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A carbocation is an ion with a positively-charged carbon atom. Among the simplest examples are methenium CH+3, methanium CH+5, and ethanium C2H+7. Some carbocations may have two or more positive charges, on the same carbon atom or on different atoms; such as theethylene dication C2H2+4.
Until the early 1970s, all carbocations were called carbonium ions. In present-day chemistry, a carbocation is any positively charged carbon atom, classified in two main categories according to thevalence of the charged carbon: three in the carbenium ions (protonated carbenes), and five or six in the carbonium ions.
The charged carbon atom in a carbocation is a "sextet", i.e. it has only six electrons in its outer valence shell instead of the eight valence electrons that ensures maximum stability (octet rule). Therefore, carbocations are often reactive, seeking to fill the octet of valence electrons as well as regain a neutral charge. One could reasonably assume a carbocation to have sp3hybridization with an empty sp3 orbital giving positive charge. However, the reactivity of a carbocation more closely resembles sp2 hybridization with a trigonal planar molecular geometry. An example is the methyl cation, CH3+.
Carbocations are often the target of nucleophilic attack by nucleophiles likehydroxide (OH−) ions or halogen ions.
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