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In chemistry, an alcohol is any organic compound in which the hydroxyl functional group (–OH) is bound to a saturated carbon atom.[2] The term alcohol originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic beverages. The suffix -ol appears in the IUPAC
IUPAC
chemical name of all substances where the hydroxyl group is the functional group with the highest priority; in substances where a higher priority group is present the prefix hydroxy- will appear in the International Union of Pure and Applied Chemistry
Chemistry
(IUPAC) name. The suffix -ol in non-systematic names (such as paracetamol or cholesterol) also typically indicates that the substance includes a hydroxyl functional group and, so, can be termed an alcohol. But many substances, particularly sugars (examples glucose and sucrose) contain hydroxyl functional groups without using the suffix. An important class of alcohols, of which methanol and ethanol are the simplest members is the saturated straight chain alcohols, the general formula for which is CnH2n+1OH.

Contents

1 History 2 Nomenclature

2.1 Etymology 2.2 Systematic names 2.3 Common names

2.3.1 Alkyl
Alkyl
chain variations in alcohols 2.3.2 Simple alcohols 2.3.3 Higher alcohols

3 Applications 4 Toxicity

4.1 Treatment

5 Physical and chemical properties 6 Occurrence in nature 7 Production

7.1 Ziegler and oxo processes 7.2 Hydration reactions 7.3 Biological routes

7.3.1 Substitution 7.3.2 Reduction 7.3.3 Hydrolysis

8 Reactions

8.1 Deprotonation 8.2 Nucleophilic substitution 8.3 Dehydration 8.4 Esterification 8.5 Oxidation

9 See also 10 Notes 11 References 12 External links

History Rhazes (854 CE – 925 CE), was a Persian[3][4][5] polymath, physician, alchemist, and philosopher who discovered numerous compounds and chemicals including "alcohol" by developing several chemical instruments and methods of distillation. Nomenclature Etymology The word "alcohol" is from the Arabic kohl (Arabic: الكحل‎, translit. al-kuḥl), a powder used as an eyeliner.[6] Al-
Al-
is the Arabic definite article, equivalent to the in English. Alcohol
Alcohol
was originally used for the very fine powder produced by the sublimation of the natural mineral stibnite to form antimony trisulfide Sb 2S 3, hence the essence or "spirit" of this substance. It was used as an antiseptic, eyeliner, and cosmetic. The meaning of alcohol was extended to distilled substances in general, and then narrowed to ethanol, when "spirits" was a synonym for hard liquor.[7] Bartholomew Traheron, in his 1543 translation of John of Vigo, introduces the word as a term used by "barbarous" (Moorish) authors for "fine powder." Vigo wrote: "the barbarous auctours use alcohol, or (as I fynde it sometymes wryten) alcofoll, for moost fine poudre."[8] The 1657 Lexicon Chymicum, by William Johnson glosses the word as "antimonium sive stibium."[9] By extension, the word came to refer to any fluid obtained by distillation, including "alcohol of wine," the distilled essence of wine. Libavius
Libavius
in Alchymia (1594) refers to "vini alcohol vel vinum alcalisatum". Johnson (1657) glosses alcohol vini as "quando omnis superfluitas vini a vino separatur, ita ut accensum ardeat donec totum consumatur, nihilque fæcum aut phlegmatis in fundo remaneat." The word's meaning became restricted to "spirit of wine" (the chemical known today as ethanol) in the 18th century and was extended to the class of substances so-called as "alcohols" in modern chemistry after 1850.[8] The term ethanol was invented 1892, combining the word ethane with the "-ol" ending of "alcohol".[10] Systematic names IUPAC
IUPAC
nomenclature is used in scientific publications and where precise identification of the substance is important, especially in cases where the relative complexity of the molecule does not make such a systematic name unwieldy. In the IUPAC
IUPAC
system, in naming simple alcohols, the name of the alkane chain loses the terminal "e" and adds "ol", e.g., as in "methanol" and "ethanol".[11] When necessary, the position of the hydroxyl group is indicated by a number between the alkane name and the "ol": propan-1-ol for CH 3CH 2CH 2OH, propan-2-ol for CH 3CH(OH)CH 3. If a higher priority group is present (such as an aldehyde, ketone, or carboxylic acid), then the prefix "hydroxy" is used,[11] e.g., as in 1-hydroxy-2-propanone (CH 3C(O)CH 2OH).[12]

Some examples of simple alcohols and how to name them

CH3–CH2–CH2–OH

n-propyl alcohol, propan-1-ol, or 1-propanol isopropyl alcohol, propan-2-ol, or 2-propanol cyclohexanol isobutyl alcohol, 2-methylpropan-1-ol, or 2-methyl-1-propanol tert-amyl alcohol, 2-methylbutan-2-ol, or 2-methyl-2-butanol

A primary alcohol A secondary alcohol A secondary alcohol A primary alcohol A tertiary alcohol

In cases where the OH functional group is bonded to an sp2 carbon on an aromatic ring the molecule is known as a phenol, and is named using the IUPAC
IUPAC
rules for naming phenols.[13] Common names In other less formal contexts, an alcohol is often called with the name of the corresponding alkyl group followed by the word "alcohol", e.g., methyl alcohol, ethyl alcohol. Propyl
Propyl
alcohol may be n-propyl alcohol or isopropyl alcohol, depending on whether the hydroxyl group is bonded to the end or middle carbon on the straight propane chain. As described under systematic naming, if another group on the molecule takes priority, the alcohol moiety is often indicated using the "hydroxy-" prefix.[14] Alcohols are then classified into primary, secondary (sec-, s-), and tertiary (tert-, t-), based upon the number of carbon atoms connected to the carbon atom that bears the hydroxyl functional group. (The respective numeric shorthands 1°, 2°, and 3° are also sometimes used in informal settings.[15]) The primary alcohols have general formulas RCH2OH. The simplest primary alcohol is methanol (CH3OH), for which R=H, and the next is ethanol, for which R=CH3, the methyl group. Secondary alcohols are those of the form RR'CHOH, the simplest of which is 2-propanol (R=R'=CH3). For the tertiary alcohols the general form is RR'R"COH. The simplest example is tert-butanol (2-methylpropan-2-ol), for which each of R, R', and R" is CH3. In these shorthands, R, R', and R" represent substituents, alkyl or other attached, generally organic groups.

 Chemical formula    IUPAC
IUPAC
Name   Common name 

Monohydric alcohols

CH3OH methanol wood alcohol

C2H5OH ethanol alcohol

C3H7OH propan-2-ol isopropyl alcohol, rubbing alcohol

C4H9OH butan-1-ol butanol, butyl alcohol

C5H11OH pentan-1-ol pentanol, amyl alcohol

C16H33OH hexadecan-1-ol cetyl alcohol

Polyhydric alcohols

C2H4(OH)2 ethane-1,2-diol ethylene glycol

C3H6(OH)2 propane-1,2-diol propylene glycol

C3H5(OH)3 propane-1,2,3-triol glycerol

C4H6(OH)4 butane-1,2,3,4-tetraol erythritol, threitol

C5H7(OH)5 pentane-1,2,3,4,5-pentol xylitol

C6H8(OH)6 hexane-1,2,3,4,5,6-hexol mannitol, sorbitol

C7H9(OH)7 heptane-1,2,3,4,5,6,7-heptol volemitol

Unsaturated aliphatic alcohols

C3H5OH Prop-2-ene-1-ol allyl alcohol

C10H17OH 3,7-Dimethylocta-2,6-dien-1-ol geraniol

C3H3OH Prop-2-yn-1-ol propargyl alcohol

Alicyclic
Alicyclic
alcohols

C6H6(OH)6 cyclohexane-1,2,3,4,5,6-hexol inositol

C10H19OH 2 - (2-propyl)-5-methyl-cyclohexane-1-ol menthol

Alkyl
Alkyl
chain variations in alcohols Short-chain alcohols have alkyl chains of 1–3 carbons. Medium-chain alcohols have alkyl chains of 4–7 carbons. Long-chain alcohols (also known as fatty alcohols) have alkyl chains of 8–21 carbons, and very long-chain alcohols have alkyl chains of 22 carbons or longer.[16] Simple alcohols "Simple alcohols" appears to be a completely undefined term. However, simple alcohols are often referred to by common names derived by adding the word "alcohol" to the name of the appropriate alkyl group. For instance, a chain consisting of one carbon (a methyl group, CH3) with an OH group attached to the carbon is called "methyl alcohol" while a chain of two carbons (an ethyl group, CH2CH3) with an OH group connected to the CH2 is called "ethyl alcohol." For more complex alcohols, the IUPAC
IUPAC
nomenclature must be used.[17] Simple alcohols, in particular ethanol and methanol, possess denaturing and inert rendering properties, leading to their use as anti-microbial agents in medicine, pharmacy, and industry.[citation needed] Higher alcohols Encyclopædia Britannica
Encyclopædia Britannica
states, "The higher alcohols—those containing 4 to 10 carbon atoms—are somewhat viscous, or oily, and they have heavier fruity odours. Some of the highly branched alcohols and many alcohols containing more than 12 carbon atoms are solids at room temperature."[18] Like ethanol, butanol can be produced by fermentation processes. Saccharomyces yeast are known to produce these higher alcohols at temperatures above 75 °F (24 °C). The bacterium Clostridium acetobutylicum
Clostridium acetobutylicum
can feed on cellulose to produce butanol on an industrial scale.[19] Applications

Total recorded alcohol per capita consumption (15+), in litres of pure ethanol[20]

Alcohol
Alcohol
has a long history of several uses worldwide. It is found in alcoholic beverages sold to adults, as fuel, and also has many scientific, medical, and industrial uses. The term alcohol-free is often used to describe a product that does not contain alcohol.

Alcoholic drinks, typically containing 3–40% alcohol by volume, have been produced and consumed by humans since pre-historic times. Natural fermentation also produces trace amounts of other alcohols such as 2-methyl-2-butanol
2-methyl-2-butanol
and γ-hydroxybutyric acid (GHB), which have psychoactive effects similar to alcohol when used as a drug. Antifreeze
Antifreeze
commonly includes a 50% v/v (by volume) solution of ethylene glycol in water. Medical: Ethanol
Ethanol
can be used as an antiseptic to disinfect the skin before injections are given, often along with iodine.[21] Ethanol-based soaps are becoming common in restaurants and are convenient because they do not require drying due to the volatility of the compound. Alcohol
Alcohol
based gels have become common as hand sanitizers.[citation needed] Alcohol
Alcohol
fuel: Some alcohols, mainly ethanol and methanol, can be used as fuel. Fuel performance can be increased in forced induction internal combustion engines by injecting alcohol into the air intake after the turbocharger or supercharger has pressurized the air. This cools the pressurized air, providing a denser air charge, which allows for more fuel, and therefore more power.[citation needed] Preservative: Alcohol
Alcohol
is often used as a preservative for biological specimens in the fields of science and medicine. Solvent: Hydroxyl
Hydroxyl
groups (-OH), found in alcohols, are polar and therefore hydrophilic (water loving) but their carbon chain portion is non-polar which make them hydrophobic. The molecule increasingly becomes overall more nonpolar and therefore less soluble in the polar water as the carbon chain becomes longer.[22] Methanol
Methanol
has the shortest carbon chain of all alcohols (one carbon atom) followed by ethanol (two carbon atoms.) Alcohols have applications in industry and science as reagents or solvents. Because of its relatively low toxicity compared with other alcohols and ability to dissolve non-polar substances, ethanol can be used as a solvent in medical drugs, perfumes, and vegetable essences such as vanilla. In organic synthesis, alcohols serve as versatile intermediates.[citation needed]

Toxicity

This section needs more medical references for verification or relies too heavily on primary sources. Please review the contents of the section and add the appropriate references if you can. Unsourced or poorly sourced material may be challenged and removed. (June 2014)

Ball-and-stick model
Ball-and-stick model
of tert-Amyl alcohol, which is 20 times more intoxicating than ethanol and like all tertiary alcohols, cannot be metabolised to toxic aldehydes.[23][24][better source needed][25][better source needed]

Ethanol
Ethanol
is thought to cause harm partly as a result of direct damage to DNA
DNA
caused by its metabolites.[26]

Most significant of the possible long-term effects of ethanol. In addition, in pregnant women it may cause fetal alcohol syndrome.

Ethanol's toxicity is largely caused by its primary metabolite, acetaldehyde (systematically ethanal)[27][28] and secondary metabolite, acetic acid.[28][29][30][31] Many primary alcohols are metabolized into aldehydes then to carboxylic acids whose toxicities are similar to acetaldehyde and acetic acid.[citation needed] Metabolite toxicity is reduced in rats fed N-acetylcysteine[27][32] and thiamine.[33] Although the mechanism is unclear, a meta-analysis of 572 studies have shown increased cancer risk from consumption of ethanol.[34][35] Tertiary alcohols cannot be metabolized into aldehydes[36] and as a result they cause no hangover or toxicity through this mechanism. Some secondary and tertiary alcohols are less poisonous than ethanol, because the liver is unable to metabolize them into toxic by-products.[37] This makes them more suitable for pharmaceutical use as the chronic harms are lower.[38] Ethchlorvynol
Ethchlorvynol
and tert-amyl alcohol are tertiary alcohols which have seen both medicinal and recreational use.[39] Other alcohols are substantially more poisonous than ethanol, partly because they take much longer to be metabolized and partly because their metabolism produces substances that are even more toxic. Methanol
Methanol
(wood alcohol), for instance, is oxidized to formaldehyde and then to the poisonous formic acid in the liver by alcohol dehydrogenase and formaldehyde dehydrogenase enzymes, respectively; accumulation of formic acid can lead to blindness or death.[40] Likewise, poisoning due to other alcohols such as ethylene glycol or diethylene glycol are due to their metabolites, which are also produced by alcohol dehydrogenase.[41][42] Methanol
Methanol
itself, while poisonous (LD50 5628 mg/kg, oral, rat[43]), has a much weaker sedative effect than ethanol. Isopropyl alcohol
Isopropyl alcohol
is oxidized to form acetone by alcohol dehydrogenase in the liver, but has occasionally been abused by alcoholics, leading to a range of adverse health effects.[44][better source needed][45][better source needed] Treatment An effective treatment to prevent toxicity after methanol or ethylene glycol ingestion is to administer ethanol. Alcohol dehydrogenase
Alcohol dehydrogenase
has a higher affinity for ethanol, thus preventing methanol from binding and acting as a substrate. Any remaining methanol will then have time to be excreted through the kidneys.[40][46][47] Physical and chemical properties Alcohols have an odor that is often described as "biting" and as "hanging" in the nasal passages. Ethanol
Ethanol
has a slightly sweeter (or more fruit-like) odor than the other alcohols. In general, the hydroxyl group makes the alcohol molecule polar. Those groups can form hydrogen bonds to one another and to other compounds (except in certain large molecules where the hydroxyl is protected by steric hindrance of adjacent groups[48]). This hydrogen bonding means that alcohols can be used as protic solvents. Two opposing solubility trends in alcohols are: the tendency of the polar OH to promote solubility in water, and the tendency of the carbon chain to resist it. Thus, methanol, ethanol, and propanol are miscible in water because the hydroxyl group wins out over the short carbon chain. Butanol, with a four-carbon chain, is moderately soluble because of a balance between the two trends. Alcohols of five or more carbons such as pentanol and higher are effectively insoluble in water because of the hydrocarbon chain's dominance. All simple alcohols are miscible in organic solvents.[citation needed] Because of hydrogen bonding, alcohols tend to have higher boiling points than comparable hydrocarbons and ethers. The boiling point of the alcohol ethanol is 78.29 °C, compared to 69 °C for the hydrocarbon hexane (a common constituent of gasoline), and 34.6 °C for diethyl ether. Alcohols, like water, can show either acidic or basic properties at the -OH group. With a pKa of around 16-19, they are, in general, slightly weaker acids than water, but they are still able to react with strong bases such as sodium hydride or reactive metals such as sodium. The salts that result are called alkoxides, with the general formula RO− M+. Meanwhile, the oxygen atom has lone pairs of nonbonded electrons that render it weakly basic in the presence of strong acids such as sulfuric acid. For example, with methanol:

Alcohols can be oxidised to give aldehydes, ketones or carboxylic acids, or they can be dehydrated to alkenes. They can react with carboxylic acids to form ester compounds, and they can (if activated first) undergo nucleophilic substitution reactions. The lone pairs of electrons on the oxygen of the hydroxyl group also makes alcohols nucleophiles. For more details, see the reactions of alcohols section below.[49] As one moves from primary to secondary to tertiary alcohols with the same backbone, the hydrogen bond strength, the boiling point, and the acidity typically decrease. Occurrence in nature Ethanol
Ethanol
occurs naturally as a byproduct of the metabolic process of yeast. As such, ethanol will be present in any yeast habitat. Ethanol can commonly be found in overripe fruit. Methanol
Methanol
is produced naturally in the anaerobic metabolism of many varieties of bacteria, and is commonly present in small amounts in the environment. Alcohols have been found outside the Solar System
Solar System
at low densities in star-forming regions of interstellar space.[50][51] Production Ziegler and oxo processes In the Ziegler process, linear alcohols are produced from ethylene and triethylaluminium followed by oxidation and hydrolysis.[52] An idealized synthesis of 1-octanol
1-octanol
is shown:

Al(C2H5)3 + 9 C2H4 → Al(C8H17)3 Al(C8H17)3 + 3 O + 3 H2O → 3 HOC8H17 + Al(OH)3

The process generates a range of alcohols that are separated by distillation. Many higher alcohols are produced by hydroformylation of alkenes followed by hydrogenation. When applied to a terminal alkene, as is common, one typically obtains a linear alcohol:[52]

RCH=CH2 + H2 + CO → RCH2CH2CHO RCH2CH2CHO + 3 H2 → RCH2CH2CH2OH

Such processes give fatty alcohols, which are useful for detergents. Hydration reactions Low molecular weight alcohols of industrial importance are produced by the addition of water to alkenes. Ethanol, isopropanol, 2-butanol, and tert-butanol are produced by this general method. Two implementations are employed, the direct and indirect methods. The direct method avoids the formation of stable intermediates, typically using acid catalysts. In the indirect method, the alkene is converted to the sulfate ester, which is subsequently hydrolyzed. The direct hydration using ethylene (ethylene hydration)[53] or other alkenes from cracking of fractions of distilled crude oil. Hydration is also used industrially to produce the diol ethylene glycol from ethylene oxide. Biological routes Ethanol
Ethanol
is obtained by fermentation using glucose produced from sugar from the hydrolysis of starch, in the presence of yeast and temperature of less than 37 °C to produce ethanol. For instance, such a process might proceed by the conversion of sucrose by the enzyme invertase into glucose and fructose, then the conversion of glucose by the enzyme complex zymase into ethanol (and carbon dioxide). Several of the benign bacteria in the intestine use fermentation as a form of anaerobic metabolism. This metabolic reaction produces ethanol as a waste product, just like aerobic respiration produces carbon dioxide and water. Thus, human bodies contain some quantity of alcohol endogenously produced by these bacteria. In rare cases, this can be sufficient to cause "auto-brewery syndrome" in which intoxicating quantities of alcohol are produced.[54][55][56] Substitution Primary alkyl halides react with aqueous NaOH or KOH mainly to primary alcohols in nucleophilic aliphatic substitution. (Secondary and especially tertiary alkyl halides will give the elimination (alkene) product instead). Grignard reagents react with carbonyl groups to secondary and tertiary alcohols. Related reactions are the Barbier reaction and the Nozaki-Hiyama reaction. Reduction Aldehydes
Aldehydes
or ketones are reduced with sodium borohydride or lithium aluminium hydride (after an acidic workup). Another reduction by aluminiumisopropylates is the Meerwein-Ponndorf-Verley reduction. Noyori asymmetric hydrogenation
Noyori asymmetric hydrogenation
is the asymmetric reduction of β-keto-esters. Hydrolysis Alkenes
Alkenes
engage in an acid catalysed hydration reaction using concentrated sulfuric acid as a catalyst that gives usually secondary or tertiary alcohols. The hydroboration-oxidation and oxymercuration-reduction of alkenes are more reliable in organic synthesis. Alkenes
Alkenes
react with NBS and water in halohydrin formation reaction. Amines can be converted to diazonium salts, which are then hydrolyzed. The formation of a secondary alcohol via reduction and hydration is shown:

Reactions Deprotonation Alcohols behave as weak acids, undergoing deprotonation, but strong bases are required. The deprotonation reaction to produce an alkoxide salt is performed with a strong base such as sodium hydride or sodium metal.

2 R-OH + 2 NaH → 2 R-O−Na+ + 2 H2

2 R-OH + 2 Na → 2 R-O−Na+ + H2

Water is similar in pKa to many alcohols, so with sodium hydroxide an equilibrium exists, which usually lies to the left:

R-OH + NaOH ⇌ R-O−Na+ + H2O (equilibrium to the left)

The acidity of alcohols is strongly affected by solvation. In the gas phase, alcohols are more acidic than is water.[57] Nucleophilic substitution The OH group is not a good leaving group in nucleophilic substitution reactions, so neutral alcohols do not react in such reactions. However, if the oxygen is first protonated to give R−OH2+, the leaving group (water) is much more stable, and the nucleophilic substitution can take place. For instance, tertiary alcohols react with hydrochloric acid to produce tertiary alkyl halides, where the hydroxyl group is replaced by a chlorine atom by unimolecular nucleophilic substitution. If primary or secondary alcohols are to be reacted with hydrochloric acid, an activator such as zinc chloride is needed. In alternative fashion, the conversion may be performed directly using thionyl chloride.[1]

Alcohols may, likewise, be converted to alkyl bromides using hydrobromic acid or phosphorus tribromide, for example:

3 R-OH + PBr3 → 3 RBr + H3PO3

In the Barton-McCombie deoxygenation
Barton-McCombie deoxygenation
an alcohol is deoxygenated to an alkane with tributyltin hydride or a trimethylborane-water complex in a radical substitution reaction. Dehydration Alcohols are themselves nucleophilic, so R−OH2+ can react with ROH to produce ethers and water in a dehydration reaction, although this reaction is rarely used except in the manufacture of diethyl ether. More useful is the E1 elimination reaction of alcohols to produce alkenes. The reaction, in general, obeys Zaitsev's Rule, which states that the most stable (usually the most substituted) alkene is formed. Tertiary alcohols eliminate easily at just above room temperature, but primary alcohols require a higher temperature. This is a diagram of acid catalysed dehydration of ethanol to produce ethene:

A more controlled elimination reaction is the Chugaev elimination
Chugaev elimination
with carbon disulfide and iodomethane. Esterification To form an ester from an alcohol and a carboxylic acid the reaction, known as Fischer esterification, is usually performed at reflux with a catalyst of concentrated sulfuric acid:

R-OH + R'-COOH → R'-COOR + H2O

In order to drive the equilibrium to the right and produce a good yield of ester, water is usually removed, either by an excess of H2SO4 or by using a Dean-Stark apparatus. Esters may also be prepared by reaction of the alcohol with an acid chloride in the presence of a base such as pyridine. Other types of ester are prepared in a similar manner – for example, tosyl (tosylate) esters are made by reaction of the alcohol with p-toluenesulfonyl chloride in pyridine. Oxidation Main article: Alcohol
Alcohol
oxidation Primary alcohols (R-CH2-OH) can be oxidized either to aldehydes (R-CHO) or to carboxylic acids (R-CO2H), while the oxidation of secondary alcohols (R1R2CH-OH) normally terminates at the ketone (R1R2C=O) stage. Tertiary alcohols (R1R2R3C-OH) are resistant to oxidation. The direct oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate (R-CH(OH)2) by reaction with water before it can be further oxidized to the carboxylic acid.

Mechanism of oxidation of primary alcohols to carboxylic acids via aldehydes and aldehyde hydrates

Reagents useful for the transformation of primary alcohols to aldehydes are normally also suitable for the oxidation of secondary alcohols to ketones. These include Collins reagent
Collins reagent
and Dess-Martin periodinane. The direct oxidation of primary alcohols to carboxylic acids can be carried out using potassium permanganate or the Jones reagent. See also

Enol Ethanol
Ethanol
fuel Fatty alcohol Index of alcohol-related articles Polyol Rubbing alcohol Sugar alcohol Transesterification

Notes

^ "alcohols". IUPAC
IUPAC
Gold Book. Retrieved 16 December 2013.  ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–) "Alcohols". ^ Hitti, Philip K. (1977). History of the Arabs from the earliest times to the present (10th ed.). London: Macmillan. p. 365. ISBN 978-0-333-09871-4. The most notable medical authors who followed the epoch of the great translators were Persian in nationality but Arab in language: 'Ali al-Tabari, al-Razi, 'Ali ibn-al-'Abbas al-Majusi and ibn-Sina.  ^ Robinson, Victor (1944), The story of medicine, New York: New Home Library  ^ Porter, Dorothy (2005), Health, civilization, and the state: a history of public health from ancient to modern times, New York: Routledge (published 1999), p. 25, ISBN 0-415-20036-9 ; Reviewed in Vaughan P (2000). "Health, civilization and the state: a history of public health from ancient to modern times". Bull World Health Organ. 78 (9): 1170. PMC 2560849 .  ^ http://www.etymonline.com/index.php?allowed_in_frame=0&search=alcohol ^ Lohninger, H. "VIAS Encyclopedia: Etymology of the Word "Alcohol"". vias.org.  ^ a b "alcohol, n." OED Online. Oxford University Press, September 2016. Web. 15 November 2016. ^ Lexicon Chymicum ^ Proc. Chem. Soc. 8 July 1892, page 128 "As ol is indicative of an OH derivative, there seems no reason why the simple word acid should not connote carboxyl, and why al should not connote COH; the names ethanol ethanal and ethanoic acid or simply ethane acid would then stand for the OH, COH and COOH derivatives of ethane." ^ a b William Reusch. "Alcohols". VirtualText of Organic Chemistry. Archived from the original on 19 September 2007. Retrieved 14 September 2007.  ^ Organic chemistry IUPAC
IUPAC
nomenclature. Alcohols Rule C-201. ^ Organic Chemistry
Chemistry
Nomenclature Rule C-203: Phenols ^ "How to name organic compounds using the IUPAC
IUPAC
rules". www.chem.uiuc.edu. THE DEPARTMENT OF CHEMISTRY AT THE UNIVERSITY OF ILLINOIS. Retrieved 14 November 2016.  ^ Reusch, William. "Nomenclature of Alcohols". chemwiki.ucdavis.edu/. Retrieved 17 March 2015.  ^ "MetaCyc Compound Class: a short-chain alcohol". Retrieved 31 December 2013.  ^ "Molecule Gallery - Alcohols". Retrieved 31 December 2013.  ^ "alcohol (chemical compound)". Encyclopædia Britannica. Retrieved 31 December 2013.  ^ Zverlov, W; Berezina, O; Velikodvorskaya, GA; Schwarz, WH (August 2006). "Bacterial acetone and butanol production by industrial fermentation in the Soviet Union: use of hydrolyzed agricultural waste for biorefinery". Applied Microbiology Technology. 71 (5): 587–97. doi:10.1007/s00253-006-0445-z. PMID 16685494.  ^ "Global Status Report on Alcohol
Alcohol
2004" (PDF). Retrieved 28 November 2010.  ^ Mahon, Connie R.; Lehman, Donald C.; Manuselis, George (2014-03-25). Textbook of Diagnostic Microbiology - E-Book. Elsevier Health Sciences. ISBN 9780323292627.  ^ "Alcohols, Phenols, Thiols, and Ethers". Chemistry
Chemistry
- Louisiana Tech University. Retrieved 31 December 2013.  ^ Hans Brandenberger; Robert A. A. Maes, eds. (1997). Analytical Toxicology for Clinical, Forensic and Pharmaceutical Chemists. p. 401. ISBN 3-11-010731-7.  ^ D. W. Yandell; et al. (1888). "Amylene hydrate, a new hypnotic". The American Practitioner and News. Louisville KY: John P. Morton & Co. 5: 88–89.  ^ Carey, Francis. Organic Chemistry
Chemistry
(4 ed.). ISBN 0072905018. Retrieved 5 February 2013.  ^ Brooks PJ (1997). " DNA
DNA
damage, DNA
DNA
repair, and alcohol toxicity-a review". Alcoholism: Clinical and Experimental Research. 21 (6): 1073–1082. doi:10.1111/j.1530-0277.1997.tb04256.x.  ^ a b Fowkes, Steven (13 December 1996). "Living with alcohol". Smart Drug News. 5. Retrieved 2 March 2012.  ^ a b Melton, Lisa. "What's your poison" (PDF). New Scientist. Archived from the original on 21 February 2012. Retrieved 10 February 2007.  ^ Maxwell CR, Spangenberg RJ, Hoek JB, Silberstein SD, Oshinsky ML (2010). Skoulakis, Efthimios M. C., ed. "Acetate causes alcohol hangover headache in rats". PLoS ONE. 5 (12): e15963. Bibcode:2010PLoSO...515963M. doi:10.1371/journal.pone.0015963. PMC 3013144 . PMID 21209842.  ^ Ramachandra Murty, B (1 October 2004). "The Biochemistry of Alcohol Toxicity" (PDF). Archived (PDF) from the original on 20 August 2012. Retrieved 21 February 2012.  ^ Cassarett, Lewis; Doull, John (1986). Toxicology: The Basic Science of Poisons (3rd ed.). pp. 648–653.  ^ Ozaras R, Tahan V, Aydin S, Uzun H, Kaya S, Senturk H (2003). "N-acetylcysteine attenuates alcohol-induced oxidative stress in the rat". World Journal of Gastroenterology. 9 (1): 125–128. doi:10.3748/wjg.9.125. PMID 12508366.  ^ Sprince, H; Parker, CM; Smith, GG; Gonzales, LJ (1974). "Protection against acetaldehyde toxicity in the rat by l-cysteine, thiamin and l-2-Methylthiazolidine-4-carboxylic acid". Agents and Actions. 4 (2): 125–130. doi:10.1007/BF01966822. PMID 4842541.  ^ Bagnardi V, Rota M, Botteri E, Tramacere I, Islami F, Fedirko V, Scotti L, Jenab M, Turati F, Pasquali E, Pelucchi C, Galeone C, Bellocco R, Negri E, Corrao G, Boffetta P, La Vecchia C (2015). " Alcohol
Alcohol
consumption and site-specific cancer risk: a comprehensive dose-response meta-analysis". British Journal of Cancer. 112 (3): 580–93. doi:10.1038/bjc.2014.579. PMC 4453639 . PMID 25422909.  ^ http://www.otago.ac.nz/news/news/otago617874.html[full citation needed] ^ Collins AS, Sumner SC, Borghoff SJ, Medinsky MA (1999). "A physiological model for tert-amyl methyl ether and tert-amyl alcohol: Hypothesis testing of model structures". Toxicological Sciences. 49 (1): 15–28. doi:10.1093/toxsci/49.1.15. PMID 10367338.  ^ "oxidation of alcohols". chemguide.co.uk.  ^ Hirsh HL, Orsinger WH (1952). "Methylparafynol--a new type hypnotic. Preliminary report on its therapeutic efficacy and toxicity". American practitioner and digest of treatment. 3 (1): 23–26. PMID 14903452.  ^ Adriani, John (1962). The Chemistry
Chemistry
and Physics of Anesthesia. Second Edition. Illinois: Thomas Books. pp. 273–274. ISBN 9780398000110.  ^ a b Schep LJ, Slaughter RJ, Vale JA, Beasley DM (30 September 2009). "A seaman with blindness and confusion". BMJ. 339: b3929. doi:10.1136/bmj.b3929. PMID 19793790.  ^ Brent J (May 2009). "Fomepizole for ethylene glycol and methanol poisoning". N. Engl. J. Med. 360 (21): 2216–23. doi:10.1056/NEJMct0806112. ISSN 0028-4793. PMID 19458366.  ^ Schep LJ, Slaughter RJ, Temple WA, Beasley DM (July 2009). " Diethylene glycol
Diethylene glycol
poisoning". Clin Toxicol. 47 (6): 525–35. doi:10.1080/15563650903086444. ISSN 1556-3650. PMID 19586352.  ^ "ChemIDplus Advanced - Chemical information with searchable synonyms, structures, and formulas". nih.gov.  ^ Wiernikowski A, Piekoszewski W, Krzyzanowska-Kierepka E, Gomułka E (1997). "Acute oral poisoning with isopropyl alcohol in alcoholics". Przeglad lekarski. 54 (6): 459–63. PMID 9333902.  ^ Mańkowski W, Klimaszyk D, Krupiński B (2000). "How to differentiate acute isopropanol poisoning from ethanol intoxication? – a case report". Przeglad lekarski. 57 (10): 588–90. PMID 11199895.  ^ Zimmerman HE, Burkhart KK, Donovan JW (1999). " Ethylene glycol
Ethylene glycol
and methanol poisoning: diagnosis and treatment". Journal of Emergency Nursing. 25 (2): 116–20. doi:10.1016/S0099-1767(99)70156-X. PMID 10097201.  ^ Lobert S (2000). "Ethanol, isopropanol, methanol, and ethylene glycol poisoning". Critical care nurse. 20 (6): 41–7. PMID 11878258.  ^ Majerza I, Natkaniec I (2006). "Experimental and theoretical IR, R, and INS spectra of 2,2,4,4-tetramethyl-3-t-butyl-pentane-3-ol". Journal of Molecular Structure. 788 (1–3): 93–101. Bibcode:2006JMoSt.788...93M. doi:10.1016/j.molstruc.2005.11.022.  ^ Sfetcu, Nicolae (2014). Health & Drugs Disease, Prescription & Medication. North Carolina: Lulu.com. ISBN 9781312039995.  ^ Charnley, S. B.; Kress, M. E.; Tielens, A. G. G. M.; Millar, T. J. (1995). "Interstellar Alcohols". Astrophysical Journal. 448: 232. Bibcode:1995ApJ...448..232C. doi:10.1086/175955.  ^ Giant cloud of space alcohol found labnews.co.uk/ ^ a b Jürgen Falbe, Helmut Bahrmann, Wolfgang Lipps, Dieter Mayer "Alcohols, Aliphatic" in Ullmann's Encyclopedia of Chemical Technology Wiley-VCH Verlag; Weinheim, 2002. doi:10.1002/14356007.a01_279 ^ Lodgsdon J.E. (1994). "Ethanol". In Kroschwitz J.I. Encyclopedia of Chemical Technology. 9 (4th ed.). New York: John Wiley & Sons. p. 820. ISBN 0-471-52677-0.  ^ P. Geertinger MD; J. Bodenhoff; K. Helweg-Larsen; A. Lund (1 September 1982). "Endogenous alcohol production by intestinal fermentation in sudden infant death". Zeitschrift für Rechtsmedizin. Springer-Verlag. 89 (3): 167–172. doi:10.1007/BF01873798.  ^ Logan BK, Jones AW (July 2000). "Endogenous ethanol 'auto-brewery syndrome' as a drunk-driving defence challenge". Medicine, science, and the law. 40 (3): 206–15. PMID 10976182.  ^ Cecil Adams (20 October 2006). "Designated drunk: Can you get intoxicated without actually drinking alcohol?". The Straight Dope. Retrieved 27 February 2013.  ^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 0-471-72091-7 

References

Metcalf, Allan A. (1999). The World in So Many Words. Houghton Mifflin. ISBN 0-395-95920-9. 

External links

Find more aboutAlcoholat's sister projects

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Alcohol
Alcohol
(Ethanol) at The Periodic Table of Videos
The Periodic Table of Videos
(University of Nottingham)

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Alcohols

Straight-chain primary alcohols (1°)

Methanol
Methanol
(C 1) Ethanol
Ethanol
(C 2) 1- Propanol (C 3) n-Butanol (C 4) 1-Pentanol
1-Pentanol
(C 5) 1-Hexanol
1-Hexanol
(C 6) 1-Heptanol
1-Heptanol
(C 7) 1-Octanol
1-Octanol
(C 8) 1-Nonanol
1-Nonanol
(C 9) 1-Decanol
1-Decanol
(C 10) Undecanol
Undecanol
(C 11) Dodecanol
Dodecanol
(C 12) Tridecan-1-ol (C 13) 1-Tetradecanol
1-Tetradecanol
(C 14) Pentadecan-1-ol (C 15) Cetyl alcohol
Cetyl alcohol
(C 16) Heptadecan-1-ol (C 17) Stearyl alcohol
Stearyl alcohol
(C 18) Nonadecan-1-ol (C 19) Arachidyl alcohol
Arachidyl alcohol
(C 20) Heneicosan-1-ol (C 21) Docosanol
Docosanol
(C 22) Tricosan-1-ol (C 23) 1-Tetracosanol
1-Tetracosanol
(C 24) Pentacosan-1-ol (C 25) 1-Hexacosanol
1-Hexacosanol
(C 26) 1-Heptacosanol
1-Heptacosanol
(C 27) 1-Octacosanol
1-Octacosanol
(C 28) 1-Nonacosanol
1-Nonacosanol
(C 29) Triacontanol
Triacontanol
(C 30)

Other primary alcohols

Isobutanol
Isobutanol
(C 4) Isoamyl alcohol
Isoamyl alcohol
(C 5) 2-Methyl-1-butanol
2-Methyl-1-butanol
(C 5) Phenethyl alcohol
Phenethyl alcohol
(C 8) Tryptophol
Tryptophol
(C 10)

Secondary alcohols (2°)

Isopropanol (C 3) 2-Butanol
2-Butanol
(C 4) 2-Pentanol
2-Pentanol
(C 5) 2-Hexanol
2-Hexanol
(C 6) 2-Heptanol
2-Heptanol
(C 7) Cyclohexanol
Cyclohexanol
(C 6) 2-Octanol
2-Octanol
(C 8)

Tertiary alcohols (3°)

tert-Butyl alcohol (C 4) tert- Amyl alcohol
Amyl alcohol
(C 5) 2-Methyl-2-pentanol
2-Methyl-2-pentanol
(C 6) 2-Methylhexan-2-ol (C 7) 2-Methylheptan-2-ol (C 8) 3-Methyl-3-pentanol
3-Methyl-3-pentanol
(C 6) 3-Methyloctan-3-ol (C 9)

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Alcohol-related topics by country

Countries

Afghanistan Australia Bangladesh Indonesia Iran Malaysia New Zealand Sudan

Cultures

Australia Korea

Types

Canada China Sweden

Laws

Australia Canada Iceland India

Prohibition

Germany Russia

Consumption

United Kingdom United States

Youth consumption

Commons Category

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Functional groups

Only carbon, hydrogen and oxygen

Hydrocarbons

Allene Alkene
Alkene
(Allyl, Vinyl) Alkyl
Alkyl
(Methyl, Ethyl, Propyl, Butyl, Pentyl) Alkyne Benzyl Carbene Cumulene Methylene bridge Methylene group Methine Phenyl

Other

Acetoxy Acetyl Acryloyl Acyl Aldehyde Alkoxy (Methoxy) Benzoyl Carbonyl Carboxyl Dioxirane Epoxide Ester Ether Ethylenedioxy Hydroxy Ketone Methylenedioxy Peroxide
Peroxide
(Organic) Ynone

Only one element apart from C, H, O

Nitrogen

Amine Azo compound Cyanate Hydrazone Imide Imine Isocyanate Isonitrile Nitrene Nitrile Nitro compound Nitroso
Nitroso
compound Organic amide Oxime

Phosphorus

Phosphonate Phosphonous

Sulfur

Disulfide Sulfone Sulfonic acid Sulfoxide Thial Thioester Thioether Thioketone Thiol

Selenium

Selenol Selenonic acid Seleninic acid Selenenic acid

Tellurium

Tellurol

Other

Isothiocyanate Phosphoramide Sulfenyl chloride Sulfonamide Thiocyanate

See also chemical classification, chemical nomenclature (inorganic, organic)

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Bioenergy

Biofuels

Alcohol Algae fuel Bagasse Babassu oil Biobutanol Biodiesel Biogas Biogasoline Corn stover Ethanol

cellulosic mixtures

Methanol Stover

Corn stover

Straw Cooking oil

Vegetable oil

Water hyacinth Wood gas

Energy from foodstock

Barley Cassava Coconut oil Grape Hemp Maize Oat Palm oil Potato Rapeseed Rice Sorghum bicolor Soybean Sugarcane Sugar beet Sunflower Wheat Yam Camelina
Camelina
sativa

Non-food energy crops

Arundo Big bluestem Camelina Chinese tallow Duckweed Jatropha curcas Millettia pinnata Miscanthus giganteus Switchgrass Salicornia Wood fuel

Technology

BECCS Bioconversion Biomass heating systems Biorefinery Fischer–Tropsch process Industrial biotechnology Pellets

mill stove

Thermal depolymerization

Concepts

Cellulosic ethanol
Cellulosic ethanol
commercialization Energy content of biofuel Energy crop Energy forestry EROEI Food vs. fuel Issues Sustainable biofuel

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Alternative fuel vehicles

Compressed-air engine

Compressed air car Compressed-air vehicle Tesla turbine

Electric motor

Battery-electric locomotive Battery electric vehicle Cater MetroTrolley Electric aircraft Electric bicycle Pedelec Electric boat Electric bus

Battery electric bus

Electric car Electric truck Electric platform truck Electric vehicle Electric motorcycles and scooters Electric kick scooter Gyro flywheel locomotive Hybrid electric vehicle Hybrid train Motorized bicycle Neighborhood Electric Vehicle Plug-in electric vehicle Plug-in hybrid
Plug-in hybrid
electric vehicle Solar vehicle

Solar car Solar bus

Biofuel
Biofuel
ICE

Alcohol
Alcohol
fuel Biodiesel Biogas Butanol fuel Common ethanol fuel mixtures E85 Ethanol
Ethanol
fuel Flexible-fuel vehicle Methanol
Methanol
economy Methanol
Methanol
fuel Wood gas

Hydrogen

Fuel cell vehicle Hydrogen
Hydrogen
economy Hydrogen
Hydrogen
vehicle Hydrogen
Hydrogen
internal combustion engine vehicle

Others

Autogas Hybrid electric vehicle Liquid nitrogen vehicle Natural gas vehicle Propane Steam car

Multiple-fuel

Bi-fuel vehicle Flexible-fuel vehicle Hybrid vehicle Multifuel Plug-in hybrid

Documentaries

Who Killed the Electric Car? What Is the Electric Car? Revenge of the Electric Car

See also

Wind-powered vehicle Zero-emissions vehicle

Authority control

GND: 41418

.