Talk:Alkyl nitrite

Merger

The following discussion is closed. Please do not modify it. Subsequent comments should be made in a new section.

Alkyl nitrates should be merged with Poppers, and the combination moved to Alkyl nitrite, no a redirect with history so takes admin intervention to accomplish. Gene Nygaard 18:17, 1 October 2006 (UTC)

Disagree. Alkyl nitrates (formula R-O-NO₂, nitroglycerine is a member of that class) are a different class of compounds than are alkyl nitrites (formula R-ONO, amyl nitrite is a well-known representative of that group). Organic nitro compounds (nitrobenzene, nitromethane) are yet another class of compounds. The reason that Alkyl nitrites got its separate article was that they are used in synthetic chemistry, and that the information here would be all but swamped in the big article on poppers, where the recreational use is discussed. Dr Zak 19:14, 2 October 2006 (UTC)

I think I replied to the original post on this in the wrong place. Sorry about that. In my other post, I mentioned some there had been a doctor who had a genuine reason for keeping these article separated, but I could not remember what it was. Now that I see his post (Dr. Zak) I remember.

I agree with Dr. Zak. 216.54.197.236 22:12, 2 October 2006 (UTC)

Well, no matter what, they need to be better cross-linked and the relationship better explained in the articles themselves. As it is, this article is a mere stub with little utility at all, and no particular reason not to be "swamped" in the other article. So if you want them separate, see what you can do about that. Gene Nygaard 00:52, 3 October 2006 (UTC)

Gene, what exactly is your argument for merging the article, apart from saying it's a "mere stub" on a class of compounds? We have stubs and short articles on all sorts of compounds and classes of compounds, and as it happens alkyl nitrites are only infrequently encountered. There is not much to be said about them apart from the fact that they can be made and that they are used on occasion for certain reactions. If you look at Organic Syntheses there are preparations for butyl [1] and isoamyl nitrite [2], which are referenced in less than a dozen preparations.

On the other hand, the focus of the two articles (poppers and alkyl nitrites) is very different. Someone who is interested in one aspect (the pharmacology and social aspects) will likely not be interested in the other (synthetic applications). We have this often. Even though introductory quantum mechanics is routinely taught to chemists hydrogen atom did not get merged into hydrogen, because someone interested in the solutions of the Schroedinger equation may at the moment not bother with the chemistry of hydrogen gas. I don't think that article length was an issue in keeping the two articles separate. Dr Zak 01:26, 3 October 2006 (UTC)

The focus may be different, but they aren't two totally different things. I'm not dead set on merging them; but unless somebody does a whole lot better job of tying the separate articles together, I shall continue to push for merger. Gene Nygaard 01:36, 3 October 2006 (UTC)

Why not try and merge ethanol and alcoholic beverage, too? Same issue there. Dr Zak 03:50, 3 October 2006 (UTC)

I strongly disagree with a merger. I think that some info from poppers should be moved to alkyl nitrites, although subsets from each other, there are some distinct differences (a nitrite with a very high boiling point is not a popper, while amylnitrite is a popper but also a useful lab-chemical). If nobody objects soon, I may have a go at that (this evening), trying to rewrite the three .. or maybe even four pages (alkyl nitrites, alkyl nitrates, nitroalkanes (right title?), and poppers. Could someone keep an eye on the 'medical/recreational' use of poppers, I am not extremely knowledgable in that field (but then I will try not to touch on that part too much, but may post some questions). --Dirk Beetstra ^{T C} 07:53, 3 October 2006 (UTC)

• I agree 'poppers' and alkyl nitrites should not be merged. But, Gene Nygaard is right, they should be tied together. I note that on the poppers page the merge notice is still at the top of the page. I'd like to delete the notice, and link out to the alkyl nitrites page from the summary on the poppers page.Lt. Dan 20:29, 1 November 2006 (UTC)

The discussion above is closed. Please do not modify it. Subsequent comments should be made on the appropriate discussion page. No further edits should be made to this discussion.

Wrong connection to other languages

de it nl fr es <-- for those the connections are wrong; the german should go to de.wikipedia.org/wiki/Amylnitrit (It don't know how to change it) --79.199.86.160 (talk) 14:51, 7 September 2009 (UTC)

Correction to quinine total synthesis mechanism?

In the mechanism shown, I think it's far more likely that the first step proceeds via an enolate, rather than the comparatively unstable carbanion shown. Is there a reason why it has been drawn in this way? 92.24.131.217 (talk) 16:56, 4 April 2012 (UTC)

New merge discussion

The following discussion is closed. Please do not modify it. Subsequent comments should be made in a new section. A summary of the conclusions reached follows.

This discussion has been open for 18 months and there is clearly no consensus to merge the two articles as was the case in 2006 SmartSE (talk) 11:47, 10 August 2014 (UTC)

---

Davidbengtenglund has proposed that Poppers be merged into this article, so I'm adding a section to discuss this.

For my part, I'm in favour in theory, but I'd like to see the issues currently flagged in the Poppers article cleaned up before any merge effort is made.

—me_and 14:50, 11 January 2013 (UTC)

• No - I think if anything Poppers have the greater notability, and the Alkyl Nitrites articles should be merged into the Poppers article. isfutile:P (talk) 17:26, 14 January 2013 (UTC)

• • I disagree on two counts: firstly, I don't think the primary article should be titled after a street name, and secondly "Alkyl nitrites" could clearly include all aspects of the chemicals, whereas "Poppers" strongly implies their use as recreational drugs only. —me_and 11:32, 17 January 2013 (UTC)

I have to agree with the previous comment against the merging. It often is bothersome with other articles when it is merged. But one is a recreational drug inference, and the other is the the chemical at that is the major component in poppers. — Preceding unsigned comment added by 184.0.79.83 (talk) 20:28, 20 January 2013 (UTC)

• Oppose merger proposal for all the reasons stated in 2006 and more recently. These are articles' separation reflects the two aspects of alkyl nitrates and poppers that would not be well-served by merging them. Argos'Dad 22:03, 20 January 2013 (UTC)

I feel like poppers should be moved to the amyl nitrite page. The page should then have a "Recreational Use" subsection noting the common use of amyl nitrite recreationally calling it poppers... The 2 pages are describing the same chemical that has multiple uses. — Preceding unsigned comment added by 99.177.244.138 (talk) 09:05, 16 September 2013 (UTC)

• Opposesee 2006 discussion V8rik (talk) 17:20, 16 September 2013 (UTC)
• Oppose The topics discuss two different aspects of the chemical. One is in terms of it as a recreational drug, the other is about a chemical compound. Idiotic suggestion. 92.26.68.193 (talk) 20:04, 1 February 2014 (UTC)Jimzip
• Oppose Leave as separate articles, but cleanup "Poppers" and move info to "Alkyl nitrites" as appropriate. Ozzieboy (talk) 02:09, 10 April 2014 (UTC)
• Oppose. The 2006 discussion of this is helpful. The key point is that each article serves a different purpose: a reader interested in "poppers" is likely to be interested in the social, cultural and in some cases sacramental phenomenon, while a reader interested in "alkyl nitrites" is likely to be interested in the chemistry. By all means have links between the two articles, but we would serve our readers better by discussing different issues in different articles. RomanSpa (talk) 07:50, 10 April 2014 (UTC)

The discussion above is closed. Please do not modify it. Subsequent comments should be made on the appropriate discussion page. No further edits should be made to this discussion.

First members?

What exactly is meant by "first few members of the series"? The fisrt to be 'discovered'/ studied/ known/ used? But then, why is this followed by "are"? Are these still the fist members? Rui ''Gabriel'' Correia (talk) 10:06, 3 February 2014 (UTC)

Like other similar series, these kinds of organic compounds are generally ordered in terms of the number of carbon atoms. So methyl nitrite contains one carbon atom, ethyl nitrite contains two carbon atoms, propyl nitrite contains three carbon atoms, and so on. If you did chemistry at school you probably learnt the list of alkanes (the saturated hydrocarbons): methane, ethane, propane, butane, etc.. You might also remember the alcohols: methanol, ethanol, propanol, and so on. Each compound in any of these (related) series is similar to its predecessor, but with the addition of an extra carbon atom (and some hydrogen atoms dangling off the side). So the series has a natural order, and methyl nitrite is the "first" in the series for the same reason that "1" is the first number.

There is, in principle, no limit to the number of carbon atoms we could add, so the series is (in principle) infinite, though I don't know of anyone who's dedicated their lives to the study of (for example) the 256-th member of the series. Because things get more complicated as you add more carbon atoms (because the atoms can be arranged in different patterns inside the compounds) it turns out that the series branches and recombines as the number of carbon atoms increases, but this is not something that would be naturally covered in this article, belonging in a more general article on organic chemistry. The emphasis here is on the properties arising from the nitrite group, which is what gives the compounds in this series their distinctive shared properties.

RomanSpa (talk) 20:21, 3 February 2014 (UTC)

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Synthesis

The best way is 1. dissolving the alcohol in a solution of sodium nitrite in water; and 2. stir this well and add dilute acid drop by drop. I used phosphoric acid, because it forms a buffer which prevents the pH from getting too low. When the solution is too acidic, a lot of NO and NO₂ is formed. So nitrous acid is lost and no more converted to the alkyl nitrite you want to prepare. Hope you know how toxic these gases are! --FK1954 (talk) 21:42, 5 May 2020 (UTC)