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For example, the pK a value of acetic acid is 4.8, while ethanol has a pK a of 16. Hence acetic acid is a much stronger acid than ethanol. Hence acetic acid is a much stronger acid than ethanol. This in turn means that for equimolar solutions of a carboxylic acid or an alcohol in water, the carboxylic acid would have a much lower pH .
Mechanism of Wolff-Kishner reduction. Aromatic carbonyls are more readily reduced to their respective alkanes than aliphatic compounds. [26] For example, ketones are reduced to their respective alkyl benzenes by catalytic hydrogenation [27] [28] or by Birch reduction [29] under mild conditions.
The Vilsmaier reagent (N,N-Dimethyl(chloromethylene)ammonium chloride; [ClHC=N + (CH 3) 2]Cl −) is a highly chemoselective agent for carboxylic acid reduction. It selectively activates the carboxylic acid to give the carboxymethyleneammonium salt, which can be reduced by a mild reductant like lithium tris( t -butoxy)aluminum hydride to afford ...
Transition metal salts, especially copper compounds, [9] facilitate decarboxylation via carboxylate complex intermediates. Metals that catalyze cross-coupling reactions thus treat aryl carboxylates as an aryl anion synthon; this synthetic strategy is the decarboxylative cross-coupling reaction. [10]
The Dakin oxidation (or Dakin reaction) is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide (H 2 O 2) in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidised, whereas the H 2 O 2 is reduced.
Carboxylation is a chemical reaction in which a carboxylic acid is produced by treating a substrate with carbon dioxide. [1] The opposite reaction is decarboxylation.In chemistry, the term carbonation is sometimes used synonymously with carboxylation, especially when applied to the reaction of carbanionic reagents with CO 2.
The simplest example is acrylic acid (CH 2 =CHCO 2 H). These compounds are prone to polymerization, giving rise to the large area of polyacrylate plastics. Acrylate polymers are derived from but do not contain the acrylate group. [4] The carboxyl group of acrylic acid can react with ammonia to form acrylamide, or with an alcohol to form an ...
Scheme 2: A mechanism of Clemmensen reduction was proposed in 1975. [7] [8] The carbonyl is first converted to radical anion (shown as blue), then to zinc carbenoid (shown as red), and then reduced to alkane. Despite the reaction being first discovered in 1914, the mechanism of the Clemmensen reduction remains obscure.