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In industry, this reaction is performed in the liquid phase at elevated pressure. Typical reaction conditions are 80 °C and 40 atm. The most widely used base is sodium methoxide. Hydrolysis of the methyl formate produces formic acid: HCO 2 CH 3 + H 2 O → HCOOH + CH 3 OH. Efficient hydrolysis of methyl formate requires a large excess of water.
Methanol and carbon monoxide react in the presence of a strong base, such as sodium methoxide: [1] CH 3 OH + CO → HCOOCH 3. Hydrolysis of methyl formate gives formic acid and regenerates methanol: HCOOCH 3 → HCOOH + CH 3 OH. Formic acid is used for many applications in industry. Formate esters often are fragrant or have distinctive odors.
On the other hand, if a chemical is a weak acid its conjugate base will not necessarily be strong. Consider that ethanoate, the conjugate base of ethanoic acid, has a base splitting constant (Kb) of about 5.6 × 10 −10, making it a weak base. In order for a species to have a strong conjugate base it has to be a very weak acid, like water.
H 2 O is a base because it accepts a proton from CH 3 COOH and becomes its conjugate acid, the hydronium ion, (H 3 O +). [9] The reverse of an acid–base reaction is also an acid–base reaction, between the conjugate acid of the base in the first reaction and the conjugate base of the acid.
An acid may also form hydrogen bonds to its conjugate base. This process, known as homoconjugation, has the effect of enhancing the acidity of acids, lowering their effective pK a values, by stabilizing the conjugate base. Homoconjugation enhances the proton-donating power of toluenesulfonic acid in acetonitrile solution by a factor of nearly 800.
An acid–base reaction is, thus, the removal of a hydrogen ion from the acid and its addition to the base. [21] The removal of a hydrogen ion from an acid produces its conjugate base, which is the acid with a hydrogen ion removed. The reception of a proton by a base produces its conjugate acid, which is the base with a hydrogen ion added.
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The carboxylate anion (R−COO − or R−CO − 2) of a carboxylic acid is usually named with the suffix -ate, in keeping with the general pattern of -ic acid and -ate for a conjugate acid and its conjugate base, respectively. For example, the conjugate base of acetic acid is acetate.