Deck 4: Isomers the Arrangement of Atoms in Space

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Question
How many asymmetric carbon centers are found in cabergoline, a drug used to treat Parkinson's disease?
<strong>How many asymmetric carbon centers are found in cabergoline, a drug used to treat Parkinson's disease?  </strong> A) 1 B) 2 C) 3 D) 4 E) 5 <div style=padding-top: 35px>

A) 1
B) 2
C) 3
D) 4
E) 5
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Question
Which of the following structures is an E isomer?
<strong>Which of the following structures is an E isomer?  </strong> A) 1 B) 2 C) 3 D) 1 and 2 E) 1 and 3 <div style=padding-top: 35px>

A) 1
B) 2
C) 3
D) 1 and 2
E) 1 and 3
Question
A sample of the disulfide L-cystine has an observed specific rotation of -14. Pure L-cystine has a specific rotation of -70. What percent of each enantiomer is present in the sample?
<strong>A sample of the disulfide L-cystine has an observed specific rotation of -14. Pure L-cystine has a specific rotation of -70. What percent of each enantiomer is present in the sample?  </strong> A) 14 (?) and 56 (+) B) 20 (?) and 80 (+) C) 60 (?) and 40 (+) D) 80 (?) and 20 (+) E) 84 (?) and 16 (+) <div style=padding-top: 35px>

A) 14 (?) and 56 (+)
B) 20 (?) and 80 (+)
C) 60 (?) and 40 (+)
D) 80 (?) and 20 (+)
E) 84 (?) and 16 (+)
Question
Which structure(s) is(are) an enantiomer of the molecule at the top left?
<strong>Which structure(s) is(are) an enantiomer of the molecule at the top left?  </strong> A)   B)   C)   D)   <div style=padding-top: 35px>

A) <strong>Which structure(s) is(are) an enantiomer of the molecule at the top left?  </strong> A)   B)   C)   D)   <div style=padding-top: 35px>
B) <strong>Which structure(s) is(are) an enantiomer of the molecule at the top left?  </strong> A)   B)   C)   D)   <div style=padding-top: 35px>
C) <strong>Which structure(s) is(are) an enantiomer of the molecule at the top left?  </strong> A)   B)   C)   D)   <div style=padding-top: 35px>
D) <strong>Which structure(s) is(are) an enantiomer of the molecule at the top left?  </strong> A)   B)   C)   D)   <div style=padding-top: 35px>
Question
Which of the following structures has the S configuration?
<strong>Which of the following structures has the S configuration?  </strong> A) 1 B) 2 C) 3 D) 4 E) 1 and 3 <div style=padding-top: 35px>

A) 1
B) 2
C) 3
D) 4
E) 1 and 3
Question
What is the relationship between the two compounds shown below? <strong>What is the relationship between the two compounds shown below?  </strong> A) enantiomers B) diastereomers C) constitutional isomers D) geometric isomers E) identical compounds <div style=padding-top: 35px>

A) enantiomers
B) diastereomers
C) constitutional isomers
D) geometric isomers
E) identical compounds
Question
Which of the following structures has the S,S configuration?
<strong>Which of the following structures has the S,S configuration?  </strong> A) 1 B) 2 C) 3 D) 1 and 3 E) none of the above Structures 1 and 3 are meso and must have R and S asymmetric centers. Structure 2 has no plane of symmetry. <div style=padding-top: 35px>

A) 1
B) 2
C) 3
D) 1 and 3
E) none of the above
Structures 1 and 3 are meso and must have R and S asymmetric centers. Structure 2 has no plane of symmetry.
Question
What is the maximum number of stereoisomers possible for nootkatone (grapefruit oil) shown below?
<strong>What is the maximum number of stereoisomers possible for nootkatone (grapefruit oil) shown below?  </strong> A) 2 B) 3 C) 4 D) 8 E) 16 <div style=padding-top: 35px>

A) 2
B) 3
C) 4
D) 8
E) 16
Question
Which of the following structures is a meso compound?
<strong>Which of the following structures is a meso compound?  </strong> A) 1 B) 2 C) 3 D) 4 E) 2 and 4 <div style=padding-top: 35px>

A) 1
B) 2
C) 3
D) 4
E) 2 and 4
Question
What is the relationship between the two compounds shown below?
<strong>What is the relationship between the two compounds shown below?  </strong> A) enantiomers B) diastereomers C) constitutional isomers D) geometric isomers E) identical compounds <div style=padding-top: 35px>

A) enantiomers
B) diastereomers
C) constitutional isomers
D) geometric isomers
E) identical compounds
Question
Using Cahn-Ingold-Prelog rules, which set of answers is correctly organized from highest to lowest priority?

A) ?CH2NH2 > ?CN > -COOH > ?NH2
B) ?COOH > ?CN > ?CH2NH2 > ?NH2
C) ?NH2 > ?CN > ?CH2NH2 > ?COOH
D) ?NH2 > ?COOH > ?CN > ?CH2NH2
E) ?CN > ?NH2 > ?CH2NH2 > ?COOH
Relative priorities are based on atomic number and the rules for multiple bonds (?C <strong>Using Cahn-Ingold-Prelog rules, which set of answers is correctly organized from highest to lowest priority?</strong> A) ?CH<sub>2</sub>NH<sub>2</sub> > ?CN > -COOH > ?NH<sub>2</sub> B) ?COOH > ?CN > ?CH<sub>2</sub>NH<sub>2</sub> > ?NH<sub>2</sub> C) ?NH<sub>2</sub> > ?CN > ?CH<sub>2</sub>NH<sub>2</sub> > ?COOH D) ?NH<sub>2</sub> > ?COOH > ?CN > ?CH<sub>2</sub>NH<sub>2</sub> E) ?CN > ?NH<sub>2</sub> > ?CH<sub>2</sub>NH<sub>2</sub> > ?COOH Relative priorities are based on atomic number and the rules for multiple bonds (?C   N is greater than ?CH<sub>2</sub>NH<sub>2</sub>). <div style=padding-top: 35px> N is greater than ?CH2NH2).
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Deck 4: Isomers the Arrangement of Atoms in Space
1
How many asymmetric carbon centers are found in cabergoline, a drug used to treat Parkinson's disease?
<strong>How many asymmetric carbon centers are found in cabergoline, a drug used to treat Parkinson's disease?  </strong> A) 1 B) 2 C) 3 D) 4 E) 5

A) 1
B) 2
C) 3
D) 4
E) 5
3
2
Which of the following structures is an E isomer?
<strong>Which of the following structures is an E isomer?  </strong> A) 1 B) 2 C) 3 D) 1 and 2 E) 1 and 3

A) 1
B) 2
C) 3
D) 1 and 2
E) 1 and 3
1 and 2
3
A sample of the disulfide L-cystine has an observed specific rotation of -14. Pure L-cystine has a specific rotation of -70. What percent of each enantiomer is present in the sample?
<strong>A sample of the disulfide L-cystine has an observed specific rotation of -14. Pure L-cystine has a specific rotation of -70. What percent of each enantiomer is present in the sample?  </strong> A) 14 (?) and 56 (+) B) 20 (?) and 80 (+) C) 60 (?) and 40 (+) D) 80 (?) and 20 (+) E) 84 (?) and 16 (+)

A) 14 (?) and 56 (+)
B) 20 (?) and 80 (+)
C) 60 (?) and 40 (+)
D) 80 (?) and 20 (+)
E) 84 (?) and 16 (+)
60 (?) and 40 (+)
4
Which structure(s) is(are) an enantiomer of the molecule at the top left?
<strong>Which structure(s) is(are) an enantiomer of the molecule at the top left?  </strong> A)   B)   C)   D)

A) <strong>Which structure(s) is(are) an enantiomer of the molecule at the top left?  </strong> A)   B)   C)   D)
B) <strong>Which structure(s) is(are) an enantiomer of the molecule at the top left?  </strong> A)   B)   C)   D)
C) <strong>Which structure(s) is(are) an enantiomer of the molecule at the top left?  </strong> A)   B)   C)   D)
D) <strong>Which structure(s) is(are) an enantiomer of the molecule at the top left?  </strong> A)   B)   C)   D)
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5
Which of the following structures has the S configuration?
<strong>Which of the following structures has the S configuration?  </strong> A) 1 B) 2 C) 3 D) 4 E) 1 and 3

A) 1
B) 2
C) 3
D) 4
E) 1 and 3
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6
What is the relationship between the two compounds shown below? <strong>What is the relationship between the two compounds shown below?  </strong> A) enantiomers B) diastereomers C) constitutional isomers D) geometric isomers E) identical compounds

A) enantiomers
B) diastereomers
C) constitutional isomers
D) geometric isomers
E) identical compounds
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7
Which of the following structures has the S,S configuration?
<strong>Which of the following structures has the S,S configuration?  </strong> A) 1 B) 2 C) 3 D) 1 and 3 E) none of the above Structures 1 and 3 are meso and must have R and S asymmetric centers. Structure 2 has no plane of symmetry.

A) 1
B) 2
C) 3
D) 1 and 3
E) none of the above
Structures 1 and 3 are meso and must have R and S asymmetric centers. Structure 2 has no plane of symmetry.
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8
What is the maximum number of stereoisomers possible for nootkatone (grapefruit oil) shown below?
<strong>What is the maximum number of stereoisomers possible for nootkatone (grapefruit oil) shown below?  </strong> A) 2 B) 3 C) 4 D) 8 E) 16

A) 2
B) 3
C) 4
D) 8
E) 16
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9
Which of the following structures is a meso compound?
<strong>Which of the following structures is a meso compound?  </strong> A) 1 B) 2 C) 3 D) 4 E) 2 and 4

A) 1
B) 2
C) 3
D) 4
E) 2 and 4
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10
What is the relationship between the two compounds shown below?
<strong>What is the relationship between the two compounds shown below?  </strong> A) enantiomers B) diastereomers C) constitutional isomers D) geometric isomers E) identical compounds

A) enantiomers
B) diastereomers
C) constitutional isomers
D) geometric isomers
E) identical compounds
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11
Using Cahn-Ingold-Prelog rules, which set of answers is correctly organized from highest to lowest priority?

A) ?CH2NH2 > ?CN > -COOH > ?NH2
B) ?COOH > ?CN > ?CH2NH2 > ?NH2
C) ?NH2 > ?CN > ?CH2NH2 > ?COOH
D) ?NH2 > ?COOH > ?CN > ?CH2NH2
E) ?CN > ?NH2 > ?CH2NH2 > ?COOH
Relative priorities are based on atomic number and the rules for multiple bonds (?C <strong>Using Cahn-Ingold-Prelog rules, which set of answers is correctly organized from highest to lowest priority?</strong> A) ?CH<sub>2</sub>NH<sub>2</sub> > ?CN > -COOH > ?NH<sub>2</sub> B) ?COOH > ?CN > ?CH<sub>2</sub>NH<sub>2</sub> > ?NH<sub>2</sub> C) ?NH<sub>2</sub> > ?CN > ?CH<sub>2</sub>NH<sub>2</sub> > ?COOH D) ?NH<sub>2</sub> > ?COOH > ?CN > ?CH<sub>2</sub>NH<sub>2</sub> E) ?CN > ?NH<sub>2</sub> > ?CH<sub>2</sub>NH<sub>2</sub> > ?COOH Relative priorities are based on atomic number and the rules for multiple bonds (?C   N is greater than ?CH<sub>2</sub>NH<sub>2</sub>). N is greater than ?CH2NH2).
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