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

Imine vs Enamine

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

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5:32 minutes

Problem 44b

Textbook Question

A chemist failed to generate the alcohol using the reaction shown here.
(b) How could the reaction conditions be modified to allow formation of the product?

Verified step by step guidance

Analyze the reaction provided in the problem. Identify the starting material, reagents, and the desired product. Pay attention to the functional groups involved and the type of reaction (e.g., reduction, oxidation, substitution, etc.).

For part (a), consider why the reaction might fail. Common reasons include the use of inappropriate reagents, incorrect reaction conditions (e.g., temperature, solvent, or pH), or the presence of competing side reactions. Evaluate whether the reagents used are suitable for the transformation of the starting material into the desired alcohol.

For part (b), propose general modifications to the reaction conditions. For example, if the reaction requires a reducing agent to convert a carbonyl group to an alcohol, ensure that a strong and selective reducing agent (e.g., NaBH₄ or LiAlH₄) is used. Alternatively, if the reaction involves a nucleophilic substitution, ensure the nucleophile and leaving group are compatible under the reaction conditions.

Consider the role of the solvent and temperature in the reaction. For instance, polar protic or aprotic solvents can influence the reactivity of reagents. Adjusting the temperature may also help drive the reaction forward or suppress side reactions.

Finally, ensure that the reaction mechanism is feasible under the proposed conditions. For example, if the reaction involves an intermediate, confirm that the intermediate can form and proceed to the desired product under the modified conditions.

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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 it describes the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the role of catalysts. A failure to generate the desired alcohol may indicate that the proposed mechanism is not feasible under the given conditions.

Reaction Conditions

Reaction conditions encompass factors such as temperature, pressure, solvent, and concentration that can significantly influence the outcome of a chemical reaction. Modifying these conditions can enhance the likelihood of product formation. For instance, increasing temperature may provide the necessary energy to overcome activation barriers.

Functional Group Reactivity

Functional group reactivity refers to how different functional groups behave in chemical reactions, influencing their ability to undergo transformations. In the context of alcohol formation, understanding the reactivity of the starting materials and the stability of the intermediates is essential. If the functional groups involved are not compatible, the reaction may not proceed as expected.

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Acetals can serve as protecting groups for 1,2-diols, as well as for aldehydes and ketones. When the acetal is formed from acetone plus the diol, the acetal is called an acetonide. Show the acetonides formed from these diols with acetone under acid catalysis.

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As discussed in Section 17.9.1, alkenes can be hydrogenated selectively in the presence of ketones. Suppose that was not the case, and suggest how you might use a protecting group strategy to generate A from B.

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Show how you would synthesize the following derivatives from appropriate carbonyl compounds.

(d)

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