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Amyl alcohol



Amyl alcohol is an organic compound with the formula C5H11OH. All eight isomers of amyl alcohol are known:

Isomers of amyl alcohol
name formula alcohol structure IUPAC Name
normal amyl alcohol primary 1-pentanol
isobutyl carbinol
or isoamyl alcohol
or isopentyl alcohol
primary 3-methyl-1-butanol
active amyl alcohol primary 2-methyl-1-butanol
tertiary butyl carbinol
or neopentyl alcohol
primary 2,2-dimethyl-1-propanol
diethyl carbinol secondary 3-pentanol
methyl (n) propyl carbinol secondary 2-pentanol
methyl isopropyl carbinol secondary 3-methyl-2-butanol
dimethyl ethyl carbinol
or tertiary amyl alcohol
tertiary 2-methyl-2-butanol

Additional recommended knowledge

Three of these alcohols, active amyl alcohol, methyl (n) propyl carbinol, and methyl isopropyl carbinol, are optically active, as they contain an asymmetric carbon atom.

The most important is isobutyl carbinol, this being the chief constituent of fermentation amyl alcohol, and consequently a constituent of fusel oil. It can be separated from fusel oil by shaking with strong brine solution, separating the oily layer from the brine layer and distilling it, the portion boiling between 125 and 140 °C. being collected. For further purification it may be shaken with hot lime water, the oily layer separated, dried with calcium chloride and fractionated, the fraction boiling between 128 and 132 °C only being collected. It may be synthezed from isobutanol by conversion into isovaleraldehyde, which is subsequently reduced to isobutyl carbinol by means of sodium amalgam.

It is a colourless liquid of density 0.8247 g/cm³ (0 °C), boiling at 131.6 °C, slightly soluble in water, easily soluble in organic solvents. It possesses a characteristic strong smell and a sharp burning taste. When pure, it is nontoxic, while the impure product is toxic. On passing its vapour through a red-hot tube, it decomposes with production of acetylene, ethylene, propylene, and other compounds. It is oxidized by chromic acid to isovaleraldehyde, and it forms crystalline addition compounds with calcium chloride and tin(IV) chloride.

The other amyl alcohols may be obtained synthetically. Of these, tertiary butyl carbinol has been the most difficult to obtain, its synthesis having first been reported in 1891, by L. Tissier (Comptes Rendus, 1891, 112, p. 1065) by the reduction of a mixture of trimethyl acetic acid and trimethylacetyl chloride with sodium amalgam. It is a solid that melts at 48 to 50 °C and boils at 112.3 °C.

References

  • This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Amyl_alcohol". A list of authors is available in Wikipedia.
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