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
1 vote
0 answers
52 views

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 ...
user avatar
  • 193
0 votes
1 answer
158 views

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?
user avatar
  • 321
2 votes
2 answers
96 views

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 ...
user avatar
2 votes
0 answers
21 views

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?...
user avatar
  • 121
2 votes
0 answers
52 views

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:...
user avatar
0 votes
2 answers
62 views

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 ...
user avatar
2 votes
0 answers
36 views

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 ...
user avatar
  • 1,349
4 votes
1 answer
115 views

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-...
user avatar
  • 442
3 votes
1 answer
93 views

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) ...
user avatar
  • 163
2 votes
1 answer
91 views

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 ...
user avatar
  • 466
4 votes
0 answers
186 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 ...
user avatar
  • 1,799
2 votes
2 answers
718 views

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 \...
user avatar
  • 187
5 votes
3 answers
461 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 ...
user avatar
  • 169
1 vote
1 answer
159 views

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 ...
user avatar
2 votes
0 answers
179 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 ...
user avatar
3 votes
1 answer
740 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 ...
user avatar
0 votes
1 answer
137 views

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 ...
user avatar
  • 1,076
3 votes
1 answer
85 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 ...
user avatar
-1 votes
1 answer
439 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 ...
user avatar
-2 votes
1 answer
51 views

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 ...
user avatar
0 votes
1 answer
249 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.
user avatar
10 votes
1 answer
590 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 ...
user avatar
  • 1,982
11 votes
1 answer
149 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 ...
user avatar
3 votes
1 answer
1k 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 ...
user avatar
  • 95
0 votes
0 answers
86 views

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 ...
user avatar
1 vote
0 answers
26 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 ...
user avatar
2 votes
0 answers
65 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 ...
user avatar
  • 1,799
1 vote
1 answer
2k 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 ...
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—...
user avatar
1 vote
2 answers
601 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 ...
user avatar
1 vote
0 answers
50 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 ...
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 ...
user avatar
0 votes
1 answer
859 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 ...
user avatar
6 votes
1 answer
1k 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 ...
user avatar
  • 261
0 votes
0 answers
121 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 ...
user avatar
  • 1
1 vote
2 answers
2k 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 ...
user avatar
  • 411
-3 votes
1 answer
29 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
user avatar
-1 votes
1 answer
50 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 ...
user avatar
  • 13
2 votes
0 answers
220 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....
user avatar
  • 199
2 votes
0 answers
62 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" (...
user avatar
-2 votes
1 answer
44 views

Nucleophilic comparison of epoxides and ketones [closed]

Why does $\ce{H+}$ attack on epoxide and not on the double bonded oxygen?
user avatar
  • 9
8 votes
1 answer
271 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 ...
user avatar
8 votes
2 answers
1k 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 $-\ce{OR}$ ...
user avatar
  • 5,166
1 vote
0 answers
123 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 ...
user avatar
  • 11
1 vote
1 answer
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 ...
user avatar
  • 119
0 votes
1 answer
230 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 ...
user avatar
4 votes
2 answers
1k 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 ...
user avatar
1 vote
1 answer
285 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 ...
user avatar
1 vote
1 answer
6k 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 ...
user avatar
  • 2,797
4 votes
0 answers
445 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 ...
user avatar