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

13. Alcohols and Carbonyl Compounds

Reducing Agent

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Reducing Agent

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2:08 minutes

Problem 39c

Textbook Question

Predict the product of the following reaction sequences.
(c)

Verified step by step guidance

Step 1: Analyze the starting material, which is a cyclic amide (lactam). The structure contains a five-membered ring with an amide group.

Step 2: The first reaction involves H2SO4, H2O, and heat. This is typically a hydrolysis reaction where the amide is converted into a carboxylic acid. The cyclic amide will open up to form a linear carboxylic acid.

Step 3: The second step involves SOCl2, which is used to convert carboxylic acids into acyl chlorides. The carboxylic acid formed in the previous step will be transformed into an acyl chloride.

Step 4: The third step uses LiAlH(Ot-Bu)3, a reducing agent that selectively reduces acyl chlorides to aldehydes. The acyl chloride from the previous step will be reduced to an aldehyde.

Step 5: Consider the overall transformation from the cyclic amide to the aldehyde, noting the changes in functional groups and the reagents used at each step.

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Key Concepts

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

Hydrolysis of Lactams

Lactams are cyclic amides that can undergo hydrolysis in the presence of acid and water, especially under heating conditions. This reaction breaks the amide bond, converting the lactam into a linear carboxylic acid and an amine. In this sequence, the use of H2SO4 and heat facilitates the hydrolysis of the lactam ring, leading to the formation of a carboxylic acid.

Conversion of Carboxylic Acids to Acyl Chlorides

Carboxylic acids can be converted into acyl chlorides using thionyl chloride (SOCl2). This reaction involves the substitution of the hydroxyl group of the carboxylic acid with a chlorine atom, forming an acyl chloride. Acyl chlorides are more reactive than carboxylic acids and are useful intermediates in organic synthesis.

Selective Reduction of Acyl Chlorides

Lithium tri-tert-butoxyaluminum hydride (LiAlH(Ot-Bu)3) is a selective reducing agent used to convert acyl chlorides to aldehydes. Unlike other hydride reagents, it does not reduce the aldehyde further to an alcohol. This selectivity is crucial for synthesizing aldehydes from acyl chlorides without over-reduction, allowing for controlled product formation in multi-step synthesis.

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Related Practice

Textbook Question

Suggest the most appropriate reagent for each synthesis, and explain your choice.

(c)

Textbook Question

Sodium triacetoxyborohydride, NaBH(OAc)₃, is a mild reducing agent that reduces aldehydes much more quickly than ketones. It can be used to reduce aldehydes in the presence of ketones, such as in the following reaction:

(a) Draw a complete Lewis structure for sodium triacetoxyborohydride.

Textbook Question

Draw the products of the following reactions. Indicate whether each reaction is an oxidation or a reduction.

Textbook Question

Propose a mechanism for the following reaction:

Textbook Question

Show how you would synthesize the following compounds from the appropriate carboxylic acids or acid derivatives.

Textbook Question

How can the following compounds be prepared from the given starting materials?

Multiple Choice

What is the product of the reaction?

Multiple Choice