Amyl alcohol

Amyl alcohols are alcohols with the formula C5H11OH.[1] Eight are known. 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 products. The name amyl alcohol without further specification applies to the normal (straight-chain) form, 1-pentanol.[2]

Amyl alcohol isomers
Common name Structure Type IUPAC name Boiling point (°C)[3]
1-pentanol
or normal amyl alcohol 		primary Pentan-1-ol 138.5
2-methyl-1-butanol
or active amyl alcohol 		primary 2-Methylbutan-1-ol 128.7
3-methyl-1-butanol
or isoamyl alcohol
or isopentyl alcohol 		primary 3-Methylbutan-1-ol 131.2
2,2-dimethyl-1-propanol
or neopentyl alcohol 		primary 2,2-Dimethylpropan-1-ol 113.1
2-pentanol
or sec-amyl alcohol
or methyl (n) propyl carbinol 		secondary Pentan-2-ol 118.8
3-methyl-2-butanol
or sec-isoamyl alcohol
or methyl isopropyl carbinol 		secondary 3-Methylbutan-2-ol 113.6
3-Pentanol secondary Pentan-3-ol 115.3
2-methyl-2-butanol
or tert-amyl alcohol 		tertiary 2-Methylbutan-2-ol 102

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

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.
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