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

11. Radical Reactions

Radical Reaction

Organic Chemistry

11. Radical Reactions

Radical Reaction

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5: minutes

Problem 23a

Textbook Question

Design a multistep synthesis to show how the following compounds can be prepared from the given starting material:
a.

Verified step by step guidance

Step 1: Begin with the starting material, cyclopentane. Introduce a halogen atom (e.g., bromine) to the molecule by performing a free radical halogenation reaction using Br₂ and light (hv). This will yield bromocyclopentane.

Step 2: Convert bromocyclopentane into cyclopentanol by performing a nucleophilic substitution reaction (SN2) using aqueous NaOH. The hydroxide ion will replace the bromine atom, forming cyclopentanol.

Step 3: Oxidize cyclopentanol to cyclopentanone using an oxidizing agent such as PCC (Pyridinium Chlorochromate) or Jones reagent (CrO₃/H₂SO₄). This step converts the alcohol group into a ketone group.

Step 4: Perform a Baeyer-Villiger oxidation on cyclopentanone using a peracid such as mCPBA (meta-Chloroperoxybenzoic acid). This reaction inserts an oxygen atom adjacent to the carbonyl group, forming the desired lactone (cyclic ester).

Step 5: Verify the structure of the product to ensure it matches the target compound, which is a cyclic ester derived from cyclopentanone.

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Key Concepts

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

Cycloalkane Reactivity

Cycloalkanes, such as cyclohexane, are saturated hydrocarbons that can undergo various reactions, including substitution and elimination. Understanding their reactivity is crucial for designing synthetic pathways, as these reactions can lead to the formation of more complex structures, such as bicyclic compounds. The stability and strain of the ring structure also influence the types of reactions that can occur.

Bicyclic Compounds

Bicyclic compounds consist of two interconnected rings and can exhibit unique chemical properties compared to their monocyclic counterparts. The synthesis of bicyclic structures often involves strategic bond formation and rearrangement, which can be achieved through various organic reactions. Recognizing the stereochemistry and potential isomerism in bicyclic systems is essential for successful synthesis.

Multistep Synthesis

Multistep synthesis refers to the process of constructing a complex molecule through a series of chemical reactions, each building upon the previous step. This approach allows chemists to introduce functional groups, create new bonds, and manipulate molecular structures systematically. Mastery of multistep synthesis is vital for organic chemists, as it enables the transformation of simple starting materials into intricate target compounds.

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