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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.
Electron donors (e.g. nucleophiles, Lewis bases) for example dimethylsulfide and dimethylsulfoxide are believed to stabilize the carbocation. The addition of salt for example a tetraalkylammonium salt, prevents dissociation of the ion pair that is the propagating reactive site. Ion dissociation into free ions lead to non-living polymerization.
[7] Carbonium ions can be thought of as protonated or alkylated alkanes, bearing the general formula CR 5 + (R = alkyl or H). A typical example is the methanium ion, CH 5 +, which is formed by protonation of methane using a superacid. By necessity of having five bonds on carbon but only four valence electron pairs available for bonding, they ...
The association is strongest as a covalent bond and weakest when the pair exists as free ions. [6] In cationic polymerization, the ions tend to be in equilibrium between an ion pair (either tight or solvent-separated) and free ions. [2] The more polar the solvent used in the reaction, the better the solvation and separation of the ions.
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.
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.
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.
If the potential carbocation can not be stabilized, ether cleavage follows a bimolecular, concerted S N 2 mechanism. In the example, the ether oxygen is reversibly protonated. The halide ion (here bromide) then nucleophilically attacks the sterically less hindered carbon atom, thereby forming methyl bromide and 1-propanol.