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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 ...
This reaction was developed by Alexander Williamson in 1850. [2] Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an S N 2 reaction. This reaction is important in the history of organic chemistry because it helped prove the structure of ethers. The general reaction mechanism is as follows: [3]
However, using an additive such as silver tetrafluoroborate allows the reaction to work on a wider range of substrates, as often seen for alkyl-halide substitutions, or they can be converted first to the corresponding alkyl tosylate. [4] [5] The reaction was initially limited to activated substrates, such as benzylic and α-halo ketones. To ...
Amine alkylation (amino-dehalogenation) is a type of organic reaction between an alkyl halide and ammonia or an amine. [1] The reaction is called nucleophilic aliphatic substitution (of the halide), and the reaction product is a higher substituted amine. The method is widely used in the laboratory, but less so industrially, where alcohols are ...
In the Menshutkin reaction, a tertiary amine is converted into a quaternary ammonium salt by reaction with an alkyl halide. Similar reactions occur when tertiary phosphines are treated with alkyl halides, the products being phosphonium salts. Menshutkin-reaction. Thiols are readily alkylated to give thioethers via the thiol-ene reaction. [4]
Vinyl, aryl and tertiary alkyl halides are unreactive; as a result, the reaction of NaI in acetone can be used as a qualitative test to determine which of the aforementioned classes an unknown alkyl halide belongs to, with the exception of alkyl iodides, as they yield the same product upon substitution.
Wittig reagents are usually prepared from a phosphonium salt, which is in turn prepared by the quaternization of triphenylphosphine with an alkyl halide. Wittig reagents are usually derived from a primary alkyl halide. Quaternization of triphenylphosphine with secondary halides is typically inefficient.
Another proposed mechanism involves single electron transfer with the generation of radicals. In reactions of secondary and tertiary alkyllithium and alkyl halides, radical species were detected by EPR spectroscopy. [9] [6] The mechanistic studies of lithium–halogen exchange are complicated by the formation of aggregates of organolithium species.