Iodoethane Ethyl iodide

The third example in Table 6.8 is particularly interesting since the product shown is an intermediate in a general method for the synthesis of various trisubsti-tuted alkenes. Thus, the alkylcopper-magnesium bromide species (the Nonnant reagent) adds to a primary alkyne so that the alkyl and metal addends are Z- (or syn-, or cis- or suprafacial) with the metal at C-1. In a second (and thus separate) step and with stereochemical retention (i), a second alkyl group can be added—as an alkyl iodide, for example, iodoethane (ethyl iodide, CH3CH2I)— which then replaces the metal (ii) a carboxylic add can be formed by treatment of the copper reagent with carbon dioxide (CO2) or (iii) iodine (I2) itself can be used so that a vinyl iodide results (Scheme 6.74). 

Scheme 1031. Alkylation on nitrogen. Benzamide (benzenecarboxamide) is alkylated by iodoethane (ethyl iodide, CH3CH2I) on nitrogen after generation of the amide anion with potassium hydride (KH). Subsequently, the AT-ethylbenzamide (Al-ethylbenzenecarboxamide) can be hydrolyzed by aqueous acid to produce benzoic acid (benzenecarboxylic acid) and thecorrespondingethylammoniumsalt.Alternatively,theAl-ethylbenzamide(Al-ethylbenzene-carboxamide) can be reduced with, for example, hthium aluminum hydride (LiAlHi) in ether [(CH3CH2)20], and, after hydrolysis, Af-benzylethanamine is produced.

Athyl-jodid, n, ethyl iodide, iodoethane. -rho-danid, n, ethyl thiocyanate, -rot, n. ethyl red. -schwefelsaure, /, ethylsulfurie acid, -senfol, n, ethyl mustard oil (CsHcNCS). -sulfhydrat, n, ethyl hydrosulfide, -verbindung, /, ethyl compound, -wasserstoff,... 

Jod-ather, m. iodo ether, -athyl, n. ethyl iodide, iodoethane. 

Meanwhile Frankland had been pursuing his own attempts to isolate free radicals. His method was to react together a metal with an organic cyanide or halide in the hope that combination would occur between the metal and the halide or cyanide, leaving the organic radical in the free state. The most important experiments involved zinc and ethyl iodide (iodoethane). The reactions occurring in terms of modem equations are ... 

Scheme 14.22 utilizes ethyl iodide (iodoethane) and the t-butyl ester of acetoacetic acid (t-butyl 3-oxobutanoate) in a similar set of condensation reactions. Here, however, the t-butyl ester is not hydrolyzed under basic conditions, and... 

Ethyl iodide (iodoethane) 19.2 Diethylene glycol monobutyl ether 20.9... 

Acidic ether cleavages are typical nucleophilic substitution reactions, either SN1 or Sn2 depending on the structure of the substrate. Ethers with only primary and secondary alkyl groups react by an S 2 mechanism, in which or Br attacks the protonated ether at the less hindered site. This usually results in a selective cleavage into a single alcohol and a single alkyl halide. For example, ethyl isopropyl ether yields exclusively isopropyl alcohol and iodoethane on cleavage by HI because nucleophilic attack by iodide ion occurs at the less hindered primary site rather than at the more hindered secondary site. 

Reaction of quinoxaline with iodoethane in refluxing acetonitrile gives ethyl quinoxalini-um iodide, and treatment of the parent base with methyl p-toluenesulfonate gives methyl quinoxalinium jt -toluenesulfonate in a high yield. ... 

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