Why is the use of tert-butyl methyl ether favoured over using diethyl ether?

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In summary, tert-butyl methyl ether is preferred over diethyl ether for its ability to dissolve trans-stilbene and its bulkiness compared to diethyl ether. It is not used for safety or cost reasons, but its specific effects are unknown.
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MagicalM
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Homework Statement


Why is the use of tert-butyl methyl ether favoured over using diethyl ether?

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The Attempt at a Solution


After the formation of trans-stilbene, tert-butyl methyl ether was used to dissolve trans-stilbene. Water was added to dissolve any impurities which was absorbed by calcium chloride pellets along with the impurities. I guess the reason why tert-butyl ether was used is due to the bulkiness of the substituents in comparison to diethyl ether, but I don't know what that would do in comparison. Why was tert-butyl ether used as opposed to diethyl ether? It is not due to safety or cost concerns is what I do know. However, I don't know what the answer is or how to find it. Please help. Much appreciated. :)
 
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1. Why is tert-butyl methyl ether considered safer than diethyl ether for laboratory use?

Tert-butyl methyl ether (MTBE) is considered safer than diethyl ether because it has a higher flash point and a lower volatility. This means that it is less likely to ignite and has a lower risk of producing explosive vapors. Additionally, MTBE has a less potent anesthetic effect compared to diethyl ether, making it safer for handling in a laboratory setting.

2. What are the advantages of using tert-butyl methyl ether over diethyl ether in organic synthesis?

MTBE is preferred over diethyl ether in organic synthesis due to its higher boiling point and better solubility in water. This makes it easier to separate from water and other polar solvents, and also allows for reactions to be carried out at higher temperatures. MTBE is also less reactive towards strong acids and bases, making it more stable in a wider range of reaction conditions.

3. Is tert-butyl methyl ether more expensive than diethyl ether?

In general, MTBE is more expensive than diethyl ether due to its more complex synthesis process. However, the cost difference is not significant and is often outweighed by the benefits of using MTBE in terms of safety and ease of use.

4. Can tert-butyl methyl ether be used as a substitute for diethyl ether in all laboratory procedures?

No, MTBE may not be a suitable substitute for diethyl ether in all laboratory procedures. While it is commonly used as a solvent in organic synthesis, it may not be compatible with certain reaction conditions or may not have the same reactivity as diethyl ether. It is important to consult with a chemist or refer to literature sources before substituting MTBE for diethyl ether.

5. Are there any environmental concerns associated with the use of tert-butyl methyl ether?

There have been some environmental concerns associated with the use of MTBE, particularly its potential to contaminate groundwater. However, these concerns have mostly been addressed through regulations and improved handling and disposal practices. Additionally, MTBE is not as commonly used as diethyl ether and is often only used in small amounts, reducing its potential impact on the environment.

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