Textbook Question
What are their common names?
12. Alcohols, Ethers, Epoxides and Thiols
Naming Ethers
Problem 87d
Textbook Question
Draw the correct structure from the following IUPAC names:
(d) (2R,3S)-methoxy-3-methylpentane
Verified step by step guidance1
Start by identifying the longest carbon chain in the name, which is 'pentane'. This indicates a five-carbon chain.
Locate the substituents on the main chain. The name indicates a 'methoxy' group and a 'methyl' group. The 'methoxy' group is an -OCH₃ group, and the 'methyl' group is a -CH₃ group.
Determine the positions of the substituents. The '3-methyl' indicates a methyl group attached to the third carbon, and 'methoxy' is not numbered, so it is assumed to be on the second carbon.
Consider the stereochemistry indicated by (2R,3S). The 'R' and 'S' configurations refer to the absolute configuration of the chiral centers. Use the Cahn-Ingold-Prelog priority rules to assign the correct stereochemistry to the second and third carbon atoms.
Draw the structure by placing the substituents on the correct carbons and ensuring the stereochemistry is accurately represented. The second carbon should have the 'R' configuration, and the third carbon should have the 'S' configuration.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
IUPAC Nomenclature
IUPAC nomenclature is a standardized system for naming chemical compounds. It provides a systematic way to describe the structure of a molecule using specific rules and conventions. Understanding IUPAC names involves recognizing prefixes, suffixes, and numbers that indicate the type and position of functional groups and substituents in the molecule.
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Stereochemistry
Stereochemistry involves the study of the spatial arrangement of atoms in molecules and its impact on chemical properties. The terms '2R,3S' refer to the configuration of chiral centers in the molecule, where 'R' and 'S' denote the absolute configuration based on the Cahn-Ingold-Prelog priority rules. Correctly identifying these configurations is crucial for drawing the accurate 3D structure.
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Functional Groups
Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the given compound, 'methoxy' refers to an -OCH3 group, which is an ether functional group. Recognizing and placing functional groups correctly is essential for constructing the molecular structure from the IUPAC name.
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