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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.
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]
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.
Here, a strong Lewis acid is required to generate either a carbocation from an alkyl halide in the Friedel-Crafts alkylation reaction or an acylium ion from an acyl halide. In the vast majority of cases, reactions that involve leaving group activation generate a cation in a separate step, before either nucleophilic attack or elimination.
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In this case one must examine the rate-limiting step and the intermediates. Often, the rate-limiting step is the initial formation of an unstable species such as a carbocation. Then, once the carbocation is formed, subsequent rearrangements can occur.
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