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

14. Synthetic Techniques

Retrosynthesis

Organic Chemistry

14. Synthetic Techniques

Retrosynthesis

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5:32 minutes

Problem 38a

Textbook Question

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.
(a) trans-cyclopentane-1,2-diol

Verified step by step guidance

Identify the target molecule: The target compound is trans-cyclopentane-1,2-diol, which is a cyclopentane ring with hydroxyl groups (-OH) attached to carbons 1 and 2 in a trans configuration (opposite sides of the ring).

Start with the given starting material: Cyclopentanol (a cyclopentane ring with a single hydroxyl group). The goal is to introduce a second hydroxyl group at the adjacent carbon in a trans configuration.

Use an oxidation reaction to convert cyclopentanol into cyclopentanone. This can be achieved using an oxidizing agent such as PCC (Pyridinium chlorochromate) or Jones reagent. The product will be cyclopentanone, a ketone.

Perform an enolate formation and hydroxylation: Treat cyclopentanone with a base (e.g., NaOH) to form the enolate ion. Then, use an electrophilic hydroxylation reagent such as MCPBA (meta-chloroperoxybenzoic acid) or a similar epoxidation reagent to introduce an epoxide across the double bond.

Open the epoxide ring under acidic or basic conditions to form the trans-diol. For example, treat the epoxide with aqueous acid (e.g., H3O+) or a base (e.g., NaOH) to yield trans-cyclopentane-1,2-diol as the final product.

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Key Concepts

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

Synthesis of Diols

Diols are compounds containing two hydroxyl (-OH) groups. The synthesis of diols can be achieved through various methods, including the reduction of carbonyl compounds or the addition of water to alkenes. Understanding the reactivity of alcohols and the mechanisms involved in these reactions is crucial for developing a synthetic route to trans-cyclopentane-1,2-diol.

Cyclopentanol as a Starting Material

Cyclopentanol is a cyclic alcohol that can serve as a versatile starting material in organic synthesis. Its structure allows for various functional group transformations, such as oxidation or substitution reactions. Recognizing how to manipulate cyclopentanol to introduce additional functional groups is essential for synthesizing the desired diol.

Reagents and Solvents in Organic Synthesis

The choice of reagents and solvents is critical in organic synthesis, as they can influence reaction rates, yields, and selectivity. Common reagents for diol synthesis include oxidizing agents and reducing agents, while solvents can affect solubility and reaction conditions. Familiarity with these components is necessary to design an effective synthesis pathway for trans-cyclopentane-1,2-diol.

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Related Practice

Textbook Question

Show how you would synthesize each compound, starting with alkenes or cycloalkenes that contain no more than six carbon atoms. You may use any additional reagents you need.

(c)

Textbook Question

Propose a synthesis of the carbonyl(s) using the (ii) dihydroxylation/periodic acid cleavage pathways.

(a)

Textbook Question

Propose a synthesis of the carbonyl(s) using the (ii) dihydroxylation/periodic acid cleavage pathways.

(b)

Textbook Question

Give the structures of the products represented by letters in this synthesis.

Part 2:

Textbook Question

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.

(c)

Textbook Question

Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:

Textbook Question

Give the structures of the intermediates represented by letters J, L, M, and N in this synthesis.

Textbook Question

Give the structures of the products represented by letters in this synthesis.

Part 1:

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Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.(a) trans-cyclopentane-1,2-diol

Key Concepts

Synthesis of Diols

Cyclopentanol as a Starting Material

Reagents and Solvents in Organic Synthesis

Watch next

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.
(a) trans-cyclopentane-1,2-diol