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The conversion of ethanol to ethylene is a fundamental example: [3] [4] CH 3 CH 2 OH → H 2 C=CH 2 + H 2 O. The reaction is accelerated by acid catalysts such as sulfuric acid and certain zeolites. These reactions often proceed via carbocation intermediates as shown for the dehydration of cyclohexanol. [5] Some alcohols are prone to dehydration.
Typically, generating a stable carbocation for a prolonged period of time is difficult, due to the possibility for the cation to be quenched by a β-protons attached to another monomer in the backbone, or in a free monomer. Therefore, a different approach is taken [4] [5] [17] This is an example of a controlled/living cationic polymerization.
Living cationic polymerization is a living polymerization technique involving cationic propagating species. [1] [2] It enables the synthesis of very well defined polymers (low molar mass distribution) and of polymers with unusual architecture such as star polymers and block copolymers and living cationic polymerization is therefore as such of commercial and academic interest.
Examples of heterocyclic monomers. Heterocyclic monomers that are cationically polymerized are lactones, lactams and cyclic amines. Upon addition of an initiator, cyclic monomers go on to form linear polymers. The reactivity of heterocyclic monomers depends on their ring strain.
An example in scheme 2 is the reaction of tert-butylbromide with potassium ethoxide in ethanol. E1 eliminations happen with highly substituted alkyl halides for two main reasons. Highly substituted alkyl halides are bulky, limiting the room for the E2 one-step mechanism; therefore, the two-step E1 mechanism is favored.
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] In the present-day definition given by the IUPAC, a carbocation is any even-electron cation with significant partial positive charge on a carbon atom.
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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.