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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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Which one is the stronger Lewis base: diethyl ether or tetrahydrofuran?

I am trying to understand Lewis bases (bear with me, I am a physicist). I was asking myself how diethyl ether and tetrahydrofuran compare with respect to their properties as solvents in electrophilic ...
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0answers
36 views

Ethyl Acetate and other Solvents in a mixture: miscibility and stability

I was wondering about a heterogeneous solvent mixture containing multiple alcohols such as IPA, Ethanol, methanol etc. Would EtOAc (Ethyl Acetate) play nice in these mixtures at low volumes such as 1 ...
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0answers
23 views

What acid halide reaction is more favorable: cleaving a methyl ether (o-demethylation) or addition to an alkene forming the alkyl halide?

Hydrobromic acid reacts with alkenes to produce alkyl halides, and they also can perform o-demethylation on methyl ethers, producing the corresponding alcohol. On a compound that has both groups, ...
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0answers
48 views

Will ether group undergo cleavage in this molecule?

So, I've got to tell what will be the product after treating with dilute acid. I'm sure that oxygen next to carbon 7 will get protonated resulting in carbon oxygen bond cleavage to generate a stable ...
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2answers
110 views

Using TBAI (tetra-butylammonium iodide) as a catalyst. Ideas on the mechanism or the driving force?

for my etherification of an alcoxide with alkylbromide I used TBAI as a catalyst. The catalyst transfers the alkylbromide into an alkyliodide which is more reactive. I was wondering, what is the ...
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1answer
24 views

Opening of ethers using acids [closed]

I got that following my solution i get the product is 3HCO2H but the given answer is 3HCHO
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1answer
23 views

How to check leaving group ability of cations?

In the reaction of an ether with a hydrogen halide (HX), the positive hydrogen ion replaces one of the alkyl groups attatched to the oxygen; but why does this happen, isn't the hydrogen ion a better ...
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0answers
101 views

Addition of NaBH4 and LiAlH4

NaBH4 and LiAlH4 will be a source for the hydride ion and reaction will begin with addition of hydride by displacing the carbonyl group. But I am not sure will it attack both the carbonyl or only one....
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0answers
32 views

Deperoxidation of ethers via alumina: what happens?

I was reading about the procedures for the removal of peroxides from ethereal solvents, and a procedure which seems to have survived to our days is filtration through a column of "activated alumina" (...
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1answer
24 views

Ethers( Stability doubt) [closed]

Why does H+ attack on epoxide and not on the double bonded carbon?
8
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1answer
95 views

Are crown ethers “recycled”, typically?

I know that crown ethers have the interesting property of strongly complexing alkali metals, which allows them to be used in organic solvents (eg. as "dissolving-activity enhancing agents" for ...
6
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2answers
241 views

Claisen rearrangement in substituted ring

This is an example of Claisen rearrangement, property of allyl vinyl/phenyl ethers. I believe that the allylic migration should take place to the position ortho to both $\ce{-CH3}$ and $-\ce{OR}$ ...
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39 views

Properties of the products of styrene chlorification

Background: When chlorinating styrene with an electrophile two products can be formed by substitution of the benzene ring. That is because the ethylene group is ortho and para directing, from the +M ...
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1answer
455 views

How to acid-wash sand?

I need some acid-washed sand to smooth out boiling in diethyl ether synthesis. I aready have pre-washed sand for general filtration purposes, but it is not labeled as acid-washed. Unfortunately, I ...
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1answer
115 views

No.of isomeric ethers of formula C3H6O

I managed to get 3 ethers:- 1.4-member ring ether(Oxetane) 2.Vinyl ether 3. Epoxy ether This question was asked in my school exam and the teacher had given its answer as 4..Could anyone please tell ...
4
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2answers
526 views

Synthesis of Polypropylene glycol

Polypropylene glycol is produced by ring-opening polymerization of propylene oxide. The initiator is an alcohol and the catalyst a base, usually potassium hydroxide. When the initiator is ethylene ...
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1answer
82 views

What will be the product of this reaction?

We have an alpha beta unsaturated ether, along with a keto group in the same compound, which is being treated with a grignard reagent shown (assume the grignard reagent is in excess). Will it only ...
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1answer
984 views

What are the products of the reaction of methoxypropane with HBr?

The products of the reaction of methoxypropane ($\ce{CH3CH2CH2OCH3}$) with $\ce{HBr}$ are? In my opinion, the products should be: bromopropane ($\ce{CH3CH2CH2Br}$) + methanol ($\ce{CH3OH}$). The ...
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0answers
188 views

Mechanism for reaction of enol ether with HBr

Please refer to the image for the question. I tried two different mechanisms for the reaction (1 and 2) and ended up with two different products. Now I can't decide which of the two mechanisms would ...
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1answer
798 views

Why are ethers treated as substituents and not as functional groups in IUPAC nomenclature?

Why are ethers not considered as functional groups in IUPAC nomenclature? Let us consider the following example: Image source The PIN for this compound is 2-ethoxy-1,1-dimethylcyclohexane. And we ...
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2answers
2k views

Why do alkanes have higher boiling point than their ether counterparts?

Based on my understanding of inter-molecular forces, I expect dipole-dipole interactions to be significantly stronger than van der Waal's interactions. Hence, I expect ethers (which obviously have ...
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1answer
10k views

Halogenation of Phenol [closed]

Why does only one $\ce{Br+}$ ion get generated in a non-polar solvent (such as $\ce{CS2}$), while more $\ce{Br+}$ ions are generated in aqueous or polar solvent (such as $\ce{H2O}$)?
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3answers
185 views

IUPAC way of writing prefix of alkyl isomers of an ether

Consider this compound: I am able to identify the base chain as propane. But, I am having trouble naming the other side of the chain. Will it be named as: 2-(isopropoxy)propane, 2-[(propan-2-yl)oxy]...
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0answers
199 views

Acidity of ethers vs alkanes

I wonder if ethers are more or less acidic at the alpha position than alkanes ($\mathrm{p}K_\mathrm{a} \approx 50$). I'm not sure if the stabilising inductive effect from oxygen or the alpha effect (...
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1answer
3k views

What is the correct name for 2,4-diethyl-4-ethoxyhexane?

A classmate asks you to draw the structure of 2,4-diethyl-4-ethoxyhexane, which he cannot find in a chemical reference manual. Draw the structure of 2,4-diethyl-4-ethoxyhexane. (Question continued.....
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1answer
1k views

Ring opening of epoxides

For the above question, here's what I'd thought: 1. H+ ion from HCl protonates the oxygen 2. Chloride ion attacks the electrophilic carbon, opening the epoxide ring 3. So the final product formed is ...
4
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1answer
209 views

Epoxide ring opens, or not? [duplicate]

Does the epoxide ring open in this case? I guessed it does, but it really doesn't. The answer given (among the four options) is another epoxide, with some sort of substitution. Could someone please ...
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0answers
62 views

Why is triethyl orthoformate stable? [duplicate]

Geminal diols or triols are very unstable and are easily converted into keto or carboxylic compounds. Triethyl orthoformate is a triether of similar structure. I want to know why the former is so ...
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2answers
153 views

How do phase transfer catalysts bring anions to organic phase?

Many anions are quite stable in the aqueous phase, but not so much in organic solvents where its necessary to perform some reaction (usually nucleophilic substitutions). I have heard that crown ethers ...
3
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0answers
292 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
407 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
557 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
89 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}\\ -> {...
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1answer
261 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
410 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 ...
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3answers
1k 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 ...
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2answers
895 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 ...
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1answer
322 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 ...
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1answer
1k 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 ...
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1answer
1k 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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1answer
3k 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 ...
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1answer
1k 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 ...
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6answers
42k views

How to determine the least stable 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{...
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1answer
3k 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 ...
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3answers
13k 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 ...
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1answer
252 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 ...