The hydroxyl (OH) functional group in an alcohol molecule

Ball-and-stick model of the hydroxyl (OH) functional group in an alcohol molecule

In chemistry, an alcohol is an organic compound in which the hydroxyl functional group (-OH) is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms.^[1]

An important class of alcohols are the simple acyclic alcohols, the general formula for which is C_nH_2n+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.

Other alcohols 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. The suffix -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, particularly sugars (examples glucose and sucrose) contain hydroxyl functional groups without using the suffix.

Simple alcohols[link]

Space filling model of the hydroxyl (OH) functional group in an alcohol molecule

The 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 spirits or "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 as 10 ml) can cause permanent blindness by destruction of the optic nerve and 30 ml (one fluid ounce) is potentially fatal.^[2]

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 (24 °C). 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.^[3]

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.^{[citation needed]}

Nomenclature[link]

Systematic names[link]

In the IUPAC system, the name of the alkane chain loses the terminal "e" and adds "ol", e.g., "methanol" and "ethanol".^[4] 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. Sometimes, the position number is written before the IUPAC name: 1-propanol and 2-propanol. If a higher priority group is present (such as an aldehyde, ketone, or carboxylic acid), then it is necessary to use the prefix "hydroxy",^[4] for example: 1-hydroxy-2-propanone (CH₃COCH₂OH).^[5]

Some examples of simple alcohols and how to name them

The IUPAC nomenclature is used in scientific publications and where precise identification of the substance is important. 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 1st or 2nd carbon on the propane chain.

Alcohols are classified into primary, secondary (sec), and tertiary (tert), based upon the number of carbon atoms connected to the carbon atom that bears the hydroxyl group. The primary alcohols have general formulas RCH₂OH; secondary ones are RR'CHOH; and tertiary ones are RR'R"COH, where R, R', and R" stand for alkyl groups. Ethanol and n-propyl alcohol are primary alcohols; isopropyl alcohol is a secondary one. The prefixes sec- (or s-) and tert- (or t-), conventionally in italics, may be used before the alkyl group's name to distinguish secondary and tertiary alcohols, respectively, from the primary one. For example, isopropyl alcohol is occasionally called sec-propyl alcohol, and the tertiary alcohol (CH₃)₃COH, or 2-methylpropan-2-ol in IUPAC nomenclature is commonly known as tert-butyl alcohol or tert-butanol.

Common names[link]

History and etymology[link]

The first alcohol (today known as ethyl alcohol) was discovered by the tenth-century Persian alchemist al-Razi.

kuḥl was originally the name given to the very fine powder, produced by the sublimation of the natural mineral stibnite to form antimony sulfide Sb₂S₃ (hence the essence or "spirit" of the substance), which was used as an antiseptic and eyeliner. Bartholomew Traheron in his 1543 translation of John of Vigo introduces the word as a term used by "barbarous" (Moorish) authors for "fine powder":

the barbarous auctours use alcohol, or (as I fynde it sometymes wryten) alcofoll, for moost fine poudre.

The word alcohol appears in English, as a term for a very fine powder, in the 16th century, loaned via French from medical Latin, ultimately from the Arabic الكحل (al-kuḥl, "the kohl, a powder used as an eyeliner"). Al- is the Arabic definitive article, equivalent to the in English.

William Johnson in his 1657 Lexicon Chymicum glosses the word as antimonium sive stibium. 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) has 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 18^th century, and was extended to the class of substances so-called as "alcohols" in modern chemistry, after 1850.

The current Arabic name for alcohol is الكحول al-kuḥūl, re-introduced into that language from western usage.

Physical and chemical properties[link]

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^[6]). 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 (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.

Alcohols, like water, can show either acidic or basic properties at the -OH group. With a pK_a 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 also undergo oxidation to give aldehydes, ketones, or carboxylic acids, or they can be dehydrated to alkenes. They can react 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.

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.

Applications[link]

Total recorded alcohol per capita consumption (15+), in litres of pure alcohol^[7]

Alcohols can be used as a beverage (ethanol only), as fuel and for many scientific, medical, and industrial utilities. Ethanol in the form of alcoholic beverages has been consumed by humans since pre-historic times. A 50% v/v solution of ethylene glycol in water is commonly used as an antifreeze.

Some alcohols, mainly ethanol and methanol, can be used as an alcohol 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.

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.

Ethanol can be used as an antiseptic to disinfect the skin before injections are given, often along with iodine. 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 is also used as a preservative for specimens.

Alcohol gels have become common as hand sanitizers.

Production[link]

In industry, alcohols are produced in several ways:

• 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 zymase into ethanol (and carbon dioxide).
• By direct hydration using ethylene (ethylene hydration)^[8] or other alkenes from cracking of fractions of distilled crude oil.

Endogenous[link]

Several of the benign bacteria^[which?] 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.^{[citation needed]}

Laboratory synthesis[link]

Several methods exist for the preparation of alcohols in the laboratory.

Substitution[link]

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[link]

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[link]

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[link]

Deprotonation[link]

Alcohols can behave as weak acids, undergoing deprotonation. The deprotonation reaction to produce an alkoxide salt is performed either with a strong base such as sodium hydride or n-butyllithium or with sodium or potassium metal.

2 R-OH + 2 NaH → 2 R-O^-Na⁺ + 2H₂↑

2 R-OH + 2 Na → 2 R-O⁻Na⁺ + H₂

2 CH₃CH₂-OH + 2 Na → 2 CH₃-CH₂-O⁻⁺ + H₂↑

Water is similar in pK_a to many alcohols, so with sodium hydroxide there is an equilibrium set-up, which usually lies to the left:

R-OH + NaOH ⇌ R-O^-Na⁺ + H₂O (equilibrium to the left)

It should be noted, however, that the bases used to deprotonate alcohols are strong themselves. The bases used and the alkoxides created are both highly moisture-sensitive chemical reagents.

The acidity of alcohols is also affected by the overall stability of the alkoxide ion. Electron-withdrawing groups attached to the carbon containing the hydroxyl group will serve to stabilize the alkoxide when formed, thus resulting in greater acidity. On the other hand, the presence of electron-donating group will result in a less stable alkoxide ion formed. This will result in a scenario whereby the unstable alkoxide ion formed will tend to accept a proton to reform the original alcohol.

With alkyl halides alkoxides give rise to ethers in the Williamson ether synthesis.

Nucleophilic substitution[link]

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[link]

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:

A more controlled elimination reaction is the Chugaev elimination with carbon disulfide and iodomethane.

Esterification[link]

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[link]

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.

Toxicity[link]

Most significant of the possible long-term effects of ethanol. In addition, in pregnant women, it causes fetal alcohol syndrome.

Ethanol in alcoholic beverages has been consumed by humans since prehistoric times for a variety of hygienic, dietary, medicinal, religious, and recreational reasons. The consumption of large doses of ethanol causes drunkenness (intoxication), which may lead to a hangover as its effects wear off. Depending upon the dose and the regularity of its consumption, ethanol can cause acute respiratory failure or death. Because ethanol impairs judgment in humans, it can be a catalyst for reckless or irresponsible behavior. The LD₅₀ of ethanol in rats is 10.3 g/kg.^[9]

Ethanol's toxicity is largely caused by its primary metabolite; acetaldehyde^[10][11] and secondary metabolite; acetic acid.^{[12][13][14][11]} All primary alcohols are broken down into aldehydes then to carboxylic acids, and whose toxicities are similar to acetaldehyde and acetic acid. Metabolite toxicity is reduced in rats fed N-acetylcysteine^[10][15] and thiamine^[16].

Some secondary and tertiary alcohols are less poisonous than ethanol because the liver is unable to metabolise them into these toxic by-products. This makes them more suitable for recreational^[17][18] and medicinal^[19] use as the chronic harms are lower. Ethchlorvynol is a good example of a tertiary alcohol which saw both medicinal and recreational use.

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 the liver by alcohol dehydrogenase and formaldehyde dehydrogenase enzymes, respectively; accumulation of formic acid can lead to blindness or death.^[20] Likewise, poisoning due to other alcohols such as ethylene glycol or diethylene glycol are due to their metabolites, which are also produced by alcohol dehydrogenase.^[21][22] An effective treatment to prevent toxicity after methanol or ethylene glycol ingestion is to administer ethanol. Alcohol dehydrogenase has a higher affinity for ethanol, thus preventing methanol from binding and acting as a substrate. Any remaining methanol will then have time to be excreted through the kidneys.^[20][23][24]

Methanol itself, while poisonous, has a much weaker sedative effect than ethanol. Some longer-chain alcohols such as n-propanol, isopropanol, n-butanol and t-butanol do, however, have stronger sedative effects, but also have higher toxicity than ethanol.^[25][26] These longer chain alcohols are found as contaminants in some alcoholic beverages and are known as fusel alcohols,^[27][28] and are reputed to cause severe hangovers although it is unclear if the fusel alcohols are actually responsible.^[29] Many longer chain alcohols are used in industry as solvents and are occasionally abused by alcoholics,^[30][31] leading to a range of adverse health effects.^[32]

Occurrence in nature[link]

Alcohol has been found outside the Solar System. It can be found in low densities in star and planetary system forming regions of space.^[33]

See also[link]

Notes[link]

References[link]

• Metcalf, Allan A. (1999). The World in So Many Words. Houghton Mifflin. ISBN 0-395-95920-9. 

External links[link]

Look up alcohol in Wiktionary, the free dictionary.

Wikimedia Commons has media related to: Alcohol

Wikiquote has a collection of quotations related to: Alcohol

Jamie Foxx
Foxx promoting Stealth in July 2005
Birth name	Eric Marlon Bishop
Born	(1967-12-13) December 13, 1967 (age 44) Terrell, Texas, United States
Medium	Stand up, Film, Television, Radio, Music
Nationality	American
Years active	1989–present
Genres	Musical comedy, Political satire, Observational comedy, Character comedy, Black comedy (as actor) R&B, hip hop, soul, pop(as singer and rapper)
Subject(s)	Race relations, Racism, African-American culture, Celebrities, Human sexuality, American politics, Current events, Self-deprecation
Influences	Redd Foxx[1]
Notable works and roles	Law Abiding Citizen Jamie King on The Jamie Foxx Show Ray Charles in Ray Nico in Rio
Website	Official site

Eric Marlon Bishop (born December 13, 1967), professionally known as Jamie Foxx, is an American actor, singer-songwriter, rapper, stand-up comedian, and talk radio host who began playing the piano when he was five years old. As an actor, his work in the film Ray earned him the Academy Award and BAFTA Award for Best Actor as well as the Golden Globe Award for Best Actor in a musical/comedy. He is also a Grammy Award winning musician, producing three albums which have charted highly on the Billboard 200: Unpredictable, which topped the chart, Best Night of My Life and Intuition.

Born in Terrell, Texas, Foxx was raised by his mother's adoptive parents. He performed in high school and was awarded with a scholarship to United States International University. In his twenties, Foxx began performing stand-up at comedy clubs, and eventually joined the cast of In Living Color in 1991; this exposure helped him land film roles and star in his own sitcom, The Jamie Foxx Show. He released his debut album, Peep This, in 1994, but he did not gain significant musical success until 2004 when he was featured in Twista's song "Slow Jamz". Also in 2004, Foxx played critically acclaimed roles in the films Collateral and Ray. He released his second album, Unpredictable, in 2005, which was helped by his collaboration on Kanye West's number-one single "Gold Digger". His third album Intuition was released in 2008 and was anchored by the single "Blame It". Foxx released his fourth studio album, Best Night of My Life, in 2010.

Biography[link]

Early life[link]

Foxx was born as Eric Marlon Bishop on December 13, 1967, in Terrell, Texas.^[2] He is the son of Louise Annette Talley Dixon and Shaheed Abdulah. Foxx was abandoned seven months after birth, and was subsequently adopted and raised in Terrell by his mother's adoptive parents. Terrell was a racially segregated community at the time.^[3] Foxx had a strict Baptist upbringing^[4][5] and began piano lessons at the age of five by his grandmother's orders. As a teenager, he was a part-time pianist and choir leader in Terrell's New Hope Baptist Church.^[3]

Foxx attended Terrell High School, where he received top grades, played basketball and football as quarterback, and had an ambition to play for the Dallas Cowboys. He was the first player in the school's history to pass for more than 1,000 yards.^[3][6] He also sang in a band called Leather and Lace.^[3] After completing high school, Foxx received a scholarship to United States International University, where he studied classical music and composition.^[3][7] He has often acknowledged his grandmother's influence in his life as one of the greatest reasons for his success.^[4][8]

[edit] 1989-94: Stand-up career, acting debut, Peep This and legal issue

After accepting a girlfriend's dare, Foxx told jokes and at a comedy club's open mic night in 1989. When he found that comediennes were often called first to perform, he changed his name to Jamie Foxx, feeling that it was an ambiguous enough name to disallow any biases.^[1][3] He chose his surname as a tribute to comedian Redd Foxx.^[1] In addition his recurrent In Living Color character LaWanda shared names with Redd's friend and co-worker, LaWanda Page.

Foxx joined the cast of In Living Color in 1991 and subsequently played a recurring role in the comedy-drama sitcom Roc.^[9] From 1996 to 2001, Foxx starred in his own sitcom The Jamie Foxx Show, and made his film debut in the 1992 comedy Toys. His first dramatic role came in Oliver Stone's 1999 film Any Given Sunday, where he portrayed a hard-partying American football player.^[4] He was cast in the role in part because of his background as a football player.^[4] Following Any Given Sunday, Foxx was featured as taxi driver Max Durocher in the film Collateral alongside Tom Cruise, for which he received outstanding reviews and a nomination for the Academy Award for Best Supporting Actor.^[4] In 1994, Foxx released an album (on the Fox record label) entitled Peep This.

In April 2003, Foxx was involved in an incident with two police officers who were attempting to escort him and his sister out of Harrah's casino in New Orleans. Employees claimed they had failed to show identification upon entry. Originally charged with trespassing, disturbing the peace, battery on police officers and resisting arrest, Foxx pleaded no contest to disturbing the peace in exchange for the other charges being dropped, and was sentenced to a six month suspended jail term with two years probation and a $1,500 fine.^[10][11]

In 2003, Foxx made a cameo in Benzino's music video for "Would You", which features LisaRaye McCoy and Mario Winans.

[edit] 2004-06: Ray, Collateral, and Unpredictable

Foxx and Kanye West performing "Gold Digger"

His music career shifted into a higher gear when, in 2004, he was featured on rapper Twista's song, "Slow Jamz", which also featured Kanye West. The song reached #1 on the U.S. Billboard Hot 100 singles chart, as well as #3 on the UK Singles chart. Foxx's second collaboration with Kanye West, "Gold Digger," in which he sang the "I Got a Woman" Ray Charles-influenced hook, went straight to #1 on the Billboard Hot 100, and remained there for 10 weeks. In 2005, Foxx was featured on the single "Georgia" by Atlanta rappers Ludacris and Field Mob. The song sampled Ray Charles' hit "Georgia on My Mind." He also had a beginning verse on Kanye's "Gold Digger."

His standout performance, however, was his portrayal of Ray Charles in the biopic Ray (2004), for which he won the Academy Award for Best Actor^[4] and the BAFTA Award for Best Actor in a Leading Role. Foxx is the second male in history to receive two acting Oscar nominations in the same year for two different movies, Collateral and Ray. The only other male actor to achieve this was Al Pacino. In 2005, Foxx was invited to join the Academy of Motion Picture Arts and Sciences.^[12]

Foxx released his second studio album, Unpredictable, in December 2005. It debuted at #2, selling 598,000 copies in its first week.^[13] The following week, the album rose to #1, selling an additional 200,000 copies.^[14] To date, the album has sold 1.98 million copies in the United States, and was certified double Platinum by the RIAA.^[15][16] The album also charted on the UK Albums Chart, where it peaked at #9.^[17] Foxx became the fourth artist to have won an Academy Award^® for an acting role and to have achieved a #1 album in the U.S. (The other three to accomplish this feat were Frank Sinatra, Bing Crosby, and Barbra Streisand.) Foxx's first single from the album, the title track "Unpredictable" (featuring Ludacris), samples "Wildflower" by New Birth. The song peaked in the Billboard Hot 100 Top 10 singles and also made the UK Top 20 singles chart. The second U.S. single from the album was "DJ Play a Love Song," which reunited Foxx with Twista. In the UK, however, the second single was "Extravaganza," which saw Foxx once again collaborate with Kanye West. He was not, however, featured in the song's music video.

At the 2006 Black Entertainment Television (BET) Awards, Foxx won Best Duet/Collaboration with Kanye West for "Gold Digger" and tied with Mary J. Blige's "Be Without You" for Video of the Year. On December 8, 2006, Foxx received four Grammy Award^® nominations, which included Best R&B Performance by a Duo or Group with Vocals for Love Changes featuring Mary J. Blige, Best R&B Album for Unpredictable, Best Rap Performance by a Duo or Group for Georgia by Ludacris & Field Mob featuring Jamie Foxx, and Best Rap/Sung Collaboration for Unpredictable featuring Ludacris.

[edit] 2006-2009: Dreamgirls, The Soloist, Intuition and Miley Cyrus incident

Foxx's star on the Hollywood Walk of Fame

Following these successes, Foxx appeared in Jarhead, Miami Vice, and Dreamgirls, which were box-office hits, and lifted his profile even higher as a bankable star in Hollywood. 2007 brought him the lead role in the film The Kingdom opposite Chris Cooper, Jason Bateman, Jennifer Garner and Ashraf Barhom. In September 2007, Foxx was awarded a star on the Hollywood Walk of Fame. He said, upon receiving the honor, "[it was] one of the most amazing days of my life."^[18]

On January 22, 2007, Foxx was on Sirius Satellite Radio, announcing his new channel The Foxxhole. The channel features talk-radio programs, stand-up comedy albums, and music primarily by African-American performers, and features much of Foxx's own material as well. The Jamie Foxx Show, Foxx's own talk-radio variety program, airs Friday evenings on The Foxxhole, and features Johnny Mack, Speedy, The Poetess, Lewis Dix, and T.D.P., as his co-hosts. Guests include popular musicians, actors, and fellow comedians. He recorded a song with country superstars Rascal Flatts entitled "She Goes All the Way" for their album, Still Feels Good. Foxx also performed background vocals for artist/songwriter Tank. He and The-Dream are featured on Plies' "Please Excuse My Hands." He also appeared on the remix of Ne-Yo's "Miss Independent" entitled "She Got Her Own." The track also features Fabolous. Foxx then collaborated with rapper The Game on the track "Around The World." In April 2009, Foxx played the lead role in the dramatic film The Soloist. A few months later in October 2009, He played a starring role along side Gerard Butler in the thriller Law Abiding Citizen. In April 2011, Foxx voiced Nico, a canary in the movie Rio.

Foxx released his third album titled Intuition in 2008, featuring such artists as Kanye West, T.I., Ne-Yo, and T-Pain. The album's first single, "Just Like Me" featuring T.I., was promoted by a video directed by Brett Ratner and featuring an appearance by Taraji P. Henson. The second single "Blame It" featured T-Pain and became a top 5 single on the Billboard Hot 100 and a number-one single on the Billboard Hot R&B/Hip-Hop Songs chart. The "Blame It" music video, directed by Hype Williams, features cameo appearances by Forest Whitaker, Samuel L. Jackson, Ron Howard, Quincy Jones, and Jake Gyllenhaal, among others. Foxx was also featured on T.I.'s single "Live in the Sky" from the album King. On April 6, 2009 Foxx performed the George Strait song "You Look So Good in Love" at the George Strait Artist of the Decade All-Star Concert. Foxx has been a fan of country music for many years. Jamie Foxx hosted the 2009 BET Awards ceremony on June 28, 2009, which featured several tributes to pop star Michael Jackson, who had died three days prior to the show. Aside from performing "Blame It" with T-Pain and "She Got Her Own" with Ne-Yo and Fabolous, Foxx opened the show with a rendition of Jackson's "Beat It" dance routine and closed the show with a cover of The Jackson 5's "I'll Be There" with Ne-Yo. Foxx stated during the ceremony, "We want to celebrate this black man. He belongs to us and we shared him with everybody else."

On the April 17, 2009 episode of The Jamie Foxx Show on Foxxhole Radio, Foxx and his co-hosts made several sexually suggestive and disparaging jokes regarding teenaged singer Miley Cyrus, in response to a caller's comment on a recent altercation between Cyrus and rock band Radiohead.^[19] Foxx issued a public apology on The Tonight Show with Jay Leno several days later in response to growing public outcry as well as televised criticism by Cyrus's father, country singer Billy Ray Cyrus.^[20]

[edit] 2010-present: Django Unchained and Best Night of My Life

In 2011, Foxx was officially cast in the title role of, Django Unchained. It will be written and directed by Quentin Tarantino, and he will star alongside his Ray co-star Kerry Washington, Christoph Waltz, Leonardo DiCaprio, and Samuel L. Jackson. As a producer, Foxx played a role in In the Flow with Affion Crockett on Fox in summer 2011.^[21]

Foxx released his fourth album, Best Night of My Life, on December 21, 2010.^[22] The first single is "Winner", featuring Justin Timberlake and T.I..^[23] The second single is "Living Better Now" featuring rapper Rick Ross and the third single is "Fall For Your Type" featuring rapper Drake.^[22] On October 7, RCA Music Group announced it was disbanding J Records along with Arista Records and Jive Records. With the shutdown, Foxx (and all other artists previously signed to these three labels) will release his future material on the RCA Records brand.^[24][25] In 2011, Jamie Foxx was featured in the rapper Pitbull's album 'Planet Pitt' in the song "Where Do We go".

Personal life[link]

This section requires expansion.

Foxx has a daughter, Corinne Bishop, who was born in 1994.^[3] Former Jamie Foxx Show co-star Garcelle Beauvais made a public announcement stating that Foxx has a second child.^[26] Foxx was spotted with the baby in Miami for New Year's Eve 2010, and it was revealed to be a girl.^[27]

Foxx performed a public service announcement for Do Something to promote food drives in local communities.^[28]

Jamie Foxx began playing the piano when he was five years old.

Discography[link]

• Peep This (1994)
• Unpredictable (2005)
• Intuition (2008)
• Best Night of My Life (2010)

Hosted Mixtapes

• Young Buck - Chronic 2006

Tours[link]

• The Unpredictable Tour (2006)
• The Blame It Tour (2009)

Filmography[link]

Awards and nominations[link]

Television Awards

• Image Awards
  • 1998, Outstanding Actor in a Comedy Series: The Jamie Foxx Show
  • 1999, Outstanding Actor in a Comedy Series: The Jamie Foxx Show (nominated)
  • 2000, Outstanding Actor in a Comedy Series: The Jamie Foxx Show (nominated)
  • 2001, Outstanding Actor in a Comedy Series: The Jamie Foxx Show (nominated)

Music awards

• American Music Awards
  • 2009, Favorite R&B/Soul Male Artist (nominated)
  • 2006, Favorite R&B/Soul Male Artist (winner)
  • 2006, Favorite R&B/Soul Album: Unpredictable (nominated)

• BET Awards
  • 2006, Best Male R&B Artist (nominated)
  • 2006, Best Collaboration ("Unpredictable") with Ludacris (nominated)
  • 2009, Best Collaboration ("Blame It") with T-Pain (Winner)
  • 2009, Video of the Year: ("Blame It") (nominated)
  • 2009, Best Male R&B Artist (nominated)

• Grammy Awards
  • 2010, Best R&B Performance by a Duo or Group ("Blame It") with T-Pain (winner)
  • 2010, Best Contemporary R&B Album (Intuition) (nominated)
  • 2010, Best R&B Song ("Blame It") (nominated)
  • 2007, Best Rap/Sung Collaboration ("Unpredictable") with Ludacris (nominated)
  • 2007, Best Rap Performance by a Duo or Group ("Georgia") with Ludacris & Field Mob (nominated)
  • 2007, Best R&B Performance by a Duo or Group ("Love Changes") with Mary J. Blige (nominated)
  • 2007, Best R&B Album (Unpredictable) (nominated)
  • 2006, Best Rap/Sung Collaboration ("Slow Jamz") with Twista & Kanye West (nominated)
  • 2006, Best Male R&B Vocal Performance ("Creepin") (nominated)

• Image Awards
  • 2009, Outstanding Male Artist (winner)
  • 2006, Outstanding Male Artist (winner)

• MOBO Awards
  • 2006, Best R&B Act (nominated)

• MTV Video Music Awards
  • 2006, Best Hip-Hop Video: "Gold Digger" with Kanye West (nominated)
  • 2006, Best Ringtone: "Gold Digger" with Kanye West (nominated)
  • 2006, Best R&B Video: "Unpredictable" featuring Ludacris (nominated)
  • 2004, MTV2 Award: "Slow Jamz" with Twista & Kanye West (nominated)