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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2
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0answers
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?...
6
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1answer
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 ...
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0answers
49 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:...
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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 ...
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2answers
56 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 ...
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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 ...
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1answer
44 views

Nucleophilic comparison of epoxides and ketones [closed]

Why does $\ce{H+}$ attack on epoxide and not on the double bonded oxygen?
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3answers
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—...
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1answer
3k 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 ...
4
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1answer
70 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-...
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1answer
79 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) ...
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1answer
71 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 ...
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1answer
36k 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 $\ce{H2O}$)?
3
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1answer
69 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 ...
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0answers
146 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 ...
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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 ...
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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,...
3
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1answer
968 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 ...
2
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2answers
544 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 \...
5
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3answers
427 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 ...
0
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1answer
806 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 ...
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1answer
123 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 ...
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2answers
4k 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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0answers
133 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 ...
2
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1answer
565 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 ...
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2answers
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 ...
0
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1answer
108 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 ...
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1answer
50 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 ...
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1answer
390 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 ...
0
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1answer
214 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.
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1answer
496 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 ...
11
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1answer
141 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 ...
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78 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 ...
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{...
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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 ...
2
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0answers
63 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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2answers
525 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 ...
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1answer
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 ...
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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 ...
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0answers
46 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 ...
7
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2answers
620 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 ...
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0answers
115 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 ...
16
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3answers
21k 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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2answers
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 ...
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1answer
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
22
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2answers
8k 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 ...
-1
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1answer
47 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 ...
3
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3answers
739 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]...
2
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0answers
205 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
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0answers
59 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" (...