Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

12. Alcohols, Ethers, Epoxides and Thiols

Naming Ethers

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Naming Ethers

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Problem 87d

Textbook Question

Draw the correct structure from the following IUPAC names:
(d) (2R,3S)-methoxy-3-methylpentane

Verified step by step guidance

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.

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.

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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