lcohol

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This article is about the class of chemical compounds. For ethanol found in alcoholic drinks, see Alcohol
(drug). For other uses, see Alcohol (disambiguation).

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)

In chemistry, alcohol is an organic compound that carries at least one hydroxyl functional group (−OH)
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 drinks. An
important class of alcohols, of which methanol and ethanol are the simplest members, includes all
compounds for which the general formula is CnH2n+1OH. Simple monoalcohols that are the subject of
this article include primary (RCH2OH), secondary (R2CHOH) and tertiary (R3COH) alcohols.

The suffix -ol appears in the IUPAC chemical name of all substances where the hydroxyl group is the
functional group with the highest priority. When a higher priority group is present in the compound, the
prefix hydroxy- is used in its IUPAC name. The suffix -ol in non-IUPAC names (such as paracetamol or
cholesterol) also typically indicates that the substance is an alcohol. However, many substances that
contain hydroxyl functional groups (particularly sugars, such as glucose and sucrose) have names which
include neither the suffix -ol, nor the prefix hydroxy-.

Contents

1 History

2 Nomenclature

2.1 Etymology

2.2 Systematic names

3 Applications

4 Toxicity

5 Physical properties

6 Occurrence in nature

7 Production

7.1 Ziegler and oxo processes

7.2 Hydration reactions

7.3 Biological routes

8 Reactions

8.1 Deprotonation

8.2 Nucleophilic substitution

8.3 Dehydration

8.4 Protonolysis

8.5 Esterification

8.6 Oxidation

9 See also

10 Notes

11 References

12 External links

History

The inflammable nature of the exhalations of wine was already known to ancient natural philosophers
such as Aristotle (384–322 BCE), Theophrastus (c. 371–287 BCE), and Pliny the Elder (23/24–79 CE).[3]
However, this did not immediately lead to the isolation of alcohol, even despite the development of
more advanced distillation techniques in second- and third-century Roman Egypt.[4] An important
recognition, first found in one of the writings attributed to Jābir ibn Ḥayyān (ninth century CE), was that
by adding salt to boiling wine, which increases the wine's relative volatility, the flammability of the
resulting vapors may be enhanced.[5] The distillation of wine is attested in Arabic works attributed to al-
Kindī (c. 801–873 CE) and to al-Fārābī (c. 872–950), and in the 28th book of al-Zahrāwī's (Latin: Abulcasis,
936–1013) Kitāb al-Taṣrīf (later translated into Latin as Liber servatoris).[6] In the twelfth century,
recipes for the production of aqua ardens ("burning water", i.e., alcohol) by distilling wine with salt
started to appear in a number of Latin works, and by the end of the thirteenth century it had become a
widely known substance among Western European chemists.[7] Its medicinal properties were studied
by Arnald of Villanova (1240–1311 CE) and John of Rupescissa (c. 1310–1366), the latter of whom
regarded it as a life-preserving substance able to prevent all diseases (the aqua vitae or "water of life",
also called by John the quintessence of wine).[8]

Nomenclature

Etymology

The word "alcohol" is from the Arabic kohl (Arabic: ‫الكحل‬, romanized: al-kuḥl), a powder used as an
eyeliner.[9] 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.[10]

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."[11]

The 1657 Lexicon Chymicum, by William Johnson glosses the word as "antimonium sive stibium."[12] 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.[11]

The term ethanol was invented in 1892, blending "ethane" with the "-ol" ending of "alcohol", which was
generalized as a libfix.[13]
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".[14] 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,[14] e.g., as in 1-hydroxy-2-propanone (CH

3C(O)CH

2OH).[15]

Some examples of simple alcohols and how to name them

CH3–CH2–CH2–OH Propan-2-ol displayed.svg Cyclohexanol displayed.svg 2-

Propan-1-ol.svg 2-Propanol.svg Cyclohexanol acsv.svg Isobutanol.svg 2-Methyl-2-butanol FormulaV1-

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-methyl-2-butanol

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

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.[16]

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.[17]

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.[18]) 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.

In archaic nomenclature, alcohols can be named as derivatives of methanol using "-carbinol" as the
ending. For instance, (CH3)3COH can be named trimethylcarbinol.

Type Formula IUPAC Name Common name

Monohydric

alcohols CH3OH Methanol Wood alcohol

C2H5OH Ethanol 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 5-Methyl-2-(propan-2-yl)cyclohexan-1-ol Menthol

Total recorded alcohol per capita consumption (15+), in litres of pure ethanol[19]

Alcohols have a long history of myriad uses. For simple mono-alcohols, which is the focus on this article,
the following are most important industrial alcohols:[20]

methanol, mainly for the production of formaldehyde and as a fuel additive

ethanol, mainly for alcoholic beverages, fuel additive, solvent

1-propanol, 1-butanol, and isobutyl alcohol for use as a solvent and precursor to solvents

C6–C11 alcohols used for plasticizers, e.g. in polyvinylchloride

fatty alcohol (C12–C18), precursors to detergents

Methanol is the most common industrial alcohol, with about 12 million tons/y produced in 1980. The
combined capacity of the other alcohols is about the same, distributed roughly equally.[20]

Toxicity

Main articles: Ethanol and Methanol

With respect to acute toxicity, simple alcohols have low acute toxicities. Doses of several milliliters are
tolerated. For pentanols, hexanols, octanols and longer alcohols, LD50 range from 2–5 g/kg (rats, oral).
Methanol and ethanol are less acutely toxic. All alcohols are mild skin irritants.[20]

The metabolism of methanol (and ethylene glycol) is affected by the presence of ethanol, which has a
higher affinity for liver alcohol dehydrogenase. In this way methanol will be excreted intact in urine.[21]
[22][23]

Physical properties

In general, the hydroxyl group makes alcohols polar. Those groups can form hydrogen bonds to one
another and to most other compounds. Owing to the presence of the polar OH alcohols are more water-
soluble than simple hydrocarbons. Methanol, ethanol, and propanol are miscible in water. Butanol, with
a four-carbon chain, is moderately soluble.
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, and 34.6 °C for diethyl ether.

Occurrence in nature

Simple alcohols are found widely in nature. Ethanol is the most prominent because it is the product of
fermentation, a major energy-producing pathway. The other simple alcohols are formed in only trace
amounts. More complex alcohols however are pervasive, as manifested in sugars, some amino acids,
and fatty acids.