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Another class of oxonium ions encountered in organic chemistry is the oxocarbenium ions, obtained by protonation or alkylation of a carbonyl group e.g. R−C= + −R′ which forms a resonance structure with the fully-fledged carbocation R− + −O−R′ and is therefore especially stable:
The IUPAC acknowledges the three divergent definitions of carbonium ion and urges care in the usage of this term. For the remainder of this article, the term carbonium ion will be used in this latter restricted sense, while non-classical carbocation will be used to refer to any carbocation with C–C and/or C–H σ-bonds delocalized by bridging.
Compared to a ketone, the polarization of an oxocarbenium ion is accentuated: they more strongly resemble a "true" carbocation, and they are more reactive toward nucleophiles. In organic reactions, ketones are commonly activated by the coordination of a Lewis acid or Brønsted acid to the oxygen to generate an oxocarbenium ion as an intermediate.
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.
Substitution reactions in organic chemistry are classified either as electrophilic or nucleophilic depending upon the reagent involved, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a free radical, and whether the substrate is aliphatic or aromatic. Detailed understanding of a reaction type helps to ...
Printable version; In other projects ... A carbocation is a compound containing a positively charged carbon atom. ... This list may not reflect recent changes. ...
In organic chemistry, a carbanion is an anion in which carbon is negatively charged. [1] [failed verification]Formally, a carbanion is the conjugate base of a carbon acid: . R 3 CH + B − → R 3 C − + HB
In order for a reaction to follow Markovnikov's rule, the intermediate carbocation of the mechanism of a reaction must be on the more-substituted carbon, allowing the substituent to bond to the more-stable carbocation and the more-substituted carbon. [2] 1,2-disubstituted Cycloalkene undergoing syn and anti addition