Talk:Alcohol (chemistry)/Archive 1

Toxicity
Why are alcohols toxic, what do they do to the body? AxelBoldt 04:50 Sep 10, 2002 (UTC)

In low amounts alcohols are not toxic. But in moderate to high amounts taken over short time periods they can be toxic. Alcohols (esp. ethanol) is quickly absorbed into the bloodstream and reaches the brain where it interferes with synaptic firing and causes the death of brain cells by changing the electrochemical properties around cells (intracellular calcium is increased which weakens the electrochemical gradient across the cell's membrane -- cells, esp. neurons, die without this gradient -- which is vital to the operation of membrane pumps and channels). There is also direct damage to cell membranes from free-radicals that are produced from alcohol metabolism.

The liver produces a special enzyme (alcohol dehydrogenase) that breaks down alcohols into acetaldehyde which is turned into acetic acid (another enzyme takes the acid and turns it into fatty acid, CO2 and water -- these are mostly deposited locally which leads to "beer bellies"). Chronic drinkers, however, so tax this metabolic pathway that things go awry; fatty acids build up as plaques in the capilaries around liver cells and those cells begin to die. This is the cause of cirrhosis of the liver. The liver is part of the body's filtration system and if it is damaged then certain toxins build up -- this leads to symptoms of jaundice. --mav

Health benefits
There really should be a subsection describing the known health benefits of alcohol. not just red wine as an antioxident, but specifically ehtonoals effect on "blood thinning", helping people with high blood presure...

I wonder if most of this would fit better in ethanol, or does it apply to all alcohols? AxelBoldt 15:05 Sep 10, 2002 (UTC)


 * It is my understanding that all alcohols would have similar effects, but I think you are right anyway since the only onw that is really consumed in any quantity is ethanol. --mav


 * In fact, alcohols are toxic to organic cells in nearly whatever amount, but it's not much of a problem for human beings except in "moderate to high amounts taken over short time periods". - Centrx 20:41, 3 Jan 2005 (UTC)


 * I believe that a large part of methanol's toxicity comes from the formaldehyde metabolite Evand 04:52, 25 Apr 2005 (UTC)

HEALTH BENIFITS? someone just mentioned the "known health benefits of alcohol"... in my humble opinion, though there may be some arguable health benifits to a unit of alcohol on its own, it is VERY irresponsible to glamorize alcohol as being somehow "healthy"... show me somebody who has yeah and mk rocks that "one" healthy drink and then we can talk. in fact, a lifetime of "one healthy drink a week" can be TOTALLY offset by only one night of binge drinking. in other words, among people who have engaged in drinking, there are ABSOLUTELY NONE that ive heard of who have somehow become more healthy as a result. people jog because it's healthy. people eat vegetables because they're healthy. people drink because they want to get drunk.

and on another note, even that "one healthy drink" of alcohol is not nearly as "healthy" as one drink of water, orange juice, etc...


 * Here's some interesting info I thought was worth including:
 * • Numerous epidemiological studies have found an association between moderate alcohol intake and reduced coronary heart disease risk and also mortality rates. However, heavy and binge intake is associated with increased mortality rate and coronary atherosclerosis.
 * • The cardioprotective effects of moderate alcohol are thought to be attributed to an increase in high-density lipoprotein cholesterol (which decreases LDL oxidation and removes cholesterol from arterial walls and transports it back to liver) a decrease in plasma fibrinogen concentrations --> decreased platelet aggregation, increased fibrinolysis, increased NO production, increased insulin sensitivity, and antioxidant activity by re-reducing vitamins with NADH.
 * • Heavy intake is associated with decreased fibrinolysis and increase or rebound of platelet aggregation, hypertension, and arrhythmias.
 * • Platelets from alcoholics are hypoaggregable, but after withdrawal there is an increase in platelet aggregability. This platelet rebound effect of alcohol drinking (particularly with binge drinking) could be associated with an excess of lipid peroxides known to increase platelet reactivity.


 * Here's a good recent review article that elaborates on what's currently out there to suggest beneficial/detrimental effects of alcohol: http://www.ncbi.nlm.nih.gov/pubmed/19075312. —Preceding unsigned comment added by 114.30.115.127 (talk) 06:23, 4 December 2009 (UTC)

---

Under the existing toxicity section, I tried to clean up the wording of the "treatment of methanol poisoning". It could use a bit more work. The methanol article has information in slightly greater detail about the treatment of methanol poisoning. --Mantispid 14:35, 5 August 2006 (UTC)

Water
Is water itself an alcohol according to the chemical/physical definition of an alcohol? Stan 10:29, 26 Feb 2004 (UTC)

The definition given on the alcohol page is:

In chemistry, an alcohol is an organic compound in which a hydroxyl group (-OH) is bound to a carbon atom, which in turn is bound to other hydrogen and/or carbon atoms; in other words, alcohol is characterized by one or more hydroxyl (OH) groups attached to a carbon atom of an alkyl group (hydrocarbon chain).

If I alter that slightly to:

An alcohol is a compound in which a hydroxyl group (-OH) is bound to zero or more carbon atom, which in turn is bound to other hydrogen and/or carbon atoms; in other words, alcohol is characterized by one or more hydroxyl (OH) groups attached to a carbon atom of an alkyl group (hydrocarbon chain), or just to a hydrogen atom.

then under this definition H-OH, i.e. water, would be the simplest alcohol.

What I've done it take out In chemistry on the preumption that perhaps in physics the definition is slightly different. What I'd be interested is to know whether water's physical characteristics can be equated to the series of alcohols ordered by the number of carbon atoms starting at zero, i.e.

H-OH CH3-OH C2H5-OH C4H9-OH and so on.

They're all colorless liquids for a start.

Matt Stan 19:24, 10 Mar 2004 (UTC)

An interesting idea, though I strongly doubt that physics would use a different definition of alcohol than chemistry (which as every physicist knows is just sub-field of physics).

Anyway, some numbers, in the order you specified (H2O, CH3OH, C2H5OH, C4H9OH, C5H11OH):

Density (g/cm3): 1.00, 0.79, 0.79, 0.80, 0.81, 0.82

Melting point (K): 273, 175, 159, 146, 184, 194

Boiling point (K): 373, 337, 351, 370, 390, 411

Water fairly clearly bucks the trend. -- DrBob 19:45, 10 Mar 2004 (UTC)


 * It should be noted that water is most definitely *NOT* an alcohol, making the "zero or more carbons," revised definition like calling an orange an apple, for experiment's sake. It's entirely inane: simply containing the hydroxyl group does not make a compound an alcohol, and the trend broken above was to be expected. It is that carbon that has been omitted from the revised definition which is essential to the alcoholic character.

An alcohol is characterized by one or more hydroxyl (OH) groups attached to the carbon atom of alkyl groups of a hydrocarbon.

pH of Alcohols
In my understanding (and from what I've been taught at my Chemistry courses), Alcohols are not acids, rather bases, and when dissolved in water raise the amount of -OH ions

They also cancel out acids in reactions with them, since the -OH from alcohol bonds with the hydrogen from acids to form water.

Would that be correct?


 * Since no real chemist bothered to answer: As said in the article, "alcohols are weakly acidic, even less acidic than water". That is sort of like like saying "Jews are weakly Muslim, even less Muslim than Christians". 8-) So I suppose that your fist sentence is correct...


 * I won't hazard an opinion on your second sentence. IIRC, that reaction does not hapen readily in water solutions, which is where "acid" and "base" have their traditional meaning. It may happen in dry reactions but then I guess that it is a bond-swapping thing, without ionization involved. But chemists have invented some weird definitions of acid and base since I went through college... Jorge Stolfi 06:36, 15 Jun 2004 (UTC)


 * Alcohols can indeed be either weakly acidic or basic, just like water. They have a pKa of around 16-19, which means that in the presence of a strong base such as NaH or NaNH2 they will form alkoxide salts (e.g., ROH + NaH -> RO- Na+).  However in the presence of a strong acid such as sulfuric acid they will protonate, for example ROH  +  H+  -->  ROH2+


 * Read http://en.wikipedia.org/wiki/Acid-base_reaction_theories, this is what is called a Brønsted base, a proton acceptor.


 * However the OH in alcohols is not free hydroxide ion, so it does not react in a simple way with acids to form water the way sodium hydroxide does.  Alcohols will NEVER raise the amount of  -OH ions in water, they are neutral if tested with pH paper.

Walkerma 22:14, 11 Mar 2005 (UTC)


 * Not true. The ROH will have a tendency to accept a proton from the water molecule, leaving an -OH with a negative charge, but this is a very weak tendency.


 * The two opinions above are correct. Alcohols are "basic", as they can be protonated. (But the resulting "water" group is rather labile). They are also "acidic" but you have to fight to get the proton off (through the use of a strong base like sodium hydride). The counterexample is an alcohol conjugated to an aromatic ring, which would be more acidic because the negatively charged alkoxide anion has its charge delocalized through the ring.

Etymology

 * See also: Wiktionary talk on etymology
 * Nils von Barth (nbarth) (talk) 20:14, 31 December 2008 (UTC)

((begin text from Talk:Al-Razi Jorge Stolfi 03:33, 15 Jun 2004 (UTC)))

As for the etymology, I have always heard that "alcohol" came from al-ghoul="spirit" which also gave the star "Algol" and the English "ghoul. this page about "ghoul" gives the Arabic translation as "&#1594;&#1608;&#1604;=(alcohol, bogey, goblin, hobgoblin, ogre)".


 * For what its worth. The word "Ghawl" &#1594;&#1608;&#1604; is mentioned in the Qur'an 37:47 in reference to wine. The context is that wine in Paradise will be different and "Free from Gawl; nor will they suffer intoxication therefrom." Gawl is translated as "headiness", but I have seen it translated as "the stuff that makes wine intoxicating = alcohol". -- KB 16:32, 2004 Jun 13 (UTC)

Jorge Stolfi 03:13, 13 Jun 2004 (UTC)
 * Well, there must be something wrong with my ears. I cannot find a single source can find only a couple of sources for al-ghoul -&gt; alcohol, all of them the others have the al-kuhul story. It sounds pretty weird, but... Jorge Stolfi 03:39, 13 Jun 2004 (UTC)


 * Merriam Webster and other sources on Etimology are wrong about al-kuhul being powdered antimony. What they are referring to is &#1575;&#1604;&#1603;&#1581;&#1604; which is indeed a black powder used medicinally (antiseptic?) and cosmetically (eye liner) from old times (and still is), and commonly used in early Islamic times. Alcohol is &#1603;&#1581;&#1608;&#1604; which is spelled differently. The inability of some Western writers to understand the consonental system of Semitic language and distinguish Semitic short vowels and long vowels have caused much confusion. -- KB 16:32, 2004 Jun 13 (UTC)

This document confirms Al-Razi as the discoverer but says that the "al-ghoul"="the devil" etymology was invented by an US anti-alcohol movement for propaganda purposes. Jorge Stolfi 04:27, 13 Jun 2004 (UTC)


 * Don't you just love Wikipedia! What a great place it is to reach beyond the limitations of stuffy authoritative sources and test their accuracy! I read all the above references (except the Qur'an, as I don't know Arabic) to get to the bottom of this question. (By the way, please use a descriptive term for the displayed text of a link, rather than "this document" or "other sources". I will repeat some of the above links as needed so it's easier for someone reading this later to know what they're clicking on before they click.)


 * Both the al-ghoul (Webster's Dictionary Online, "ghoul") or al-kohl (Kevin Scheel's "Alcohol the Chemical" paper, p. 8, 1st full paragraph) and the al-kuhul (Webster's Dictionary Online "Word Origin" entry from American Heritage) arguments have plausibility, although the "spirit" version seems more likely, as KB argues. Unfortunately, Scheel's paper doesn't provide references for his assertions. (Incidentally, Scheel states [p. 9, last paragraph] that it was the Temperance Movement &mdash; a political movement primarily consisting of women, often actively opposed to the US government &mdash; who used the al-ghul "spirit" interpretation to demonize alcohol.)


 * The "antimony powder" argument makes use of a broadening of the concept of ore refinement into distillation, as practiced in European countries with Latin-influenced languages. This is not at all unusual in etymology. But etymology is more art than science, especially considering the relative dearth of written materials many centuries old, from which etymology derives its understanding of changing languages. It's easy to see how European scholarship would miss the significance of Arabic sources, but the same parochial view in the general population would encourage a belief in a non-Arabic transmutation of "alkuhul". It's even possible that the parallel changes (European powder->refinement->distallation and Arabic ghost->infused spirit->drink) reinforced each other through the ages. In any case, I'd say one cannot accept the "antimony" derivation at face value without more documentation, and any such research should include an assessment of the Arabic derivation to have any credibility.


 * I would suggest that further discussion of this intriguing topic be moved either to Wikipedia's "alcohol" article or, better yet, Wiktionary's entry, which doesn't even have a definition yet, let alone a proper etymology! -- Jeff Q 20:01, 13 Jun 2004 (UTC)


 * P.S. Please forgive the reformatting of your above comments, JS and KB, but both old and new Wiki styles use colons to provide visual separation of Talk page comments. Using bullets for separation tends to make dialogs hard to read, especially as comments often include bulleted or numbered lists. Also, one shouldn't insert one's comments between two pieces of a single posting (or between the text and the signature) because it makes it hard to tell who said what later on. -- Jeff Q 20:01, 13 Jun 2004 (UTC)


 * I must apologize for misreading Jorge Stolfi's mention of the US movement propagandizing the Arabic "spirit" derivation. I thought he'd said it was a government movement, but clearly he did not say that. -- Jeff Q 20:07, 13 Jun 2004 (UTC)

Wow, thanks for the research! Jorge Stolfi 02:18, 14 Jun 2004 (UTC)

((end text from Talk:Al-Razi))


 * Thank you, Jorge Stolfi and KB! You folks did all the research. &#9786; All I did was read it, summarize it, and comment. -- Jeff Q 03:49, 15 Jun 2004 (UTC)


 * Nice etymology write-up in the article, JS! I inserted some spaces in your Arabic-to-English sequences because, at least in the current Monobook sans-serif font and to this non-Arabic reader's eye, it's hard to distinguish between Arabic script and the equals sign, so the Roman-character transliteration looks jammed up against the Arabic. Thanks again for your work. -- Jeff Q 05:17, 15 Jun 2004 (UTC)


 * Jorge, I've been trying to fill in the Hebrew reference, but I've only found the following:
 * &#x5df;&#x5d5;&#x5de;&#x5d9;&#x5d8;&#x5e0;&#x5d0; = antimon (antimun?)
 * which sounds like a modern word for antimony &mdash; probably not the Biblical reference, presumably for stibnite ore. Where did you come up with the Hebrew connection? Do you know where in the Hebrew Bible stibnite is mentioned? Also, I found a reference to a "Mesopotamian name for eye-paint, guhlu, usually translated as stibium powder&hellip; [which] passed into Arabic as kuhl". It mentions no period or specific language or people. -- Jeff Q 07:53, 15 Jun 2004 (UTC)


 * Jeffq, I have to leave now, but I found these references to "stibio" in the Latin Vulgate:
 * Jeremiah 4:30 tu autem vastata quid facies cum vestieris te coccino cum ornata fueris monili aureo et pinxeris stibio oculos tuos frustra conponeris contempserunt te amatores tui animam tuam quaerent
 * Ezekiel 23:40 miserunt ad viros venientes de longe ad quos nuntium miserant itaque ecce venerunt quibus te lavisti et circumlevisti stibio oculos tuos et ornata es mundo muliebri
 * 2Kings 9:30 venit Hieu Hiezrahel porro Hiezabel introitu eius audito depinxit oculos suos stibio et ornavit caput suum et respexit per fenestram
 * Hope it helps...
 * BTW, from those quotes it would seems that kohl in Israel was a fairly late imported "perversion".
 * BTW, the claim that kohl was prepared by sublimation or distillation seems bogus, I can't find any reference. Stibnite boils at arouns 1100 C, but unless air is excluded it will probably burn. All refs say that kohl was (still is) powdered by grinding the natural mineral. Jorge Stolfi 08:18, 15 Jun 2004 (UTC)


 * If you're getting the "kohl preparation by sublimation/distillation" from my statement above about "European powder->refinement->distallation", please let me clarify. I meant that "distillation" was seen as morphologically analogous to "refinement", not that stibnite/antimony was processed by sublimation or distillation. (That's the problem with summaries &mdash; they're so short, they can leave out important distinctions or imply things they shouldn't. Sorry 'bout that.) The mutation of meaning would have taken decades or centuries and would be similar to the modern mutation of the word "computer" from its 19th century connotation of "accountant" to its current exclusive connotation of a machine whose most noticeable 21st century use is communication. And thanks for the Latin Vulgate quotes! I'll check them out. -- Jeff Q 19:07, 15 Jun 2004 (UTC)


 * Jeff Q, I saw the story about "alkuhul" being extened to "distilled essence" in other sources too. Perhaps there is also some chemical confusion going on, besides the linguistic one.  It seems that antimony was quite popular among alchemists, because it has a colorful chemistry with many volatile compounds. Alchemical books and modern alchemy sites have many recipes for such compounds. They all start with stibnite (alkuhul), mixed with other substances and either melted (e.g. to prepare metallic antimony) or distilled (e.g. to prepare the reddish antimony trioxide, or "butter of antimony", etc).  However the "alkuhul" itself is never produced by distillation, since it oxidizes readily.  So it would be quite strange for its name to be assigned to "distilled essence".  It may be that whomever "deduced" the folk etymology was not an alchemist himself...


 * Another page said that the linguistic confusion alkuhul/alcohol led to one of the Bible verses above being translated as "women who alcoholize their eyes". I will try to find that quote (I can't recall whether the page was in English, spanish, or what.) Jorge Stolfi 00:36, 16 Jun 2004 (UTC)


 * This may just be hearsay, but growing up among Iranians I've always heard that it was the Persians that discovered alcohol. Since Islam grew rapidly threw Persia during the centuries mentioned above (mainly 12th century) it seems likely. I wonder if anyone has heard of this or has found any supporting evidence. I'm not suggesting it is true, but growing up everyone I was around took this as a fact. - User:djKianoosh 1 Jan 2005

Etymology from the OED: [a. med.L. alcohol, ad. Arab. al-ko{hdotbl}'l ‘collyrium,’ the fine powder used to stain the eyelids, f. ka{hdotbl}ala, Heb. k{amac}khal to stain, paint: see Ezekiel xxiii. 40. It appeared in Eng., as in most of the mod. langs. in 16th c. Cf. Fr. alcohol, now alcool.]

Eclectic origin history from EB:
 * Before 6000 BC, beer was made from barley in Sumeria and Babylonia.
 * Vitis vinifera was being cultivated in the Middle East by 4000 BC, and probably earlier. Egyptian records dating from 2500 BC refer to the use of grapes for wine making, and numerous Old Testament references to wine indicate the early origin and significance of the industry in the Middle East.
 * Because the two ingredients necessary to alcoholic fermentation are widely spread and always appear together, civilizations in almost every part of the world developed some form of alcoholic beverage very early in their history.

Note also that it depends on what you mean by discovery. The beer was made then but that does not necessarily mean that they knew what was going on or what was in the beer that made them inebriated. Also, as the last one indicates, alcohol is a pretty common thing to come about so it's hard to say who first used it, and it might be that it was known to be Sumeria and Babylonia simply because they kept better records than the early peoples who didn't have writing, in Africa, for - Centrx 20:50, 3 Jan 2005 (UTC)

I just removed the line "along with the substance itself" from the sentence "It was introduced to Europe in the 12th century along with the art of distillation and the substance itself." because that was completely ridiculous. It's beyond question that beer and wine flowed freely throughout Europe thousands of years earlier. I dare say that the author of that line intended to mean that distilled spirits (whiskey/grain alcholol) were introduced at this time, but the wording didn't mean that at all. If someone wants to rework it to mean that, fine by me...assuming it's accurate. I have no way of verifying that, but have plenty of references to conclude that the sentence prior to my change was definitely not correct. I mean, at the very least, the still-existant winery Corton-Charlemagne was founded by Charlemagne, who lived in the 8th and 9th centuries.


 * The article is talking about a wronge meaning of الغول in the Quranic verse, the Quranic verse describes heaven's wine telling us that "la ghaul feha" "لا غول فيها" "no ghaul in it", but ghual here doesn't mean spirit or evil, but from the Arabic root يغتال which means, among its other meanings, hides, So, the verse means "it doesn't contain the material that hides the mind" --Khaled hosny 18:14, 20 June 2007 (UTC)


 * Thanks for all the contributions!
 * The best place for further discussion would be:
 * Wiktionary talk on etymology
 * Nils von Barth (nbarth) (talk) 20:15, 31 December 2008 (UTC)

Link suggestions
An automated Wikipedia link suggester has some possible wiki link suggestions for the Alcohol article, and they have been placed on this page for your convenience. Tip: Some people find it helpful if these suggestions are shown on this talk page, rather than on another page. To do this, just add to this page. &mdash; LinkBot 00:53, 18 Dec 2004 (UTC)


 * Here thea are: Cacycle 12:19, 12 Mar 2005 (UTC)

Alcohol is clearly older than the 12th century. References to wine and mead abound in classical literature. Also, since the 7th century, alcohol has been banned in Islamic culture. Clearly, some more work and research needs to be done on this portion of the article.

New chemistry section
I think the idea of a reactions section is great, thanks Andrew for all your hard work. I don't really have time to do all of the wikifying, though I did a few edits, but I was going to suggest the following: 1. My impression is that this page gets a lot of hits, much more than most chemistry pages. Most readers will not be looking for details of the iodoform reaction (which strictly is more of a reaction of methyl ketones than alcohols)! There are probably loads of things that could go on the page- and as an organic chemist I know where my sympathies lie, but we need to consider all readers. Therefore the page needs to cover material concisely, which means that much of the reactions section needs to be edited to make it take up less space. The only other way would be to create a new page called Chemistry of alcohols or something similar.

2. Personally I prefer organic reactions drawn on a program like IsisDraw (you can see my contributions in Image:Alcohol_reaction_examples.gif and Image:Alcohol examples.gif. (Though I didn't show carbons & Hs explicitly in the naming image, that would be better for beginners- one day I will correct that.) What do others think?

3. The chemical properties section of the phys/chem props section and the chemistry (prepn & rxns) sections need to be mostly combined. When I added some content to the former, I did it mainly to correct an error, and I always felt that a separate section on chemistry would be much better- now someone has done it (thanks!). But it is ludicrous for us now to have two separate sections giving two separate examples of preparation of alkyl halides. These need to be combined and unnecessary repetition removed. If I wasn't planning a holiday from Wikipedia I'd do it myself!

Walkerma 23:18, 2 Apr 2005 (UTC)

I suggest you add a stub "buthanol" and re-direct it to this article.

--Jeff letourneau 19:20, 23 July 2006 (UTC)

Major rewrite
I have just uploaded a major rewrite of this page covering all parts except the Etymology part (which I know little about, and which seems pretty good) and the Chemistry of alcohols part (which I will work on). It seems to me that this page is probably a page receiving many hits, so it needs to be clear and concise. Unfortunately it seemed to show the worst signs of having been "written by a committee", such that although much of the content was true and at relevant, it led to the page being very long and containing many obsure facts. It also meant that there was no overall balance, having (it seemed) never had one single person edit the whole thing.

I hope that this edit makes the page a lot clearer and "punchier". Here is a summary of what I did:


 * I rewrote much of the first few sections, taking out errors, and adding a couple of pictures to clarify the text. I decided that the general formula didn't warrant its own section, so I made this one sentence, especially as the formula doesn't apply to many alcohols such as cyclohexanol, benzyl alcohol or ethylene glycol.  It was organised such that the picture near the top could serve two sections, the methanol & ethanol section as well as the primary secondary & tertiary section.
 * I have spun off the fatty alcohols on to their own page. These are not important enough to warrant a whole screen full of information one has to scroll though on such a busy page- as evidenced by the fact that it seems that none of the compounds listed has its own page.  I moved the key info up into the "Other common alcohols" section with a link to the new page.
 * I re-did the image in the properties section, so that there are other structures besides the line-angle formula. This should make the structures more readable for beginners.
 * I also took out a big chunk of specific chemistry from the properties section and put it in the chemistry section further down. I felt what was need instead was a general overview of what alcohols are like chemically, so I wrote one, and added an image to explain things.  I think general aspects like acidity and nucleophilicity are dealt with best in a section like this, while specific examples of these are best covered in the chemistry section.
 * I plan to do a major rewrite of the chemistry section in the next few days, but thought I should put up what I had so far. Please add any comments you have right after this message. Walkerma 17:27, 15 Apr 2005 (UTC)

I have finished off the rewrite. It turns out to be only slightly shorter in terms of number of screenfulls, and slightly larger in terms of kB, but I think it flows rather better and is much more evenly balanced. I have taken out a lot of duplication. Much of the growth comes from putting in important information that was missing before- such as on dehydration to alkenes, acylation by RCOCl/py. I also added short verbal explanations where before there was just a list of equations. Walkerma 19:15, 18 Apr 2005 (UTC)

Acidity and Electron Withdrawing Groups
Doesn't there need to be a section explaining the correlation between electron withdrawing groups and the acidity of alcohols? The effect is much more well-known for carboxylic acids, but it also exists for alcohols. See McMurry Organic Chemistry

antifreeze
I thought I remembered that alcohols not only have a higher boiling point but also a lower freezing point than water. Wrong? It's not discussed in the article.


 * You are right about the freezing point but not so on the boiling point. It would depend on the type of alcohol in question but in general the boiling point is lower than that of water.  See University College Cork Alcohol site, or search Google for some figures. -Onceler 18:37, 27 February 2006 (UTC)


 * A better answer: there is no need to go so far afield for figures--see ethanol, methanol, and isopropanol. However, the butanol family does exhibit lower melting point/higher boiling points than water. MP/BP are not the only target characteristics of an antifreeze though--see antifreeze article for other features and the early use of alcohol for this purpose.  Note that the common antifreeze Propylene Glycol is referred to as a diol alcohol.  Some mention in this article as historical detail or negative example  would not be unwarranted--it's probably just waiting for the motivated editor ... maybe that's you? :) Incidentally, I can't edit this discussion section and see previous text without editing the whole (long) page.  Is that a bug or a feature?  Anyone else seeing this? -Onceler 14:01, 28 February 2006 (UTC)

It should be noted that this article isn't the easiest to digest after consuming alcohol. --24.85.132.177 04:41, 16 March 2006 (UTC)

Odorless and Alcoholism
Added "odorless" (because pure alcohol is odorless) and the comment about alcoholism being hotly debated because it is. Some alcohol recovery programs which don't consider it a disease but merely a pattern of disruptive behaviors which can be rapidly unleared report success rates in excess of 65%. Compare that to the average program's rate of between 25% and 40%. The rates of most programs that consider it a disease are generally less than 20% with some averaging less than 5%.

I work with ethanol regularly (I'm an organic chemist, I used some in the lab about 3 hours ago), and to my nose it does have a smell (albeit quite mild). I can't see anything about smell on the ethanol page, which is the main page about this compound. What do others say? Regarding alcoholism, the proper place for that discussion is probably the alcoholism page. This article is supposed to be about the functional group in organic chemistry, not about alcoholism! Thanks, Walkerma 01:12, 20 May 2006 (UTC)


 * Most alcohol in the lab is about 5% water. I don't know if the water would add a smell or not, but it seems unlikely.  Try the Alcohol in a bio lab, which is supposed to be 100% pure.


 * I use ethanol regularly, too, and agree with Walkerma that it (both 100% and 95% with water) has a definite smell which, to me, is quite strong. --Ed (Edgar181) 15:27, 1 September 2006 (UTC)


 * It is impossible to smell 100% alcohol. As soon as you do so, the water vapor from your nose will be absorbed by the alcohol, thus a 100% alcohol is definately not smellable and most likely stinks as hell considering that water does not actually add a smell Tourskin (talk) 21:10, 12 January 2008 (UTC)

Contradiction tag: Two etymology sections?
And they appear to contradict each other. --Lukobe 07:23, 27 May 2006 (UTC)
 * Aye, they do. This should be fixed- mastodon 12:27, 27 May 2006 (UTC)
 * I've tried to fix it, though someone seems to have removed the contradiction tag already. -- Narge (talk|contribs) 14:06, 8 November 2006 (UTC)

boiling point
I'm a bit rusty on my chemistry so I'll abstain from adding myself, but could someone include the boiling point of alcohol. From everything I've seen it's about 79.5°C but I'm not sure if it varies for different types of alcohol. Vicarious 23:31, 30 May 2006 (UTC)


 * Ethanol b.p. 78.29 °C - CRC Handbook of Chemistry and Physics, 85th Ed. And yes, it does vary for different alcohols. --Rifleman 82 23:53, 30 May 2006 (UTC)

Introduction
I changed "odorless, colorless liquid" in the introduction paragraph to "colorless liquid with a strong smell" because as far as I know, ethanol isn't odorless.


 * Is it? see above, someone commented that pure alcohol is oderless


 * How exactly can any fool smell pure alcohol? As soon as you expose it to the air it will absorb water. It requires a water-free environment - something that kinda renders your sense of smell non-existent. —Preceding unsigned comment added by Tourskin (talk • contribs) 21:08, 12 January 2008 (UTC)

LD50
What *is* the LD50 of alcohol? -- Tompsci 00:53, 21 July 2006 (UTC)
 * 11,300 mg/kg, I've added it to the article. Vicarious 07:29, 29 September 2006 (UTC)

Vodka and Impotency
Does Vodka consumption have an impact on the potency of a guy?
 * Extremely doubtful. Vicarious 05:53, 12 October 2006 (UTC)

Toxicity bullocks?
This is from a British nurse of my acquaintance - she contests the paragraph in the Toxicity section dealing with drinking ethanol to avoid methanol poisoning. I asked her because I thought that that paragraph could be useful to remember for first aid purposes, but I figured I should verify it with a medical professional first. Can SOMEBODY, PLEASE, verify one over the other? I know Wikipedia is not a doctor, but for Chrissakes my age group will read this and think, Oh, Johnny's dying of Listerine ingestion, we'll just get some Jager into him... --207.216.10.77 08:28, 31 October 2006 (UTC)

Ethanol is toxic, and the body begins to dispose of it immediately upon its consumption. Over 90% of it is processed by the liver. In the liver, the alcohol dehydrogenase enzyme converts ethanol into acetaldehyde, which is itself toxic. Acetaldehyde is destroyed almost immediately by the aldehyde dehydrogenase enzyme, which converts it to acetate ions.

The hydrogen atoms represented by these equations are not unattached, but are picked up by another biologically important compound, nicotinamide-adenine dinucleotide (NAD), whose function is to carry hydrogen atoms. NAD is involved in both of the above processes, being converted to NADH.

NAD + H = NADH

NADH must be recycled to NAD for the disposal of ethanol to continue. If the amount of ethanol consumed is not great, the recycling can keep up with the disposal of ethanol. The ethanol disposal rate in a 150-pound human is about 0.5 ounce of ethanol per hour, which corresponds to 12 ounces of beer, 4 ounces of wine, or 1 ounce of hard liquor. The figure shows how the blood alcohol level changes with time for various doses of ethanol.

Ethanol acts as a drug affecting the central nervous system. Its behavioral effects stem from its effects on the brain and not on the muscles or senses themselves. It is a depressant, and depending on dose, can be a mild tranquilizer or a general anesthetic. It suppresses certain brain functions. At very low doses, it can appear to be a stimulant by suppressing certain inhibitory brain functions. However, as concentration increases, further suppression of brain functions produce the classic symptoms of intoxication: slurred speech, unsteady walk, disturbed sensory perceptions, and inability to react quickly. At very high concentrations, ethanol produces general anesthesia; a highly ntoxicated person will be asleep and very difficult to wake, and if awakened, unable to move voluntarily.

Alcohol levels in the brain are difficult to measure, and so blood alcohol levels are used to assess degree of intoxication. Most people begin to show measurable mental impairment at around 0.05 percent blood alcohol. At around 0.10 percent, mental impairment will show obvious physical signs, such as an unsteady walk. Slurred speech shows up at around 0.15 percent. Unconsciousness results by 0.4 percent. Above 0.5 percent, the breathing center of the brain or the beating action of the heart can be anesthetized, resulting in death.

Bees and inebriation
Please take a look at my rough draft at User talk:Filll/beedrunk and give me your opinion.--Filll 21:29, 13 January 2007 (UTC)

Uses of alcohol
is the phrase "Alcohol is used to become intoxicated and/or seduce women." needed —The preceding unsigned comment was added by 72.142.84.43 (talk) 04:02, 26 January 2007 (UTC).
 * It looks like that was already removed. --Afluent Rider 04:04, 26 January 2007 (UTC)

More Vandalism
More vandalism at the start of the page —The preceding unsigned comment was added by 192.198.151.130 (talk) 11:45, 26 January 2007 (UTC).

Metabolising
"Other alcohols are substantially more poisonous than ethanol, partly because they take much longer to be metabolized"

"It is said, by Russ Heiser, that alcohol stays in the human system and inhibits neural function for 30 days following consumption."

I'm seeing some logical contradiction here. Frigo 19:44, 27 January 2007 (UTC)


 * maybe they mean methanol, which is why its poisonous?Tourskin (talk) 17:32, 14 January 2008 (UTC)

Oxidation section changed
I changed the whole section, following the principle that only established common reactions should be included. I will expand the contents of this section in two new articles entitled "Oxidation of alcohols to aldehydes and ketones" and "Oxidation of Primary Alcohols to Carboxylic Acids." These articles will contain many references.

As soon as possible, I will add in this section a few lines about the oxidative breakage of 1,2-diols and the transformation of diols into lactones.

In my opinion, no other alcohol oxidations should be included, as they would possess a very minor importance in Synthetic Organic Chemistry.

Gabriel Tojo

New Article: Oxidation of Primary Alcohols to Carboxylic Acids
I started a new article related to Alcohols entitled Oxidation of Primary Alcohols to Carboxylic Acids. I hope to finish it in a few weeks.

Gabriel Tojo

Alcohol Powder?
I saw this Alcohol Powder Article and 1st thought that this must be physically impossible (but the article cites 2 other cases), and 2nd thought to check Wikipedia. But there's nothing here. Any help? 82.141.187.170 09:57, 7 June 2007 (UTC)
 * It seems legit, so the best thing would maybe be to wait for more news/citations for this product before writing anything? --BiT 10:14, 15 June 2007 (UTC)
 * IIRC these are salts, which give upon hydrolysis ethanol and an innocent inorganic salt (in general an oxide). Would be interesting to have an article on that.  --Dirk Beetstra T  C 10:55, 15 June 2007 (UTC)

The 109 degree angle applies to the [C] not the [O]
The 109 degress applies to the [C]. Lone pairs on an atom typically generate angles of 107 or 104 degrees. Dresj@aol.comDresj 18:08, 18 September 2007 (UTC)


 * According to March Advanced Organic Chemistry 3rd ed p21 the COH bond angle in methanol is 107-109 degrees. Silverchemist 18:49, 18 September 2007 (UTC)

alcohol as a beverage
i dont feel like this article is complete. there should be a part with alcohol used as a beverage.this is definetely missing. i know there's another article for that. but they shoud be a short thing about this on the main article 71.255.59.245 15:48, 11 October 2007 (UTC)


 * This article is about the functional group, and no one uses a functional group as a beverage. ;-) The very first sentence of the article already has clear links to ethanol and to alcoholic beverage, in case a reader is in the wrong place. --Itub 09:51, 13 October 2007 (UTC)

Ketone into diol
Should we add a image showing how ketone form into a diol? Raymond Giggs 04:10, 3 November 2007 (UTC)

nmr
Nothing is mentioned of the effect of rapid proton exchange with NMR.Tourskin (talk) 21:04, 12 January 2008 (UTC)

Etymology question
From this article, I wonder if we have not got the etymology of the word "alcohol" slightly garbled?

--Filll (talk | wpc ) 17:48, 8 July 2008 (UTC)

Whichever it may be, I don't think the transliteration is right. Shouldn't الغول‎ be "al-ġul," not "al-ġuḥl," since there's no ح involved? 128.151.25.85 (talk) 02:33, 24 September 2008 (UTC)

Specimens
"used as a preservative for specimens" goes to a page about the band. should be changed but Im not registered —Preceding unsigned comment added by 222.155.179.35 (talk) 02:40, 16 July 2008 (UTC)

Superprimary?
There is also a subset which is called superprimary (O°). The only compound in this subset is methyl alcohol. This information should be incorporated into the article. Fuzzform (talk) 23:45, 24 September 2008 (UTC)


 * Who uses this superprimary term? It seems to be extremely obscure: the only places where I have seen it used are a 1955 article (The Hydrolysis of Sodium Alkyl Sulfates in Basic Aqueous Solution. George M. Calhoun, Robert L. Burwell,, Jr.; J. Am. Chem. Soc.; 1955; 77(24); 6441-6447.) and some class notes at http://people.bu.edu/birubio/ch203/pdfs/l06.pdf . Not notable enough in my opinion. Although the term has some logic to it, most chemists I know simply call the methyl group, well, methyl. --Itub (talk) 10:38, 28 October 2008 (UTC)

LD50 incorrect in article.
Hopefully the contributing editor was just having an off day. The reference cited (^ Robert S. Gable (2004). "Comparison of acute lethal toxicity of commonly abused psychoactive substances" (reprint). Addiction 99 (6): 686–696. ) states "Non-human animal studies reported oral LD 50 doses of mice at 168 and 137 mg/kg, and rats at 162 mg/kg (National Toxicology Program 1991)." So WP has been misinforming readers for over 2 years. The figure presently used in the article is that for mice (not rats) multiplied by ten. Perhaps some of the Fundamentalist Skeptics should forgo the thrills of chasing down non-mainstream belief systems and do a bit of proof-reading? My confidence as a user of Wikipedia is slipping more and more - if this "encyclopdia" can't even get the basics correct - as in accurately report data - then it will be just more unwanted static in the flow of information. 203.206.57.3 (talk) 23:24, 27 October 2008 (UTC)
 * In Table 1 on page 689 of the cited reference, it states that the oral rat LD50 is 10300 mg/kg, which is what the article states. —Preceding unsigned comment added by 71.246.31.235 (talk) 23:49, 27 October 2008 (UTC)

etomology
The word alcohol was introduced into the English language circa 1543 from the الغول, "al-ġuḥl". I removed this from the intro as it is not supported by reliable third partiesJ8079s (talk) 19:03, 15 March 2009 (UTC)

Proposing Merge of Chemistry and Toxicology section.
Wikipedia has articles specifically detailing Alcohol's chemistry (ie. alcohol), and seperately, toxic effects (drunkeness, binge drinking, etcetera). Article alcoholic beverages' section entitled "chemistry and toxicology" seems to need merging, and "main article" links added.James Chenery (talk) 08:23, 9 June 2009 (UTC)


 * Sounds like a good idea.Wahrmund (talk) 22:40, 9 June 2009 (UTC)


 * I don't understand; surely that section is concerned with ethanol (called "alcohol" in the vernacular)? This page is concerned with family of ALCOHOLS such as methanol, menthol, things like that - even sugar counts as an alcohol.  Surely it's more to add the chemistry of ethanol into the ethanol article, not into the family article?  The fact that you use the word alcohol as a singular suggests that you haven't read this article at all! Most alcohols will usually cause death or irritation, not drunkenness! Walkerma (talk) 18:33, 15 June 2009 (UTC)


 * I do not think that the merge would be useful. There is a great deal of technical information about alcohols as a class (see above) that is not relevant to toxicity and there is specific toxicity information about compounds other than ethanol which might also get lost.  The more reasonable approach would be to create cross references in the two documents. Wgm1945 (talk) 11:00, 30 July 2009 (UTC)

Methanol hazards
Cut from article:


 * Methanol is intoxicating but not directly poisonous. It is toxic by its breakdown (toxication) by the enzyme alcohol dehydrogenase in the liver by forming formic acid and formaldehyde which cause permanent blindness by destruction of the optic nerve.

I find the phrase "not directly poisonous" misleading. I'm sitting next to a medical doctor (a native speaker of Japanese), who pointed out that methanol causes blindness.

In case someone is trying to figure out which of the three kinds of alcohol he can safely drink, can we find a better phrase than "not ... poisonous"? I'm afraid someone might skip the rest of the paragraph and assume it was safe to drink! --Uncle Ed (talk) 18:09, 9 June 2009 (UTC)

Alcohol Image
The legend beneath the image of a generic alcohol says that it is Methanol which is pictured, but the pictured image doesn't have hydrogen atoms at the ends of the bonds from the C. Indeed, in organic chemistry, it is common for a bond with no specified terminal atom to be considered a methyl group, rendering the image as tBuOH, tert-butanol. Should the image or the legend be corrected. Spuddddddd 12Jun09 —Preceding unsigned comment added by 86.26.7.49 (talk) 20:45, 12 June 2009 (UTC)

Saturated Carbon Atoms
I am not a member of the MMORPG that is Wikipedia and do not wish to become one. Since this page is protected I can only suggest that one of you modify the first sentence of the article to mention that the hydroxyle group needs to be bound to a SATURATED carbon atom, otherwise it might not be an alcohol group. —Preceding unsigned comment added by 69.159.97.223 (talk) 03:44, 10 July 2009 (UTC)

LD50
editsemiprotected

Please change 10,300 mg/kg to 10.3 g/kg

Perhaps in volume also (13 ml/kg or .2 oz/lb) Ethanol's mass is 789mg per ml. SAP

142.177.65.176 (talk) 22:28, 13 October 2009 (UTC)

✅   Set Sail   For The   Seven Seas    342° 31' 15" NET    22:50, 13 October 2009 (UTC)

LD50
If the liquor is 40% achohol by volume then it's 1/2 oz per pound of body weight. for a rat.

Typing mistake
The sentence "An important group of acohols is formed by the simple acyclic alcohols, the general formula for which is CnH2n+1OH" is writen in the first section of the article. —Preceding unsigned comment added by 93.172.42.45 (talk) 16:53, 23 October 2009 (UTC)

Inclusion of Mamaherb.com accredited information as external links
Dear editor,

My name is Rukmani Agrawal and I'm working for Mamaherb.com (http://www.mamaherb.com/). Mamaherb.com is the world's largest free Home Remedies database, who's intention is to allow users to upload and rate what actually works in the field of natural health. The data is accumulated very much in the spirit of Wikipedia - with users allowed to add and edit ingredients and create Home Remedies based on these Ingredients.

Some numbers and facts:

Home Remedies: 19,614 (growing by 100+ every day). Natural Ingredients: 1,414 Conditions Treated: 1,324

Mamaherb.com has won the prestigious (though rather new) United Nation's WSA award for 2009 for making the world a healthier place, being ".... one of the most outstanding examples of creative and innovative e-Content in the world!". The WSA was called by Prof. Nicholas Negroponte, initiator of the 'One Laptop per Child', the “The Nobel Prize of Multimedia”.

What we'd like to receive your consent to is adding relevant links from Mamaherb.com to this article, under the External Links section (qualifying with all of Wikipedia’s guide-lines as to what should be included under this section):

Here, under: http://en.wikipedia.org/wiki/Alcohol, we’d add: http://www.mamaherb.com/Alcohol (note the links to the 20 related treatments and remedies).

Surely you'd agree Mamaherb.com's content is very value-adding in this External links section.

Thanks in advance,

Rukmani

Dollyagrawal (talk) 06:36, 27 November 2009 (UTC)


 * This is the wrong page to add this; if you read the article, you'll see it's not about the same topic at all - it's about organic compounds containing a hydroxy group. You should instead ask this question at ethanol.  Personally, I don't think the Mamaherb page on this topic adds much to the ethanol page, since it represents a minor use tested by a handful of people in an unscientific way, so personally I would oppose adding the link.  However, others may think differently. Walkerma (talk) 07:27, 27 November 2009 (UTC)

Pharmacokinetics
Like any other drug, I think many people would be interested to know how alcohol is absorbed (w/ and w/o other factors like food), distributed, metabolised and excreted; or at have a link to the "Metabolism and excretion" section in "Blood alcohol content". However, although the section deals with alcohol dehydrogenase saturation at low BACs it doesn't mention the other metabolising pathway that plays a bigger role in alcohol metabolism at higher BACs, namely the microsomal pathway (or MEOS). In addition to being induced by alcohol (leading to pharmacokinetic interactions with other drugs), this pathway contributes significantly to the production of reactive oxygen species by alcohol. —Preceding unsigned comment added by 114.30.115.127 (talk) 06:47, 4 December 2009 (UTC)

New species
Under Occurence in nature, why does it say (New Species) next to Astrophysical maser? —Preceding unsigned comment added by 70.96.164.170 (talk) 19:31, 7 December 2009 (UTC)

== The etimology should mention Old Spanish =

Etymology: New Latin, from Medieval Latin, powdered antimony, from Old Spanish, from Arabic al-kuḥul the powdered antimony, from kuḥl kohl Date: 1672

A lot of words came to English from French (France), and many of this words came from other sources you should mention. So it'd fair to say the whole route words have done to come to English. Alcohol comes from الكحل(Arabic), then Old Spanish took it (introduction to the Latin spelling as "alcohol"), introduced to Medieval Latin and New Latin, then taken by the French language, and finally taken by the English language. 92.0.226.39 (talk) 15:59, 13 December 2009 (UTC)