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 87f

Textbook Question

Draw the correct structure from the following IUPAC names:
(f) (S)-4-isopropoxypent-2-yne.

Verified step by step guidance

Identify the main chain: The name 'pent-2-yne' indicates a five-carbon chain with a triple bond starting at the second carbon. Draw a linear chain of five carbon atoms and place a triple bond between the second and third carbon atoms.

Determine the stereochemistry: The '(S)' configuration indicates the stereochemistry at a chiral center. Identify the chiral center in the structure, which is the fourth carbon in this case.

Add the isopropoxy group: The '4-isopropoxy' part of the name indicates an isopropoxy group attached to the fourth carbon. Draw an isopropoxy group (a propyl group with an oxygen atom replacing one hydrogen) and attach it to the fourth carbon.

Assign priorities for stereochemistry: Assign priorities to the groups attached to the chiral center (fourth carbon) based on atomic number and connectivity. The groups are the isopropoxy group, the rest of the carbon chain, and the hydrogen atom.

Determine the (S) configuration: Arrange the molecule so that the lowest priority group (usually hydrogen) is pointing away from you. Then, observe the order of the remaining groups. If they decrease in priority in a counterclockwise direction, the configuration is (S). Adjust the structure if necessary to ensure the correct stereochemistry.

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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 identifying the main chain, functional groups, and stereochemistry, which are crucial for drawing the correct structure.

Stereochemistry

Stereochemistry refers to the spatial arrangement of atoms in molecules and its impact on chemical properties. The '(S)' designation in the name indicates the specific configuration of the chiral center, which is determined using the Cahn-Ingold-Prelog priority rules. Correctly identifying stereochemistry is essential for accurately representing the molecule's 3D structure.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for characteristic chemical reactions. In the name '4-isopropoxypent-2-yne,' the isopropoxy group is an ether functional group, and the 'yne' suffix indicates a triple bond. Recognizing these groups helps in constructing the correct molecular structure.

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