Amyl alcohol

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An amyl alcohol is any of eight alcohols with the formula C5H12O. [1] A mixture of amyl alcohols (also called amyl alcohol) can be obtained from fusel alcohol. Amyl alcohol is used as a solvent and in esterification, by which is produced amyl acetate and other important products. The name amyl alcohol without further specification applies to the normal (straight-chain) form, 1-pentanol. [2]

These are the 8 alcohols that are structural isomers with molecular formula C5H12O:

Amyl alcohol isomers
Common nameStructureType IUPAC name Boiling point (°C) [3]
1-pentanol
or normal amyl alcohol
Pentan-1-ol-2D-skeletal.png primary Pentan-1-ol 138.5
2-methyl-1-butanol
or active amyl alcohol
2-Methyl-1-butanol.svg primary 2-Methylbutan-1-ol 128.7
3-methyl-1-butanol
or isoamyl alcohol
or isopentyl alcohol
Isoamyl alcohol.svg primary 3-Methylbutan-1-ol 131.2
2,2-dimethyl-1-propanol
or neopentyl alcohol
Neopentyl-alcohol-2D-skeletal.png primary 2,2-Dimethylpropan-1-ol 113.1
2-pentanol
or sec-amyl alcohol
or methyl (n) propyl carbinol
Pentan-2-ol-2D-skeletal.png secondary Pentan-2-ol 118.8
3-methyl-2-butanol
or sec-isoamyl alcohol
or methyl isopropyl carbinol
3-methylbutan-2-ol-2D-skeletal.png secondary 3-Methylbutan-2-ol 113.6
3-Pentanol Pentan-3-ol-2D-skeletal.png secondary Pentan-3-ol 115.3
2-methyl-2-butanol
or tert-amyl alcohol
Tert-pentyl-alcohol-2D-skeletal.png tertiary 2-Methylbutan-2-ol 102

Three of these alcohols, 2-methyl-1-butanol, 2-pentanol, and 3-methyl-2-butanol (methyl isopropyl carbinol), are therefore optically active.

The most important amyl alcohol is isoamyl alcohol, the chief one generated by fermentation in the production of alcoholic beverages and a constituent of fusel oil. The other amyl alcohols may be obtained synthetically.

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In chemistry, a structural isomer of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term metamer was formerly used for the same concept.

1-Pentanol, (or n-pentanol, pentan-1-ol), is an alcohol with five carbon atoms and the molecular formula C5H11OH. 1-Pentanol is a colourless liquid with a distinctive aroma. It is the straight-chain form of amyl alcohol, one of 8 isomers with that formula.

Fusel alcohols or fuselol, also sometimes called fusel oils in Europe, are mixtures of several higher alcohols produced as a by-product of alcoholic fermentation. The word Fusel[ˈfuːzl̩] is German for "bad liquor".

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

2-Butanol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol. isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-butanol and (S)-(+)-2-butanol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

<span class="mw-page-title-main">Lucas' reagent</span>

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<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

<span class="mw-page-title-main">Pentyl group</span> Chemical compound

Pentyl is a five-carbon alkyl group or substituent with chemical formula -C5H11. It is the substituent form of the alkane pentane.

<span class="mw-page-title-main">Isobutanol</span> Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<span class="mw-page-title-main">Isoamyl alcohol</span> Chemical compound

Isoamyl alcohol is a colorless liquid with the formula C
5
H
12
O
, specifically (H3C–)2CH–CH2–CH2–OH. It is one of several isomers of amyl alcohol (pentanol). It is also known as isopentyl alcohol, isopentanol, or (in the IUPAC recommended nomenclature) 3-methyl-butan-1-ol. An obsolete name for it was isobutyl carbinol.

<span class="mw-page-title-main">1-Butanol</span> Chemical compound

1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.

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The molecular formula C5H12O (molar mass: 88.15 g/mol, exact mass: 88.088815) may refer to:

The molecular formula C6H14O may refer to:

<i>tert</i>-Amyl alcohol Chemical compound

tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol.

<span class="mw-page-title-main">2-Methyl-1-butanol</span> Chemical compound

2-Methyl-1-butanol is an organic compound with the formula CH3CH2CH(CH3)CH2OH. It is one of several isomers of amyl alcohol. A colorless liquid, it occurs naturally in trace amounts and has attracted some attention as a potential biofuel, exploiting its hydrophobic (gasoline-like) and branched structure. It is chiral.

<span class="mw-page-title-main">2-Pentanol</span> Chemical compound

2-Pentanol is an organic chemical compound. It is used as a solvent and an intermediate in the manufacturing of other chemicals. 2-Pentanol is a component of many mixtures of amyl alcohols sold industrially. 2-Pentanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-pentanol and (S)-(+)-2-pentanol.

<span class="mw-page-title-main">2-Methyl-2-pentanol</span> Chemical compound

2-Methyl-2-pentanol is an organic chemical compound. It can be added to a gas chromatograph to help distinguish between branched compounds, especially alcohols. Its presence in urine can be used to test for exposure to 2-methylpentane. As with many other short-chain alcohols, 2-methyl-2-pentanol can produce intoxication and sedative effects similar to those of ethanol, though it is more irritating to mucous membranes and generally more toxic to the body.

<span class="mw-page-title-main">Prenderol</span> Chemical compound

Prenderol (Diethylpropanediol) is a simple alkyl diol which has sedative, anticonvulsant and muscle relaxant effects. It is closely related in structure to meprobamate and numerous other alkyl alcohols and diols with generally comparable activity.

References

  1. Merriam-Webster's Collegiate Dictionary 11th Ed. 2004
  2. Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter (2000). "Alcohols, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a01_279. ISBN   3527306730.
  3. Calculated boiling points from ChemSpider.