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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4:37 minutes

Problem 56g

Textbook Question

Show how you would synthesize octanal from each compound. You may use any necessary reagents.
(g) ethyl octanoate

Verified step by step guidance

Step 1: Begin with ethyl octanoate, which is an ester. The goal is to convert this ester into an aldehyde (octanal). To achieve this, you need to reduce the ester selectively to the aldehyde without over-reducing it to the alcohol.

Step 2: Use a reducing agent that can selectively reduce esters to aldehydes. One such reagent is diisobutylaluminum hydride (DIBAL-H). Add DIBAL-H to ethyl octanoate at low temperatures (e.g., -78°C) to ensure selective reduction to the aldehyde.

Step 3: After the reaction with DIBAL-H, perform a quenching step by adding water or a weak acid to hydrolyze the intermediate and release the aldehyde (octanal).

Step 4: Isolate the product (octanal) by using standard organic workup techniques, such as extraction and purification (e.g., distillation or chromatography).

Step 5: Confirm the structure of the synthesized octanal using spectroscopic methods such as IR (look for the C=O stretch of the aldehyde) and NMR (look for the aldehyde proton signal around 9-10 ppm).

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Key Concepts

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

Synthesis of Aldehydes

The synthesis of aldehydes, such as octanal, often involves the oxidation of primary alcohols or the reduction of carboxylic acids. In this case, ethyl octanoate can be hydrolyzed to octanoic acid, which can then be reduced to octanal. Understanding the functional group transformations and the reagents required for these reactions is crucial for effective synthesis.

Reagents and Reaction Conditions

Different reagents and conditions are essential for achieving specific transformations in organic synthesis. For example, using sodium borohydride (NaBH4) or lithium aluminum hydride (LiAlH4) can reduce carboxylic acids to aldehydes. Familiarity with these reagents and their mechanisms helps in planning the synthesis route from ethyl octanoate to octanal.

Functional Group Interconversion

Functional group interconversion is a fundamental concept in organic chemistry that involves transforming one functional group into another. In this synthesis, converting the ester group in ethyl octanoate to an aldehyde requires specific reactions, such as hydrolysis followed by reduction. Mastery of these transformations is key to successfully synthesizing octanal.

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Predict the major products of the following reactions.

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Textbook Question

(a) Outline the syntheses indicated in Solved Problem 18-2, beginning with aldehydes and alkyl halides.

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Textbook Question

Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:

Textbook Question

Show how you would synthesize octanal from each compound. You may use any necessary reagents.

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Textbook Question

Show how you would accomplish the following syntheses efficiently and in good yield. You may use any necessary reagents.

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