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Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen (F, Cl, Br, I). Haloalkanes have been known for centuries. Chloroethane was produced in the 15th century. The systematic synthesis of such compounds developed in the 19th century in step with the ...
In the Williamson ether reaction there is an alkoxide ion (RO −) which acts as the nucleophile, attacking the electrophilic carbon with the leaving group, which in most cases is an alkyl tosylate or an alkyl halide. The leaving site must be a primary carbon, because secondary and tertiary leaving sites generally prefer to proceed as an ...
When there are different alkyl groups, they are listed in alphabetical order. In addition, each position on an alkyl chain can be described according to how many other carbon atoms are attached to it. The terms primary, secondary, tertiary, and quaternary refer to a carbon attached to one, two, three, or four other carbons respectively.
The reaction involves a carbocation intermediate and is commonly seen in reactions of secondary or tertiary alkyl halides under strongly basic conditions or, under strongly acidic conditions, with secondary or tertiary alcohols. With primary and secondary alkyl halides, the alternative S N 2 reaction occurs.
For example, reaction of 1-bromooctane with ammonia yields almost equal amounts of the primary amine and the secondary amine. [3] Therefore, for laboratory purposes, N-alkylation is often limited to the synthesis of tertiary amines. An exception is the amination of alpha-halo carboxylic acids that do permit synthesis of primary amines with ...
Furthermore, the reaction is only useful for primary alkyl halides in an intramolecular sense when a 5- or 6-membered ring is formed. For the intermolecular case, the reaction is limited to tertiary alkylating agents, some secondary alkylating agents (ones for which carbocation rearrangement is degenerate), or alkylating agents that yield ...
tert-Butyl bromide used to study the massive deadenylation of adenine based-nucleosides induced by halogenated alkanes (alkyl halides) under physiological conditions. 2-Bromo-2-methylpropane causes the massive deguanylation of guanine based-nucleosides and massive deadenylation of adenine based-nucleosides.
The Corey-House synthesis is preceded by two preliminary steps to prepare the requisite Gilman reagent from an alkyl halide. In the first step, the alkyl halide is treated with lithium metal in dry ether to prepare an alkyllithium reagent, RLi. The starting alkyl halide for the lithiation step can be a primary, secondary or tertiary alkyl ...