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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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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32 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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332 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 ...
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0answers
320 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
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0answers
54 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
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0answers
174 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....
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0answers
49 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
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0answers
452 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
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1answer
218 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 ...
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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 ...
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37 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 ...
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0answers
77 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 ...
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0answers
116 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}\\ -> {...
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1answer
49 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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62 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 ...
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0answers
104 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 ...