Isobutyl chloride

One drawback to Fnedel-Crafts alkylation is that rearrangements can occur espe cially when primary alkyl halides are used For example Friedel-Crafts alkylation of benzene with isobutyl chloride (a primary alkyl halide) yields only tert butylbenzene... 

Chloro 2 methylpropane Isobutyl chloride or 2 methylpropyl chloride 2 Chloro 2 methylpropane tert Butyl chloride or 1 1 dimethylethyl chloride... 

Isobutyl chloride (l-chloro-2-methylpropane) [513-36-0] n 1.398. Same methods as described under isoamyl chloride. 

C,HifC 60736-79-0) see Ibuprofen isobutyl bromide (QH Br 78-77-3) see Butalbital isobutyl chloride... 

Isobutane Isobutyl chloride (63%) tert-butyl chloride (37%)... 

Isobutyl bromide, b371 Isobutyl chloride, cl79 Isobutyl chlorocarbonate, i68 Isobutyl ether, d458 Isobutyl mercaptan, m3 9 5 Isobutyl methyl ketone, m3 70... 

Recently, the radical cation of PBN has been characterized by matrix spectroscopy and its reactivity has been studied by fast spectroscopic methods (Zubarev and Brede, 1994), and found to conform to the behaviour deduced from the OsCU and TBPA + studies. y-Radiolysis of PBN in a glassy matrix of isobutyl chloride or Freon-113 (CF2C1CFC12) at 77 K produced an intensely green glass containing PBN +, the epr spectrum of which had an anisotropic nitrogen coupling constant Ay = 2.75 mT and gy = 2.0037. Tlie mechanism of the radiolysis reaction is well established (Neta, 1976) and involves the formation of solvated electrons (e ), which add to the matrix species and produce chloride ion, and positive holes (h+) which eventually come to rest at the matrix component of lowest Ip (Symons, 1997), in this case PBN (see reactions (30) and (31)). 

The reaction of isobutyl chloride at —50° with 2% water present leads to a mixture of 13% n-butane which has exchanged 0 9 protons and 87% isobutane which essentially has not exchanged any. With 5% water, unexchanged isobutane is again recovered, but the n-butane has exchanged nearly two protons with the acid, even though the reaction was run at —78°. 

The behaviour of the butyl system provides important information on the nature of the intermediate formed during the rearrangement of the isobutyl to the 2-butyl cation. Thus, from the observation that isobutyl chloride yields n-butane which has exchanged one proton with the acid, while the solvolysis of 2-butyl chloride in the same acid (2% HjO), yields unexchanged n-butane one might deduce that an intermediate was formed during the former s solvolysis which exchanged one proton with the acid before it converted to a secondary butyl ion. A reasonable mechanism is shown in Scheme 1. 

Isobutyl chloride FALSE FALSE FALSE FALSE... 

Problem 4,33 Synthesize (a) 2-methylpentane from CH,CH=CH—CH(CH,), (b) isobutane from isobutyl chloride, (c) 2-methyl-2-deuterobutane from 2-chloro-2-methylbutane. Show all steps. ... 

Problem 6.53 Outline the steps needed for the following syntheses in reasonable yield. Inorganic reagents and solvents may also be used, (a) IXhloropentane to 1,2-dichloropentane. (b) IXhloropentane to 2-chloro-pentane. (c) IXhloropentane to 1-bromopentane. (d) l-Bromobutane to 1.2-dihydroxybutane. (e) Isobutyl chloride to... 

Probl0in 7.2 Give the structural formula and lUPAC name for (a) isobutyl chloride, (f>) f-amyl bromide (amyls pentyl). 

Methylpropane l-Chloro-2-methylpropane (63%) (isobutyl chloride) 2-Chloro-2-methylpropane (37%) (rert-butyl chloride)... 

Isobutyl chloride- rerr-Butyl cation Tetrachloroaluminate... 

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