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 7e

Textbook Question

Draw the structure that corresponds to the name provided.
(e) (1S,4S)-4-isopropylcyclopent-2-enethiol

Verified step by step guidance

Start by identifying the main structure: cyclopent-2-ene. This indicates a cyclopentane ring with a double bond between the second and third carbon atoms.

Next, consider the stereochemistry indicated by (1S,4S). This means that the first and fourth carbon atoms in the ring have specific stereochemistry. Use wedge and dash bonds to represent these stereocenters, with 'S' indicating the counterclockwise arrangement of substituents when viewed from the front.

Add the isopropyl group to the fourth carbon atom. An isopropyl group is a branched alkyl group with the formula \( \text{C}_3\text{H}_7 \), typically represented as \( \text{-CH(CH}_3\text{)}_2 \). Attach this group to the fourth carbon, considering the stereochemistry.

Include the thiol group (\( \text{-SH} \)) on the second carbon atom. Thiol groups are similar to alcohols but contain sulfur instead of oxygen. Ensure the thiol group is correctly positioned relative to the double bond.

Verify the structure by checking the placement of all groups and the stereochemistry. Ensure that the double bond, isopropyl group, and thiol group are correctly positioned according to the IUPAC name provided.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and its impact on chemical properties. In this context, the (1S,4S) notation indicates the specific 3D orientation of the substituents on the cyclopentene ring, which is crucial for accurately drawing the molecule's structure.

IUPAC Nomenclature

IUPAC nomenclature is a standardized system for naming chemical compounds. Understanding this system is essential for interpreting the name '4-isopropylcyclopent-2-enethiol,' which describes the molecule's structure, including the cyclopentene ring, the isopropyl group at position 4, and the thiol group at position 2.

Functional Groups

Functional groups are specific groups of atoms within molecules that determine the chemical reactivity and properties of those molecules. In this case, the thiol group (-SH) is a key functional group that must be correctly positioned on the cyclopentene ring to accurately represent the compound's structure.

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