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In order for the S N 2 reaction to take place there must be a good leaving group which is strongly electronegative, commonly a halide. [4] 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 ...
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 mechanism of reduction itself depends on the nature of the reducing agent. One-electron reducing agents, such as d 6 or d 1 transition metal complexes, initially donate a single electron to the halo ketone. Fragmentation of the resulting radical anion yields an organic radical and halide anion.
Traditionally, alkyl halides are substrates for dehydrohalogenations. The alkyl halide must be able to form an alkene, thus halides having no C–H bond on an adjacent carbon are not suitable substrates. Aryl halides are also unsuitable. Upon treatment with strong base, chlorobenzene dehydrohalogenates to give phenol via a benzyne intermediate.
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 ...
The classic Finkelstein reaction entails the conversion of an alkyl chloride or an alkyl bromide to an alkyl iodide by treatment with a solution of sodium iodide in acetone. Sodium iodide is soluble in acetone while sodium chloride and sodium bromide are not; [ 3 ] therefore, the reaction is driven toward products by mass action due to the ...
Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li[Al H 4] or LiAlH 4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. [4] This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides.
β-Hydride elimination is a reaction in which a metal-alkyl centre is converted into the corresponding metal-hydride-alkene. [1] β-Hydride elimination can also occur for many alkoxide complexes as well. The main requirements are that the alkyl group possess a C-H bond β to the metal and that the metal be coordinatively unsaturated.