Everything about 1-hexanol totally explained
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1-Hexanol is an organic
alcohol with a six
carbon chain and a condensed structural formula of CH
3(CH
2)
5OH. This colorless liquid is slightly soluble in water, but
miscible with
ether and
ethanol. Two additional straight chain isomers of 1-hexanol exist,
2-hexanol and 3-hexanol, both of which differ by the location of the hydroxyl group. Many isomeric alcohols have the formula C
6H
13OH. 1-hexanol is believed to be a component of the odour of freshly mowed grass. It is used in the
perfume industry.
Preparation
Hexanol is produced industrially by the oligomerization of
ethylene using
triethylaluminium followed by oxidation of the
alkylaluminium products. An idealized synthesis is shown:
» Al(C
2H
5)
3 + 6 C
2H
4 → Al(C
6H
13)
3
Al(C
6H
13)
3 + 3 O + 3 H
2O → 3 HOC
6H
13 + Al(OH)
3
The process generates a range of oligomers that are separated by
distillation.
Alternative methods
Another method of preparation entails
hydroformylation of
1-pentene followed by
hydrogenation of the resulting aldehydes. This method is practiced industrially to produce mixtures of isomeric C6-alcohols, which are precursors to
plasticizers.
[
In principle, 1-hexene could be converted to 1-hexanol by hydroboration (diborane in tetrahydrofuran followed by treatment with hydrogen peroxide and sodium hydroxide):]
This method is instructive and useful in laboratory synthesis but of no practical relevance because of the commercial availability of inexpensive 1-hexanol from ethylene.
2-Hexanol
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2-Hexanol (or hexan-2-ol) is a six carbon alcohol in which the OH group is located on the second carbon atom. It is an isomer of 1-hexanol, 3-hexanol, 2-methylpentanol, 3-methylpentanol, 2,3-dimethylbutanol, 2-ethylbutanol and many more compounds. Its chemical formula is C6H14O or C6H13OH. 2-Hexanol has a chiral center and can be resolved into enantiomers.
Further Information
Get more info on '1-hexanol'.
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