Tert-Butyl chloride

Chembox new
ImageFileL1 = Tert-butyl-chloride-2D-skeletal.png ImageSizeL1 = 100px
ImageFileR1 = Tert-butyl-chloride-3D-balls.png ImageSizeR1 = 120px
IUPACName = 2-chloro-2-methylpropane
OtherNames = 1,1-dimethylethyl chloride
1-chloro-1,1-dimethylethane
2-chloroisobutane
2-methyl-2-chloropropane
chlorotrimethylmethane
trimethylchloromethane
t-butyl chloride
tert-butyl chloride
t-BuCl
UN 1127
Section1 = Chembox Identifiers
CASNo = 507-20-0
EINECS = 208-066-4
PubChem = 10486
SMILES = CC(C)(C)Cl
InChI = 1/C4H9Cl/c1-4(2,3)5/h1-3H3
RTECS = TX5040000
Section2 = Chembox Properties
Formula = C₄H₉Cl
MolarMass = 92.57 g/mol
Appearance = Colorless liquid
Density = 0.89 g cm⁻³
MeltingPt = −26 °C
BoilingPt = 51 °C
Solubility =
VaporPressure = 34.9 kPa (20 °C)
Section3 = Chembox Hazards
EUClass = Flammable (F)
MainHazards =
FlashPt = −9 °C (open cup)
−23 °C (closed cup)
Autoignition = 540 °C
NFPA-H = 2
NFPA-F = 3
NFPA-R = 0
NFPA-O =
RPhrases = R12, R36/37/38
SPhrases = S7, S9, S16, S29, S33

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 water, a polar and protic solvent, the bulky chloride substituent is carried away by it, and isolated from the aliphatic chain, causing an heterolitic 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.

ynthesis

"tert"-Butyl chloride can be synthesized in the laboratory by the S_N1 reaction of "tert"-Butanol with concentrated hydrochloric acid, 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 S_N1 mechanism to be followed, whereas a primary alcohol would follow an S_N2 mechanism.

See also

* Isobutane

External links

* [http://physchem.ox.ac.uk/MSDS/CH/2-chloro-2-methylpropane.html Safety MSDS data]
* [http://wwwchem.uwimona.edu.jm:1104/lab_manuals/c10expt20.html Preparation 2-chloro-2-methylpropane]
* [http://www.cerlabs.com/experiments/10875407331.pdf http://www.cerlabs.com/experiments/10875407331.pdf]