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The vinyl cation is a carbocation with the positive charge on an alkene carbon. Its empirical formula of the parent ion is C 2 H + 3.Vinyl cation are invoked as reactive intermediates in solvolysis of vinyl halides, [1] [2] as well as electrophilic addition to alkynes and allenes.
However, reactions that would require the formation of unstable carbocations (methyl, vinyl, aryl or primary carbon) proceed via S N 2 mechanism. The hydrohalic acid also plays an important role, as the rate of reaction is greater with hydroiodic acid than with hydrobromic acid. Hydrochloric acid only reacts under more rigorous conditions.
Based on hydride ion affinity, the parent vinyl cation is less stable than even a primary sp 2-hybridized carbocation, while an α alkyl-substituted vinyl cation has a stability that is comparable to the latter. Hence, vinyl cations are relatively uncommon intermediates.
A carbocation is an ion with a positively charged carbon atom. Among the simplest examples are the methenium CH + 3, methanium CH + 5, acylium ions RCO +, and vinyl C 2 H + 3 cations. [2] Until the early 1970s, carbocations were called carbonium ions. [3]
Most chemical reactions take more than one elementary step to complete, and a reactive intermediate is a high-energy, hence unstable, product that exists only in one of the intermediate steps. The series of steps together make a reaction mechanism .
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This forms a carbocation intermediate, and the X then bonds to the positive carbon that is available, as in the following two-step reaction. [4] CH 2 CH 2 + HX → CH 2 CH + 3 + X − CH 2 CH + 3 + X − → CH 2 XCH 3. Similarly, in an H 2 O addition reaction, the pi bond of an alkene acts as a nucleophile and bonds with the proton of an [H 3 ...