Talk:Ether

As a Drug
It is used as a drug. Any information about that? —The preceding unsigned comment was added by 203.97.178.2 (talk) 00:03, 3 January 2007 (UTC).
 * Yeah I was searching for information on ether as a drug, but all I found was its chemical properties. Someone should add it. CheesePlease NL 11:38, 26 September 2007 (UTC)

Agreed. There should be some information regarding its use as a general anesthetic. —Preceding unsigned comment added by 70.162.18.223 (talk) 07:18, 21 July 2008 (UTC)


 * Yeah I came here to find out more about it's use as an anaesthetic, but it's just a page of scientific forumula and information only useful to scientists. -NeF (talk) 01:13, 25 July 2008 (UTC)


 * There's a very brief mention of ether used as an anesthetic in the article Chloroform. There's also a not very satisfactory discussion of ether at History of general anesthesia, and a somewhat better discussion at Anesthesia. None of these mention that ether was still used occasionally for surgery until the mid-20th century. All of these articles badly need some knowledgeable help. Milkunderwood (talk) 20:52, 1 May 2016 (UTC)

Well, I know of a site called erowid.org that has information on pretty much every type of drug that you could imagine, and ones you couldn't. It has some stories about trips on Ether and the like, that I've been currently reading up on. Here's the link to the Ether section of the site:

http://www.erowid.org/chemicals/ether/

Along with the first time recreational use stories that people have posted:

http://www.erowid.org/experiences/subs/exp_Ether_First_Times.shtml

The first link has a link to the general trip stories, as well as links to info about the history of the drug and the like. The first story I read about Ether usage was this (and another one listed below it to show others ways it effects people):

http://www.erowid.org/experiences/exp.php?ID=10737 http://www.erowid.org/experiences/exp.php?ID=42973

Some pretty interesting stuff, but I don't see why people would use stuff like Ether and Dizocilpine for recreational uses. They seem way too dangerous and unstable for that sort of usage. KiwiMaddog (talk) 03:08, 14 March 2009 (UTC)
 * Probably because they just read or watched Fear and Loathing in Las Vegas —Slicing (talk) 03:42, 22 July 2012 (UTC)


 * I'm suprised no one has mentioned this, but ether refers to a whole class of organic compounds. The drug known in colloquial use as "ether" refers specifically as diethyl ether i.e. the one with medical and recreation drug use. This is mentioned at the start of the article, though it might not have been when this discussion started. — Preceding unsigned comment added by J1812 (talk • contribs) 04:59, 10 January 2013 (UTC)

Various remarks
How does it smell?

In the sidebar, furan is shown as an aromatic compound that is not an ether. Furan is the prototypical aromatic ether and is the unsaturated form of THF (hence tetrahydrofuran)

The funny thing about the Michaelson-Morely experiment is that Einstein was already formulating relativity before he knew anything about it.

Also, wasn't the root of the english word "ether" the Latin word "aether", which means "air" as in "the sky".

You sure aether doesn't refer specifically to the upper air, which corresponds to the fifth element that fills all of space? Its Greek equivalent does, at least.


 * Despite their comparably attenuated reactivity, ethers can act as Lewis acids (see Acid-base reaction theories). For instance, diethyl ether forms a complex with boron compounds, such as boron trifluoride etherate, F3B:O(CH2CH3)2

Wouldn't the ether be the Lewis base here? Josh Cherry 00:59, 23 Oct 2003 (UTC)

The article states that the "x y ether" nomenclature is official IUPAC nomenclature; I don't want to edit the article as I may be wrong, but I'm sure that I was taught (at degree level) that this was trivial nomenclature and the only IUPAC nomenclature was the "x-oxy-y" type, such as "methoxyethane" - please correct me if I'm wrong, but I'm going to do a bit of research and find out, and possibly edit the article if I'm right - ta :) edd 08:33, 5 Jul 2004 (UTC)

should this be a disambig page?
what do people think? a discussion of diethly ether belongs on a separate page to discussion of ether's in general... jsut a thought... Erich 06:38, 15 Jul 2004 (UTC)

Williamson ether synthesis
The equation given for the Williamson ether synthesis shows an alkyl halide as a reactant, but what follows gives sulfonate esters as an example of a leaving group. Either the equation is not general enough or this example is incorrect. Josh Cherry 15:53, 26 Dec 2004 (UTC)

Space theory
Should some mention be made of early astronomical/astrological claims of space consisting of heavenly bodies suspended in "ether?" 153.104.16.114 17:29, 14 November 2005 (UTC)

I was wondering the same thing, I found it under "aether theories" — Preceding unsigned comment added by 72.67.68.139 (talk) 21:13, 23 March 2014 (UTC)

What came first?
If the known chemical was named after the ancient concept of "ether" or "aether", being what fills the void, or the universal solvent, then shouldn't this be the main entry for the word "ether"? All other entries may branch from this one. The article makes no mention of the ethymology of the chemical. Odraxir 00:17, 30 December 2005 (UTC)

The problem is that most of the article is relevant to chemistry alone and to include every association with "ether" will make it confusing to read. As wil alcohol, maybe a "Chemistry of.." page is better and to help produce a whole new specialist chemical section.

Aminal
The illustration of the aminal does not have the same structure on this page, as on the aminal page... (Which one is correct?) ChristianB 13:44, 18 August 2007 (UTC)


 * the image on the ether page is technically a hemiaminal but the distinction is not always made. I have no objections against the current image V8rik 17:54, 18 August 2007 (UTC)
 * I think what is shown is NOT a hemiaminal but an aminal-acetal --kupirijo (talk) 01:09, 22 October 2008 (UTC)
 * Actually according to IUPAC it is an α-aminoether and it is recommnded that the word aminal should not be used AT ALL.--kupirijo (talk) 13:03, 9 November 2008 (UTC)
 * Recomienda... 190.51.183.15 (talk) 13:03, 8 March 2012 (UTC)

Needs a message that directs people to the Ether of classic physics
I think there needs to be a message that says something along the line of "for the Ether in classic physics that is believed to be the medium of which light travels, see [link]" at the top. RegalStar (talk) 21:28, 16 January 2008 (UTC)


 * Isn't it enough with the link to the disambiguation page that is already at the top of the article? --Itub (talk) 09:34, 17 January 2008 (UTC)

Origin of name
Why are they called ethers? Did early chemists believe these newly discovered substances were the "aether" (either the luminifarious one or the Fifth Element), or is it more complicated than that? Daibhid C (talk) 21:22, 6 June 2008 (UTC)


 * The name was introduced (though not necessarily coined) in 1730 (1729 O.S.) by German chemist August Sigmund Frobenius either for the compound's purity, transparency, lightness and lack of color   or its high volatility . --84.41.34.154 (talk) 21:29, 28 April 2017 (UTC)

That picture is massive
we need to find a different illustration, the one currently one the site is needlessly large--66.210.54.83 (talk) 19:54, 26 September 2008 (UTC)


 * Which one? There are sixteen images in this article at present.


 * Ben (talk) 12:34, 28 September 2008 (UTC)

The one that appeared in previous versions of the article such as here:http://en.wikipedia.org/w/index.php?title=Ether&direction=next&oldid=240861814. Worth a look. You can't miss it. Meltyman (talk) 23:59, 2 October 2008 (UTC)


 * I think this edit was enough to fix the problem.


 * I'd prefer to undo this revision by Meltyman because the image is now too small to read easily.


 * Ben (talk) 12:02, 3 October 2008 (UTC)

I re-sized the image in the commons and then put it in a frame rather than a thumbnail in the article, i.e. pic on page is now actual size but that actual size is a fraction of the actual size of the previous image. This edit was OK but it bled into the next section a bit, I thought. Meltyman (talk) 19:54, 3 October 2008 (UTC)


 * It's legible now but it's the aspect ratio has changed so the image is stretched. Ask the original author to recreate it in the required shape.


 * Ben (talk) 22:12, 3 October 2008 (UTC)

The aspect ratio has changed and the image has been stretched, but neither change is important to the understanding of the article or to the ease with which it can be read. It could look better but it's far from the mess that prompted me to edit this article in the first place. If the current edit bothers you, you might try following your own orders. Meltyman (talk) 23:00, 3 October 2008 (UTC)

Dibutyl Ether
If Dibutyl Ether is going to redirect to this page, then there should be more info on it in the article. Boiling point, structure, etc. —Preceding unsigned comment added by 98.173.141.129 (talk) 14:50, 29 July 2009 (UTC)

Possible error in page, at least an inconsistency?
In the 'Structure and bonding' section the C-O-C bond angle is said to be about 120 degrees. In the 'Physical Properties' section it is said the C-O-C bond angle is about 110 degrees. I believe it's exactly 109.5 degrees because of the sp3 hybridization, but I'm just a first semester o-chem student so wanted someone to verify this error before correcting it. —Preceding unsigned comment added by Jusmai77 (talk • contribs) 18:39, 21 January 2010 (UTC)
 * The average bond angle in sp3 hybridization is 109.5 degrees, but in practice this is not always the case. Note that water is 104.5 degrees even though it is sp3 hybridized. This is due to the fact that the lone pairs take up more space than the hydrides. Intermolecular forces and intramolecular forces must also be considered. As it happens, I modeled a couple molecules with ether groups on avogadro, and found that the optimization produced angles between 110 and 115 degrees. CH3CH2OCH2CH3 had an angle of 113.2, and CH3CH2OCH2CH2OCH2CH3 had an angle of 111.4. Adam.braley (talk) 16:55, 28 October 2010 (UTC)

Rather than computational models that are hard to cite, can we use some real world data? --Rifleman 82 (talk) 16:42, 28 October 2010 (UTC)

That's a good point. I'll see if I can't get a better citation, but any first semester organic student can tell that 120 degrees is at least unlikely.Adam.braley (talk) 17:05, 28 October 2010 (UTC)

Yes, 120 ° is certainly strange. I was just thinking about how best to cite this source. --Rifleman 82 (talk) 00:49, 29 October 2010 (UTC)

Hybridization
I'm not a specialist but afaik 120deg angle is for sp2-hybridization, not for sp3. sp3-hybridization has a 109deg angle. Am I wrong? Wizardist (talk) 06:50, 4 June 2010 (UTC)

Polyethers: is it fair to refer to crown ethers as polyethers?
I'm not at all confident that the initial explanation of polyethers is accurate. Polyethers are definitely NOT molecules with multiple ether groups, they are polymers that contain repeating ether groups from their propagated monomers. What I'm not sure of is whether it's fair to call crown ethers polyethers. My instinct is no, but I can't back it up since I don't "know" that large crown ethers aren't synthesized by polymerization techniques. I doubt it, since neither step reaction polymerization nor chain reaction polymerization makes any sense for them as far as I can see. Anyway, I submit the question to you my fellow Wikipedians.Adam.braley (talk) 16:51, 28 October 2010 (UTC)

R'
I changed the general formula to R-O-R'. This is consistent with the picture but the online iupac goldbook reference uses R-O-R. A different references that alludes to both R-O-R and R-O-R' is http://docs.google.com/viewer?a=v&q=cache:C8gFvmb-ls8J:chemistry.csudh.edu/faculty/jim/ethers.ppt+ethers+ror&hl=en&gl=us&pid=bl&srcid=ADGEESgZXYBidUi-rktMmIlMZnRmQLeFV_-PZPgdYkNNV-PeAPl7RpK7vAu9kLE9cHGRYmdNCH7413us4yOepqxtM0JwQcOqISSD6Q4KpJr3cyRhmGAOPW0zYSiQraRmmifCPB_hqOke&sig=AHIEtbTm3E1O2QEz8jxkVdlvAayTicHpGQ which is a google view version of http://chemistry.csudh.edu/faculty/jim/ethers.ppt

Peroxide formation
I think some clarification is needed about how the tendency of ethers to form explosive peroxides depends on their structure. The Sept 20th, 2011 version of this section in the ether article contained the statement "Primary and secondary ethers with a CH group next to the ether oxygen form peroxides....For this reason, diisopropyl ether and THF are often avoided as solvents.".

All the common ethers, including diethyl ether, tetrahydrofuran (THF) and diisopropyl ether contain a CH group adjacent to the oxygen. The first two are primary ethers containing CH2 groups adjacent to the oxygen, while diisopropyl ether is a secondary ether. THF and diethyl ether are very widely used as solvents, with precautions recommended such as storing in the dark and not distilling to dryness because of the danger of peroxides. The article diisopropyl ether says it is more prone to peroxide formation than diethyl ether, and less so than methyl t-butyl ether (MTBE). To totally avoid a CH group adjacent to the oxygen one would need to go a highly hindered (crowded) compound such as bis (t-butyl) ether, which may be too hindered to even exist as a stable compound.

Pending further clarification of the relation of peroxide formation to structure, I will change the text in the main article to say simply that ethers are susceptible to forming explosive peroxides, unless appropriate precautions are taken.CharlesHBennett (talk) 20:49, 20 September 2011 (UTC)

Actually MTBE has 3 primary Hydrogens, diethyl ether has 2 secondary Hydrogens, and 2 tertiary Hydrogens in diisopropyl ether. The C-H bond strength is tertiary<secondary<primary which applies to free radical reactions like Bromination and Peroxide formation. Peroxide formation, like combustion, is a chain reaction. (Triplet) Oxygen removes a Hydrogen to form Hydroperoxide and Carbon radical that reacts with Oxygen, and that Peroxide radical reacts with and takes the Hydrogen (from the lowest energy bond) and the chain continues. Isooctane has high flash point (compared diesel's cetane number of secondary C-H bonds) because it is mostly higher energy primary C-H bonds and hindered Tertiary and Secondary C-H bonds which don't propagate the combustion chain reaction. Historically, we were cleaning out a lab connected to an EPA Superfund site and found a clear bottle labeled "isoPropyl Ether" with large clear (peroxide) crystals in it. We gingerly took that bottle to a vacant area and detonated it. Shjacks45 (talk) 12:01, 4 July 2019 (UTC)

By the way, Eucalyptol (natural oil) structure is basically a di-tert-Butyl Ether, Shjacks45 (talk) 12:09, 4 July 2019 (UTC)

Trivial Names: "X Y ether" or "Y X ether"?
Sometimes, as if following IUPAC rules, we put X and Y in alphabetical order, as in e thyl m ethyl ether, tert- a myl m ethyl ether (TAME). But then sometimes the reverse order seems more usual, as in m ethyl tert- b utyl ether (MTBE), e thyl tert- b utyl ether (ETBE). I know these are not systematic names and as such anything could happen, but is there any (historical?) reason behind this inconsistency? It would be greatly appreciated if this was clarified in the article(s), since these names are rather confusing for average (non-advanced) readers including myself. Textbook says that butyl-, ethyl-, methyl- must be said in this (alphabetical) order, but then we have a name like methyl tert-butyl ether, which may mislead you into believing that tert-butyl is alphabetized under “t” (a wrong assumption which will only confuse you even more). — Gyopi (talk) 09:39, 3 July 2015 (UTC)

Typical Wiki
This is what I hate about wikipedia. Saw the term ether on a TV show, wanted to find out what it was, come here and the entire article is chemistry mumbo jumbo. The average person isn't going to understand any of this. How about explaining what kind of chemical it is and its uses, in a way that isn't chock full of chemistry terms? Wiki articles tend to be way too literal. — Preceding unsigned comment added by 24.137.115.238 (talk) 04:46, 12 November 2015 (UTC)
 * AN unsigned commenter is actually right for once. You morons need to quit being so smart and realize that your article for ether contains virtually none of the information that the general public would come here to find... like uses and history and stuff. Of course that is kinda contained in the article for diethyl ether, but is little help to the average person who arrives here by searching "Ether" wanting to find out about civil war medicine. Try to view the article from the vantage point of someone who has seen a member of the opposite sex without clothes on. Nerds. 206.113.15.122 (talk) 21:09, 11 January 2018 (UTC)

Assessment comment
Substituted at 14:43, 29 April 2016 (UTC)

R?
what kind of element is R? 108.65.81.190 (talk) 17:42, 2 November 2016 (UTC)
 * In typical organic chemistry nomenclature, R is used to denote an alkyl or aryl group, or other substituent. I have added the missing definitions of R and R' to the article.  -- Ed (Edgar181) 18:18, 2 November 2016 (UTC)

Not everyone writes that that way.
Example: in English, we say pentyl phenyl ether. But here we say phenyl pentyl ether (fenil-pentil éter). Alfa-ketosav (talk) 14:31, 27 April 2018 (UTC)

Add MTBE to list of ethers
Methyl T-Butyl Ether was a controversial gasoline additive competing to "Oxygenate" gasoline, but Ethanol (and Iowa) won. Also more electrophilic that Ethyl ether, advantages for complexing Grignard reagents and Lithium compounds. Shjacks45 (talk) 11:04, 4 July 2019 (UTC)