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Complete the following Fischer diagram so that it represents (2R,3R)-butane-2,3-diol. Complete the following Fischer diagram so that it represents (2R,3R)-butane-2,3-diol.

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


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

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

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How many stereoisomers of 2,3-dimethylbutane, (CH3) 2CHCH(CH3) 2, exist?


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

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

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How many stereoisomers of 2,4-pentanediol, CH3CH(OH) CH2CH(OH) CH3, exist?


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

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

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

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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) None of the above

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

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The number of chiral centers in progesterone (shown below) is ______. The number of chiral centers in progesterone (shown below) is ______.

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Complete the following Newman projection so that it represents (2S,3S)-2,3-butanediol. Complete the following Newman projection so that it represents (2S,3S)-2,3-butanediol.

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The terms that best describe the relationship between (2R,3S)-2,3-butanediol and (2S,3S)-2,3-butanediol are configurational and diastereomers.

A) True
B) False

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Complete the following Fischer diagram so that it represents (2R,3R)-3-bromobutan-2-ol. Complete the following Fischer diagram so that it represents (2R,3R)-3-bromobutan-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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A solution of 0.1 g/mL of a pure R enantiomer in a 1 dm polarimeter rotates plane polarized light by +4.8 \circ . What is the rotation observed on this solution in a 2 dm polarimeter?


A) +2.4 \circ
B) +4.8 \circ
C) +9.6 \circ
D) +19.2 \circ

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

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Which of the following structures has a center of symmetry (i.e., center of inversion) ? Which of the following structures has a center of symmetry (i.e., center of inversion) ?   A) 1 B) 2 C) 3 D) 4


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

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

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The specific rotation of the S-enantiomer of a compound is -120º. What is the enantiomeric excess of a sample of the compound that has a measured specific rotation of -30º.

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ee = 25% o...

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Complete the following Fischer diagram so that it represents (2R,3S)-3-bromobutan-2-ol. Complete the following Fischer diagram so that it represents (2R,3S)-3-bromobutan-2-ol.

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How many chiral centers are there in the following molecule (the naturally occurring stereoisomer is the male hormone testosterone) ? How many chiral centers are there in the following molecule (the naturally occurring stereoisomer is the male hormone testosterone) ?   A) Three B) Four C) Six D) Seven


A) Three
B) Four
C) Six
D) Seven

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

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A pure sample of the R enantiomer of a compound has a specific rotation, [ α\alpha ], of +20 \circ . A solution containing 0.2 g/mL of a mixture of enantiomers rotates plane polarized light by -2 \circ in a 1 dm polarimeter. What is the enantiomeric excess (%ee) of the mixture?


A) 25% R
B) 40% S
C) 50% S
D) 70% R

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

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Which of the following statements regarding optical rotation is not true?


A) All (+) enantiomers are dextrorotatory.
B) All R enantiomers are dextrorotatory.
C) All (-) enantiomers rotate plane-polarized light in a counterclockwise direction.
D) All (+) and (-) enantiomers rotate plane-polarized light in opposite directions.

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

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What mass of (S)-(-)-mandelic acid is present in a 10 g sample which has an enantiomeric excess of 30% of the S-enantiomer?

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