|Jmol-3D images||Image 1|
|Molar mass||92.57 g/mol|
|Density||0.84 g cm−3|
|Melting point||−26 °C (−15 °F; 247 K)|
|Boiling point||51 °C (124 °F; 324 K)|
|Solubility in water||Sparingly sol in water, miscible with alcohol and ether|
|Vapor pressure||34.9 kPa (20 °C)|
|EU classification||Flammable (F)|
|S-phrases||S7, S9, S16, S29, S33|
|Flash point||−9 °C (open cup)
−23 °C (closed cup)
|Related alkyl halides||tert-Butyl bromide|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
tert-Butyl chloride is a colorless, liquid organic compound at room temperature. It is sparingly soluble in water, with a tendency to undergo spontaneous solvolysis when dissolved into it. The compound is flammable and volatile, and its main use is as a starting molecule to carry out nucleophilic substitution reactions, to produce different substances, ranging from alcohols to alkoxide salts.
When tert-butyl chloride is dissolved in a polar and protic solvent, like water, it undergoes a solvolysis reaction. The chloride groups leaves, causing an heterolytic rupture of the compound, giving rise to a carbocation which eventually becomes a tertiary alcohol after a water molecule reacts with it, releasing hydrochloric acid as the final product. If a different, stronger nucleophilic agent is present at the moment of reaction, reaction product may not be an alcohol, but a tertiary carbon with the nucleophile as a substituent. Because of the steric hindrance of the tert-butyl group the solvolysis reaction follows the SN1 mechanism nad not the SN2 mechanism.
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.