El alcohol

This article is about the generic chemistry term. For the kind of alcohol found in alcoholic beverages, see Ethanol. For beverages containing alcohol, see Alcoholic beverage. For other uses, see Alcohol (disambiguation).

The hydroxyl (OH) functional group in an alcohol molecule
Ball-and-stick model of the hydroxyl (OH) functional group in an alcohol moleculeIn chemistry, an alcohol is anyorganic compound in which a hydroxyl functional group (-OH) is bound to a carbon atom, usually connected to other carbon or hydrogen atoms.

An important class are the simple acyclic alcohols, the general formula for which is CnH2n+1OH. Of those, ethanol (C2H5OH) is the type of alcohol found in alcoholic beverages, and in common speech the word alcohol refers specifically to ethanol.

Otheralcohols are usually described with a clarifying adjective, as in isopropyl alcohol (propan-2-ol) or wood alcohol (methyl alcohol, or methanol). 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 higher priority group is present the prefix hydroxy- will appear in the IUPAC name. Thesuffix -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 (such as citric acid, lactic acid, and sucrose) contain one or more hydroxyl functional groups without using the suffix.

Contents [hide]
1 Simple alcohols
2 Nomenclature
2.1 Systematicnames
2.2 Common Names
2.3 Etymology
3 Physical and chemical properties
4 Applications
5 Production
5.1 Endogenous
6 Laboratory synthesis
6.1 Substitution
6.2 Reduction
6.3 Hydrolysis
7 Reactions
7.1 Deprotonation
7.2 Nucleophilic substitution
7.3 Dehydration
7.4 Esterification
7.5 Oxidation
8 Toxicity
9 Occurrence in nature
10 See also
11 References
12 BibliographySimple alcohols
Space filling model of the hydroxyl (OH) functional group in an alcohol moleculeThe most commonly used alcohol is ethanol, C2H5OH, with the ethane backbone. Ethanol has been produced and consumed by humans for millennia, in the form of fermented and distilled alcoholic beverages. It is a clear flammable liquid that boils at 78.4 °C, which is used as an industrial solvent, car fuel,and raw material in the chemical industry. In the US and some other countries, because of legal and tax restrictions on alcohol consumption, ethanol destined for other uses often contains additives that make it unpalatable (such as Bitrex) or poisonous (such as methanol). Ethanol in this form is known generally as denatured alcohol; when methanol is used, it may be referred to as methylated spiritsor "surgical spirits".

The simplest alcohol is methanol, CH3OH, which was formerly obtained by the distillation of wood and, therefore, is called "wood alcohol". It is a clear liquid resembling ethanol in smell and properties, with a slightly lower boiling point (64.7 °C), and is used mainly as a solvent, fuel, and raw material. Unlike ethanol, methanol is extremely toxic: One sip (as little as10 ml) can cause permanent blindness by destruction of the optic nerve and 30 ml (one fluid ounce) is potentially fatal.[1]

Two other alcohols whose uses are relatively widespread (though not so much as those of methanol and ethanol) are propanol and butanol. Like ethanol, they can be produced by fermentation processes. (However, the fermenting agent is a bacterium, Clostridium acetobutylicum,that feeds on cellulose, not sugars like the Saccharomyces yeast that produces ethanol.) Saccharomyces yeast are known to produce these higher alcohols at temperatures above 75 F. These alcohols are called fusel alcohols or fusel oils in brewing and tend to have a spicy or peppery flavor. They are considered a fault in most styles of beer.[citation needed]

Simple alcohols, in particular,...