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

21. Aldehydes and Ketones: Nucleophilic Addition

Oxidizing and Reducing Agents

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Oxidizing and Reducing Agents

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1:44 minutes

Problem 36f

Textbook Question

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).
(f)

Verified step by step guidance

Step 1: Recognize the transformation. The starting material is a carboxylic acid (-COOH), and the product is a primary alcohol (-CH2OH). This indicates a reduction reaction is required.

Step 2: Select an appropriate reducing agent. Carboxylic acids can be reduced to primary alcohols using strong reducing agents such as lithium aluminum hydride (LiAlH4). Sodium borohydride (NaBH4) is not strong enough for this transformation.

Step 3: Write the reaction conditions. The reduction of the carboxylic acid to the alcohol typically involves treating the carboxylic acid with LiAlH4 in an anhydrous solvent like diethyl ether or tetrahydrofuran (THF). After the reaction, the mixture is quenched with water or a mild acid to complete the process.

Step 4: Consider the mechanism. LiAlH4 donates hydride ions (H⁻) to the carbonyl carbon of the carboxylic acid, reducing it first to an aldehyde intermediate and then further to the primary alcohol.

Step 5: Verify the product. The final product should be cyclopentylmethanol (CH2OH group attached to the cyclopentane ring), which matches the desired synthesis.

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Key Concepts

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

Synthetic Pathways

Synthetic pathways refer to the series of chemical reactions and transformations that convert starting materials into desired products. Understanding these pathways is crucial for planning efficient syntheses, as it involves selecting appropriate reagents and conditions to achieve the target molecule with minimal steps and byproducts.

Reagents and Their Functions

Reagents are substances used in chemical reactions to facilitate the transformation of reactants into products. Each reagent has specific roles, such as acting as a catalyst, providing functional groups, or promoting certain reaction mechanisms. Knowledge of common reagents and their functions is essential for designing effective synthetic routes.

Reaction Mechanisms

Reaction mechanisms describe the step-by-step sequence of elementary reactions that occur during a chemical transformation. Understanding these mechanisms helps predict the outcomes of reactions, including the formation of intermediates and the stereochemistry of products, which is vital for successful synthesis in organic chemistry.

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