tert-Butyl chloride
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| Names | |||
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| IUPAC name
2-chloro-2-methylpropane
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| Other names
1,1-dimethylethyl chloride
1-chloro-1,1-dimethylethane chlorotrimethylmethane trimethylchloromethane t-butyl chloride |
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| Identifiers | |||
507-20-0  |
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| ChEMBL | ChEMBL346997 |
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| ChemSpider | 10054 |
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| EC Number | 208-066-4 | ||
| Jmol 3D model | Interactive image | ||
| PubChem | 10486 | ||
| RTECS number | TX5040000 | ||
| UN number | 1127 | ||
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| Properties | |||
| C4H9Cl | |||
| Molar mass | 92.57 g/mol | ||
| Appearance | Colorless liquid | ||
| Density | 0.851 g/mL | ||
| Melting point | −26 °C (−15 °F; 247 K) | ||
| Boiling point | 51 °C (124 °F; 324 K) | ||
| Sparingly sol in water, miscible with alcohol and ether | |||
| Vapor pressure | 34.9 kPa (20 °C) | ||
| Vapor pressure | {{{value}}} | ||
| Related compounds | |||
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Related alkyl halides
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tert-Butyl bromide | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is  ?) |
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| Infobox references | |||
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 and not the SN2 mechanism.
Synthesis
tert-Butyl chloride can be synthesized in the laboratory by the SN1 reaction of tert-Butanol with concentrated hydrochloric acid, as shown below.
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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.
