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Chemical compound
"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. In the laboratory, concentrated hydrochloric acid is used. The conversion entails a SN1 reaction as shown below.
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 neohexyl chloride.