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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]
The 2-norbornyl cation is one of the best characterized carbonium ion. It is the prototype for non-classical ions. As indicated first by low-temperature NMR spectroscopy and confirmed by X-ray crystallography, [1] it has a symmetric structure with an RCH 2 + group bonded to an alkene group, stabilized by a bicyclic structure.
The chemical basis for Markovnikov's Rule is the formation of the most stable carbocation during the addition process. Adding the hydrogen ion to one carbon atom in the alkene creates a positive charge on the other carbon, forming a carbocation intermediate.
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.
For example, (C 6 H 5)(CH 3) 2 C + is referred to as a "benzylic" carbocation. The benzyl free radical has the formula C 6 H 5 CH 2 •. The benzyl cation or phenylcarbenium ion is the carbocation with formula C 6 H 5 CH + 2; the benzyl anion or phenylmethanide ion is the carbanion with the formula C 6 H 5 CH − 2.
It is a carbocation and an enium ion, making it the simplest of the carbenium ions. [3] ... The carbon atom is a prototypical (and exact) example of sp 2 hybridization.
This arises from the fact that polar solvents stabilize the formation of the carbocation intermediate to a greater extent than the non-polar-solvent conditions. This is apparent in the ΔE a, ΔΔG ‡ activation. On the right is an S N 2 reaction coordinate diagram. Note the decreased ΔG ‡ activation for the non-polar-solvent reaction ...
For example, when pentan-3-ol is heated with aqueous HCl, the initially formed 3-pentyl carbocation rearranges to a mixture of the 3-pentyl and 2-pentyl. These cations react with chloride ion to produce 3-chloropentane and 2-chloropentane in a ratio of approximately 1:2.