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Ferf-butyl chloride

Use curved arrows to track electron movement in the dehydro-] halogenation of ferf-butyl chloride by sodium methoxide by the E2 mechanism. J... [Pg.215]

The ether-forming step is an S -like reaction of the alkoxide ion on the silicon atom, with concurrent loss of the leaving chloride anion. Unlike most Sn2 reactions, though, this reaction takes place at a tertiary center—a trialJkyl-substituted silicon atom. The reaction occurs because silicon, a third-row atom, is larger than carbon and forms longer bonds. The three methyl substituents attached to silicon thus offer less steric hindrance to reaction than they do in the analogous ferf-butyl chloride. [Pg.627]

In a 250 ml. separatory funnel place 25 g. of anhydrous ZerZ.-butyl alcohol (b.p. 82-83°, m.p. 25°) (1) and 85 ml. of concentrated hydrochloric acid (2) and shake the mixture from time to time during 20 minutes. After each shaking, loosen the stopper to relieve any internal pressure. Allow the mixture to stand for a few minutes until the layers have separated sharply draw off and discard the lower acid layer. Wash the halide with 20 ml. of 5 per cent, sodium bicarbonate solution and then with 20 ml. of water. Dry the preparation with 5 g. of anhydrous calcium chloride or anhydrous calcium, sulphate. Decant the dried liquid through a funnel supporting a fluted Alter paper or a small plug of cotton wool into a 100 ml. distilling flask, add 2-3 chips of porous porcelain, and distil. Collect the fraction boiling at 49-51°. The yield of ferf.-butyl chloride is 28 g. [Pg.276]

Although GC-C-IRMS systems that can measure the chlorine isotopic composition of individual chlorinated hydrocarbons are currently unavailable, it is clear that chlorine isotope analysis is also a useful technique to consider for study [614,677,678]. Measurement of chlorine stable isotope ratios in natural samples such as rocks and waters has become routine [626,679,680], but few measurements of chlorine isotopes in chlorinated aliphatic hydrocarbons have been reported [614]. A chlorine isotope effect was found in ferf-butyl chloride [681], demonstrating that 37Cl is more strongly bound to carbon than is 35Cl. Significant differences in the <5i7Cl values of some atmospheric chlorinated... [Pg.85]

Recent work (Brown and Pearsall, 15) has indicated that while hydrogen aluminum tetrachloride is nonexistent, interaction of aluminum chloride and hydrogen chloride does occur in the presence of substances (such as benzene and presumably, olefins) to which basic properties may be ascribed. It may be concluded that while hydrogen aluminum tetrachloride is an unstable acid, its esters are fairly stable. Further evidence in support of the hypothesis that metal halides cause the ionization of alkyl halides (the products of the addition of the hydrogen halide promoters to the olefins) is found in the fact that exchange of radioactive chlorine atoms for ordinary chlorine atoms occurs when ferf-butyl chloride is treated with aluminum chloride containing radioactive chlorine atoms the hydrogen chloride which is evolved is radioactive (Fair-brother, 16). [Pg.28]

The alkylation of phenylacetylene with ferf-butyl chloride, benzyl chloride, and diphenylmethyl chloride follows an AdE2 mechanism57-59 with the involvement of the open vinyl cationic intermediate 17 ... [Pg.227]

Chloro-2-methy lpropane Isobutyl chloride or 2-methylpropyl chloride 2-Chloro-2-methylpropane ferf-Butyl chloride or 1,1-dimethylethyl chloride... [Pg.1212]

Exercise 8-5 The rate of solvolysis of ferf-butyl chloride in aqueous solution is... [Pg.218]

The equilibrium constant Kp for the gas-phase thermal decomposition of ferf-butyl chloride is 3.45 at 500 K ... [Pg.571]

Propane and cyclopentane give isopropyl chloride and cyclopentyl chloride, respectively, whereas isobutane is transformed to ferf-butyl chloride under the same reaction conditions (yields are 69%, 74%, and 76%, respectively). Neopentane undergoes isomerization to yield 2-chloro-2-butane (88%). When saturated, hydrocarbons were allowed to react with methylene bromide and SbF5 bromoalkanes were obtained in comparable yields (64-75%). Formation of the halogenated product can be best explained by the mechanistic pathway (I) depicted in Scheme 5.55. Since SbF5 always contains some HF, mechanism (II) may also contribute to product formation (Scheme 5.55). [Pg.651]

Preparation by way of the nitrile will not be feasible. Rather than react with sodium cyanide by substitution, ferf-butyl chloride will undergo elimination exclusively. The SN2 reaction with cyanide ion is limited to primary and secondary alkyl halides. [Pg.505]

Hydrochloric acid (HC1) reacts with alcohols in much the same way that hydrobromic acid does. For example, concentrated aqueous HC1 reacts with ferf-butyl alcohol to give ferf-butyl chloride. [Pg.481]

For example, aluminum chloride catalyzes the alkylation of benzene by ferf-butyl chloride. HC1 gas is evolved. [Pg.777]

This alkylation is a typical electrophilic aromatic substitution, with the ferf-butyl cation acting as the electrophile. The ferf-butyl cation is formed by reaction of ferf-butyl chloride with the catalyst, aluminum chloride. The ferf-butyl cation reacts with benzene to form a sigma complex. Loss of a proton gives the product, fm-butylbenzenc. The aluminum chloride catalyst is regenerated in the final step. [Pg.777]

With regard to the sulfmyl chlorides needed for sulfinate ester synthesis, a large number of them are readily accessible by oxidation of the corresponding disulfide according to the Young and Herrmann procedure."4 However, in the case of the more hindered ferf-butyl chloride, Netscher and Prinzbach s method gives better... [Pg.90]

There is direct evidence, from ir and nmr spectra, that the fert-butyl cation is quantitatively formed when ferf-butyl chloride reacts with AICI3 in anhydrous liquid HCl. In the case of alkenes, Markovnikov s rule (p. 1019) is followed. Carbocation formation is particularly easy from some reagents, because of the stability of the cations. Triphenylmethyl chloride and 1-chloroadamantane alkylate activated aromatic rings (e.g., phenols, amines) with no catalyst or solvent. Ions as stable as this are less reactive than other carbocations and often attack only active substrates. The tropylium ion, for example, alkylates anisole, but not benzene. It was noted on p. 476 that relatively stable vinylic cations can be generated from certain vinylic compounds. These have been used to introduce vinylic groups into aryl substrates. Lewis acids, such as BF3 or AIEta, can also be used to alkylation of aromatic rings with alkene units. [Pg.711]

PPM If crystals of A are treated again with more ferf-butyl chloride and aluminium chloride, a new oily compound B may be isolated, this time with a molecular mass of 246. Its H NMR spectrum is similar to that of A, but not quite the same ... [Pg.8]

Benzylic halides resemble allylic halides in the readiness with which they form carbocations. On comparing the rate of S l hydrolysis in aqueous acetone of the following two tertiary chlorides, we find that the benzylic chloride reacts over 600 times faster than does ferf-butyl chloride. [Pg.418]


See other pages where Ferf-butyl chloride is mentioned: [Pg.177]    [Pg.589]    [Pg.303]    [Pg.255]    [Pg.255]    [Pg.594]    [Pg.595]    [Pg.859]    [Pg.859]    [Pg.859]    [Pg.571]    [Pg.571]    [Pg.104]    [Pg.649]    [Pg.649]    [Pg.96]    [Pg.505]    [Pg.320]    [Pg.146]    [Pg.249]    [Pg.280]    [Pg.481]    [Pg.811]    [Pg.149]    [Pg.381]    [Pg.382]    [Pg.104]    [Pg.399]    [Pg.451]   
See also in sourсe #XX -- [ Pg.589 ]




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