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Reaction mechanism for the bromination of acetone while in the presence of acetic acid. Basic (in aqueous NaOH): Reaction mechanism for the bromination of acetone while in the presence of aqueous NaOH. In acidic solution, usually only one alpha hydrogen is replaced by a halogen, as each successive halogenation is slower than the first.
In chemistry, the haloform reaction (also referred to as the Lieben haloform reaction) is a chemical reaction in which a haloform (CHX 3, where X is a halogen) is produced by the exhaustive halogenation of an acetyl group (R−C(=O)CH 3, where R can be either a hydrogen atom, an alkyl or an aryl group), in the presence of a base.
The photo-Favorskii reaction has been used in the photochemical unlocking of certain phosphates (for instance those of ATP) protected by p-hydroxyphenacyl groups. [13] The deprotection proceeds through a triplet diradical ( 3 ) and a dione spiro intermediate ( 4 ) although the latter has thus far eluded detection.
The reduction of α-halo ketones generates a variety of product structures that may exhibit unique substitution patterns and reactivity. For instance, reduction of α,α'-dihalo ketones leads to 2-oxyallyl metal complexes, which participate in [4+3] and [3+2] cycloaddition reactions as the 2π component.
As with all ketones, acetone enolizes in the presence of acids or bases. The alpha carbon then undergoes electrophilic substitution with bromine. The main difficulty with this method is over-bromination, resulting in di- and tribrominated products. If a base is present, bromoform is obtained instead, by the haloform reaction. [5]
The reaction is much slower with ketones than aldehydes. [42] For example, in Nicolaou's epothilones synthesis, asymmetric allylboration (with an allylborane derived from chiral alpha-pinene ) is the first step in a two-carbon homologation to acetogenin : [ 43 ]
Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids. [1] A variety of oxidants can be used.
Since, aldehydes reduce more easily than ketones, they require milder reagents and milder conditions. At the other extreme, carboxylic acids, amides, and esters are poorly electrophilic and require strong reducing agents. [17] The idealized equation for the reduction of a ketone by sodium borohydride is: 4 RCOR' + NaBH 4 → NaB(OCHRR') 4