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.

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0answers
478 views

Why are thioethers not better leaving groups than ethers?

Why are thioethers ($\ce{RSR}$) not better leaving groups than ethers ($\ce{ROR}$)? I learnt that better bases are poorer leaving groups. Here, clearly the poorer base is thioether, as the lone pair ...
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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.
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2answers
891 views

How can isotope labelling be used to determine the mechanism of ether cleavage with hydrogen iodide?

When methyl tert-butyl ether (MTBE) is treated with one equivalent of hydrogen iodide, the ether C–O bond is cleaved. I read that if the oxygen in MTBE is isotopically labelled, it is possible to ...
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0answers
119 views

Synthesis of para-chloroanisole using diazotisation followed by chlorination with aluminium chloride

Is this a legitimate reaction scheme to synthesise para-chloroanisole from benzene and methanol as the only organic reactants? $$\ce{C6H6 -> HNO3/H2SO4 -> H2/Pd -> HONO/{Ethanol}\\ -> {...
3
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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 ...
6
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1answer
489 views

Do crown ethers have to have two carbons between the oxygens? If so, why?

I just began learning about ethers and I have noticed that pictures of crown ethers, no matter what size they are, always have two carbon atoms left and right of each oxygen atom before you reach ...
8
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3answers
2k views

Preventing build-up of Diethyl Ether Peroxides

I've never stored Diethyl Ether before but am thinking of producing minor amounts myself and storing said Ether inside of glass/PTFE bottles. I am aware of possible pressure build-up due to vapors ...
10
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2answers
2k views

Most stable conformational isomer of 3-methoxycyclohexan-1-ol

Among the following, the most stable isomer is? I am aware of the fact that equatorial substituents are more stable than axial substituents but couldn't proceed to apply it here. However the answer ...
2
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1answer
515 views

Will Sodium Amide react with Epoxides in the same manner as Grignard Reagents?

I have been unable to find the reaction anywhere on the internet so I'm assuming the answer is no, although I would like an explanation as to why. I can't seem to find any reason why it would not ...
5
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1answer
2k views

How to prevent dripping when using a Pasteur pipette with solvents like diethyl ether?

I'm trying to use a Pasteur pipette for pipetting diethyl ether and regardless of the angle I hold the pipette at, the diethyl ether will automatically start dispensing itself (I am unsure of what ...
5
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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 ...
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2answers
4k views

Test for diethylether or tertiary alcohol?

What is a simple chemical test to tell the difference between a tertiary alcohol (e.g. 2-methylpropan-2-ol) and an ether (specifically diethylether/ethoxyethane)? Neither of them can be oxidised by ...
6
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1answer
2k views

Reaction of cyclohexane-1,2,4-triol with acetone

What is the product formed when cyclohexane-1,2,4-triol reacts with 1 equivalent of acetone in an acidic medium? There are 3 possible hemiacetal products. The major one is formed via nucleophilic ...
16
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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{...
5
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2answers
5k views

Heating of Ethers with HI and Cleavage of Ethers

Question: Give the major product formed by the heating of the following ether with HI. CH3 | CH3-CH2-CH-CH2-O-CH2-CH3 My Attempt: According to me,...
4
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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 ...
14
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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 ...
1
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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 ...

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