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.
16
questions with no upvoted or accepted answers
5
votes
1answer
807 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
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
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
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
373 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
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
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 ...
1
vote
0answers
119 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}\\ -> {...
1
vote
1answer
64 views
Shape of PEG in water
According to the chemical formula $\ce{Hā(OāCH2āCH2)_nāOH}$ 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 ...
0
votes
0answers
63 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 ...
0
votes
0answers
105 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 ...