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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 ...
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 ...
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.
It is a colorless liquid with a pleasant odor. Because the carbon atom connected to the bromine is connected to two other carbons the molecule is referred to as a secondary alkyl halide. 2-Bromobutane is chiral and thus can be obtained as either of two enantiomers designated as (R)-(−)-2-bromobutane and (S)-(+)-2-bromobutane.
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.
Formation of the diradical pair 3 allows for radical decarboxylation to form the diradical pair 4, which recombines to form the organic halide 5. The trend in the yield of the resulting halide is primary > secondary > tertiary. [2] [3]
Likewise, this method only gives the best yields for primary halides. Secondary and tertiary halides are prone to undergo E2 elimination on exposure to the basic alkoxide anion used in the reaction due to steric hindrance from the large alkyl groups. In a related reaction, alkyl halides undergo nucleophilic displacement by phenoxides. The R–X ...