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane?


A) 3
B) 4
C) 5
D) 6

E) A) and D)
F) B) and C)

Correct Answer

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A pure sample of the R enantiomer of a compound has a specific rotation, [α], of −15°. A solution containing 0.6 g/mL of a mixture of enantiomers rotates plane polarized light by −3° in a 1 dm polarimeter. What is the enantiomeric excess (%ee) of the mixture?


A) 33% R
B) 33% S
C) 50% R
D) 75% R

E) B) and D)
F) A) and B)

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What is the configuration of the two chiral centers in the following molecule? What is the configuration of the two chiral centers in the following molecule? A) 3R,5R B) 3R,5S C) 3S,5R D) 3S,5S


A) 3R,5R
B) 3R,5S
C) 3S,5R
D) 3S,5S

E) B) and C)
F) C) and D)

Correct Answer

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Which of the following structures represent the same stereoisomer? Which of the following structures represent the same stereoisomer? A) only 1 and 2 B) only 1 and 3 C) only 2 and 3 D) 1, 2 and 3


A) only 1 and 2
B) only 1 and 3
C) only 2 and 3
D) 1, 2 and 3

E) A) and C)
F) All of the above

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What mass of (S)-(-)-mandelic acid is present in a 10 g sample which has an enantiomeric excess of 20% of the S-enantiomer?

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Which of the following structures does not have a plane of symmetry? Which of the following structures does not have a plane of symmetry? A) only 2 B) only 1 and 2 C) only 3 and 4 D) only 1, 2 and 4


A) only 2
B) only 1 and 2
C) only 3 and 4
D) only 1, 2 and 4

E) All of the above
F) A) and B)

Correct Answer

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Which of the following structures has a center of symmetry? Which of the following structures has a center of symmetry? A) 1 B) 2 C) 3 D) 4


A) 1
B) 2
C) 3
D) 4

E) A) and B)
F) A) and C)

Correct Answer

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