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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Mechanism of ring expansion of epoxide

The below transformation is from J. Am. Chem. Soc. 1990, 112, 14, 5583–5601 What does the treatment with lithium anion of ethoxyacetylene in the presence of the lewis acid do to epoxides? How does ...
wayrese's user avatar
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Which hydrogens are the most acidic in a THF molecule?

Which hydrogens are the most acidic in a THF molecule? I understand the main factors that influence acidity, but I can't seem to figure this one out and I have not gotten any answers on the internet. ...
Shiv Mehrotra's user avatar
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1 answer
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Williamson Ether synthesis use of particular solvent [closed]

In Williamson ether synthesis conjugate acid of corresponding alkoxide ion is taken as solvent instead of any other alcohol. Why it is like that?
user138137's user avatar
2 votes
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Crown ether complex formation with cesium carbonate

I am searching for some papers which form complex between crown ether and caesium carbonate. But Most papers only use caesium carbonate as a base in the synthesis of crown ether, not ionic compound ...
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How to name ether with ketone and carboxyl groups?

Carboxylic acid is the main functional group due to higher priority, but since it's an ether, what's the proper way to name the following compound? My attempt: 2-(1-methyl oxo propyl ether) ethanoic ...
Chuck's user avatar
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Does boric acid really rearrange phenols?

This reaction was on prepchem.com and I want to know whether it could work. Most of their reactions are well sourced but this is rather scant (and can't find the patent referenced). It is possible ...
TWiz's user avatar
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1H-NMR: How does the oxygen in ethers act as a spin coupling barrier while the oxygen in hydroxy groups doesn't?

It is possible to observe coupling between a hydroxyl proton and other protons. Why does the oxygen atom in ethers prevent any further coupling and act as a sort of barrier between spin systems? Or is ...
hebabla's user avatar
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Ion from unsaturated ether

As far as I am concerned, from unsaturated primary/secondary amines (enamines) we obtain imines, like we do obtain carbonyls from enols, by tautomerism. For tertiary enamines, we have a corresponding ...
MathStackExchange's user avatar
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Favoured reaction product in acid catalysed addition of methanol to alkene [closed]

I would like to add methanol to an alkene RCH=CH2, catalysed by conc. sulphuric acid. I would like to know which of these endproducts will be preferentially produced: RCH(OMe)-CH3 RCH2-CH2OMe Many ...
Purple Pixie's user avatar
2 votes
1 answer
243 views

How does 81-crown-27 complexes itself with alkali metal with its size?

The biggest crown ether experimentally confirmed is 81-crown-27 1 How can this molecule form complexes when the distance between the 27 oxygen atoms which complexes with the cation inside seems ...
Evamentality's user avatar
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How do mechanisms of acidic cleavage of ethers differ for anhydrous, concentrated, and aqueous HI?

I have seen the usage of anhydrous, concentrated, and aqueous HI for the acidic cleavage of ethers. What is the difference in the mechanisms and which will follow either of SN1/SN2 mechanism? Once the ...
Sung Jin-Woo's user avatar
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Selectivity in dehydration of isopropyl alcohol to diisopropyl ether

Can isopropyl alcohol be dehydrated by sulfuric acid to diisopropyl ether in a similar way as to how ethanol can? Is there a way to avoid or at least minimize the inevitable dehydration to propylene?
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When does an aromatic ether break its bonds?

I was reading some reactions of ethers and I came across Zeisel determination. Later that day, I was asked to determine the products of the reaction : And I made the product: This reaction is ...
Damstridium's user avatar
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DEG monobutyl ether pH change

We are using DEG monobutyl ether (CAS 112-34-5) in our production. Normally it is pH neutral, however suddenly we noticed that it has shifted to being acidic (pH=3.4). What has changed in the material?...
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Synthesis of allylic ether, starting with phenalene

I stumbled across a retro-synthesis question, for which I don't know the exact answer; I prepared two synthesis ways, but I don't know if they could be realized in a lab. The question is the following:...
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Doubt in a question on cleavage of ethers (Solomons Practice problem 11.18) [closed]

I have reffered to the mechanism shown in the text which is: But I am not able to figure out how this took place: Please help me with it. Though it is a homework question but I have tried my best to ...
Joe Janiak's user avatar
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What is the reaction mechanism involved in the ring opening seen in 3,3-diphenyloxiran-2-ide?

I have an epoxide with a negative (-) charge on one of the carbons. In which of the two ways should I open the epoxide? I am not able to understand which one to prefer. (The general way I think of ...
Ashish's user avatar
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Which has higher priority between unsaturated ring and unsaturated chain in the nomenclature of organic compounds?

According to the IUPAC rules of nomenclature, alkenes have higher priority over rings but what if the ring also contains a double or a triple bond? For eg: Is this compound going to be named as 1-(2-...
Neha's user avatar
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Products of the reaction between ethoxyethene and HI

Problem The products formed in the reaction $$\ce{CH2=CHOCH2CH3 + HI ->}$$ are (a) $\ce{CH2=CHI}$ and $\ce{CH3CH2I}$ (b) $\ce{CH2=CHI}$ and $\ce{CH3CH2OH}$ (c) $\ce{CH3CHO}$ and $\ce{CH3CH2I}$ (d) ...
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Why is the ether linkage breaking here?

I have been asked to find the major product of the following reaction: This is my thought process: the lone pairs of the oxygen atom connected to $\ce{-Et}$ are less delocalised than the other oxygen ...
Aniruddha's user avatar
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What is the mechanism of benzyl ether hydrogenolysis?

The mechanism for the hydrogenation of alkenes or alkynes using Pd/C is fairly well explained to involve the absorption of hydrogen onto a metal's surface followed by the addition of that hydrogen ...
Eli Jones's user avatar
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2 answers
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What are the products formed in acidic hydrolysis of a tetrahydropyranyl ester?

Find the major product of the following reaction: My approach From my knowledge of reagents, I figured out that that the acid will protonate the oxygen(s) in the reactant and after that $\ce{C-O \...
Shriom707's user avatar
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Synthesing tetrahydropyran from ethylene oxide

I thought that the first step must be using a Grignard reagent to add carbons, but I need a hydroxyl group on the carbon on the other side to make it a diol and produce the product given, but nothing ...
Katia's user avatar
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Shape of PEG in water

According to the chemical formula $\ce{H−(O−CH2−CH2)_n−OH}$ of polyethylene glycol, or PEG, I assume that this organic compound has a long chain structure when it is dry and in powder form. (This is ...
Michael Gao's user avatar
2 votes
0 answers
358 views

Reaction of multiple diols with sulphuric acid [closed]

Find the total number of possible products I can think of atleast three reactions that will take place in the acidic medium: Pinacol-Pinacolone rearrangement Intermolecular dehydration (leading to ...
Aniruddha Deb's user avatar
3 votes
1 answer
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Why does H+ attack alkene first in this reaction?

The reaction is: Why is the double bond attacked here even though it is in conjugation with the lone pairs of O thereby making it harder to extract. Also,don't the 2 lone pairs on OH have more ...
TheQuestioner's user avatar
1 vote
1 answer
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Acidic cleavage of an ether

In the following question; Apparently, an SN2 reaction ensues, where the iodine atom's supposed to cleave off with the less sterically hindered alkyl branch from both the oxygens. This is the ...
harry's user avatar
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3 votes
1 answer
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Grignard alkoxide intermediate as starting material for ether or ester synthesis

I'm having a Grignard reaction between a ketone or aldehyde with RMgX in mind. The average workup uses water to hydrolize the intermediate alkoxide. But could this intermediate be used without ...
elchemiste's user avatar
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1 answer
590 views

A reaction of Hydrogen Iodide and Ether

The problem is: 1,2,3-trimethoxy-cyclohexane reacts with $x$ moles of $\ce{HI}$ to give $y$ moles of $\ce{CH3I}$ and iodo-cyclohexane as product. Then find the value of $\frac{x+1}{y+1}$. I am not ...
Arnav Mahajan's user avatar
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1 answer
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Comparing between cleavage of ethers

We have to find out which ether would undergo cleavage faster. My Attempt IV. I couldn't figure out, so i carried out simple SN1 cleavage. Since +M effect of OH > OCH3 1st reactant seemed right ...
Aditya suresh's user avatar
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1 answer
299 views

Can Cyanide ion substitute methoxide? [closed]

Question Attempt Since CN is better nucleophile than both OMe and Cl, I believe that it should replace both. But none of the options match my answer. Where am I wrong? Please help.
Aditya suresh's user avatar
10 votes
1 answer
781 views

Effect of substituents on arene oxide-phenol rearrangement

When I was learning about the reactions of epoxides from my textbook, I came across the following mechanism for arene oxide-phenol rearrangement in the presence of acid: NIH Shift - National ...
Vishnu's user avatar
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12 votes
1 answer
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The Evasive Ether: Existence of diethynyl ether?

I tried to find online whether the compound diethynyl ether, $\ce{HC#COC#CH}$, exists in a stable state at STP, mainly out of curiosity, but also because it would be interesting to study the ...
mpprogram6771's user avatar
4 votes
1 answer
2k views

Reactivity of different alcohols with NaNH2 and CH3I

Identify the final product (B) in the following reaction: I'm not sure how $\ce{NaNH2}$ and $\ce{CH3I}$ will react with the different types of alcohol present here. According to my solution,ether was ...
student's user avatar
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0 answers
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Why can't strong bases cleave ethers?

I'm imagining a strong base like NaNH2 attacking the adjacent carbon of the ether, giving the oxygen a lone pair and forming an alkoxide. NH3 has a pKa of 36 while an alcohols (conjugate acid of ...
anonymous12345's user avatar
1 vote
0 answers
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Benzannulation of 18-crown-6

I know crown ethers can be used to complex metal ions. Question: What important properties do 18-crown-6 change during the benzannulation from 18-crown-6 to DB18C6 (dibenzo-18-crown-6)? How do these ...
Kemono Chen's user avatar
2 votes
0 answers
74 views

Do tertiary ethers tolerate oxidative workup of an ozonolysis reaction?

I am attempting to cleave a double bond into a carboxylic acid and carbon dioxide using an ozonolysis reaction followed by an oxidative workup. I am concerned with the presence of a tertiary ether in ...
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1 vote
1 answer
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Reaction of ether with HCl

Most of the reactions undergo ring expansion whenever favourable. But this reaction [1, p. 514] doesn't seems to do so: Practice Problem 11.18 Provide a mechanism for the following reaction. Could ...
Dheeraj Kamath's user avatar
3 votes
3 answers
4k 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—...
Garima Singh's user avatar
1 vote
2 answers
822 views

Acidic cleavage of ether with a 2° alkyl group

I know that an ether with a 3° alkyl group and a 1° alkyl group is cleaved by $\mathrm{S_N1}$ mechanism to give a tertiary alkyl halide and a 1° alcohol. And an ether with a two 1° alkyl groups is ...
Debarghya Basak's user avatar
1 vote
0 answers
59 views

What lubricant can be used for mechanical parts in a system containing diethyl ether?

I make a thermal actuator that works with the expansion of diethyl ether at its boiling point of around 34 °C. For sealing and lubrication of the polypropylene piston and barrel, I need a lubricant ...
J. Bowden's user avatar
6 votes
2 answers
2k views

Is cyclic ether oxidised by periodic acid?

Is the three member ring of cyclic ether oxidised by periodic acid? As this also has oxygen attached to adjacent carbon so I think that cyclic ether of three members should be oxidised by periodic ...
Smit Patel's user avatar
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1 answer
1k views

Role of zinc chloride in reaction of ether

I am trying to do a reaction between acetyl chloride $\ce{CH3COCl}$ with diethyl ether. I know that upon using anhydrous $\ce{ZnCl2}$ and heat, I'll get an ester and an alkyl chloride, but I'm not ...
Aditya Prakash's user avatar
6 votes
1 answer
2k views

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 ...
oliver's user avatar
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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 ...
ChemQ4's user avatar
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1 vote
2 answers
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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 ...
Inselino's user avatar
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-3 votes
1 answer
30 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
Rituraj Tripathy's user avatar
-1 votes
1 answer
59 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 ...
SLADE's user avatar
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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....
kiv's user avatar
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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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