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In it, Zaytsev proposed a purely empirical rule for predicting the favored regiochemistry in the dehydrohalogenation of alkyl iodides, though it turns out that the rule is applicable to a variety of other elimination reactions as well. While Zaytsev's paper was well referenced throughout the 20th century, it was not until the 1960s that ...
Dehydrohalogenation to give an alkene In chemistry , dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate . The reaction is usually associated with the synthesis of alkenes , but it has wider applications.
Such reactions give alkenes in the case of vicinal alkyl dihalides: [2] R 2 C(X)C(X)R 2 + M → R 2 C=CR 2 + MX 2. Most desirable from the perspective of remediation are dehalogenations by hydrogenolysis, i.e. the replacement of a C−X bond by a C−H bond. Such reactions are amenable to catalysis: R−X + H 2 → R−H + HX
Using a carboxylate-to-iodine ratio of 1:1 leads to an alkyl iodide product, in line with Borodin's findings and the modern understanding of the Hunsdiecker reaction. However, a 2:1 ratio favours the formation of an ester product that arises from decarboxylation of one carboxylate and coupling the resulting alkyl chain with the other. [9] [10]
In chemistry, halogenation is a chemical reaction which introduces one or more halogens into a chemical compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. [1]
The iodide anion is a good nucleophile and will displace chloride, tosylate, bromide and other leaving groups, as in the Finkelstein reaction. Alcohols can be converted to the corresponding iodides using phosphorus triiodide. Illustrative is the conversion of methanol to iodomethane: [15] PI 3 + 3 CH 3 OH → 3 CH 3 I + "H 3 PO 3 "
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E1 typically takes place with tertiary alkyl halides, but is possible with some secondary alkyl halides. The reaction rate is influenced only by the concentration of the alkyl halide because carbocation formation is the slowest step, as known as the rate-determining step. Therefore, first-order kinetics apply (unimolecular).