Alcohol: This Article Is About The Class of Chemical Compounds. For Found In, See - For Other Uses, See
Alcohol: This Article Is About The Class of Chemical Compounds. For Found In, See - For Other Uses, See
Ball-and-stick model of an alcohol molecule (R3COH). The red and white balls represent the hydroxyl
group (-OH). The three "R's" stand for carbon substituents or hydrogen atoms.[1]
The bond angle between a hydroxyl group (-OH) and a chain of carbon atoms (R)
1History
2Nomenclature
2.1Etymology
2.2Systematic names
2.3Common names
3Applications
4Toxicity
5Physical properties
6Occurrence in nature
7Production
8Reactions
8.1Deprotonation
8.2Nucleophilic substitution
8.3Dehydration
8.4Protonolysis
8.5Esterification
8.6Oxidation
9See also
10Notes
11References
12External links
History
Alcohol distillation possibly originated in the Indus valley civilization as early
as 2000 BCE. The people of India used an alcoholic drink called Sura made
from fermented rice, barley, jaggery, and flowers of the madhyaka tree.
[3] Alcohol distillation was known to Islamic chemists as early as the eighth
century.[4][5]
The Arab chemist al-Kindi unambiguously described the distillation of wine in
a treatise titled as "The Book of the chemistry of Perfume and Distillations". [6]
[7][8]
Nomenclature
Etymology
The word "alcohol" is from the Arabic kohl (Arabic: الكحل, romanized: al-kuḥl), a
powder used as an eyeliner.[11] 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 Sb
2S
3.It was considered to be the essence or "spirit" of this mineral. 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.[12]
Bartholomew Traheron, in his 1543 translation of John of Vigo, introduces the
word as a term used by "barbarous" authors for "fine powder." Vigo wrote:
"the barbarous auctours use alcohol, or (as I fynde it sometymes wryten)
alcofoll, for moost fine poudre."[13]
The 1657 Lexicon Chymicum, by William Johnson glosses the word as
"antimonium sive stibium."[14] 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. [13]
The term ethanol was invented in 1892, blending "ethane" with the "-ol"
ending of "alcohol", which was generalized as a libfix.[15]
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 naming simple alcohols, the name of the alkane chain loses the
terminal e and adds the suffix -ol, e.g., as in "ethanol" from the alkane chain
name "ethane".[16] 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,[16] e.g., as in 1-hydroxy-2-
propanone (CH
3C(O)CH
2OH).[17]
CH3–CH2–CH2–
OH
tert-amyl
isobutyl
n-propyl isopropyl alcohol,
alcohol,
alcohol, alcohol, 2-
2-methylpropan-
propan-1-ol, propan-2- cyclohexanol methylbutan-
1-ol, or
or ol, or 2-ol, or
2-methyl-1-
1-propanol 2-propanol 2-methyl-2-
propanol
butanol
A primary A secondary A secondary A primary A tertiary
alcohol alcohol alcohol alcohol alcohol
In cases where the OH functional group is bonded to an sp carbon on
2