Chapter 4: Problem 15
Draw \((2 R, 3 S)-2,3\)-dichloropentane. Draw the enantiomer of \((2 R\), \(3 S)-2,3\)-dichloropentane. Draw a diastereomer of \((2 R, 3 S)-2,3\)-dichloropentane.
Short Answer
Expert verified
Draw (2R, 3S)-2,3-dichloropentane. Draw its mirror image for the enantiomer. For a diastereomer, change (3S) to (3R).
Step by step solution
01
- Understand the molecule structure
The given molecule is 2,3-dichloropentane, meaning it has a five-carbon chain with chlorine atoms on the second and third carbons.
02
- Assign the given stereochemistry
The molecule has the stereochemistry (2R, 3S). For carbon 2, assign the priorities to substituents: chlorine > ethyl (CH3CH2) > methyl (CH3) > hydrogen (H). Similarly for carbon 3: chlorine > ethyl (CH3CH2) > hydrogen (H) > methyl (CH3).
03
- Draw the molecule with appropriate stereochemistry
Draw the pentane chain. Place chlorine atoms with R configuration at carbon 2 (clockwise) and S configuration at carbon 3 (counterclockwise).
04
- Draw the enantiomer
Draw the mirror image of (2R, 3S)-2,3-dichloropentane. The enantiomer will have configurations (2S, 3R).
05
- Draw a diastereomer
A diastereomer has one stereocenter that stays the same and one that is different. Keep the 2R configuration and change the 3S to 3R, resulting in a (2R, 3R)-2,3-dichloropentane.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Chiral Centers
To understand 2,3-dichloropentane, we need clarity about chiral centers. A chiral center, often a carbon atom, has four different substituents. It lacks symmetry, which is crucial for stereochemistry. For example, in 2,3-dichloropentane, carbon atoms 2 and 3 each have four distinct groups attached: a chlorine atom, a part of the pentane chain, and different hydrogen atoms. This makes them chiral centers. Chiral centers are essential because they lead to the formation of unique 3D arrangements, affecting the chemical's properties and interactions with other molecules. Visualize a chiral center like a hand: just as your left and right hands are not superimposable, molecules with chiral centers are not identical to their mirror images.
Enantiomers
Enantiomers are pairs of molecules that are mirror images but not superimposable. Think of them like your left and right hands. For 2,3-dichloropentane, the molecule (2R, 3S)-2,3-dichloropentane can be mirrored to form its enantiomer, (2S, 3R)-2,3-dichloropentane. Despite having the same atomic makeup, their spatial arrangements differ, making them unique. Enantiomers often have distinct biological activities. For instance, one enantiomer might be therapeutic, while its mirror image could be less effective or even harmful. Identifying and understanding enantiomers is critical in fields like pharmaceuticals where the 3D orientation of a molecule can dramatically affect how it interacts with biological systems.
Diastereomers
Diastereomers are stereoisomers that are not mirror images of each other. They occur when a molecule has multiple chiral centers. For 2,3-dichloropentane, a diastereomer of (2R, 3S)-2,3-dichloropentane could be (2R, 3R)-2,3-dichloropentane. Here, one stereocenter (carbon 3) changes configuration while the other (carbon 2) remains the same. Unlike enantiomers, diastereomers often have different physical properties, like melting points. This makes them easier to separate in a laboratory setting. Understanding diastereomers helps in synthesizing and identifying different forms of a compound, particularly in drugs where the potency and safety of a drug might depend on specific stereochemical configurations.
R/S Configuration
R/S configuration describes the exact spatial arrangement of atoms around a chiral center. The rules for determining R and S configurations are based on the Cahn-Ingold-Prelog priority order. To assign R or S, follow these steps:
- Assign priorities to each group attached to the chiral center based on atomic number: higher numbers get higher priority.
- Orient the molecule so the group with the lowest priority is positioned away from you.
- Observe the ordered sequence of the remaining groups. If it is clockwise, the configuration is R (Rectus). If counterclockwise, it is S (Sinister).