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

The Cataracs are an American hip hop indie-pop duo formed in Berkeley, California, consisting of David “Campa” Benjamin Singer-Vine, a songwriter and vocalist and Niles “Cyrano” Hollowell-Dhar, a songwriter, vocalist, and producer. The duo started out as an independent group, during their years at Berkeley High School. The two were first signed to the label Indie-Pop. They are currently based in Los Angeles, California.

Biography[link]

Early days[link]

The duo met in their sophomore year while attending Berkeley High School. Singer-Vine was featured in a rap CD that was being passed around campus. When Dhar eventually heard the CD, he subsequently created a response. However, the “diss” response brought the two together and they soon became friends. In 2003, the two joined together to create what is now The Cataracs (named after the phrase “Who smoke ‘til your eyes get cataracts” from Snoop Dogg's song “What's my name Pt. 2”).^[1] In the summer of 2006, they released their first album, Technohop Vol. 1. In August 2006, the group joined with The Pack to make the single “Blueberry Afghani”. The song soon became a hit and was chosen as a “Download of the Week” by 106 KMEL and many music sites such as The Fader, UK’s Hip Hop Connection and XLR8R praised it.^[2]

Dhar went on to attend Lehigh University in Bethlehem, Pennsylvania and Singer-Vine attended Columbia College Chicago, in Chicago, Illinois.^[3] Niles Dhar is also a member of Pi Kappa Phi Fraternity. But in order to pursue their dreams and career in music, they both decided that they would have to leave school. The duo then packed their bags and moved to Los Angeles, CA, where they began working on their music full-time, creating songs like "Club Love" and “Baby Baby", the latter which went on to be featured on the hit reality series Keeping Up with the Kardashians in early 2010.^[4] By 2007, they released their second album, Technohop Vol. 2, and in 2008 they released their third album The 13th Grade.^[5]

Rise to fame[link]

In their new stage, they discovered Manteca, California native, Dev, a singer who posted much of her work on MySpace. Dhar asked if she would like to sing for them, which led to the song "2Nite." The Cataracs, along with Dev, signed to the Indie-Pop Label, which also features musicians such as Young L.^[6] They were later signed to a major label, Universal Records.^[7] Through Universal, they began producing music for artists such as Far East Movement and Glasses Malone. As artists, The Cataracs received recognition through their 2010 single "Club Love", which received air play at clubs and on many different radio stations. Despite such accomplishments, the Cataracs have had their most mainstream success with the song "Like a G6" which was written by Singer-Vine/Dhar and produced by Dhar.^[8] and also went on to peak at #1 on the Billboard charts.^[9] The chorus for the song is sampled from lyrics in the song "Booty Bounce" by Dev, which they also produced. They were featured on two of Shwayze's songs on his 2010 mixtape Love Stoned. The duo also produced songs for albums such as The Pack new album, Wolfpack Party. In early December 2010, a collaboration with Snoop Dogg, the inspiration behind the group's name, had leaked and is rumored to become Snoop Dogg's second single for his upcoming album Doggumentary. Produced "Kick Us Out" for pop trio Hyper Crush. On July 17, 2011 Campa released a free album on his website, campaiscold.com titled Would You Hate Me If I Took a Sip? along with 3 music videos to go along with it.

Discography[link]

Studio albums

• Technohop Vol. 1 (2006)
• Technohop Vol. 2 (2007)
• The 13th Grade (2008)
• Songs We Sung in Showers (2009)
• 12 (TBA)

Extended plays

• Lingerie (2008)

Mixtapes

• Kids - Presented by DJ Eleven (2008)
• Yeah Buddy! - Mixed by DJ Excel (2009)
• The Stimulating Package (2009)
• I Thought They Were Black?! - Presented by DJ Greg Street (2010)

Singles[link]

As featured artist[link]

Guest appearances[link]

Production credits[link]

• 2009: " Back It Up" Colette Carr
• 2010: "Fireball" (Dev)
• 2010: "Wet" (Snoop Dogg)
• 2010: "Booty Bounce" (Dev)
• 2010: "Bass Down Low" (Dev feat. The Cataracs)
• 2010: "Like a G6" (Far East Movement feat. The Cataracs and Dev)
• 2010: "Kick Us Out" (Hyper Crush)
• 2010: "Backseat" (New Boyz)
• 2010: "Malibu Is Poppin'" Colette Carr
• 2011: "Better with the Lights Off" (New Boyz feat. Chris Brown)
• 2011: "Love Letter" (Shwayze feat. The Cataracs and Dev)
• 2011: "In the Dark" (Dev)
• 2011: "I'm On It" (50 Cent)
• 2011: "City Nights" (Mistah F.A.B. feat. T-Pain)
• 2011: "Whiplash" ([Lisa D'Amato feat. Loco Ninja])
• 2012: "Naked" (Dev feat. Enrique Iglesias)

Music videos[link]

References[link]

External links[link]

• The Cataracs

References[link]

Brad Paisley
Brad Paisley performing on August 19, 2007
Background information
Birth name	Brad Douglas Paisley
Born	(1972-10-28) October 28, 1972 (age 39)
Origin	Glen Dale, West Virginia, United States
Genres	Country, Country Rock
Occupations	Singer-songwriter, musician
Instruments	Vocals, guitar, mandolin
Years active	1997–present
Labels	Arista Nashville
Associated acts	Alison Krauss, Dolly Parton, Carrie Underwood, Keith Urban, Martina McBride, Chely Wright, Scotty McCreery
Website	BradPaisley.com

Brad Douglas Paisley (born October 28, 1972) is an American singer-songwriter and musician. His style crosses between traditional country music and Southern rock, and his songs are frequently laced with humor and pop culture references.

Paisley was the 2008 CMA and ACM Male Vocalist of the Year winner. Starting with the release of his 1999 album Who Needs Pictures, Paisley has recorded seven studio albums and a Christmas compilation on the Arista Nashville label, with all of his albums certified gold or higher by the RIAA.^[1] In addition, he has charted 25 singles on the U.S. Billboard Hot Country Songs chart, 16 of which have reached #1 with a record 10 consecutive singles reaching the top spot on the chart.^[2] On November 10, 2010, Paisley won the Entertainer of the Year award at the 44th annual CMA Awards.^[3]

Biography[link]

Paisley was born on October 28, 1972 in Glen Dale, West Virginia to Douglas Edward "Doug" Paisley, who worked for the West Virginia Department of Transportation, and Sandra Jean "Sandy" (née Jarvis) Paisley, a teacher.^[4] He was raised in Glen Dale, West Virginia. He has stated that his love of country music stems from his maternal grandfather, Warren Jarvis, who gave Paisley his first guitar, a Sears Danelectro Silvertone^[5] at 8-years-old and taught him how to play. At age 10, he performed for the first time in public by singing in his church. He later recalled that, "Pretty soon, I was performing at every Christmas party and Mother's Day event. The neat thing about a small town is that when you want to be an artist, by golly, they'll make you one".^[5] At age 12, Paisley wrote his first song, entitled, "Born on Christmas Day".^[5] He had been taking lessons with local guitarist Clarence "Hank" Goddard.^[5] By age 13, Goddard and Paisley formed a band called "Brad Paisley and the C-Notes", with the addition of two of Paisley's adult friends.^[5]

While in junior high, his principal heard him perform "Born On Christmas Day" and invited him to play at the local Rotary Club meeting. In attendance was Tom Miller, the program director of a radio station in Wheeling, West Virginia. Miller asked him if he would like to be a guest on Jamboree USA. After his first performance, he was asked to become a member of the show's weekly lineup. For the next eight years, he opened for country singers such as The Judds, Ricky Skaggs and George Jones. He would become the youngest person inducted into the Jamboree USA Hall of Fame. He also performed at the Jamboree in the Hills.^[6]

Paisley graduated from John Marshall High School in Glen Dale, West Virginia in 1991,^[7] studied for 2 years at West Liberty University (WV) and later was awarded a full-paid ASCAP scholarship to Belmont University, in Nashville, Tennessee (from 1993 to 1995). He interned at ASCAP, Atlantic Records, and the Fitzgerald-Hartley management firm. While in college, he met Frank Rogers, a fellow student who went on to serve as his producer. Paisley also met Kelley Lovelace, who became his songwriting partner. He also met Chris DuBois in college, and he too would write songs for him.^[6]

After graduating from Belmont with a Bachelor's degree in music business, within a week Paisley signed a songwriting contract with EMI Music Publishing;^[6] and, he wrote David Kersh's "Top 5" hit, "Another You", as well as David Ball's 1999 single, "Watching My Baby Not Come Back." The latter song was also co-written by Ball.^[8]

[edit] 1999–2001: Who Needs Pictures

His debut as a singer was with the label Arista Nashville, with the song "Who Needs Pictures" (released February 22, 1999). In May of that same year, he made his first appearance on the Grand Ole Opry.^[1] Seven months later he had his first #1 hit with "He Didn't Have to Be," which detailed the story of Paisley's frequent co-writer Kelley Lovelace and Lovelace's stepson, McCain Merren.^[9] We Danced also was a hit for Paisley off the debut album, reaching #1 on the U.S. Billboard Hot Country Singles & Tracks chart. By February 2001, the album was certified platinum.^[10]

In 2000, Paisley's mainstream notoriety received a huge boost when he was exposed to his first national non-country music oriented audience on the TLC special, "Route 66: Main Street America." Producer, Todd Baker, tapped the young musician to appear on this show when he was a relative unknown outside the world of country music. It featured Paisley and band doing rare live and acoustic versions of Route 66. The international and home video versions of this program end with a full, un-cut acoustic rendition of the piece, which was performed live on Rainbow Bridge in Riverton, KS.^[11] The show accurately predicted that Paisley would become a legendary musician, and also featured blues artist, Buddy Guy.^[12]

Later in 2000, Paisley won the Country Music Association's (CMA) Horizon Award and the Academy of Country Music's best new male vocalist trophy. He received his first Grammy Award nomination a year later for Best New Artist. On February 17, 2001, Paisley was inducted into the Grand Ole Opry^[1] He was 28 when he accepted the invitation, and was the youngest member ever to join. PBS did a 75th anniversary concert special, which saw Paisley pair up with Chely Wright and sing a song called Hard to Be a Husband, Hard to Be a Wife, and would be included on the album Backstage at the Opry, It would get a CMA nomination for Vocal Event of the Year.^[13]

[edit] 2001–2003: Part II

In 2002, he won the CMA Music Video of the Year for "I'm Gonna Miss Her (The Fishin' Song)." Several celebrities made notable guest appearances in the video, including Little Jimmy Dickens, Kimberly Williams, Dan Patrick, and Jerry Springer. His three other singles off the Part II album, "I Wish You'd Stay", "Wrapped Around", and "Two People Fell in Love", all charted in the top 10. The album stayed in the charts for more than 70 weeks and was certified platinum in August 2002. To support his album, he toured the country as the opening act for Lonestar.^[14]

[edit] 2003–2005: Mud on the Tires

Paisley released his third album, Mud on the Tires (2003), following Who Needs Pictures and Part II. The album features the hit song "Celebrity", the video of which parodies reality shows such as Fear Factor, American Idol, The Bachelorette and According to Jim, and included such celebrities as Jason Alexander, James Belushi, Little Jimmy Dickens, Trista Rehn and William Shatner. (Paisley later contributed to Shatner's album Has Been.) The album's title track, "Mud on the Tires", reached Billboard #1 in 2004.^[15]

In addition, the ninth track from Mud on the Tires, "Whiskey Lullaby", a duet with Alison Krauss reached #3 on the Billboard Hot Country Singles & Tracks (now Hot Country Songs) charts, and #41 on the Billboard Hot 100. The music video for Whiskey Lullaby also won several awards and was rated #2 on the 100 Greatest Music Videos by CMT in 2008. The album would be certified double platinum.^[14]

[edit] 2005–2007: Time Well Wasted

In 2005, after touring with Reba McEntire and Terri Clark on the "Two Hats and a Redhead Tour," he released Time Well Wasted, containing 15 tracks. This album includes "Alcohol," two duets — "When I Get Where I'm Going" with Dolly Parton and "Out in the Parking Lot" with Alan Jackson — and a bonus track, "Cornography." On November 6, 2006, the album "Time Well Wasted" won the Country Music Association CMA Award for Best Album. "Time Well Wasted" also won album of the year at the 2006 ACM Awards.

Paisley also contributed two original songs to the Disney film Cars. These can be found on the film's soundtrack. This was in recognition of his contribution to the "Route 66: Main Street America" television special.

At the 2006 Grammy Awards, Paisley received four nominations: Best Country Album (for Time Well Wasted), Best Country Song (for "Alcohol"), Best Country Instrumental (for "Time Warp") and Best Country Vocal, Male (for "Alcohol").

[edit] 2007–2008: 5th Gear

Paisley's fifth studio album, 5th Gear, was released in the United States on June 19, 2007. The first four singles from the album, "Ticks", "Online", "Letter to Me", and "I'm Still a Guy", all reached number one on the country music single charts, making seven straight number one hits for Paisley."^[16] "Online" featured the Brentwood High School marching band playing toward the end of the song, a cameo by Jason Alexander, and again featured a cameo by William Shatner. Throttleneck would also reach number one, which would get Paisley his first Grammy.^[17]

The fifth single from 5th Gear actually came from a reissued version of the album – a new recording of "Waitin' on a Woman", a track cut from Time Well Wasted. The reissued version received unsolicited airplay in late 2006, and features less prominent string guitar and violin parts and a more "muted" musical tone. For the chart week of September 20, 2008, the song became Paisley's twelfth number-one single and his eighth straight number-one hit, making him the artist with the most consecutive Number One country hits since the inception of Nielsen SoundScan in 1990.^[18]

In July 2006, producer Todd Baker tapped Brad for a television appearance as an animated character in The Wonder Pets, Daddy Armadillo. The yet-to-be-broadcast episode features Brad's wife, Kimberly Williams, as Mama Armadillo.

Paisley toured April 26, 2007 through February 24, 2008 in support of 5th Gear on the Bonfires & Amplifiers Tour. The tour visited 94 cities over a 10 month period and played for over 1,000,000 fans. The tour was so successful that it was extended past its original end date to February 2008. Some of the opening acts who appeared during the tour were Taylor Swift, Kellie Pickler, Jack Ingram, Rodney Atkins and Chuck Wicks.

Paisley was nominated for three 2008 Grammy Awards related to 5th Gear: Best Country Album (for 5th Gear), Best Country Collaboration (for "Oh Love" with Carrie Underwood), and Best Country Instrumental (for "Throttleneck"). On February 10, 2008, he won his first Grammy award for Best Country Instrumental for "Throttleneck".

In March 2008, Brad Paisley announced his next tour, "The Paisley Party," a 42-date tour sponsored by Hershey's. The tour kicked off on June 11, 2008, in Albuquerque, New Mexico with Chuck Wicks, Julianne Hough and Jewel as the opening acts.^[16]

[edit] 2008–2009: Play

A sixth, largely instrumental album, titled Play, was released on November 4, 2008.^[19] Brad Paisley and Keith Urban released to country radio their first duet together on September 8, 2008, "Start a Band." It was the first and only single from Play, and it went on to become Paisley's thirteenth number one hit and his ninth in a row. The album also features collaborations with James Burton, Little Jimmy Dickens, Vince Gill, John Jorgenson, B.B. King, Albert Lee, Brent Mason, Buck Owens, Redd Volkaert and Steve Wariner. Paisley and Urban both received Entertainer of the Year nominations from the CMA on September 10, 2008. On November 12, 2008 Brad Paisley won Male Vocalist of the Year and Music Video of the Year for "Waitin' on a Woman" during the CMA's.

[edit] 2009–2010: American Saturday Night

Brad Paisley performing at the White House.

Brad Paisley announced on January 26, 2009 his new tour named "American Saturday Night." Dierks Bentley and Jimmy Wayne will be opening in the majority of the shows. Brad Paisley's newest album, American Saturday Night was released on June 30, 2009. The album's lead off single, "Then" was released in March 2009 and performed for the first time on American Idol on March 18. It went on to become Paisley's 14th number one single and his tenth in a row.

On May 6, 2009, Paisley gave an exclusive performance^[20] to a small group of members from his fan club in Studio A of the Grand Ole Opry in Nashville, TN as he and his band taped an episode of CMT Invitation Only. The show gives fans a chance to see their favorite artists in a more intimate setting up close and personal. There was a Q & A session and interaction between Paisley and his fans. The show aired on Monday, August 3 at 9:00 p.m. on CMT.

On July 21, 2009, Paisley performed at the White House in celebration of country music. "Country Music at the White House " was streamed live on the White House web-site as well as a special on Great American Country.

On November 11, 2009, Paisley co-hosted the CMA Awards for the second straight year. He also performed "Welcome to the Future", and won both Male Vocalist of the Year and Musical Event of the Year for Start a Band with Keith Urban.

On March 1, 2010, Paisley was the first musical performance with "American Saturday Night" for the second tenure of the Tonight Show with Jay Leno.

On Friday March 5, 2010, Paisley slipped and fell performing his last song of the set, "Alcohol," at a concert at the North Charleston Coliseum in Charleston, South Carolina, on the final date of the American Saturday Night Tour. Fearing a broken rib, he was held overnight at an area hospital, but was released when a CT scan was negative.^[21]

On July 31, 2010 Brad performed alongside Carrie Underwood at the inaugural Greenbrier Classic PGA Tour Event in Lewisburg, W.Va. An estimated 60,000 people attended the outdoor event to watch Carrie and Brad perform in the pouring rain.

On August 4, 2010, it was announced on his official website that Paisley would release his first official greatest hits package, entitled Hits Alive. Released on November 2, 2010, Hits Alive is a double-disc collection, with one disc containing studio versions of Paisley's hit singles, while the companion disc features previously unreleased live versions of his songs.^[22]

Brad Paisley cohosted the 44th Annual CMA Awards on November 10, 2010, where he was also awarded the CMA's top award, Entertainer of the Year.^[23] During his acceptance speech, Paisley emotionally honored his grandfather, who inspired him to play the guitar.

In 2012, MSN.com listed American Saturday Night as one of the 21 Essential 21st-Century Albums.^[24]

[edit] 2011-present: This Is Country Music

In December 2010, Paisley released "This Is Country Music" as the title track to his eighth studio album, released May 23, 2011. The album's second single, "Old Alabama" (with Alabama), released to country radio on March 14, 2011 and became Paisley's nineteenth number one hit. "Remind Me," with Carrie Underwood, was released May 23, 2011 to radio.

On March 22, 2011, Paisley's website announced a new beta game titled "Brad Paisley World." The game is modeled after other Facebook games such as Farmville or Mafia Wars and features original animation. The game provides a new way for fans to interact with each other and view exclusive material that would otherwise be unavailable.

On May 12, 2011, Paisley's website announced that he would release two songs on the soundtrack for the film Cars 2. One of them would be a collaboration with British pop singer Robbie Williams.

On October 19, 2011, Paisley made a voice cameo as various background characters in the South Park episode "Bass to Mouth". ^[25]

On January 14, 2012, Paisley was a guest on Garrison Keillor's Prairie Home Companion, during which he did a rendition of "Life's Railway to Heaven" by Charles Davis Tillman.^[26]

Brad also tweeted that he has started recording his upcoming album.

On April 25, 2012, Paisley was featured on the South Park episode "Cartman Finds Love", in which he voiced himself,^[27] sang "The National Anthem", and helped Cartman sing the 90's hit song "I Swear", which was popularized in 1994 by the country musician John Michael Montgomery and the pop group All-4-One. ^[28]

Paisley extended his "Virtual Realty" tour throughout the summer of 2012. He will be touring the country and making pit stops at local country music festivals. The goal of these outdoor concerts is to give the audience the full experience of Brad Paisley's music, as many of his songs contain outdoor elements. ^[29]

Tours[link]

• Brooks & Dunn's Neon Circus & Wild West Show 2003
• Mud & Suds Tour 2004 (w/ Sara Evans, Andy Griggs)
• Two Hats & A Redhead Tour 2005 (w/ Reba McEntire, Terri Clark)
• Time Well Wasted Tour 2006 (w/ Sara Evans, Sugarland, Carrie Underwood, Jake Owen, Josh Turner, Billy Currington)
• Bonfires & Amplifiers Tour 2007–2008 (w/ Taylor Swift, Jack Ingram, Kellie Pickler, Rodney Atkins, Chuck Wicks)
• The Paisley Party Tour 2008 (w/ Chuck Wicks, Julianne Hough, Jewel)
• The Paisley Party Tour 2009 (w/ Dierks Bentley, Darius Rucker, Crystal Shawanda)
• American Saturday Night Tour 2009 (w/ Dierks Bentley, Jimmy Wayne)
• American Saturday Night Tour 2010 (w/ Miranda Lambert, Justin Moore)
• The H2O Tour 2010 (w/ Darius Rucker, Justin Moore, Easton Corbin, Steel Magnolia, Josh Thompson)
• The H2O Frozen Over Tour 2011 (w/ Darius Rucker, Jerrod Niemann)
• H2O II: Wetter and Wilder World Tour (w/ Darius Rucker, Blake Shelton, Jerrod Niemann, Sunny Sweeney, The JaneDear Girls, Brent Anderson, Edens Edge)
• Virtual Reality Tour 2012 (w/ The Band Perry, Scotty McCreery)

Band[link]

Paisley records his studio albums, in most part, with the backing of his live band, The Drama Kings. Their first gig together was May 7, 1999. The only changes have been Randel Currie's addition on the steel guitar in 2000 and Jimmy Heffernan's departure in 2001. Also, Jody Harris worked as Paisley's guitar tech until officially becoming a bandmember for the American Saturday Night Tour. As of 2010, the lineup is:

• Brad Paisley – lead vocals, lead guitar
• Gary Hooker – rhythm guitar
• Randle Currie – steel guitar
• Kendal Marcy – keyboards, banjo, mandolin
• Justin Williamson – fiddle, mandolin
• Kenny Lewis – bass guitar
• Ben Sesar – drums

Personal life[link]

Paisley performing in 2006.

Brad Paisley has been married to actress Kimberly Williams since 2003. Paisley had first seen Kimberley Williams in Father of the Bride with a former girlfriend. Brad and his former girlfriend broke up prior to the release of Father of the Bride Part II, which Brad went to see alone.^[30] Brad has stated that he watched Kimberly Williams' performance and thought "She seems like a great girl — smart and funny and all those things that are so hard to find."^[30]

Paisley and Williams began dating in 2001. In 2002, Williams appeared in a video for the song "I'm Gonna Miss Her (The Fishin' Song)," the last release from his Part II album. The two married on March 15, 2003, at Stauffer Chapel on the campus of Pepperdine University after a nine month engagement. They live in Franklin, Tennessee, and have another home in Malibu.

Paisley and Williams first son, William Huckleberry, or "Huck", was born on February 22, 2007, in Nashville, Tennessee.^[31] Their second son, Jasper Warren (named after his grandfather who bought Brad his first guitar), was born on April 17, 2009.^[32]

In the last months of 2000, Paisley had a relationship with fellow country music singer Chely Wright,^[33][34][35] even though Wright and her female lover had moved together into a new home earlier in the year. Wright was touring together with Paisley, with whom she had co-written one song the previous year, and he had been enamored of her ever since. Although she felt no sexual attraction to Paisley, as to all men,^[36][37] she recounts why Paisley was the man she decided to have a relationship with, "he’s wickedly smart, which is one of the reasons why I made the decision to spend time with him. I loved Brad. I never had the capacity to fall in love with him, but I figured if I’m gonna live a less than satisfied life, this is the guy I could live my life with. If I’m gonna be with a boy, this is the boy."^[38] Her actions were further fueled by the fact that she held him in high esteem and great affection in every way other than sexual attraction.^[36][39] In her autobiography she expresses remorse for how she treated him.^[40]

Paisley is a member of the Southern Jurisdiction of the Scottish Rite of Freemasonry,^[41] and a Noble of the AAONMS,^[42] also known as Shriners. He was accompanied by his father, Doug Paisley (32º), for the ceremony on October 28, 2006.^[41]