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
22
votes
2answers
5k 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 ...
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{...
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 ...
13
votes
2answers
3k 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 ...
11
votes
1answer
131 views

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 ...
10
votes
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 ...
8
votes
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 ...
8
votes
1answer
284 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 ...
8
votes
1answer
160 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 ...
7
votes
2answers
429 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 ...
6
votes
2answers
1k 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 ...
6
votes
2answers
921 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 $-\ce{OR}$ ...
6
votes
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 ...
6
votes
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 ...
6
votes
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 ...
5
votes
3answers
381 views

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 ...
5
votes
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,...
5
votes
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
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 ...
5
votes
1answer
3k 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 ...
5
votes
1answer
806 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 ...
4
votes
2answers
911 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 ...
4
votes
1answer
296 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 ...
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 ...
4
votes
0answers
68 views

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 ...
4
votes
0answers
348 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 ...
3
votes
3answers
485 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]...
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 ...
3
votes
1answer
55 views

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 ...
3
votes
0answers
341 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 (...
2
votes
1answer
274 views

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 ...
2
votes
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 ...
2
votes
0answers
57 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 ...
2
votes
0answers
178 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....
2
votes
0answers
52 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" (...
2
votes
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 ...
2
votes
1answer
372 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 ...
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 ...
1
vote
2answers
1k 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 ...
1
vote
1answer
4k 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 ...
1
vote
1answer
1k views

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 ...
1
vote
1answer
6k 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.....
1
vote
1answer
2k 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 ...
1
vote
1answer
202 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 ...
1
vote
0answers
90 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 ...
1
vote
0answers
23 views

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 ...
1
vote
2answers
400 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 ...
1
vote
0answers
39 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 ...
1
vote
0answers
81 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 ...