View source for Tert-Butyl chloride

{{DISPLAYTITLE:''tert''-Butyl chloride}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 309623926
| Name=''tert''-Butyl chloride
| 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<br/>1-chloro-1,1-dimethylethane<br/>chlorotrimethylmethane<br/>trimethylchloromethane<br/>''t''-butyl chloride
| Section1 = {{Chembox Identifiers
|   CASNo = 507-20-0
|    CASNo_Ref = {{cascite}}
|   EC-number = 208-066-4
|   ChemSpiderID = 10054
|   PubChem = 10486
|   SMILES = CC(C)(C)Cl
|   RTECS = TX5040000
|   UNNumber = 1127
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>4</sub>H<sub>9</sub>Cl
|   MolarMass = 92.57 g/mol
|   Appearance = Colorless liquid
|   Density = 0.84 g cm<sup>−3</sup>
|   MeltingPtC = −26
|   BoilingPtC = 51
|   Solubility = Sparingly sol in water, miscible with alcohol and ether
|   VaporPressure = 34.9 kPa (20 °C)
  }}
| Section3 = {{Chembox Hazards
|   EUClass = Flammable ('''F''')
|   MainHazards = 
|   FlashPt = −9 °C (open cup)<br>−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 [[solvation|dissolved]] into it. The compound is [[flammable]] and [[Volatile organic compound|volatile]], and its main use is as a starting molecule to carry out [[nucleophilic substitution|nucleophilic substitution reactions]], to produce different substances, ranging from [[alcohols]] to [[alkoxide]] [[salts]].

When ''tert''-butyl chloride is dissolved in water, a [[chemical polarity|polar]] and [[protic solvent]], the bulky [[chloride]] [[substituent]] is carried away by it, and isolated from the [[aliphatic compound|aliphatic chain]], 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.

==Synthesis==
''tert''-Butyl chloride can be synthesized in the laboratory by the S<sub>N</sub>1 reaction of [[Tert-Butanol|''tert''-Butanol]] with concentrated [[hydrochloric acid]], as shown below.

{|align="center"  class="wikitable"
|<center>'''Step 1'''</center>||<center>'''Step 2'''</center>||<center>'''Step 3'''</center>
|-
|<center>[[Image:1-HCl-protonates-tBuOH-2D-skeletal.png|250px]]</center>||<center>[[Image:2-water-leaves-protonated-tBuOH-2D-skeletal.png|250px]]</center>||<center>[[Image:3-chloride-attacks-tBu-cation-2D-skeletal.png|250px]]</center>
|-
|<center>The acid protonates the alcohol, forming a good [[leaving group]] (water).</center>||<center>Water leaves the protonated <em>t</em>-BuOH, forming a relatively stable tertiary [[carbocation]].</center>||<center>The chloride ion attacks the carbocation, forming <em>t</em>-BuCl.</center>
|}

The overall reaction, therefore, is:

[[Image:0-SN1-tBuOH-to-tBuCl-2D-skeletal.png|250px]]

Because ''tert''-butanol is a tertiary alcohol, the relative stability of the ''tert''-butyl carbocation in the Step 2 allows the [[SN1|S<sub>N</sub>1]] mechanism to be followed, whereas a primary alcohol would follow an [[SN2|S<sub>N</sub>2]] 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]

{{DEFAULTSORT:Butyl chloride, tert-}}
[[Category:Organochlorides]]

[[de:2-Chlor-2-methylpropan]]
[[nl:2-chloor-2-methylpropaan]]
[[zh:叔丁基氯]]
[[Category:2Fix]]