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In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids (R−C(=O)OH). A specific example of an acyl chloride is acetyl chloride, CH 3 COCl. Acyl chlorides are the ...
Diacyl peroxides are typically prepared by treating hydrogen peroxide with acid chlorides or acid anhydrides in the presence of base: [1] H 2 O 2 + 2 RCOCl → (RCO 2) 2 + 2 HCl H 2 O 2 + (RCO) 2 O → (RCO 2) 2 + H 2 O. The reaction competes with hydrolysis of the acylating agent but the hydroperoxide anion is a superior nucleophile relative ...
Hydroxylamine (also known as hydroxyammonia) is an inorganic compound with the chemical formula N H 2 OH.The compound exists as hygroscopic colorless crystals. [4] Hydroxylamine is almost always provided and used as an aqueous solution or more often as one of its salts such as hydroxylammonium sulfate, a water-soluble solid.
Acetyl chloride is a reagent for the preparation of esters and amides of acetic acid, used in the derivatization of alcohols and amines. One class of acetylation reactions are esterification, for example the reaction with ethanol to produce ethyl acetate and hydrogen chloride: CH 3 COCl + HO−CH 2 −CH 3 → CH 3 −COO−CH 2 −CH 3 + HCl
Another common example is the reaction of a primary amine or secondary amine with a carboxylic acid or with a carboxylic acid derivative to form an amide. This reaction is widely used, especially in the synthesis of peptides. On the simple addition of an amine to a carboxylic acid, a salt of the organic acid and base is obtained.
Substituted ketenes can be prepared from acyl chlorides by an elimination reaction in which HCl is lost: Formation of a ketene from an acyl chloride. In this reaction, a base, usually triethylamine, removes the acidic proton alpha to the carbonyl group, inducing the formation of the carbon-carbon double bond and the loss of a chloride ion:
All react with amines to form amides and with alcohols to form esters by nucleophilic acyl substitution. Acylation can be used to prevent rearrangement reactions that would normally occur in alkylation. To do this an acylation reaction is performed, then the carbonyl is removed by Clemmensen reduction or a similar process. [3]
Several metal hydroperoxide complexes have been characterized by X-ray crystallography, for example: triphenylsilicon and triphenylgermanium hydroperoxides can be obtained by reaction of initial chlorides with excess of hydrogen peroxide in presence of base. [17] [18] Some form by the reaction of metal hydrides with oxygen gas: [19]