''tert''-Butyl chloride is the
organochloride
An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalent bond, covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens subst ...
with the formula . It is a colorless, flammable liquid. It is sparingly soluble in
water
Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as a ...
, with a tendency to undergo
hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
to the corresponding ''tert''-butyl alcohol. It is produced industrially as a precursor to other organic compounds.
[M. Rossberg et al. "Chlorinated Hydrocarbons" in ''Ullmann's Encyclopedia of Industrial Chemistry'' 2006, Wiley-VCH, Weinheim. ]
Synthesis
''tert''-Butyl chloride is produced by the reaction of ''tert''-butyl alcohol with
hydrogen chloride
The compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colourless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hydrogen chloride ga ...
.
[ In the laboratory, concentrated ]hydrochloric acid
Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid
Acid strength is the tendency of an acid, symbol ...
is used. The conversion entails a SN1 reaction as shown below.[James F. Norris and Alanson W. Olmsted "''tert''-Butyl Chloride" Org. Synth. 1928, volume 8, pp. 50. ]
The overall reaction, therefore, is:
:
Because ''tert''-butanol is a tertiary alcohol, the relative stability of the ''tert''-butyl carbocation in the step 2 allows the SN1 mechanism to be followed, whereas a primary alcohol would follow an SN2 mechanism.
Reactions
When ''tert''-butyl chloride is dissolved in water, it undergoes a hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
to ''tert''-butyl alcohol. When dissolved in alcohols, the corresponding t-butyl ethers are produced.
Uses
''tert''-Butyl chloride is used to prepare the antioxidant ''tert''-butylphenol and the fragrance neohexyl chloride.[
]
See also
* Isobutane
Isobutane, also known as ''i''-butane, 2-methylpropane or methylpropane, is a chemical compound with molecular formula HC(CH3)3. It is an isomer of butane. Isobutane is a colourless, odourless gas.
It is the simplest alkane with a tertiary carbon a ...
References
External links
Safety MSDS data
http://www.cerlabs.com/experiments/10875407331.pdf
{{DEFAULTSORT:Butyl chloride, tert-
Chloroalkanes
Tert-butyl compounds