''tert''-Butyl chloride is the
organochloride
Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds that contain one or more carbon–chlorine bonds. The chloroalkane class (alkanes with one or more hydrogens substituted ...
with the formula . It is a colorless, flammable liquid. It is sparingly soluble in
water
Water is an inorganic compound with the chemical formula . It is a transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance. It is the main constituent of Earth's hydrosphere and the fluids of all known liv ...
, 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 Chemical compound, compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hyd ...
.
[ In the laboratory, concentrated ]hydrochloric acid
Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungency, pungent smell. It is classified as a acid strength, strong acid. It is ...
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 colorless, odorless 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