Deck 6: Sterechemistry at Tetrahedral Centers
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Deck 6: Sterechemistry at Tetrahedral Centers
1
Instructions: Consider the structure of streptimidone below to answer the following question(s).
Refer to instructions. Assign R or S configuration to each chirality center indicated in streptimidone.
Refer to instructions. Assign R or S configuration to each chirality center indicated in streptimidone.
2
Which of the following has a plane of symmetry?
A) boot
B) laboratory beaker
C) hammer
D) both b and c
E) none of these
A) boot
B) laboratory beaker
C) hammer
D) both b and c
E) none of these
D
3
The biological importance of enantiomers arises from?
A) Biological reactions involve receptor molecules.
B) Biological receptors are chiral.
C) Biological receptors require a specific enantiomer for reaction.
D) Each enantiomer has different biological properties.
E) all of these
A) Biological reactions involve receptor molecules.
B) Biological receptors are chiral.
C) Biological receptors require a specific enantiomer for reaction.
D) Each enantiomer has different biological properties.
E) all of these
E
4
Which of the following is the definition of a pair of enantiomers?
A) A pair of structures that are superimposable mirror images of one another
B) A pair of stereoisomers that are non-superimposable mirror images of one another
C) A pair of stereoisomers that are not mirror images of one another
D) A pair of stereoisomers that have equal specific rotations
A) A pair of structures that are superimposable mirror images of one another
B) A pair of stereoisomers that are non-superimposable mirror images of one another
C) A pair of stereoisomers that are not mirror images of one another
D) A pair of stereoisomers that have equal specific rotations
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5
Which of the following physical properties can be used to identify a compound?
A) R
B) S
C) a
D) [a]D
A) R
B) S
C) a
D) [a]D
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6
Instructions: Place asterisks at all the chirality centers in each molecule below.
Place asterisks:

Place asterisks:

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7
Instructions: In the molecules below, assign R, S configurations to the chirality center indicated with an arrow.
Refer to instructions. The configuration of the carbon atom labeled 19 is _____.
Refer to instructions. The configuration of the carbon atom labeled 19 is _____. Unlock Deck
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8
Instructions: Place asterisks at all the chirality centers in each molecule below.
Place asterisks:

Place asterisks:

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9
Instructions: In the molecules below, assign R, S configurations to the chirality center indicated with an arrow.
Refer to instructions. The configuration of the carbon atom labeled 20 is _____.
Refer to instructions. The configuration of the carbon atom labeled 20 is _____. Unlock Deck
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10
If (+)-sucrose has a specific rotation of +66.47, what is the specific rotation of (-)-sucrose?
A) +66.47
B) -66.47
C) +33.43
D) -33.43
E) Must be determined with a polarimeter.
A) +66.47
B) -66.47
C) +33.43
D) -33.43
E) Must be determined with a polarimeter.
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11
Which of the following is the definition of a pair of diastereomers?
A) A pair of structures that are superimposable mirror images of one another
B) A pair of stereoisomers that are non-superimposable mirror images of one another
C) A pair of stereoisomers that are not mirror images of one another
D) A pair of stereoisomers that have equal specific rotations
A) A pair of structures that are superimposable mirror images of one another
B) A pair of stereoisomers that are non-superimposable mirror images of one another
C) A pair of stereoisomers that are not mirror images of one another
D) A pair of stereoisomers that have equal specific rotations
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12
Rank the following substituent groups from highest to lowest priority according to the sequencing rules.
CO2CH3 CO2H OH Cl
CO2CH3 CO2H OH Cl
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13
Which of the following is the definition of a meso compound?
A) A molecule with chirality centers which is chiral
B) A molecule with chirality centers which is not chiral
C) A diastereomer with no chirality centers
D) A chiral compound with more than one chirality center
A) A molecule with chirality centers which is chiral
B) A molecule with chirality centers which is not chiral
C) A diastereomer with no chirality centers
D) A chiral compound with more than one chirality center
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14
(-)-cholesterol
A) does not have a chiral center.
B) is dextrorotatory.
C) rotates the plane of polarized light counterclockwise.
D) does not rotate polarized light.
A) does not have a chiral center.
B) is dextrorotatory.
C) rotates the plane of polarized light counterclockwise.
D) does not rotate polarized light.
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15
Instructions: Place asterisks at all the chirality centers in each molecule below.
Place asterisks:

Place asterisks:

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16
2.10 g of an unknown compound was dissolved in 15.00 mL of ethanol. The sample was placed in a 10.0 cm cell in a polarimeter and the angle of rotation was determined to be -18.48 . What is the specific rotation of this unknown and specify if the compound is levorotatory or dextrorotatory?
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17
The numbers on the carbon center of the following molecule represent atomic numbers.
The molecule is in
A) the R configuration.
B) the S configuration.
C) The carbon is not a chiral center in this molecule.
D) The exact configuration cannot be determined without knowing additional atomic numbers.
The molecule is inA) the R configuration.
B) the S configuration.
C) The carbon is not a chiral center in this molecule.
D) The exact configuration cannot be determined without knowing additional atomic numbers.
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18
Instructions: Consider the structure of streptimidone below to answer the following question(s).
Refer to instructions. Does streptimidone have a meso stereoisomer? Explain.
Refer to instructions. Does streptimidone have a meso stereoisomer? Explain. Unlock Deck
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19
Which of the following statements is true regarding pairs of enantiomers?
A) They have identical melting points
B) They have identical boiling points.
C) They rotate plane-polarized light in opposite directions
D) They produce different products in reactions with chiral reagents
E) all of these
A) They have identical melting points
B) They have identical boiling points.
C) They rotate plane-polarized light in opposite directions
D) They produce different products in reactions with chiral reagents
E) all of these
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20
Which of the following correctly describes a molecule that is achiral?
A) Non-superimposability of the molecule on its mirror image
B) Superimposability of the molecule on its mirror image
C) Contains a carbon atom with four different substituents
D) Does not have a plane of symmetry
E) Both b and d
A) Non-superimposability of the molecule on its mirror image
B) Superimposability of the molecule on its mirror image
C) Contains a carbon atom with four different substituents
D) Does not have a plane of symmetry
E) Both b and d
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21
How many stereoisomers of 3-bromo-2-butanol exist? 
A) 1
B) 2
C) 3
D) 4

A) 1
B) 2
C) 3
D) 4
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22
Which of the following have the R configuration? 
A) only 1
B) only 2
C) only 1 and 2
D) 1, 2 and 3

A) only 1
B) only 2
C) only 1 and 2
D) 1, 2 and 3
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23
Instructions:
Refer to the structure below to answer the following questions.
Refer to instructions. Give the complete name of the enantiomer of (S)-(-)-serine.
Refer to the structure below to answer the following questions.
Refer to instructions. Give the complete name of the enantiomer of (S)-(-)-serine. Unlock Deck
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24
Which of the following compounds is (are) achiral? 
A) only 1
B) only 1 and 2
C) only 2 and 3
D) 1, 2 and 3

A) only 1
B) only 1 and 2
C) only 2 and 3
D) 1, 2 and 3
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25
What is the relationship between the following pair of structures? 
A) They are enantiomers
B) They are diastereomers
C) The are constitutional isomers
D) They are identical

A) They are enantiomers
B) They are diastereomers
C) The are constitutional isomers
D) They are identical
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26
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
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27
How many stereoisomers of 2,3-dimethylbutane exist? 
A) 1
B) 2
C) 3
D) 4

A) 1
B) 2
C) 3
D) 4
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28
Which of the following structures contain a plane of symmetry? 
A) 1
B) 2
C) 3
D) All three contain a plane of symmetry

A) 1
B) 2
C) 3
D) All three contain a plane of symmetry
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29
How many stereoisomers of 3-chloro-2-methylbutane exist? 
A) 1
B) 2
C) 3
D) 4

A) 1
B) 2
C) 3
D) 4
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30
What is the relationship between the following pair of structures? 
A) They are enantiomers
B) They are diastereomers
C) The are constitutional isomers
D) They are identical

A) They are enantiomers
B) They are diastereomers
C) The are constitutional isomers
D) They are identical
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31
Which of the following have the S configuration? 
A) only 1
B) only 2
C) only 1 and 2
D) 1, 2 and 3

A) only 1
B) only 2
C) only 1 and 2
D) 1, 2 and 3
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32
Instructions:
Refer to the structure below to answer the following questions.
Refer to instructions. Draw the enantiomer of (S)-(-)-serine in a wedge-dash projection.
Refer to the structure below to answer the following questions.
Refer to instructions. Draw the enantiomer of (S)-(-)-serine in a wedge-dash projection. Unlock Deck
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33
A natural product having [a]D = +40.3 has been isolated and purified. This information indicates that the natural product:
a. is racemic
b. doanot rotate plene-polarized light
c. is levaratetary.
d. is dextarotatory.
a. is racemic
b. doanot rotate plene-polarized light
c. is levaratetary.
d. is dextarotatory.
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35
Match between columns
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