Deck 6: Sterechemistry at Tetrahedral Centers

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Question
Instructions: Consider the structure of streptimidone below to answer the following question(s).
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.<div style=padding-top: 35px> Refer to instructions. Assign R or S configuration to each chirality center indicated in streptimidone.
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Question
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
Question
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
Question
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
Question
Which of the following physical properties can be used to identify a compound?

A) R
B) S
C) a
D) [a]D
Question
Instructions: Place asterisks at all the chirality centers in each molecule below.
Place asterisks:
Instructions: Place asterisks at all the chirality centers in each molecule below. Place asterisks:  <div style=padding-top: 35px>
Question
Instructions: In the molecules below, assign R, S configurations to the chirality center indicated with an arrow.
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 _____.<div style=padding-top: 35px> Refer to instructions. The configuration of the carbon atom labeled 19 is _____.
Question
Instructions: Place asterisks at all the chirality centers in each molecule below.
Place asterisks:
Instructions: Place asterisks at all the chirality centers in each molecule below. Place asterisks:  <div style=padding-top: 35px>
Question
Instructions: In the molecules below, assign R, S configurations to the chirality center indicated with an arrow.
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 _____.<div style=padding-top: 35px> Refer to instructions. The configuration of the carbon atom labeled 20 is _____.
Question
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.
Question
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
Question
Rank the following substituent groups from highest to lowest priority according to the sequencing rules.
CO2CH3 CO2H OH Cl
Question
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
Question
(-)-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.
Question
Instructions: Place asterisks at all the chirality centers in each molecule below.
Place asterisks:
Instructions: Place asterisks at all the chirality centers in each molecule below. Place asterisks:  <div style=padding-top: 35px>
Question
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 °\degree . What is the specific rotation of this unknown and specify if the compound is levorotatory or dextrorotatory?
Question
The numbers on the carbon center of the following molecule represent atomic numbers. <strong>The numbers on the carbon center of the following molecule represent atomic numbers.   The molecule is in</strong> 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. <div style=padding-top: 35px> 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.
Question
Instructions: Consider the structure of streptimidone below to answer the following question(s).
Instructions: Consider the structure of streptimidone below to answer the following question(s).   Refer to instructions. Does streptimidone have a meso stereoisomer? Explain.<div style=padding-top: 35px> Refer to instructions. Does streptimidone have a meso stereoisomer? Explain.
Question
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
Question
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
Question
How many stereoisomers of 3-bromo-2-butanol exist? <strong>How many stereoisomers of 3-bromo-2-butanol exist?  </strong> A) 1 B) 2 C) 3 D) 4 <div style=padding-top: 35px>

A) 1
B) 2
C) 3
D) 4
Question
Which of the following have the R configuration? <strong>Which of the following have the R configuration?  </strong> A) only 1 B) only 2 C) only 1 and 2 D) 1, 2 and 3 <div style=padding-top: 35px>

A) only 1
B) only 2
C) only 1 and 2
D) 1, 2 and 3
Question
Instructions:
Refer to the structure below to answer the following questions. Instructions: Refer to the structure below to answer the following questions.   Refer to instructions. Give the complete name of the enantiomer of (S)-(-)-serine.<div style=padding-top: 35px> Refer to instructions. Give the complete name of the enantiomer of (S)-(-)-serine.
Question
Which of the following compounds is (are) achiral? <strong>Which of the following compounds is (are) achiral?  </strong> A) only 1 B) only 1 and 2 C) only 2 and 3 D) 1, 2 and 3 <div style=padding-top: 35px>

A) only 1
B) only 1 and 2
C) only 2 and 3
D) 1, 2 and 3
Question
What is the relationship between the following pair of structures? <strong>What is the relationship between the following pair of structures?  </strong> A) They are enantiomers B) They are diastereomers C) The are constitutional isomers D) They are identical <div style=padding-top: 35px>

A) They are enantiomers
B) They are diastereomers
C) The are constitutional isomers
D) They are identical
Question
Which of the following structures represent the same stereoisomer? <strong>Which of the following structures represent the same stereoisomer?  </strong> A) only 1 and 2 B) only 1 and 3 C) only 2 and 3 D) 1, 2 and 3 <div style=padding-top: 35px>

A) only 1 and 2
B) only 1 and 3
C) only 2 and 3
D) 1, 2 and 3
Question
How many stereoisomers of 2,3-dimethylbutane exist? <strong>How many stereoisomers of 2,3-dimethylbutane exist?  </strong> A) 1 B) 2 C) 3 D) 4 <div style=padding-top: 35px>

A) 1
B) 2
C) 3
D) 4
Question
Which of the following structures contain a plane of symmetry? <strong>Which of the following structures contain a plane of symmetry?  </strong> A) 1 B) 2 C) 3 D) All three contain a plane of symmetry <div style=padding-top: 35px>

A) 1
B) 2
C) 3
D) All three contain a plane of symmetry
Question
How many stereoisomers of 3-chloro-2-methylbutane exist? <strong>How many stereoisomers of 3-chloro-2-methylbutane exist?  </strong> A) 1 B) 2 C) 3 D) 4 <div style=padding-top: 35px>

A) 1
B) 2
C) 3
D) 4
Question
What is the relationship between the following pair of structures? <strong>What is the relationship between the following pair of structures?  </strong> A) They are enantiomers B) They are diastereomers C) The are constitutional isomers D) They are identical <div style=padding-top: 35px>

A) They are enantiomers
B) They are diastereomers
C) The are constitutional isomers
D) They are identical
Question
Which of the following have the S configuration? <strong>Which of the following have the S configuration?  </strong> A) only 1 B) only 2 C) only 1 and 2 D) 1, 2 and 3 <div style=padding-top: 35px>

A) only 1
B) only 2
C) only 1 and 2
D) 1, 2 and 3
Question
Instructions:
Refer to the structure below to answer the following questions. 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.<div style=padding-top: 35px> Refer to instructions. Draw the enantiomer of (S)-(-)-serine in a wedge-dash projection.
Question
A natural product having [a]D = +40.3 °\degree 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.
Question
Match between columns
Are stereoisomers that are not mirror images.
enantiomers or optically active
Are stereoisomers that are not mirror images.
racemates
Are stereoisomers that are not mirror images.
diastereomers
Are stereoisomers that are not mirror images.
chirality center
Are stereoisomers that are not mirror images.
meso compounds
Are stereoisomers that are not mirror images.
prochirality center
Is an atom in a molecule that is bonded to four different atoms or groups of atoms.
enantiomers or optically active
Is an atom in a molecule that is bonded to four different atoms or groups of atoms.
racemates
Is an atom in a molecule that is bonded to four different atoms or groups of atoms.
diastereomers
Is an atom in a molecule that is bonded to four different atoms or groups of atoms.
chirality center
Is an atom in a molecule that is bonded to four different atoms or groups of atoms.
meso compounds
Is an atom in a molecule that is bonded to four different atoms or groups of atoms.
prochirality center
Are designated either (±) or d,l.
enantiomers or optically active
Are designated either (±) or d,l.
racemates
Are designated either (±) or d,l.
diastereomers
Are designated either (±) or d,l.
chirality center
Are designated either (±) or d,l.
meso compounds
Are designated either (±) or d,l.
prochirality center
Are molecules which contain both chirality centers and a plane of symmetry.
enantiomers or optically active
Are molecules which contain both chirality centers and a plane of symmetry.
racemates
Are molecules which contain both chirality centers and a plane of symmetry.
diastereomers
Are molecules which contain both chirality centers and a plane of symmetry.
chirality center
Are molecules which contain both chirality centers and a plane of symmetry.
meso compounds
Are molecules which contain both chirality centers and a plane of symmetry.
prochirality center
Describes organic molecules which rotate plane-polarized light.
enantiomers or optically active
Describes organic molecules which rotate plane-polarized light.
racemates
Describes organic molecules which rotate plane-polarized light.
diastereomers
Describes organic molecules which rotate plane-polarized light.
chirality center
Describes organic molecules which rotate plane-polarized light.
meso compounds
Describes organic molecules which rotate plane-polarized light.
prochirality center
Describes an sp3-hybridized atom that can become a chirality center by changing one of its attached groups.
enantiomers or optically active
Describes an sp3-hybridized atom that can become a chirality center by changing one of its attached groups.
racemates
Describes an sp3-hybridized atom that can become a chirality center by changing one of its attached groups.
diastereomers
Describes an sp3-hybridized atom that can become a chirality center by changing one of its attached groups.
chirality center
Describes an sp3-hybridized atom that can become a chirality center by changing one of its attached groups.
meso compounds
Describes an sp3-hybridized atom that can become a chirality center by changing one of its attached groups.
prochirality center
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Deck 6: Sterechemistry at Tetrahedral Centers
1
Instructions: Consider the structure of streptimidone below to answer the following question(s).
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
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
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
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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
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6
Instructions: Place asterisks at all the chirality centers in each molecule below.
Place asterisks:
Instructions: Place asterisks at all the chirality centers in each molecule below. Place asterisks:
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7
Instructions: In the molecules below, assign R, S configurations to the chirality center indicated with an arrow.
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 _____.
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8
Instructions: Place asterisks at all the chirality centers in each molecule below.
Place asterisks:
Instructions: Place asterisks at all the chirality centers in each molecule below. Place asterisks:
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9
Instructions: In the molecules below, assign R, S configurations to the chirality center indicated with an arrow.
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 _____.
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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.
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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
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12
Rank the following substituent groups from highest to lowest priority according to the sequencing rules.
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
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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.
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15
Instructions: Place asterisks at all the chirality centers in each molecule below.
Place asterisks:
Instructions: Place asterisks at all the chirality centers in each molecule below. 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 °\degree . 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. <strong>The numbers on the carbon center of the following molecule represent atomic numbers.   The molecule is in</strong> 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 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.
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18
Instructions: Consider the structure of streptimidone below to answer the following question(s).
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.
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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
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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
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21
How many stereoisomers of 3-bromo-2-butanol exist? <strong>How many stereoisomers of 3-bromo-2-butanol exist?  </strong> 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? <strong>Which of the following have the R configuration?  </strong> 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. 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 instructions. Give the complete name of the enantiomer of (S)-(-)-serine.
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24
Which of the following compounds is (are) achiral? <strong>Which of the following compounds is (are) achiral?  </strong> 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? <strong>What is the relationship between the following pair of structures?  </strong> 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? <strong>Which of the following structures represent the same stereoisomer?  </strong> 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? <strong>How many stereoisomers of 2,3-dimethylbutane exist?  </strong> 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? <strong>Which of the following structures contain a plane of symmetry?  </strong> 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? <strong>How many stereoisomers of 3-chloro-2-methylbutane exist?  </strong> 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? <strong>What is the relationship between the following pair of structures?  </strong> 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? <strong>Which of the following have the S configuration?  </strong> 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. 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 instructions. Draw the enantiomer of (S)-(-)-serine in a wedge-dash projection.
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33
A natural product having [a]D = +40.3 °\degree 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.
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35
Match between columns
Are stereoisomers that are not mirror images.
enantiomers or optically active
Are stereoisomers that are not mirror images.
racemates
Are stereoisomers that are not mirror images.
diastereomers
Are stereoisomers that are not mirror images.
chirality center
Are stereoisomers that are not mirror images.
meso compounds
Are stereoisomers that are not mirror images.
prochirality center
Is an atom in a molecule that is bonded to four different atoms or groups of atoms.
enantiomers or optically active
Is an atom in a molecule that is bonded to four different atoms or groups of atoms.
racemates
Is an atom in a molecule that is bonded to four different atoms or groups of atoms.
diastereomers
Is an atom in a molecule that is bonded to four different atoms or groups of atoms.
chirality center
Is an atom in a molecule that is bonded to four different atoms or groups of atoms.
meso compounds
Is an atom in a molecule that is bonded to four different atoms or groups of atoms.
prochirality center
Are designated either (±) or d,l.
enantiomers or optically active
Are designated either (±) or d,l.
racemates
Are designated either (±) or d,l.
diastereomers
Are designated either (±) or d,l.
chirality center
Are designated either (±) or d,l.
meso compounds
Are designated either (±) or d,l.
prochirality center
Are molecules which contain both chirality centers and a plane of symmetry.
enantiomers or optically active
Are molecules which contain both chirality centers and a plane of symmetry.
racemates
Are molecules which contain both chirality centers and a plane of symmetry.
diastereomers
Are molecules which contain both chirality centers and a plane of symmetry.
chirality center
Are molecules which contain both chirality centers and a plane of symmetry.
meso compounds
Are molecules which contain both chirality centers and a plane of symmetry.
prochirality center
Describes organic molecules which rotate plane-polarized light.
enantiomers or optically active
Describes organic molecules which rotate plane-polarized light.
racemates
Describes organic molecules which rotate plane-polarized light.
diastereomers
Describes organic molecules which rotate plane-polarized light.
chirality center
Describes organic molecules which rotate plane-polarized light.
meso compounds
Describes organic molecules which rotate plane-polarized light.
prochirality center
Describes an sp3-hybridized atom that can become a chirality center by changing one of its attached groups.
enantiomers or optically active
Describes an sp3-hybridized atom that can become a chirality center by changing one of its attached groups.
racemates
Describes an sp3-hybridized atom that can become a chirality center by changing one of its attached groups.
diastereomers
Describes an sp3-hybridized atom that can become a chirality center by changing one of its attached groups.
chirality center
Describes an sp3-hybridized atom that can become a chirality center by changing one of its attached groups.
meso compounds
Describes an sp3-hybridized atom that can become a chirality center by changing one of its attached groups.
prochirality center
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