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 name Structure Type 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.

Notes[edit]

  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.