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

22. Carboxylic Acid Derivatives: NAS

Acid-Catalyzed Ester Hydrolysis

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Acid-Catalyzed Ester Hydrolysis

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7:16 minutes

Problem 64

Textbook Question

Describe how the target molecule (butanone) can be synthesized in a high yield from butane.

Verified step by step guidance

Step 1: Begin by understanding the transformation required. The target molecule, butanone (CH3COCH2CH3), is a ketone, while the starting material, butane (C4H10), is an alkane. This means the process will involve oxidation to introduce a carbonyl group.

Step 2: Perform a controlled oxidation of butane. First, convert butane into butanol (an alcohol) by reacting it with oxygen in the presence of a catalyst, such as cobalt or manganese-based catalysts. This step is crucial to introduce a functional group that can be further oxidized.

Step 3: Oxidize the butanol to butanal (an aldehyde). This can be achieved using a mild oxidizing agent such as PCC (Pyridinium chlorochromate) or by carefully controlling the reaction conditions with stronger oxidizing agents like KMnO4 or CrO3.

Step 4: Further oxidize butanal to butanone. This step involves converting the aldehyde group (-CHO) into a ketone group (-CO-). A strong oxidizing agent such as potassium dichromate (K2Cr2O7) in acidic conditions can be used for this transformation.

Step 5: Ensure high yield by carefully controlling reaction conditions at each step. For example, avoid over-oxidation of butanone to carboxylic acids by monitoring the reaction time and using appropriate catalysts. Purify the final product using distillation or other separation techniques.

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Key Concepts

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

Hydrocarbon Functional Groups

Understanding the functional groups in hydrocarbons is essential for organic synthesis. Butane is an alkane, characterized by single bonds between carbon atoms, while butanone is a ketone, which contains a carbonyl group (C=O) flanked by two carbon atoms. Recognizing these functional groups helps in determining the necessary reactions to convert butane into butanone.

Oxidation Reactions

Oxidation reactions involve the loss of electrons or an increase in oxidation state, which is crucial for converting alkanes to ketones. In the case of butane to butanone, a common method is the oxidation of butane using reagents like potassium permanganate or chromic acid, which facilitates the transformation of the alkane into the corresponding ketone while maximizing yield.

Reaction Conditions and Yield

The conditions under which a reaction occurs significantly affect the yield of the desired product. Factors such as temperature, pressure, and the presence of catalysts can influence the efficiency of the oxidation process. Optimizing these conditions is vital for achieving a high yield of butanone from butane, ensuring that side reactions are minimized and the desired product is favored.

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