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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1:45 minutes

Problem 84b

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the starting material and the target compound. The starting material is a methyl ester (cyclopentanecarboxylic acid methyl ester), and the target compound is an aldehyde (cyclopentanecarboxaldehyde). This indicates that the transformation involves the reduction of the ester group to an aldehyde.

Step 2: Identify the appropriate reagent for the reduction. To selectively reduce an ester to an aldehyde, a mild reducing agent such as DIBAL-H (Diisobutylaluminum hydride) is commonly used. DIBAL-H can stop the reduction at the aldehyde stage under controlled conditions.

Step 3: Describe the reaction conditions. The reaction is typically carried out at low temperatures (e.g., -78°C) to prevent over-reduction of the aldehyde to a primary alcohol. After the reaction, hydrolysis is performed to quench the reaction and isolate the aldehyde.

Step 4: Write the reaction mechanism. The mechanism involves the nucleophilic attack of DIBAL-H on the carbonyl carbon of the ester, forming an intermediate aluminum complex. Upon hydrolysis, the intermediate is converted into the aldehyde.

Step 5: Summarize the process. The methyl ester is treated with DIBAL-H at low temperature, followed by hydrolysis, to yield the desired aldehyde. This method ensures selective reduction without over-reduction to the alcohol.

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Key Concepts

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

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. This process is crucial for modifying aromatic compounds, allowing for the introduction of various functional groups. Understanding the mechanisms of EAS, including the role of catalysts and the stability of intermediates, is essential for predicting the outcomes of reactions involving aromatic compounds.

Reactivity of Carbonyl Compounds

Carbonyl compounds, characterized by the presence of a carbon-oxygen double bond (C=O), exhibit distinct reactivity patterns due to the polarization of the carbonyl bond. They can undergo nucleophilic addition, condensation, and oxidation-reduction reactions. Recognizing how these compounds interact with nucleophiles and electrophiles is vital for synthesizing complex organic molecules from simpler starting materials.

Protecting Groups in Organic Synthesis

Protecting groups are temporary modifications used in organic synthesis to prevent unwanted reactions at specific functional groups during multi-step synthesis. For example, methoxy (OCH3) can serve as a protecting group for alcohols or carbonyls, allowing selective reactions to occur without interference. Understanding how to effectively use and remove protecting groups is essential for achieving desired transformations in complex organic synthesis.

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