text:
Earth's orbit
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The Earth at different points in its orbit
Earth's orbit is the trajectory along which Earth travels around the Sun. The average distance between the Earth and the Sun is 149.60 million km (92.96 million mi),[1] and one complete orbit takes 365.256 days (1 sidereal year), during which time Earth has traveled 940 million km (584 million mi).[2] Earth's orbit has an eccentricity of 0.0167.
As seen from Earth, the planet's orbital prograde motion makes the Sun appear to move with respect to other stars at a rate of about 1° (or a Sun or Moon diameter every 12 hours) eastward per solar day.[nb 1] Earth's orbital speed averages about 30 km/s (108,000 km/h; 67,000 mph), which is fast enough to cover the planet's diameter in 7 minutes and the distance to the Moon in 4 hours.[3]
From a vantage point above the north pole of either the Sun or Earth, Earth would appear to revolve in a counterclockwise direction around the Sun. From the same vantage point, both the Earth and the Sun would appear to rotate also in a counterclockwise direction about their respective axes.
Contents
[hide]
1 History of study
2 Influence on Earth
3 Events in the orbit
4 Future
5 See also
6 Notes
7 References
8 External links
History of study[edit]
Main article: Heliocentrism
Heliocentric Solar System
Heliocentrism (lower panel) in comparison to the geocentric model (upper panel)
Heliocentrism is the scientific model that first placed the Sun at the center of the Solar System and put the planets, including Earth, in its orbit. Historically, heliocentrism is opposed to geocentrism, which placed the Earth at the center. Aristarchus of Samos already proposed a heliocentric model in the 3rd century BC. In the 16th century, Nicolaus Copernicus' De revolutionibus presented a full discussion of a heliocentric model of the universe[4] in much the same way as Ptolemy had presented his geocentric model in the 2nd century. This "Copernican revolution" resolved the issue of planetary retrograde motion by arguing that such motion was only perceived and apparent. "Although Copernicus's groundbreaking book...had been [printed] over a century earlier, [the Dutch mapmaker] Joan Blaeu was the first mapmaker to incorporate his revolutionary heliocentric theory into a map of the world."[5]
Influence on Earth[edit]
Main article: Season
Because of Earth's axial tilt (often known as the obliquity of the ecliptic), the inclination of the Sun's trajectory in the sky (as seen by an observer on Earth's surface) varies over the course of the year. For an observer at a northern latitude, when the north pole is tilted toward the Sun the day lasts longer and the Sun appears higher in the sky. This results in warmer average temperatures, as additional solar radiation reaches the surface. When the north pole is tilted away from the Sun, the reverse is true and the weather is generally cooler. Above the Arctic Circle and below the Antarctic Circle, an extreme case is reached in which there is no daylight at all for part of the year. This is called a polar night. This variation in the weather (because of the direction of the Earth's axial tilt) results in the seasons.[6]
Events in the orbit[edit]
By astronomical convention, the four seasons are determined by the solstices – the two points in the Earth's orbit of the maximum tilt of the Earth's axis, towards the Sun or away from the Sun – and the equinoxes – the two points in the Earth's orbit where the Earth's tilted axis and an imaginary line drawn from the Earth to the Sun are exactly perpendicular to one another. The solstices and equinoxes divide the year up into four approximately equal parts. In the northern hemisphere winter solstice occurs on or about December 21; summer solstice is near June 21; spring equinox is around March 20; and autumnal equinox is about September 23.[7] The effect of the Earth's axial tilt in the southern hemisphere is the opposite of that in the northern hemisphere, thus the seasons of the solstices and equinoxes in the southern hemisphere are the reverse of those in the northern hemisphere (e.g. the northern summer solstice is at the same time as the southern winter solstice).
In modern times, Earth's perihelion occurs around January 3, and the aphelion around July 4 (for other eras, see precession and Milankovitch cycles). The changing Earth–Sun distance results in an increase of about 6.9%[8] in total solar energy reaching the Earth at perihelion relative to aphelion. Since the southern hemisphere is tilted toward the Sun at about the same time that the Earth reaches the closest approach to the Sun, the southern hemisphere receives slightly more energy from the Sun than does the northern over the course of a year. However, this effect is much less significant than the total energy change due to the axial tilt, and most of the excess energy is absorbed by the higher proportion of water in the southern hemisphere.[9]
The Hill sphere (gravitational sphere of influence) of the Earth is about 1,500,000 kilometers (0.01 AU) in radius, or approximately 4 times the average distance to the moon.[10][nb 2] This is the maximal distance at which the Earth's gravitational influence is stronger than the more distant Sun and planets. Objects orbiting the Earth must be within this radius, otherwise they can become unbound by the gravitational perturbation of the Sun.
Orbital characteristics
epoch J2000.0[nb 3]
aphelion 152.10×10^6 km (94.51×10^6 mi)
1.0167 AU[nb 4]
perihelion 147.10×10^6 km (91.40×10^6 mi)
0.98329 AU[nb 4]
semimajor axis 149.60×10^6 km (92.96×10^6 mi)
1.000001018 AU[11]
eccentricity 0.0167086[11]
inclination 7.155° to Sun's equator
1.578690°[12] to invariable plane
longitude of the ascending node 174.9°[11]
longitude of perihelion 102.9°[11]
argument of periapsis 288.1°[11][nb 5]
period 365.256363004 days[13]
average speed 29.78 km/s (18.50 mi/s)[3]
107,200 km/h (66,600 mph)
The following diagram shows the relation between the line of solstice and the line of apsides of Earth's elliptical orbit. The orbital ellipse goes through each of the six Earth images, which are sequentially the perihelion (periapsis — nearest point to the Sun) on anywhere from January 2 to January 5, the point of March equinox on March 19, 20, or 21, the point of June solstice on June 20, 21, or 22, the aphelion (apoapsis — farthest point from the Sun) on anywhere from July 3 to July 5, the September equinox on September 22, 23, or 24, and the December solstice on December 21, 22, or 23.[7] The diagram shows an exaggerated shape of Earth's orbit; the actual orbit is less eccentric than pictured.
Because of the axial tilt of the Earth in its orbit, the maximal intensity of Sun rays hits the Earth 23.4 degrees north of equator at the June Solstice (at the Tropic of Cancer), and 23.4 degrees south of equator at the December Solstice (at the Tropic of Capricorn).[14]
Future[edit]
Main article: Stability of the Solar System
Mathematicians and astronomers (such as Laplace, Lagrange, Gauss, Poincaré, Kolmogorov, Vladimir Arnold, and Jürgen Moser) have searched for evidence for the stability of the planetary motions, and this quest led to many mathematical developments and several successive "proofs" of stability for the Solar System.[15] By most predictions, Earth's orbit will be relatively stable over long periods.[16]
In 1989, Jacques Laskar's work indicated that the Earth's orbit (as well as the orbits of all the inner planets) can become chaotic and that an error as small as 15 meters in measuring the initial position of the Earth today would make it impossible to predict where the Earth would be in its orbit in just over 100 million years' time.[17] Modeling the Solar System is a subject covered by the n-body problem.
See also[edit]
Astronomy portal
Astronomical unit
Barycenter
Earth's axial tilt
Earth's rotation
Geocentric orbit – the orbit of any object orbiting the Earth, such as the Moon or an artificial satellite
Satellite
Space station
Notes[edit]
Jump up ^ Our planet takes about 365 days to orbit the Sun. A full orbit has 360°. That fact demonstrates that each day, the Earth travels roughly 1° in its orbit. Thus, the Sun will appear to move eastward across the sky relative to the stars by that same amount.
Jump up ^ For the Earth, the Hill radius is
R H = a ( m 3 M ) 1 / 3 , {\displaystyle R_{H}=a\left({\frac {m}{3M}}\right)^{1/3},}
where m is the mass of the Earth, a is an astronomical unit, and M is the mass of the Sun. So the radius in AU is about ( 1 3 ⋅ 332 946 ) 1 / 3 ≈ 0.01 {\displaystyle \left({\frac {1}{3\cdot 332\,946}}\right)^{1/3}\approx 0.01} .[citation needed]
Jump up ^ All astronomical quantities vary, both secularly and periodically. The quantities given are the values at the instant J2000.0 of the secular variation, ignoring all periodic variations.
^ Jump up to: a b aphelion = a × (1 + e); perihelion = a × (1 – e), where a is the semi-major axis and e is the eccentricity.
Jump up ^ The reference lists the longitude of perihelion, which is the sum of the longitude of the ascending node and the argument of perihelion. Subtracting from that (102.937°) the node longitude of 174.873° gives −71.936°. Adding 360° gives 288.064°. That addition does not change the angle but expresses it in the usual 0–360° range for longitudes.
References[edit]
Jump up ^ "Sun: Facts & Figures". Solar System Exploration. National Aeronautics and Space Administration. Retrieved July 29, 2015.
Jump up ^ Jean Meeus, Astronomical Algorithms 2nd ed, ISBN 0-943396-61-1 (Richmond, VA: Willmann-Bell, 1998) 238. See Ellipse#Circumference. The formula by Ramanujan is accurate enough.
^ Jump up to: a b Williams, David R. (2004-09-01). "Earth Fact Sheet". NASA. Retrieved 2007-03-17.
Jump up ^ De revolutionibus orbium coelestium. Johannes Petreius. 1543.
Jump up ^ Jerry Brotton, A History of the World in Twelve Maps, London: Allen Lane, 2012, ISBN 9781846140990 p. 262.
Jump up ^ "What causes the seasons? (NASA)". Retrieved January 22, 2015.
^ Jump up to: a b "Date & Time of Solstices & Equinoxes". August 28, 2013. Retrieved Jan 22, 2015.
Jump up ^ Aphelion is 103.4% of the distance to perihelion. See "Orbital characteristics" table. Due to the inverse square law, the radiation at perihelion is about 106.9% of the radiation at aphelion.[citation needed]
Jump up ^ Williams, Jack (2005-12-20). "Earth's tilt creates seasons". USAToday. Retrieved 2007-03-17.
Jump up ^ Vázquez, M.; Montañés Rodríguez, P.; Palle, E. (2006). "The Earth as an Object of Astrophysical Interest in the Search for Extrasolar Planets" (PDF). Instituto de Astrofísica de Canarias. Retrieved 2007-03-21.
^ Jump up to: a b c d e Simon, J.L.; Bretagnon, P.; Chapront, J.; Chapront-Touzé, M.; Francou, G.; Laskar, J. (February 1994). "Numerical expressions for precession formulae and mean elements for the Moon and planets". Astronomy and Astrophysics. 282 (2): 663–683. Bibcode:1994A&A...282..663S.
Jump up ^ Allen, Clabon Walter; Cox, Arthur N. (2000). Allen's Astrophysical Quantities. Springer. p. 294. ISBN 0-387-98746-0.
Jump up ^ The figure appears in multiple references, and is derived from the VSOP87 elements from section 5.8.3, p. 675 of the following: Simon, J. L.; Bretagnon, P.; Chapront, J.; Chapront-Touzé, M.; Francou, G.; Laskar, J. (February 1994). "Numerical expressions for precession formulae and mean elements for the Moon and planets". Astronomy and Astrophysics. 282 (2): 663–683. Bibcode:1994A&A...282..663S.
Jump up ^ "What is the significance of the Tropic of Cancer, Tropic of Capricorn, Arctic Circle and Antarctic Circle?". Retrieved Jan 22, 2015.
Jump up ^ Laskar, J. (2001). "Solar System: Stability". In Murdin, Paul. Encyclopedia of Astronomy and Astropvhysics. Bristol: Institute of Physics Publishing. article 2198. [permanent dead link]
Jump up ^ Gribbin, John (2004). Deep simplicity : bringing order to chaos and complexity (1st U.S. ed.). New York: Random House. ISBN 978-1-4000-6256-0.
Jump up ^ "Earth-Venus smash-up possible". June 11, 2009. Retrieved Jan 22, 2015.
External links[edit]
Media related to Earth's orbit at Wikimedia Commons
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text:
Where Do We Come From? What Are We? Where Are We Going?
From Wikipedia, the free encyclopedia
Jump to: navigation, search
Where Do We Come From? What Are We? Where Are We Going?
Artist
Paul Gauguin
Year
1897–1898
Medium
Oil on canvas
Dimensions
139 cm × 375 cm (55 in × 148 in)
Location
Museum of Fine Arts, Boston
Where Do We Come From? What Are We? Where Are We Going? is a painting by French artist Paul Gauguin. Gauguin inscribed the original French title in the upper left corner: D'où Venons Nous / Que Sommes Nous / Où Allons Nous. The inscription the artist wrote on his canvas has no question mark, no dash, and all words are capitalized. In the upper right corner he signed and dated the painting: P. Gauguin / 1897.[1] The painting was created in Tahiti, and is in the Museum of Fine Arts in Boston, Massachusetts, US.
Contents
[hide]
1 Background
2 Style and analysis
3 Reception and provenance
4 References and sources
5 Further reading
6 External links
Background[edit]
Gauguin had been a student at the Petit Séminaire de La Chapelle-Saint-Mesmin, just outside Orléans, from the age of eleven to the age of sixteen. His subjects there included a class in Catholic liturgy; the teacher for this class was the Bishop of Orléans, Félix-Antoine-Philibert Dupanloup. Dupanloup had devised his own catechism to be lodged in the minds of the young schoolboys, and to lead them towards proper spiritual reflections on the nature of life. The three fundamental questions in this catechism were: "Where does humanity come from?" "Where is it going to?", "How does humanity proceed?". Although in later life Gauguin was vociferously anticlerical, these questions from Dupanloup's catechism obviously had lodged in his mind, and "where?" became the key question that Gauguin asked in his art.[2][3]
Looking for a society more simple and elemental than that of his native France, Gauguin left for Tahiti in 1891. In addition to several other paintings that express his highly individualistic mythology, he completed this painting in 1897 or 1898. Gauguin considered it a masterpiece and the grand culmination of his thought. He was in despair when he undertook the painting, mourning the tragic death of his favourite daughter earlier in the year and oppressed by debts, and had planned to kill himself on finishing it. He subsequently made an unsuccessful attempt with an overdose of arsenic. Thomson thinks it quite possible that he only painted in the inscription while recovering from the attempt.[4][5][6]
Style and analysis[edit]
Gauguin indicated that the painting should be read from right to left, with the three major figure groups illustrating the questions posed in the title. The three women with a child represent the beginning of life; the middle group symbolizes the daily existence of young adulthood; and in the final group, according to the artist, "an old woman approaching death appears reconciled and resigned to her thoughts"; at her feet, "a strange white bird...represents the futility of words" or "the uselessness of vain words".[7] The blue idol in the background apparently represents what Gauguin described as "the Beyond." Of its entirety he said, "I believe that this canvas not only surpasses all my preceding ones, but that I shall never do anything better—or even like it."
The painting is an accentuation of Gauguin's trailblazing post-impressionistic style; his art stressed the vivid use of colors and thick brushstrokes, tenets of the impressionists (though the Impressionists focused on quick brushstrokes), while it aimed to convey an emotional or expressionistic strength. It emerged in conjunction with other avant-garde movements of the twentieth century, including cubism and fauvism.
Reception and provenance[edit]
In 1898, Gauguin sent the painting to Georges-Daniel de Monfreid in Paris. Monfreid passed it to Ambroise Vollard along with eight other thematically related pictures shipped earlier. They went on view at Vollard's gallery from November to December 1898.[8] The exhibition was a success, although D'où Venons Nous? received mixed reviews. The critic Andre Fontainas of the Mercure de France acknowledged a grudging respect for the work but thought the allegory impenetrable were it not for the inscription, and compared the painting unfavourably to the murals of Pierre Puvis de Chavannes who had died recently. Vollard had already purchased the other works as a job lot from Monfreid for 1,000 francs (Gauguin was furious when he found out),[9] but refrained from purchasing the larger monumental work and had difficulty selling it on.
Charles Morice (fr) two years later tried to raise a public subscription to purchase the painting for the nation. To assist this endeavour, Gauguin wrote a detailed description of the work concluding with the messianic remark that he spoke in parables: "Seeing they see not, hearing they hear not". The subscription nevertheless failed. Vollard eventually sold the painting for 2,500 francs (about $10,000 in year 2000 US dollars) in 1901 to Gabriel Frizeau (fr), of which Vollard's commission was perhaps as much as 500 francs.[10]
Subsequently, the painting was consigned and sold to several other Parisian and European merchants and collectors until it was purchased by the Marie Harriman Gallery in New York City in 1936. The Museum of Fine Arts, Boston, acquired it from the Marie Harriman Gallery on 16 April 1936.[1]
References and sources[edit]
References
^ Jump up to: a b Where Do We Come From? What Are We? Where Are We Going?, Museum of Fine Arts, Boston. Retrieved 23 February 2015.
Jump up ^ Gayford pp. 99-100.
Jump up ^ Stuckey p. 129.
Jump up ^ Mathews pp. 225-6.
Jump up ^ Thomson p. 194.
Jump up ^ Boime p. 143.
Jump up ^ Boime p. 140.
Jump up ^ "Gauguin - Tahiti, The Workshop of the Tropics". musee-orsay.fr. Musée d'Orsay.
Jump up ^ Mathews p. 229.
Jump up ^ Thomson pp. 198-200.
Sources
Boime, Albert. (2008) Revelation of Modernism: Responses to the Cultural Crisis in Fin-de-Siécle. University of Missouri Press, ISBN 9780826266255
Gayford, Martin. (2006) The Yellow House: Van Gogh, Gauguin, and Nine Turbulent Weeks in Arles, London: Penguin Books, ISBN 0-670-91497-5.
Mathews, Nancy Mowll (2001). Paul Gauguin, an Erotic Life. New Haven, Connecticut: Yale University Press, ISBN 0-300-09109-5
Stuckey, Charles. "Gauguin Inside Art" in Eric M. Zafran. Ed., Gauguin's Nirvana: Painters at Le Pouldu 1889-90. New Haven: Wadsworth Atheneum Museum of Art, Hartford in association with Yale University Press, 2001, ISBN 0300089546.
Thomson, Belinda (1987). Gauguin. London: Thames and Hudson. ISBN 0-500-20220-6.
Further reading[edit]
Rewald, John (1956; revised 1978). History of Post-Impressionism: From Van Gogh to Gauguin, London: Secker & Warburg.
Rewald, John. (1946) History of Impressionism.
External links[edit]
Media related to Paul Gauguin at Wikimedia Commons
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v
t
e
Paul Gauguin
Paintings
Study of a Nude (1880)
Still Life with Profile of Laval (1886)
Vision after the Sermon (1888)
The Painter of Sunflowers (1888)
Landscape near Arles (1888)
Fruits on a Table (1889)
The Flageolet Player on the Cliff (1889)
The Yellow Christ (1889)
The Green Christ (1889)
Christ on the Mount of Olives (1889)
Self-Portrait with Halo and Snake (1889)
Still Life with Head-Shaped Vase and Japanese Woodcut (1889)
Tahitian Women on the Beach (1891)
Vahine no te vi (1892)
Fatata te Miti (By the Sea) (1892)
Arearea (1892)
Spirit of the Dead Watching (1892)
When Will You Marry? (1892)
Aha Oe Feii? (1892)
Arii Matamoe (1892)
Merahi metua no Tehamana (1893)
Nave Nave Mahana (1896)
Where Do We Come From? What Are We? Where Are We Going? (1897/1898)
Two Tahitian Women (1899)
Other works
Jug in the Form of a Head, Self-Portrait (1889)
Soyez amoureuses vous serez heureuses (wood panel, 1889)
Objet décoratif carré avec dieux tahitiens (sculpture, 1893-1895)
Oviri (ceramic sculpture, 1895)
Periodicals
Le Sourire (1899-1900)
Exhibitions
Les XX, 1889
The Volpini Exhibition, 1889
Museums
Paul Gauguin Museum (Tahiti)
Paul Gauguin Cultural Center
People
Jean René Gauguin (son)
Flora Tristan (grandmother)
Émile Bernard
Vincent van Gogh
Meijer de Haan
Charles Laval
George-Daniel de Monfreid
Camille Pissarro
Émile Schuffenecker
Theo van Gogh
Ambroise Vollard
Related
Lust for Life (1956 film)
Rebel in Paradise (1960 film)
The Wolf at the Door (1986 film)
Paradise Found (2003 film)
Authority control
BNF: cb13750370t (data)
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Alcohol
From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
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 grey balls represent the hydroxyl group (-OH). The three "R's" stand for carbon substituents or hydrogen atoms.[1]
The bond angle between an hydroxyl group (-OH) and a chain of carbon atoms (R)
In chemistry, an alcohol is any organic compound in which the hydroxyl functional group (–OH) is bound to a carbon.[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. An important class of alcohols, of which methanol and ethanol are the simplest members, includes all compounds the general formula for which is CnH2n+1OH. It is these simple monoalcohols that are the subject of this article.
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
2.3 Common 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
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
Alcohol distillation was known to Islamic chemists as early as the eighth century.[3][4]
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".[5][6][7]
The Persian physician, alchemist, polymath and philosopher Rhazes (854 CE – 925 CE)[8] is credited with the discovery of ethanol.[9][10]
Nomenclature
Etymology
The word "alcohol" is from the Arabic kohl (Arabic: الكحل, translit. 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" (Moorish) 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 1892, combining the word ethane with the "-ol" ending of "alcohol".[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]
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 rules for naming phenols.[18]
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.[19]
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.[20]) 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.
Type
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 5-Methyl-2-(propan-2-yl)cyclohexan-1-ol Menthol
Applications
Total recorded alcohol per capita consumption (15+), in litres of pure ethanol[21]
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:[22]
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.[22]
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.[22]
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.[23][24][25]
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 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 are pervasive, as manifested in sugars, some amino acids, and fatty acids.
Production
Ziegler and oxo processes
In the Ziegler process, linear alcohols are produced from ethylene and triethylaluminium followed by oxidation and hydrolysis.[22] 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:[22]
RCH=CH2 + H2 + CO → RCH2CH2CHO
RCH2CH2CHO + 3 H2 → RCH2CH2CH2OH
Such processes give fatty alcohols, which are useful for detergents.
Hydration reactions
Some 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)[26] 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 species of the benign bacteria in the intestine use fermentation as a form of anaerobic metabolism. This metabolic reaction produces ethanol as a waste product. 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.[27][28][29]
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.[30]
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
Deprotonation
With a pKa of around 16–19, they are, in general, slightly weaker acids than water. With strong bases such as sodium hydride or sodium they form salts called alkoxides, with the general formula RO− M+.
2 R-OH + 2 NaH → 2 R-O−Na+ + 2 H2
2 R-OH + 2 Na → 2 R-O−Na+ + H2
The acidity of alcohols is strongly affected by solvation. In the gas phase, alcohols are more acidic than is water.[31]
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
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:
Upon treatment with strong acids, alcohols undergo the E1 elimination reaction 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 ethylene:
A more controlled elimination reaction is the with carbon disulfide and iodomethane.
Esterification
Alcohol and carboxylic acids react in the so-called Fischer esterification. The reaction usually requires a catalyst, such as concentrated sulfuric acid:
R-OH + R'-CO2H → R'-CO2R + H2O
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 oxidation
Primary alcohols (R-CH2OH) can be oxidized either to aldehydes (R-CHO) or to carboxylic acids (R-CO2H). 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
Ethanol fuel
Fatty alcohol
Index of alcohol-related articles
Polyol
Rubbing alcohol
Sugar alcohol
Transesterification
Notes
Jump up ^ "alcohols". IUPAC Gold Book. Retrieved 16 December 2013.
Jump up ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "Alcohols".
Jump up ^ Al-Hassani, Salim; Abattouy, Mohammed. "The Advent of Scientific Chemistry". Muslim Heritage. Retrieved 17 May 2018.
Jump up ^ Curzon, George Nathaniel (7 July 2010). "The History of Alcohol in Islam". Coming Anarchy. Retrieved 17 May 2018.
Jump up ^ Forbes, R. J. (1970). A Short History of the Art of Distillation. Brill Publishers. p. 87. ISBN 9004006176.
Jump up ^ Multhauf, Robert (1966). The Origins of Chemistry. London. pp. 204–6.
Jump up ^ Hill, Donald Routledge (1993). Islamic science and engineering. Edinburgh University Press. ISBN 9780748604555.
Jump up ^ Hitti, Philip K. (1977). History of the Arabs from the earliest times to the present (10th ed.). London: Macmillan Publishers. 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.
Jump up ^ Modanlou, Houchang D. (November 2008). "A tribute to Zakariya Razi (865 - 925 AD), an Iranian pioneer scholar" (PDF). Archives of Iranian Medicine. 11 (6): 673–677. PMID 18976043. Retrieved 17 May 2018. Abu Bakr Mohammad Ibn Zakariya al-Razi, known in the West as Rhazes, was born in 865 AD in the ancient city of Rey, Near Tehran. A musician during his youth he became an alchemist. He discovered alcohol and sulfuric acid. He classified substances as plants, organic, and inorganic.
Jump up ^ Schlosser, Stefan (May 2011). "Distillation – from Bronze Age till today". Retrieved 17 May 2018. Al-Razi (865–925) was the preeminent Pharmacist and physician of his time [5]. The discovery of alcohol, first to produce acids such as sulfuric acid, writing up extensive notes on diseases such as smallpox and chickenpox, a pioneer in ophthalmology, author of first book on pediatrics, making leading contributions in inorganic and organic chemistry, also the author of several philosophical works.
Jump up ^ Harper, Douglas. "Alcohol". Etymonline. MaoningTech. Retrieved 17 May 2018.
Jump up ^ Lohninger, H. (21 December 2004). "Etymology of the Word "Alcohol"". VIAS Encyclopedia. Retrieved 17 May 2018.
^ Jump up to: a b "alcohol, n.". OED Online. Oxford University Press. 15 November 2016.
Jump up ^ Johnson, William (1652). Lexicon Chymicum.
Jump up ^ Armstrong, Henry E. (8 July 1892). "Contributions to an international system of nomenclature. The nomenclature of cycloids". Proc. Chem. Soc. 8 (114): 128. doi:10.1039/PL8920800127. 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.
^ Jump up to: a b William Reusch. "Alcohols". VirtualText of Organic Chemistry. Archived from the original on 19 September 2007. Retrieved 14 September 2007.
Jump up ^ Organic chemistry IUPAC nomenclature. Alcohols Rule C-201.
Jump up ^ Organic Chemistry Nomenclature Rule C-203: Phenols
Jump up ^ "How to name organic compounds using the IUPAC rules". www.chem.uiuc.edu. THE DEPARTMENT OF CHEMISTRY AT THE UNIVERSITY OF ILLINOIS. Retrieved 14 November 2016.
Jump up ^ Reusch, William. "Nomenclature of Alcohols". chemwiki.ucdavis.edu/. Retrieved 17 March 2015.
Jump up ^ "Global Status Report on Alcohol 2004" (PDF). Retrieved 28 November 2010.
^ Jump up to: a b c d e Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter (2005), "Alcohols, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a01_279 .
Jump up ^ 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.
Jump up ^ 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. PMID 10097201.
Jump up ^ Lobert S (2000). "Ethanol, isopropanol, methanol, and ethylene glycol poisoning". Critical care nurse. 20 (6): 41–7. PMID 11878258.
Jump up ^ 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.
Jump up ^ 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.
Jump up ^ 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. doi:10.1177/002580240004000304. PMID 10976182.
Jump up ^ Cecil Adams (20 October 2006). "Designated drunk: Can you get intoxicated without actually drinking alcohol?". The Straight Dope. Retrieved 27 February 2013.
Jump up ^ 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 and Biotechnology. 71 (5): 587–97. doi:10.1007/s00253-006-0445-z. PMID 16685494.
Jump up ^ 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.
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Alcohol (Ethanol) at The Periodic Table of Videos (University of Nottingham)
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Alcohols
Straight-chain
primary
alcohols (1°)
Methanol (C
1)
Ethanol (C
2)
1-Propanol (C
3)
n-Butanol (C
4)
1-Pentanol (C
5)
1-Hexanol (C
6)
1-Heptanol (C
7)
1-Octanol (C
8)
1-Nonanol (C
9)
1-Decanol (C
10)
Undecanol (C
11)
Dodecanol (C
12)
Tridecan-1-ol (C
13)
1-Tetradecanol (C
14)
Pentadecan-1-ol (C
15)
Cetyl alcohol (C
16)
Heptadecan-1-ol (C
17)
Stearyl alcohol (C
18)
Nonadecan-1-ol (C
19)
Arachidyl alcohol (C
20)
Heneicosan-1-ol (C
21)
Docosanol (C
22)
Tricosan-1-ol (C
23)
1-Tetracosanol (C
24)
Pentacosan-1-ol (C
25)
1-Hexacosanol (C
26)
1-Heptacosanol (C
27)
1-Octacosanol (C
28)
1-Nonacosanol (C
29)
Triacontanol (C
30)
Other primary
alcohols
Isobutanol (C
4)
Isoamyl alcohol (C
5)
2-Methyl-1-butanol (C
5)
Phenethyl alcohol (C
8)
Tryptophol (C
10)
Secondary
alcohols (2°)
Isopropanol (C
3)
2-Butanol (C
4)
2-Pentanol (C
5)
2-Hexanol (C
6)
2-Heptanol (C
7)
Cyclohexanol (C
6)
2-Octanol (C
8)
Tertiary
alcohols (3°)
tert-Butyl alcohol (C
4)
tert-Amyl alcohol (C
5)
2-Methyl-2-pentanol (C
6)
2-Methylhexan-2-ol (C
7)
2-Methylheptan-2-ol (C
8)
3-Methyl-3-pentanol (C
6)
3-Methyloctan-3-ol (C
9)
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See also chemical classification, chemical nomenclature (inorganic, organic)
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Bioenergy
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NARA: 10640163
NDL: 00560350
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values: Featured content – the best of Wikipedia

values: Find background information on current events

values:
/wiki/Special:Random
Load a random article [ctrl-alt-x]
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values: portal navigation p-navigation p-navigation-label

values: Guidance on how to use and edit Wikipedia

values: About the project, what you can do, where to find things

values: A list of recent changes in the wiki [ctrl-alt-r]

values: portal navigation p-interaction p-interaction-label

values: List of all English Wikipedia pages containing links to this page [ctrl-alt-j]

values: Recent changes in pages linked from this page [ctrl-alt-k]

values:
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u

values: A list of all special pages [ctrl-alt-q]

values: Permanent link to this revision of the page

values: Link to connected data repository item [ctrl-alt-g]

values: Printable version of this page [ctrl-alt-p]

values: portal navigation p-wikibase-otherprojects p-wikibase-otherprojects-label

values:
https://af.wikipedia.org/wiki/Alkohol
Alkohol – Afrikaans
af
af
interlanguage-link-target

values:
interlanguage-link interwiki-af
display: none;

values:
https://als.wikipedia.org/wiki/Alkohole
Alkohole – Alemannisch
als
als
interlanguage-link-target

values:
interlanguage-link interwiki-als
display: none;

values:
https://an.wikipedia.org/wiki/Alcohol
Alcohol – Aragonese
an
an
interlanguage-link-target

values:
interlanguage-link interwiki-an
display: none;

values:
interlanguage-link interwiki-roa-rup
display: none;

values:
interlanguage-link interwiki-as
display: none;

values:
https://ast.wikipedia.org/wiki/Alcohol
Alcohol – Asturian
ast
ast
interlanguage-link-target

values:
interlanguage-link interwiki-ast
display: none;

values:
interlanguage-link interwiki-az
display: none;

values:
interlanguage-link interwiki-azb
display: none;

values: অ্যালকোহল – Bangla

values:
interlanguage-link interwiki-bn
display: none;

values:
interlanguage-link interwiki-zh-min-nan
display: none;

values:
interlanguage-link interwiki-ba
display: none;

values:
interlanguage-link interwiki-be
display: none;

values: Сьпірт – Belarusian (Taraškievica orthography)

values:
interlanguage-link interwiki-be-x-old
display: none;

values:
interlanguage-link interwiki-bg
display: none;

values:
https://bs.wikipedia.org/wiki/Alkohol
Alkohol – Bosnian
bs
bs
interlanguage-link-target

values:
interlanguage-link interwiki-bs
display: none;

values:
https://br.wikipedia.org/wiki/Alkool
Alkool – Breton
br
br
interlanguage-link-target

values:
interlanguage-link interwiki-br
display: none;

values:
https://ca.wikipedia.org/wiki/Alcohol
Alcohol – Catalan
ca
ca
interlanguage-link-target

values:
interlanguage-link interwiki-ca
display: none;

values:
https://cs.wikipedia.org/wiki/Alkoholy
Alkoholy – Czech
cs
cs
interlanguage-link-target

values:
interlanguage-link interwiki-cs
display: none;

values:
https://cy.wikipedia.org/wiki/Alcohol
Alcohol – Welsh
cy
cy
interlanguage-link-target

values:
interlanguage-link interwiki-cy
display: none;

values:
interlanguage-link interwiki-da
display: none;

values:
https://de.wikipedia.org/wiki/Alkohole
Alkohole – German
de
de
interlanguage-link-target

values:
interlanguage-link interwiki-de
display: none;

values:
https://et.wikipedia.org/wiki/Alkoholid
Alkoholid – Estonian
et
et
interlanguage-link-target

values:
interlanguage-link interwiki-et
display: none;

values: Αλκοόλες – Greek

values:
interlanguage-link interwiki-el
display: none;

values:
https://es.wikipedia.org/wiki/Alcohol
Alcohol – Spanish
es
es
interlanguage-link-target

values:
https://eo.wikipedia.org/wiki/Alkoholo
Alkoholo – Esperanto
eo
eo
interlanguage-link-target

values:
interlanguage-link interwiki-eo
display: none;

values:
https://eu.wikipedia.org/wiki/Alkohol
Alkohol – Basque
eu
eu
interlanguage-link-target

values:
interlanguage-link interwiki-eu
display: none;

values:
interlanguage-link interwiki-fa
display: none;

values:
https://hif.wikipedia.org/wiki/Alcohol
Alcohol – Fiji Hindi
hif
hif
interlanguage-link-target

values:
interlanguage-link interwiki-hif
display: none;

values:
https://fo.wikipedia.org/wiki/Alkohol
Alkohol – Faroese
fo
fo
interlanguage-link-target

values:
interlanguage-link interwiki-fo
display: none;

values:
interlanguage-link interwiki-fr
display: none;

values:
interlanguage-link interwiki-ga
display: none;

values:
https://gv.wikipedia.org/wiki/Alcoal
Alcoal – Manx
gv
gv
interlanguage-link-target

values:
interlanguage-link interwiki-gv
display: none;

values:
https://gd.wikipedia.org/wiki/Alcol
Alcol – Scottish Gaelic
gd
gd
interlanguage-link-target

values:
interlanguage-link interwiki-gd
display: none;

values:
https://gl.wikipedia.org/wiki/Alcohol
Alcohol – Galician
gl
gl
interlanguage-link-target

values:
interlanguage-link interwiki-gl
display: none;

values: આલ્કોહોલ – Gujarati

values:
interlanguage-link interwiki-gu
display: none;

values:
interlanguage-link interwiki-ko
display: none;

values:
interlanguage-link interwiki-hy
display: none;

values: अल्कोहल – Hindi

values:
https://hr.wikipedia.org/wiki/Alkoholi
Alkoholi – Croatian
hr
hr
interlanguage-link-target

values:
interlanguage-link interwiki-hr
display: none;

values:
https://io.wikipedia.org/wiki/Alkoholo
Alkoholo – Ido
io
io
interlanguage-link-target

values:
interlanguage-link interwiki-io
display: none;

values:
https://ilo.wikipedia.org/wiki/Alkohol
Alkohol – Iloko
ilo
ilo
interlanguage-link-target

values:
interlanguage-link interwiki-ilo
display: none;

values:
https://id.wikipedia.org/wiki/Alkohol
Alkohol – Indonesian
id
id
interlanguage-link-target

values:
https://ia.wikipedia.org/wiki/Alcohol
Alcohol – Interlingua
ia
ia
interlanguage-link-target

values:
interlanguage-link interwiki-ia
display: none;

values:
interlanguage-link interwiki-is
display: none;

values:
https://it.wikipedia.org/wiki/Alcoli
Alcoli – Italian
it
it
interlanguage-link-target

values:
interlanguage-link interwiki-it
display: none;

values:
https://jv.wikipedia.org/wiki/Alkohol
Alkohol – Javanese
jv
jv
interlanguage-link-target

values:
interlanguage-link interwiki-jv
display: none;

values: ಆಲ್ಕೋಹಾಲ್ – Kannada

values:
interlanguage-link interwiki-kn
display: none;

values:
interlanguage-link interwiki-ka
display: none;

values: Алкогольдер – Kazakh

values:
interlanguage-link interwiki-kk
display: none;

values:
https://sw.wikipedia.org/wiki/Alkoholi
Alkoholi – Swahili
sw
sw
interlanguage-link-target

values:
interlanguage-link interwiki-sw
display: none;

values:
interlanguage-link interwiki-ht
display: none;

values:
https://ku.wikipedia.org/wiki/Alkol
Alkol – Kurdish
ku
ku
interlanguage-link-target

values:
interlanguage-link interwiki-ku
display: none;

values: Спирт – Kyrgyz

values:
interlanguage-link interwiki-ky
display: none;

values:
interlanguage-link interwiki-lad
display: none;

values:
https://la.wikipedia.org/wiki/Alcohol
Alcohol – Latin
la
la
interlanguage-link-target

values:
interlanguage-link interwiki-la
display: none;

values:
https://lv.wikipedia.org/wiki/Spirti
Spirti – Latvian
lv
lv
interlanguage-link-target

values:
https://lb.wikipedia.org/wiki/Alkoholen
Alkoholen – Luxembourgish
lb
lb
interlanguage-link-target

values:
interlanguage-link interwiki-lb
display: none;

values:
https://lt.wikipedia.org/wiki/Alkoholis
Alkoholis – Lithuanian
lt
lt
interlanguage-link-target

values:
https://li.wikipedia.org/wiki/Alcohol
Alcohol – Limburgish
li
li
interlanguage-link-target

values:
interlanguage-link interwiki-li
display: none;

values:
https://ln.wikipedia.org/wiki/Lotoko
Lotoko – Lingala
ln
ln
interlanguage-link-target

values:
interlanguage-link interwiki-ln
display: none;

values:
https://lmo.wikipedia.org/wiki/Alcol
Alcol – Lombard
lmo
lmo
interlanguage-link-target

values:
interlanguage-link interwiki-lmo
display: none;

values:
https://hu.wikipedia.org/wiki/Alkoholok
Alkoholok – Hungarian
hu
hu
interlanguage-link-target

values:
interlanguage-link interwiki-hu
display: none;

values:
interlanguage-link interwiki-mk
display: none;

values: ചാരായം (രസതന്ത്രം) – Malayalam

values:
interlanguage-link interwiki-ml
display: none;

values:
https://ms.wikipedia.org/wiki/Alkohol
Alkohol – Malay
ms
ms
interlanguage-link-target

values: အယ်လ်ကိုဟော – Burmese

values:
interlanguage-link interwiki-my
display: none;

values:
interlanguage-link interwiki-nl
display: none;

values: अल्कोहल – Nepali

values:
interlanguage-link interwiki-ne
display: none;

values:
interlanguage-link interwiki-ja
display: none;

values:
https://frr.wikipedia.org/wiki/Alkohol
Alkohol – Northern Frisian
frr
frr
interlanguage-link-target

values:
interlanguage-link interwiki-frr
display: none;

values:
https://no.wikipedia.org/wiki/Alkoholer
Alkoholer – Norwegian
no
no
interlanguage-link-target

values:
interlanguage-link interwiki-no
display: none;

values:
https://nn.wikipedia.org/wiki/Alkohol
Alkohol – Norwegian Nynorsk
nn
nn
interlanguage-link-target

values:
interlanguage-link interwiki-nn
display: none;

values:
interlanguage-link interwiki-oc
display: none;

values:
https://uz.wikipedia.org/wiki/Spirtlar
Spirtlar – Uzbek
uz
uz
interlanguage-link-target

values:
interlanguage-link interwiki-uz
display: none;

values: ਅਲਕੋਹਲ – Punjabi

values:
interlanguage-link interwiki-pa
display: none;

values:
interlanguage-link interwiki-pnb
display: none;

values:
https://jam.wikipedia.org/wiki/Alkoal
Alkoal – Jamaican Creole English
jam
jam
interlanguage-link-target

values:
interlanguage-link interwiki-jam
display: none;

values:
https://nds.wikipedia.org/wiki/Alkohol
Alkohol – Low German
nds
nds
interlanguage-link-target

values:
interlanguage-link interwiki-nds
display: none;

values:
https://pl.wikipedia.org/wiki/Alkohole
Alkohole – Polish
pl
pl
interlanguage-link-target

values:
interlanguage-link interwiki-pl
display: none;

values:
https://ksh.wikipedia.org/wiki/Alkohol
Alkohol – Colognian
ksh
ksh
interlanguage-link-target

values:
interlanguage-link interwiki-ksh
display: none;

values:
https://ro.wikipedia.org/wiki/Alcool
Alcool – Romanian
ro
ro
interlanguage-link-target

values:
interlanguage-link interwiki-ro
display: none;

values:
https://qu.wikipedia.org/wiki/Alkul
Alkul – Quechua
qu
qu
interlanguage-link-target

values:
interlanguage-link interwiki-qu
display: none;

values: Алкоголы – Rusyn

values:
interlanguage-link interwiki-rue
display: none;

values: Спирты – Russian

values: interlanguage-link interwiki-ru badge-Q17437796 badge-featuredarticle

values:
https://sco.wikipedia.org/wiki/Alcohol
Alcohol – Scots
sco
sco
interlanguage-link-target

values:
interlanguage-link interwiki-sco
display: none;

values:
https://sq.wikipedia.org/wiki/Alkooli
Alkooli – Albanian
sq
sq
interlanguage-link-target

values:
interlanguage-link interwiki-sq
display: none;

values:
https://scn.wikipedia.org/wiki/Alcool
Alcool – Sicilian
scn
scn
interlanguage-link-target

values:
interlanguage-link interwiki-scn
display: none;

values:
interlanguage-link interwiki-simple
display: none;

values:
interlanguage-link interwiki-sk
display: none;

values:
https://sl.wikipedia.org/wiki/Alkohol
Alkohol – Slovenian
sl
sl
interlanguage-link-target

values:
interlanguage-link interwiki-sl
display: none;

values:
interlanguage-link interwiki-ckb
display: none;

values: Алкохол – Serbian

values:
interlanguage-link interwiki-sr
display: none;

values:
https://sh.wikipedia.org/wiki/Alkoholi
Alkoholi – Serbo-Croatian
sh
sh
interlanguage-link-target

values:
interlanguage-link interwiki-sh
display: none;

values:
https://su.wikipedia.org/wiki/Alkohol
Alkohol – Sundanese
su
su
interlanguage-link-target

values:
interlanguage-link interwiki-su
display: none;

values:
https://fi.wikipedia.org/wiki/Alkoholit
Alkoholit – Finnish
fi
fi
interlanguage-link-target

values:
https://sv.wikipedia.org/wiki/Alkoholer
Alkoholer – Swedish
sv
sv
interlanguage-link-target

values:
interlanguage-link interwiki-sv
display: none;

values:
https://tl.wikipedia.org/wiki/Alkohol
Alkohol – Tagalog
tl
tl
interlanguage-link-target

values:
interlanguage-link interwiki-tl
display: none;

values: மதுசாரம் – Tamil

values:
interlanguage-link interwiki-ta
display: none;

values: Спиртлар – Tatar

values:
interlanguage-link interwiki-tt
display: none;

values: ఆల్కహాలు – Telugu

values:
interlanguage-link interwiki-te
display: none;

values: แอลกอฮอล์ – Thai

values:
interlanguage-link interwiki-th
display: none;

values:
https://tr.wikipedia.org/wiki/Alkol
Alkol – Turkish
tr
tr
interlanguage-link-target

values:
interlanguage-link interwiki-tr
display: none;

values:
interlanguage-link interwiki-uk
display: none;

values: الکحل – Urdu

values:
https://vi.wikipedia.org/wiki/Ancol
Ancol – Vietnamese
vi
vi
interlanguage-link-target

values:
interlanguage-link interwiki-vi
display: none;

values:
https://vls.wikipedia.org/wiki/Alcool
Alcool – West Flemish
vls
vls
interlanguage-link-target

values:
interlanguage-link interwiki-vls
display: none;

values:
https://war.wikipedia.org/wiki/Arkohol
Arkohol – Waray
war
war
interlanguage-link-target

values:
interlanguage-link interwiki-war
display: none;

values:
interlanguage-link interwiki-wuu
display: none;

values: אלקאהאל – Yiddish

values:
interlanguage-link interwiki-yi
display: none;

values:
interlanguage-link interwiki-yo
display: none;

values:
interlanguage-link interwiki-zh-yue
display: none;

values:
interlanguage-link interwiki-bat-smg
display: none;

values:
https://zh.wikipedia.org/wiki/%E9%86%87
醇 – Chinese
zh
zh
interlanguage-link-target

values:
interlanguage-link interwiki-kbp
display: none;

values: All languages (initial selection from common choices by you and others)

values: /static/images/wikimedia-button-1.5x.png 1.5x, /static/images/wikimedia-button-2x.png 2x

values: /static/images/poweredby_mediawiki_132x47.png 1.5x, /static/images/poweredby_mediawiki_176x62.png 2x

values:
suggestions
display: none; font-size: 13px;

values: mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject page-Alcohol rootpage-Alcohol skin-vector action-view