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

Acetal Protecting Group

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Acetal Protecting Group

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6:19 minutes

Problem 29e

Textbook Question

Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.
(e)

Verified step by step guidance

Step 1: Begin with the starting material, cyclopentanone. The goal is to convert the ketone group into a hydroxyl group while introducing a benzoyl group (C=O attached to a phenyl group) at the alpha position.

Step 2: Perform an alpha-alkylation reaction. First, generate the enolate of cyclopentanone by treating it with a strong base such as LDA (Lithium Diisopropylamide). This enolate will act as a nucleophile.

Step 3: Introduce the benzoyl group by reacting the enolate with benzyl bromide (PhCH2Br) in an SN2 reaction. This will add the benzyl group to the alpha position of the cyclopentanone.

Step 4: Oxidize the benzyl group to a benzoyl group. Use an oxidizing agent such as PCC (Pyridinium Chlorochromate) or Jones reagent to convert the CH2 group into a C=O group.

Step 5: Reduce the ketone group in cyclopentanone to a hydroxyl group. Use a reducing agent such as NaBH4 (Sodium Borohydride) or LiAlH4 (Lithium Aluminum Hydride) to achieve this transformation, yielding the final product.

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Key Concepts

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

Organic Synthesis

Organic synthesis is the process of constructing organic compounds through chemical reactions. It involves the strategic selection of starting materials and reagents to achieve a desired product. Understanding the principles of synthesis is crucial for designing pathways that efficiently convert reactants into target molecules while considering factors like yield and selectivity.

Reaction Mechanisms

A reaction mechanism describes the step-by-step sequence of elementary reactions that occur during a chemical transformation. It provides insight into how bonds are broken and formed, and the intermediates that may be involved. Familiarity with mechanisms is essential for predicting the outcomes of reactions and for selecting appropriate reagents in synthesis.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups is vital in organic chemistry as they dictate the reactivity and properties of compounds. Understanding how different functional groups interact can guide the selection of reagents and conditions for successful synthesis.

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