Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Tert-Butyl chloride: Difference between pages

{{DISPLAYTITLE:''tert''-Butyl chloride}}

| Watchedfields = changed

| verifiedrevid = 470602836

| Name =''tert''-Butyl chloride

| ImageFile2 = Tert butyl chloride.jpg

| ImageSize2 = 50px

| PIN = 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

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = JN2YO95TZ0

| EC_number = 208-066-4

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| PubChem = 10486

| SMILES = ClC(C)(C)C

| RTECS = TX5040000

| UNNumber = 1127

}}

|Section2={{Chembox Properties

| Formula = C₄H₉Cl

| MolarMass = 92.57 g/mol

| Appearance = Colorless liquid

| Density = 0.851 g/ml

| MeltingPtC = −26

| BoilingPtC = 51

| Solubility = Sparingly soluble in water, miscible with alcohol and ether

| VaporPressure = 34.9 kPa (20 °C)

}}

|Section3={{Chembox Hazards

| FlashPtC = −9

| FlashPt_notes = (open cup)<br>−23 °C (closed cup)

| AutoignitionPtC = 540

| NFPA-H = 2

| NFPA-F = 3

| NFPA-R = 0

| GHSPictograms = {{GHS02}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|225}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|280|303+361+353|370+378|403+235|501}}

}}

|Section8={{Chembox Related

| OtherFunction_label = [[alkyl halide]]s

| OtherFunction = [[tert-Butyl bromide]]

}}

'''''tert''-Butyl chloride''' is the [[organochloride]] with the formula {{chem2|(CH3)3CCl}}. 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.<ref name=Ullmann>M. Rossberg et al. "Chlorinated Hydrocarbons" in ''Ullmann's Encyclopedia of Industrial Chemistry'' 2006, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a06_233.pub2}}</ref>

== Synthesis ==

''tert''-Butyl chloride is produced by the reaction of ''tert''-butyl alcohol with [[hydrogen chloride]].<ref name=Ullmann/> In the laboratory, concentrated [[hydrochloric acid]] is used. The conversion entails a S_N1 reaction as shown below.<ref>James F. Norris and Alanson W. Olmsted "''tert''-Butyl Chloride" Org. Synth. 1928, volume 8, pp. 50. {{doi|10.15227/orgsyn.008.0050}}</ref>

{| class="wikitable" style="text-align:center;"

| '''Step 1'''||'''Step 2'''||'''Step 3'''

|-

| [[File:1-HCl-protonates-tBuOH-2D-skeletal.png|250px]]||[[File:2-water-leaves-protonated-tBuOH-2D-skeletal.png|250px]]||[[File:3-chloride-attacks-tBu-cation-2D-skeletal.png|250px]]

|-

| 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:

:{{chem2|(CH3)3COH + HCl -> (CH3)3CCl + H2O}}

Because ''tert''-butanol is a tertiary alcohol, the relative stability of the ''tert''-butyl carbocation in the step 2 allows the [[SN1|S_N1]] mechanism to be followed, whereas a primary alcohol would follow an [[SN2|S_N2]] mechanism.

==Reactions==

When ''tert''-butyl chloride is dissolved in water, it undergoes a [[hydrolysis]] to [[tert-Butyl alcohol|''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.<ref name=Ullmann/>

== See also ==

* [[Isobutane]]

==References==

<references />

== External links ==

* [https://web.archive.org/web/20160303234638/http://faculty.uscupstate.edu/labmanager/MSDS%20files/1097%20-%202-Chloro-2-methylpropane%20(tert%20butyl%20chloride).pdf Safety MSDS data]

* [https://web.archive.org/web/20070501061548/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:Chloroalkanes]]

[[Category:Tert-butyl compounds]]