Podcast
Questions and Answers
Which statement accurately describes the relationship between enantiomers and diastereomers?
Which statement accurately describes the relationship between enantiomers and diastereomers?
- Enantiomers and diastereomers are both constitutional isomers.
- Enantiomers are non-superimposable mirror images, while diastereomers are superimposable mirror images.
- Enantiomers have different physical properties, while diastereomers have the same physical properties.
- Enantiomers are stereoisomers that are mirror images, while diastereomers are stereoisomers that are not mirror images. (correct)
Consider a molecule with two chiral centers. If one chiral center is R and the other is S, how would you describe its enantiomer?
Consider a molecule with two chiral centers. If one chiral center is R and the other is S, how would you describe its enantiomer?
- Both chiral centers would still be R and S, respectively.
- One center would be S and the other would be S.
- One center would be R and the other would be R.
- One center would be S and the other would be R. (correct)
A molecule has three chiral centers. What is the maximum number of possible stereoisomers?
A molecule has three chiral centers. What is the maximum number of possible stereoisomers?
- 4
- 8 (correct)
- 10
- 6
How does the presence of a plane of symmetry affect the chirality of a molecule?
How does the presence of a plane of symmetry affect the chirality of a molecule?
Which type of symmetry is irrelevant when determining whether a compound is chiral or achiral?
Which type of symmetry is irrelevant when determining whether a compound is chiral or achiral?
A compound has two chiral centers and exhibits reflectional symmetry. What type of compound is it?
A compound has two chiral centers and exhibits reflectional symmetry. What type of compound is it?
What is the relationship between two stereoisomers if all chiral centers have the opposite configuration?
What is the relationship between two stereoisomers if all chiral centers have the opposite configuration?
Which statement is true about diastereomers?
Which statement is true about diastereomers?
Consider a compound with four chiral centers. What is the maximum number of pairs of enantiomers that can exist for this compound?
Consider a compound with four chiral centers. What is the maximum number of pairs of enantiomers that can exist for this compound?
A stereoisomer has a specific rotation of +30°. What is the specific rotation of its enantiomer?
A stereoisomer has a specific rotation of +30°. What is the specific rotation of its enantiomer?
Flashcards
Enantiomers
Enantiomers
Stereoisomers that are non-superimposable mirror images of each other.
Diastereomers
Diastereomers
Stereoisomers that are non-superimposable and not mirror images of each other.
Chiral Center
Chiral Center
A carbon atom bonded to four different groups.
Rotational Symmetry
Rotational Symmetry
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Reflectional Symmetry
Reflectional Symmetry
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Center of Inversion
Center of Inversion
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Meso Compounds
Meso Compounds
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Fischer Projections
Fischer Projections
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Configuration
Configuration
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Stereoisomers
Stereoisomers
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Study Notes
- Stereoisomers share the same atomic connectivity but differ in spatial arrangement. They are categorized as enantiomers or diastereomers
Enantiomers
- Stereoisomers are mirror images of each other
Diastereomers
- Stereoisomers aren't mirror images of one another
- Have distinct physical properties
Cis-trans isomers
- Classified as diastereomers rather than enantiomers
- Differences between enantiomers and diastereomers become relevant in compounds with multiple chiral centers
- A molecule with two chiral centers can have four stereoisomers
- Two pairs of enantiomers
- Stereoisomers in a molecular family include one enantiomer (mirror-image twin) and two diastereomers (siblings).
- The maximum number of stereoisomers in a family is calculated as 2ⁿ, where n is the number of chiral centers.
- Cholesterol, with eight chiral centers, can have 256 stereoisomers, but only one is produced by nature
Symmetry and Chirality
- Chirality isn't guaranteed by a single chiral center
- Trans isomers are chiral, while cis isomers aren't
- Chirality is determined by the types of symmetry
- The compound must be explored
Types of Symmetry
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Rotational Symmetry
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Reflectional Symmetry
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Rotational symmetry doesn't affect chirality
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Reflectional symmetry does
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A plane of symmetry makes a compound achiral
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Compounds lacking a plane of symmetry are usually chiral
Meso Compounds
- Occur when a compound exhibits reflectional symmetry despite possessing chiral centers.
- A family of stereoisomers containing a meso compound will have fewer than 2ⁿ stereoisomers
Fischer Projections
- A drawing style used for compounds with multiple chiral centers
- Horizontal lines represent bonds coming out of the page, while vertical lines represent bonds going behind the page
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