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

Nitrile to Ketone

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Nitrile to Ketone

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3:34 minutes

Problem 55f

Textbook Question

Show how you would synthesize octan-2-one from each compound. You may use any necessary reagents.
(f) CH₃(CH₂)₅CN

Verified step by step guidance

Step 1: Begin by hydrolyzing the nitrile group (-CN) in CH3(CH2)5CN to convert it into a carboxylic acid. Use acidic or basic hydrolysis conditions, such as H3O+ (acidic) or NaOH followed by acidification. This will yield CH3(CH2)5COOH.

Step 2: Convert the carboxylic acid (CH3(CH2)5COOH) into an acid chloride (CH3(CH2)5COCl) using a reagent like thionyl chloride (SOCl2). This step activates the carboxylic acid for further reactions.

Step 3: Perform a Friedel-Crafts acylation reaction to introduce the ketone functionality. React the acid chloride (CH3(CH2)5COCl) with ethane (CH3CH3) in the presence of a Lewis acid catalyst, such as AlCl3. This will yield octan-2-one.

Step 4: Purify the product octan-2-one using techniques like distillation or chromatography to ensure the desired compound is isolated.

Step 5: Confirm the structure of octan-2-one using spectroscopic methods such as IR (to check for the carbonyl group) and NMR (to verify the positions of the protons and carbons).

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Key Concepts

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

Nitrile Chemistry

Nitriles, such as CH3(CH2)5CN, can be converted into ketones through hydrolysis. This process involves the addition of water in the presence of an acid or base, leading to the formation of a carboxylic acid, which can then be further reduced to yield the corresponding ketone. Understanding the reactivity of nitriles is crucial for synthesizing octan-2-one from this starting material.

Reduction Reactions

Reduction reactions are essential in organic synthesis, where a compound gains electrons or hydrogen, often resulting in the formation of alcohols or ketones. In the context of synthesizing octan-2-one, the reduction of a carboxylic acid derived from the nitrile can be achieved using reagents like lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4), which convert the acid to the desired ketone.

Synthesis Pathways

Synthesis pathways refer to the step-by-step methods used to convert starting materials into target compounds. For octan-2-one, a clear pathway from CH3(CH2)5CN involves hydrolysis to form a carboxylic acid followed by reduction to the ketone. Understanding these pathways allows chemists to design efficient and effective routes for synthesizing complex organic molecules.

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