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.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. In the laboratory, concentrated hydrochloric acid 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.
Step 1Step 2Step 3 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 .
See also Isobutane
References
External links Safety MSDS data Preparation 2-chloro-2-methylpropane http://www.cerlabs.com/experiments/10875407331.pdf