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

Oxidation of Alcohols

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Oxidation of Alcohols

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4:29 minutes

Problem 60d

Textbook Question

Show how you would accomplish the following syntheses.
(d)

Verified step by step guidance

Step 1: Begin by oxidizing the primary alcohol group (-CH2OH) in the starting material, Ph-(CH2)4-OH, to an aldehyde (-CHO). This can be achieved using an oxidizing agent such as PCC (Pyridinium Chlorochromate). The product will be Ph-(CH2)3-CHO.

Step 2: Perform an intramolecular aldol condensation. Under basic conditions (e.g., NaOH or KOH), the aldehyde group (-CHO) will react with the alpha-hydrogen of the adjacent methylene group (-CH2-) to form a cyclic intermediate. This step creates the six-membered ring structure.

Step 3: Dehydrate the aldol intermediate to form the conjugated enone. This step involves the elimination of water, typically under acidic or basic conditions, resulting in the formation of the double bond in the ring structure.

Step 4: Hydrogenate the double bond in the enone selectively to form the saturated ketone. This can be achieved using a catalyst such as palladium on carbon (Pd/C) under hydrogen gas (H2). The product will be tetralone.

Step 5: Verify the structure of tetralone by analyzing its chemical properties or using spectroscopic techniques such as NMR or IR to confirm the presence of the ketone group and the cyclic structure.

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Key Concepts

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

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. A clear grasp of mechanisms helps predict the outcomes of reactions and the conditions required for successful 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 essential for predicting reactivity and understanding how different compounds can be synthesized or transformed. Each functional group has unique properties that influence the overall behavior of the molecule.

Synthesis Strategies

Synthesis strategies involve planning a series of chemical reactions to construct a desired compound from simpler starting materials. This includes selecting appropriate reagents, reaction conditions, and understanding the order of reactions. Effective synthesis requires knowledge of various reactions and the ability to foresee potential challenges and side reactions.

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