Neophyl chloride: Difference between revisions

{{chembox

| verifiedrevid = 400323784

| ImageFile = Neophyl chloride.png

| IUPACName = (2-chloro-1,1-dimethylethyl)benzene

| OtherNames = (Chloro-tert-butyl)benzene

| Section1 = {{Chembox Identifiers

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

| SMILES = ClCC(c1ccccc1)(C)C

| CASNo = 515-40-2

| CASNo_Ref =

| EINECS =

| RTECS =

| Section2 = {{Chembox Properties

| Formula = C₁₀H₁₃Cl

| MolarMass = 168.663 g/mol

| Appearance = colorless liquid

| Density = 1.047 g/cm³

| Solubility = organic solvents

| BoilingPt = 223 °C

'''Neophyl chloride''', C₆H₅C(CH₃)₂CH₂Cl, is a halogenated [[organic compound]] with unusual nucleophilic substitution properties. Neophyl chloride is used to form a versatile [[organolithium reagent]], neophyl lithium, by reaction with lithium.<ref>Lide, R. D.; ''CRC Handbook of Chemistry and Physics''. 2003, 590. ISBN 0849305950</ref><ref>[[Andrew Streitwieser]] and [[Clayton H. Heathcock]]. ''Introduction to Organic Chemistry''. 3rd ed. New York: Macmillan Co., 1985. ISBN 0029467209</ref>

Neophyl chloride was first synthesized by Haller and Ramart by reacting the chlorinating reagent [[thionyl chloride]] with neophyl alcohol:{{Fact|date=May 2009}}

It is easily prepared on a large scale by combining [[benzene]] and [[methallyl chloride]] in the presence of a [[catalysis|catalytic]] quantity of [[sulfuric acid]].<ref>{{OrgSynth | prep = cv4p0702 | year = 1963 | title = Neophyl chloride | author = W. T. Smith, Jr. and J. T. Sellas}}</ref> The reaction is an example of an [[electrophilic aromatic substitution]].

:H₂C=C(CH₃)₂CH₂Cl + C₆H₆ → C₆H₅C(CH₃)₂CH₂Cl

Alternatively ''tert''-butylbenzene can be [[chlorination|chlorinated]] with [[sulfuryl chloride]].

Neophyl chloride can be used to form an organolithium reagent, neophyl lithium, by reaction with [[lithium]]. Organolithium reagents are useful due to their [[nucleophile|nucleophilic]] properties and their ability to form carbon to carbon bonds, like in reactions with [[carbonyl]]s.

:C₆H₅C(CH₃)₂CH₂Cl + Li → C₆H5C(CH₃)₂CH₂Li

Neophyl chloride is of interest to organic chemists due to its substitution properties. Neophyl chloride is a [[neopentane|neopentyl]] [[halide]] which means it is subject to the [[neopentyl effect]]. This effect makes SN₂ [[nucleophilic substitution]] highly unlikely because of [[steric effects|steric interaction]]s due to the branching of the β-carbon. No [[conformational isomerism|rotamer]] of the molecule would allow a backside attack of the α carbon.

[[beta-Hydride elimination|&beta;-Hydride elimination]] also does not occur with neophyl derivatives as this group lacks hydrogens at the β positions. These factors make neophyl chloride a precursor to intermediates that resist common substitution and [[elimination reaction]]s.

[[Category:Aromatic compounds]]