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Tert-Butyl chloride

1-chloro-1,1-dimethylethane chlorotrimethylmethane trimethylchloromethane t-butyl chloride −23 °C (closed cup) | NFPA-H = 2 | NFPA-F = 3 | NFPA-R = 0

tert-Butyl chloride is the organochloride with the formula . It is a colorless, flammable liquid. It is sparingly soluble in water, with a tendency to undergo hydrolysis to the corresponding tert-butyl alcohol. It is produced industrially as a precursor to other organic compounds.

Synthesis

tert-Butyl chloride is produced by the reaction of tert-butyl alcohol with hydrogen chloride.

The acid protonates the alcohol, forming a good leaving group (water).	Water leaves the protonated t-BuOH, forming a relatively stable tertiary carbocation.	The chloride ion attacks the carbocation, forming t-BuCl.

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 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 base .

References

M. Rossberg et al. "Chlorinated Hydrocarbons" in ''Ullmann's Encyclopedia of Industrial Chemistry'' 2006, Wiley-VCH, Weinheim. {{doi. 10.1002/14356007.a06_233.pub2
In the laboratory, concentrated [[hydrochloric acid]] is used. The conversion entails a S_N1 reaction as shown below.James F. Norris and Alanson W. Olmsted "''tert''-Butyl Chloride" Org. Synth. 1928, volume 8, pp. 50. {{doi. 10.15227/orgsyn.008.0050

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chloroalkanes tert-butyl-compounds

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