Questions tagged [ethers]

This tag is for questions relating to ethers: compounds containing an $\ce{R-O-R}$ fragment. It can be applied to the synthesis of, synthesis from and properties of ethers. If one of the $\ce{R}$ groups noted above is a carbonyl group, use *esters* instead. If both are, *carbonyl-compounds* is appropriate. This tag should not be used if the ether functionality is minor compared to others, or if it does not take part in the reaction in question.

Filter by
Sorted by
Tagged with
5
votes
1answer
2k views

Phenol or ethanol as a nucleophile for ether formation?

If we react phenol with $\ce{C2H5I}$ in $\ce{C2H5O- Na+}$ (excess), $\ce{C2H5OH}$ (anhydrous) solutions . In this reaction why is diethyl ether not formed and the actual product is phenyl ethyl ...
14
votes
3answers
19k views

Why are acetals stable to bases and nucleophiles?

Why are acetals stable to bases and nucleophiles? Could it be due to electronic effects? Lone pairs on the two oxygen atoms create an unfavorable environment for the approaching nucleophiles and ...
16
votes
4answers
53k views

How to determine the worst resonance structures out of a given set?

So I was "happily" doing organic chemistry homework when I came across this question: For 1-methoxy-1,3-butadiene, which of the following resonating structure is the least stable? $$\begin{...
4
votes
1answer
4k views

How is it possible, that the hydrolysis of ethers proceed via a SN2 mechanism?

Ethers on hydrolysis with dilute $\ce{H2SO4}$ under pressure produce alcohols. This is basically a type of acidic cleavage of ethers by the SN2 mechanism. (source) There is inversion of ...
3
votes
2answers
3k views

How many ether metamers are possible for C4H10O?

How many ether metamers are possible for $\ce{C4H10O}?$ According to me, the answer should be 2 but it was given 3. I know 3 structures can be made: $$\ce{CH3—O—CH2—CH2—CH3}\tag{1}$$ $$\ce{CH3—CH2—...
3
votes
1answer
420 views

How to make p-chloroanisole from methanol and benzene?

I am tasked to synthesise para-chloroanisole from methanol and benzene. Other reagents are permitted. Would it be correct to have the benzene attack the methanol $\ce{H}$ and then attack the ...
1
vote
1answer
573 views

Which mechanism do ethers follow when cleaved by hydrogen halides?

Ethers can be cleaved under acidic conditions by treatment with hydrogen halides (HX, where X = Cl/Br/I). Some of these reactions proceed by SN1 mechanisms and some by SN2 mechanisms. How can I tell ...
0
votes
3answers
670 views

Is there an intramolecular hydrogen bond in guaiacol?

Is there a hydrogen bond between the $\ce{H}$ atom of $\ce{-OH}$ group and the $\ce{O}$ atom of the $\ce{-OCH3}$ group in ortho-methoxyphenol? I was told no. But I want to know why.