Tert-Butyl chloride
# Tert-Butyl chloride

tert-Butyl chloride is the organochloride with the formula $(CH_3)_3CCl.$ 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 $S_N1$ reaction as shown below.

| Step 1 | Step 2 | Step 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:

    $(CH_3)_3COH$ + HCl → $(CH_3)_3CCl$ + $H_2O$

Because tert-butanol is a tertiary alcohol, the relative stability of the tert-butyl carbocation in the step 2 allows the $S_N1$ mechanism to be followed, whereas a primary alcohol would follow an $S_N2$ 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.

