Vous êtes sur la page 1sur 14

1/15/2018 Alcohol - Wikipedia

Alcohol
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 chemical name of all substances where the
hydroxyl group is the functional group with the highest priority; in substances where a
Ball-and-stick model of the
higher priority group is present the prefix hydroxy­ will appear in the International
hydroxyl (-OH) functional
Union of Pure and Applied Chemistry (IUPAC) name. The suffix ­ol in non-systematic group in an alcohol molecule
names (such as paracetamol or cholesterol) also typically indicates that the substance (R3COH). The three "R's"
includes a hydroxyl functional group and, so, can be termed an alcohol. But many stand for carbon substituents
substances, particularly sugars (examples glucose and sucrose) contain hydroxyl or hydrogen atoms.[1]
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
History The hydroxyl (-OH) functional
Nomenclature group with bond angle
Etymology
Systematic names
Common names
Applications
Toxicity
Treatment
Physical and chemical properties
Occurrence in nature
Production
Ziegler and oxo processes
Hydration reactions
Biological routes
Reactions
Deprotonation
Nucleophilic substitution
Dehydration
Esterification
Oxidation
See also
Notes
References

https://en.wikipedia.org/wiki/Alcohol 1/14
1/15/2018 Alcohol - Wikipedia

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: ‫ا‬, translit. al­kuḥl), a powder used as an eyeliner.[6] Al- is the Arabic
definite article, equivalent to the in English. Alcohol was originally used for the very fine powder produced by the
sublimation of the natural mineral stibnite to form antimony trisulfide Sb2S3, 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
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, based on combining the word ethane with "ol" the last part of "alcohol".[10]

Systematic names
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 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 CH3CH2CH2OH, propan-2-ol for CH3CH(OH)CH3. 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 (CH3C(O)CH2OH).[12]

https://en.wikipedia.org/wiki/Alcohol 2/14
1/15/2018 Alcohol - Wikipedia

Some examples of simple alcohols and how to name them

CH3–CH2–CH2–OH

n-propyl alcohol, isopropyl alcohol, isobutyl alcohol, tert-amyl alcohol,


propan-1-ol, or propan-2-ol, or cyclohexanol 2-methylpropan-1-ol, or 2-methylbutan-2-ol, or
1-propanol 2-propanol 2-methyl-1-propanol 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 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 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.

https://en.wikipedia.org/wiki/Alcohol 3/14
1/15/2018 Alcohol - Wikipedia

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

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

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 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.

https://en.wikipedia.org/wiki/Alcohol 4/14
1/15/2018 Alcohol - Wikipedia

Higher alcohols
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 can feed on cellulose to produce
butanol on an industrial scale.[19]

Applications
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 alcohol­free is often used to describe a product that
does not contain alcohol.

Alcoholic beverages, typically containing 3–40% alcohol by volume, have


Total recorded alcohol per capita
been produced and consumed by humans since pre-historic times. Natural
fermentation also produces trace amounts of other alcohols such as 2-methyl- consumption (15+), in litres of
2-butanol and γ-hydroxybutyric acid (GHB), which have psychoactive effects pure ethanol[20]
similar to alcohol when used as a drug.
Antifreeze commonly includes a 50% v/v (by volume) solution of ethylene
glycol in water.
Medical: 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 based gels have become common as hand sanitizers.
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.
Preservative: Alcohol is often used as a preservative for biological specimens in the fields of science and medicine.
Solvent: 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 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.

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

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. 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.

https://en.wikipedia.org/wiki/Alcohol 5/14
1/15/2018 Alcohol - Wikipedia

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 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 (wood alcohol), for
instance, is oxidized to formaldehyde and then to the poisonous formic acid in Ball-and-stick model of tert-Amyl
the liver by alcohol dehydrogenase and formaldehyde dehydrogenase enzymes, alcohol, which is 20 times more
intoxicating than ethanol and like all
respectively; accumulation of formic acid can lead to blindness or death.[40]
tertiary alcohols, cannot be
Likewise, poisoning due to other alcohols such as ethylene glycol or diethylene
metabolised to toxic
glycol are due to their metabolites, which are also produced by alcohol aldehydes.[23][24][25]
dehydrogenase.[41][42]

Methanol itself, while poisonous (LD50 5628 mg/kg, oral, rat[43]), has a much
weaker sedative effect than ethanol.

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][45]

Treatment
Most significant of the possible long-
An effective treatment to prevent toxicity after methanol or ethylene glycol
term effects of ethanol. In addition,
ingestion is to administer ethanol. Alcohol dehydrogenase has a higher affinity in pregnant women it may cause
for ethanol, thus preventing methanol from binding and acting as a substrate. fetal alcohol syndrome.
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 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.

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.

https://en.wikipedia.org/wiki/Alcohol 6/14
1/15/2018 Alcohol - Wikipedia

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 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 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 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 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.

https://en.wikipedia.org/wiki/Alcohol 7/14
1/15/2018 Alcohol - Wikipedia

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 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 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 is the asymmetric reduction of β-keto-esters.

Hydrolysis
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 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
https://en.wikipedia.org/wiki/Alcohol 8/14
1/15/2018 Alcohol - Wikipedia

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 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:

https://en.wikipedia.org/wiki/Alcohol 9/14
1/15/2018 Alcohol - Wikipedia

A more controlled elimination reaction is the 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
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 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 Rubbing alcohol
Ethanol fuel Sugar alcohol
Fatty alcohol Transesterification
Polyol

https://en.wikipedia.org/wiki/Alcohol 10/14
1/15/2018 Alcohol - Wikipedia

Notes
1. "alcohols" (http://goldbook.iupac.org/A00204.html). IUPAC Gold Book. Retrieved 16 December 2013.
2. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version:  (2006–)
"Alcohols (http://goldbook.iupac.org/A00204.html)".
3. 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."
4. Robinson, Victor (1944), The story of medicine, New York: New Home Library
5. 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" (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC
2560849). Bull World Health Organ. 78 (9): 1170. PMC 2560849 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2560
849)  .
6. http://www.etymonline.com/index.php?allowed_in_frame=0&search=alcohol
7. Lohninger, H. "VIAS Encyclopedia: Etymology of the Word "Alcohol" " (http://www.vias.org/encyclopedia/Alcohol_004.
html). vias.org.
8. "alcohol, n." OED Online. Oxford University Press, September 2016. Web. 15 November 2016.
9. Lexicon Chymicum (https://books.google.com/books/about/Lexicon_Chymicum.html?id=d645AAAAcAAJ)
10. 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."
11. William Reusch. "Alcohols" (https://web.archive.org/web/20070919162404/http://www.cem.msu.edu/~reusch/VirtualTe
xt/alcohol1.htm#alcnom). VirtualText of Organic Chemistry. Archived from the original (http://www.cem.msu.edu/~reus
ch/VirtualText/alcohol1.htm#alcnom) on 19 September 2007. Retrieved 14 September 2007.
12. Organic chemistry IUPAC nomenclature. Alcohols Rule C-201 (http://www.acdlabs.com/iupac/nomenclature/79/r79_20
2.htm).
13. Organic Chemistry Nomenclature Rule C-203: Phenols (http://www.acdlabs.com/iupac/nomenclature/79/r79_212.htm)
14. "How to name organic compounds using the IUPAC rules" (http://www.chem.uiuc.edu/GenChemReferences/nomencla
ture_rules.html). www.chem.uiuc.edu. THE DEPARTMENT OF CHEMISTRY AT THE UNIVERSITY OF ILLINOIS.
Retrieved 14 November 2016.
15. Reusch, William. "Nomenclature of Alcohols" (http://chemwiki.ucdavis.edu/Organic_Chemistry/Alcohols/Nomenclature
_of_Alcohols). chemwiki.ucdavis.edu/. Retrieved 17 March 2015.
16. "MetaCyc Compound Class: a short-chain alcohol" (http://www.ecocyc.org/META/NEW-IMAGE?object=Short-Chain-Al
cohols). Retrieved 31 December 2013.
17. "Molecule Gallery - Alcohols"
(http://www.angelo.edu/faculty/kboudrea/molecule_gallery/05_alcohols/00_alcohols.htm). Retrieved 31 December
2013.
18. "alcohol (chemical compound)" (http://www.britannica.com/EBchecked/topic/13366/alcohol). Encyclopædia Britannica.
Retrieved 31 December 2013.
19. 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 (https://doi.org/10.1007%2Fs00253-006-04
45-z). PMID 16685494 (https://www.ncbi.nlm.nih.gov/pubmed/16685494).
20. "Global Status Report on Alcohol 2004" (http://www.who.int/entity/substance_abuse/publications/global_status_report
_2004_overview.pdf) (PDF). Retrieved 28 November 2010.

https://en.wikipedia.org/wiki/Alcohol 11/14
1/15/2018 Alcohol - Wikipedia

21. Mahon, Connie R.; Lehman, Donald C.; Manuselis, George (2014-03-25). Textbook of Diagnostic Microbiology - E-
Book (https://books.google.com/books?id=VloMBAAAQBAJ&pg=PA65&dq=Ethanol+can+be+used+as+an+antiseptic
+to+disinfect+the+skin+before+injections+are+given,+often+along+with+iodine&hl=en&sa=X&ved=0ahUKEwiG_4ntnI
LXAhWhjFQKHYVaDMsQ6AEIMDAC#v=onepage&q=Ethanol%20can%20be%20used%20as%20an%20antiseptic%2
0to%20disinfect%20the%20skin%20before%20injections%20are%20given,%20often%20along%20with%20iodine&f=
false). Elsevier Health Sciences. ISBN 9780323292627.
22. "Alcohols, Phenols, Thiols, and Ethers" (http://www.chem.latech.edu/~deddy/chem121/Alcohols.htm). Chemistry -
Louisiana Tech University. Retrieved 31 December 2013.
23. Hans Brandenberger; Robert A. A. Maes, eds. (1997). Analytical Toxicology for Clinical, Forensic and Pharmaceutical
Chemists (https://books.google.com/books?id=ZhYtynyC4kAC&pg=PA401#v=onepage&q&f=false). p. 401. ISBN 3-
11-010731-7.
24. D. W. Yandell; et al. (1888). "Amylene hydrate, a new hypnotic" (https://books.google.com/books?id=Ra5YAAAAMAAJ
&pg=PA88#v=onepage). The American Practitioner and News. Louisville KY: John P. Morton & Co. 5: 88–89.
25. Carey, Francis. Organic Chemistry (http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch15oxidationalcohols.
html) (4 ed.). ISBN 0072905018. Retrieved 5 February 2013.
26. Brooks PJ (1997). "DNA damage, 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 (https://doi.org/10.1111%2Fj.1530-0277.1997.t
b04256.x).
27. Fowkes, Steven (13 December 1996). "Living with alcohol" (http://www.ceri.com/alcohol.htm). Smart Drug News. 5.
Retrieved 2 March 2012.
28. Melton, Lisa. "What's your poison" (http://www.cheerzhangover.com/Cheerz_ATH-NewScience.pdf) (PDF). New
Scientist. Archived from the original (https://www.newscientist.com/article/mg19325901.700-whats-your-poison.html)
on 21 February 2012. Retrieved 10 February 2007.
29. Maxwell CR, Spangenberg RJ, Hoek JB, Silberstein SD, Oshinsky ML (2010). Skoulakis, Efthimios M. C., ed.
"Acetate causes alcohol hangover headache in rats" (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3013144). PLoS
ONE. 5 (12): e15963. Bibcode:2010PLoSO...515963M (http://adsabs.harvard.edu/abs/2010PLoSO...515963M).
doi:10.1371/journal.pone.0015963 (https://doi.org/10.1371%2Fjournal.pone.0015963). PMC 3013144 (https://www.nc
bi.nlm.nih.gov/pmc/articles/PMC3013144)  . PMID 21209842 (https://www.ncbi.nlm.nih.gov/pubmed/21209842).
30. Ramachandra Murty, B (1 October 2004). "The Biochemistry of Alcohol Toxicity" (http://www.ias.ac.in/resonance/Oct2
004/pdf/Oct2004p41-47.pdf) (PDF). Archived (https://www.webcitation.org/6A3YbjpaK?url=http://www.ias.ac.in/resona
nce/Oct2004/pdf/Oct2004p41-47.pdf) (PDF) from the original on 20 August 2012. Retrieved 21 February 2012.
31. Cassarett, Lewis; Doull, John (1986). Toxicology: The Basic Science of Poisons (3rd ed.). pp. 648–653.
32. 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 (https://doi.org/1
0.3748%2Fwjg.9.125). PMID 12508366 (https://www.ncbi.nlm.nih.gov/pubmed/12508366).
33. 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 (https://doi.org/10.1007%2FBF01966822). PMID 4842541 (https://www.ncbi.nlm.nih.gov/pu
bmed/4842541).
34. 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 consumption and site-specific
cancer risk: a comprehensive dose-response meta-analysis" (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC445363
9). British Journal of Cancer. 112 (3): 580–93. doi:10.1038/bjc.2014.579 (https://doi.org/10.1038%2Fbjc.2014.579).
PMC 4453639 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4453639)  . PMID 25422909 (https://www.ncbi.nlm.nih.
gov/pubmed/25422909).
35. http://www.otago.ac.nz/news/news/otago617874.html
36. 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 (https://doi.org/10.1093%2Ftoxsci%2F49.1.15). PMID 10367338 (https://www.ncbi.nlm.nih.
gov/pubmed/10367338).

https://en.wikipedia.org/wiki/Alcohol 12/14
1/15/2018 Alcohol - Wikipedia

37. "oxidation of alcohols" (http://www.chemguide.co.uk/organicprops/alcohols/oxidation.html). chemguide.co.uk.


38. 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 (https://www.ncbi.nlm.nih.g
ov/pubmed/14903452).
39. Adriani, John (1962). The Chemistry and Physics of Anesthesia. Second Edition. Illinois: Thomas Books. pp. 273–
274. ISBN 9780398000110.
40. Schep LJ, Slaughter RJ, Vale JA, Beasley DM (30 September 2009). "A seaman with blindness and confusion" (http://
www.bmj.com/cgi/content/full/339/sep30_1/b3929). BMJ. 339: b3929. doi:10.1136/bmj.b3929 (https://doi.org/10.113
6%2Fbmj.b3929). PMID 19793790 (https://www.ncbi.nlm.nih.gov/pubmed/19793790).
41. Brent J (May 2009). "Fomepizole for ethylene glycol and methanol poisoning". N. Engl. J. Med. 360 (21): 2216–23.
doi:10.1056/NEJMct0806112 (https://doi.org/10.1056%2FNEJMct0806112). ISSN 0028-4793 (https://www.worldcat.or
g/issn/0028-4793). PMID 19458366 (https://www.ncbi.nlm.nih.gov/pubmed/19458366).
42. Schep LJ, Slaughter RJ, Temple WA, Beasley DM (July 2009). "Diethylene glycol poisoning". Clin Toxicol. 47 (6):
525–35. doi:10.1080/15563650903086444 (https://doi.org/10.1080%2F15563650903086444). ISSN 1556-3650 (http
s://www.worldcat.org/issn/1556-3650). PMID 19586352 (https://www.ncbi.nlm.nih.gov/pubmed/19586352).
43. "ChemIDplus Advanced - Chemical information with searchable synonyms, structures, and formulas" (http://chem.sis.
nlm.nih.gov/chemidplus/). nih.gov.
44. 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 (https://www.ncbi.nlm.nih.gov/pubmed/93339
02).
45. 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 (https://www.ncbi.nlm.nih.gov/pub
med/11199895).
46. Zimmerman HE, Burkhart KK, Donovan JW (1999). "Ethylene glycol and methanol poisoning: diagnosis and
treatment". Journal of Emergency Nursing. 25 (2): 116–20. doi:10.1016/S0099-1767(99)70156-X (https://doi.org/10.10
16%2FS0099-1767%2899%2970156-X). PMID 10097201 (https://www.ncbi.nlm.nih.gov/pubmed/10097201).
47. Lobert S (2000). "Ethanol, isopropanol, methanol, and ethylene glycol poisoning". Critical care nurse. 20 (6): 41–7.
PMID 11878258 (https://www.ncbi.nlm.nih.gov/pubmed/11878258).
48. 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 (http://adsabs.harva
rd.edu/abs/2006JMoSt.788...93M). doi:10.1016/j.molstruc.2005.11.022 (https://doi.org/10.1016%2Fj.molstruc.2005.11.
022).
49. Sfetcu, Nicolae (2014). Health & Drugs Disease, Prescription & Medication. North Carolina: Lulu.com.
ISBN 9781312039995.
50. Charnley, S. B.; Kress, M. E.; Tielens, A. G. G. M.; Millar, T. J. (1995). "Interstellar Alcohols" (http://hdl.handle.net/206
0/19970007168). Astrophysical Journal. 448: 232. Bibcode:1995ApJ...448..232C (http://adsabs.harvard.edu/abs/1995
ApJ...448..232C). doi:10.1086/175955 (https://doi.org/10.1086%2F175955).
51. Giant cloud of space alcohol found (http://www.labnews.co.uk/news/giant-cloud-of-space-alcohol-found-04-04-2006)
labnews.co.uk/
52. 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 (https://doi.org/10.1002%2
F14356007.a01_279)
53. 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.
54. 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 (https://doi.org/10.1007%2FBF01873798).
55. 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 (https://www.ncbi.nlm.nih.gov/pubmed/10
976182).
https://en.wikipedia.org/wiki/Alcohol 13/14
1/15/2018 Alcohol - Wikipedia

56. Cecil Adams (20 October 2006). "Designated drunk: Can you get intoxicated without actually drinking alcohol?" (http://
www.straightdope.com/columns/read/2677/designated-drunk). The Straight Dope. Retrieved 27 February 2013.
57. Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (https://
books.google.com/books?id=JDR-nZpojeEC&printsec=frontcover) (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
Alcohol (Ethanol) (http://www.periodicvideos.com/videos/mv_alcohol.htm) at The Periodic Table of Videos (University
of Nottingham)

Retrieved from "https://en.wikipedia.org/w/index.php?title=Alcohol&oldid=820172723"

This page was last edited on 13 January 2018, at 13:04.

Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may apply. By using this
site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation,
Inc., a non-profit organization.

https://en.wikipedia.org/wiki/Alcohol 14/14