tert-Butyl chloride
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| Template:Longitem | Template:Unbulleted list |
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| UN number | 1127 |
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| Template:Longitem | C4H9Cl |
| Molar mass | 92.57 g/mol |
| Appearance | Colorless liquid |
| Density | 0.851 g/ml |
| Melting point | Template:Chembox CalcTemperatures |
| Boiling point | Template:Chembox CalcTemperatures |
| Vapor pressure | 34.9 kPa (20 °C) |
| Template:Longitem | tert-Butyl bromide |
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tert-Butyl chloride is the organochloride with the formula Template:Chem2. 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.[1]
Synthesis
tert-Butyl chloride is produced by the reaction of tert-butyl alcohol with hydrogen chloride.[1] In the laboratory, concentrated hydrochloric acid is used. The conversion entails a SN1 reaction as shown below.[2]
| Step 1 | Step 2 | Step 3 |
| File:1-HCl-protonates-tBuOH-2D-skeletal.png | File:2-water-leaves-protonated-tBuOH-2D-skeletal.png | File:3-chloride-attacks-tBu-cation-2D-skeletal.png |
| 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 neohexyl chloride.[1]
See also
References
- ↑ a b c M. Rossberg et al. "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. Script error: No such module "CS1 identifiers".
- ↑ James F. Norris and Alanson W. Olmsted "tert-Butyl Chloride" Org. Synth. 1928, volume 8, pp. 50. Script error: No such module "CS1 identifiers".