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

12. Alcohols, Ethers, Epoxides and Thiols

Naming Ethers

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Naming Ethers

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5:48 minutes

Problem 35

Textbook Question

(A true story.) An inexperienced graduate student moved into a laboratory and began work. He needed some diethyl ether for a reaction, so he opened an old, rusty 1-gallon can marked 'ethyl ether' and found there was half a gallon left. To purify the ether, the student set up a distillation apparatus, started a careful distillation, and went to the stockroom for the other reagents he needed. While he was at the stockroom, the student heard a muffled "boom." He quickly returned to his lab to find a worker from another laboratory putting out a fire. Most of the distillation apparatus was embedded in the ceiling.
(a) Explain what probably happened.
(b) Explain how this near-disaster might have been prevented.

Verified step by step guidance

Step 1: Understand the chemical properties of diethyl ether. Diethyl ether is highly volatile and flammable, with a low boiling point. Over time, it can form peroxides when exposed to air and light. These peroxides are highly explosive and can detonate during distillation or heating.

Step 2: Analyze the situation described. The student used an old, rusty can of diethyl ether, which likely had been stored for a long time. This storage condition increases the likelihood of peroxide formation. During distillation, the heat applied to the ether could have caused the peroxides to detonate, leading to the explosion.

Step 3: Explain how the explosion occurred. The distillation process involves heating the liquid to separate components based on boiling points. If peroxides were present in the ether, the heat could have triggered their decomposition, releasing a large amount of energy and causing the explosion.

Step 4: Suggest preventive measures. To prevent such incidents, diethyl ether should always be tested for peroxide formation before use, especially if it has been stored for a long time. Peroxide test strips or chemical tests can be used to detect their presence. If peroxides are found, the ether should be disposed of safely according to hazardous waste protocols.

Step 5: Recommend proper storage and handling practices. Diethyl ether should be stored in tightly sealed containers, away from light and heat, and used within a reasonable timeframe. Laboratories should maintain a chemical inventory system to track the age of chemicals and ensure safe disposal of old or potentially hazardous substances.

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Key Concepts

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

Volatility of Diethyl Ether

Diethyl ether is a highly volatile organic compound, meaning it readily evaporates at room temperature. This property can lead to the accumulation of flammable vapors in the air, especially in poorly ventilated spaces. When these vapors come into contact with an ignition source, they can ignite, causing explosions or fires. Understanding the volatility of diethyl ether is crucial for safe handling and storage.

Distillation Process

Distillation is a separation technique that relies on differences in boiling points to purify liquids. In this process, the liquid is heated to create vapor, which is then cooled to form a liquid again. If not properly monitored, distillation can lead to overheating and the formation of flammable vapors, especially with substances like diethyl ether. Knowledge of the distillation process is essential to prevent accidents during purification.

Laboratory Safety Protocols

Laboratory safety protocols are guidelines designed to minimize risks associated with chemical handling and experiments. These include proper ventilation, the use of fume hoods, and the importance of not leaving distillation setups unattended. Adhering to these protocols can significantly reduce the likelihood of accidents, such as fires or explosions, by ensuring that hazardous materials are managed safely and effectively.

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