Propiolic acid
Encyclopedia
Propiolic acid, or acetylene mono-carboxylic acid, is an unsaturated
Saturation (chemistry)
In chemistry, saturation has six different meanings, all based on reaching a maximum capacity...

 organic acid
Organic acid
An organic acid is an organic compound with acidic properties. The most common organic acids are the carboxylic acids, whose acidity is associated with their carboxyl group –COOH. Sulfonic acids, containing the group –SO2OH, are relatively stronger acids. The relative stability of the conjugate...

 prepared by boiling acetylenedicarboxylic acid
Acetylenedicarboxylic acid
Acetylenedicarboxylic acid or butynedioic acid is an organic compound with the formula C4H2O4 or HO2C-C≡C-CO2H. It is a crystalline solid that is soluble in diethyl ether....

, obtained by the action of alcoholic potash
Potash
Potash is the common name for various mined and manufactured salts that contain potassium in water-soluble form. In some rare cases, potash can be formed with traces of organic materials such as plant remains, and this was the major historical source for it before the industrial era...

 on dibromosuccinic acid, or its acid potassium salt with water. It forms silky crystals which melt at 9 °C, and boil at about 144 °C with decomposition. It is soluble in water and possesses an odor resembling that of acetic acid
Acetic acid
Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...

. Exposure to sunlight
Sunlight
Sunlight, in the broad sense, is the total frequency spectrum of electromagnetic radiation given off by the Sun. On Earth, sunlight is filtered through the Earth's atmosphere, and solar radiation is obvious as daylight when the Sun is above the horizon.When the direct solar radiation is not blocked...

 converts it into trimesic acid
Trimesic acid
Trimesic acid, formally known as benzene-1,3,5-tricarboxylic acid, is a benzene derivative with three carboxylic acid groups.Trimesic acid is a planar molecule ....

 (benzene-1,3,5-tricarboxylic acid). Bromine
Bromine
Bromine ") is a chemical element with the symbol Br, an atomic number of 35, and an atomic mass of 79.904. It is in the halogen element group. The element was isolated independently by two chemists, Carl Jacob Löwig and Antoine Jerome Balard, in 1825–1826...

 converts it into dibromoacrylic acid, and it gives with hydrochloric acid
Hydrochloric acid
Hydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric acid....

 O-chloracrylic acid. It forms a characteristic explosive silver
Silver
Silver is a metallic chemical element with the chemical symbol Ag and atomic number 47. A soft, white, lustrous transition metal, it has the highest electrical conductivity of any element and the highest thermal conductivity of any metal...

 salt
Salt
In chemistry, salts are ionic compounds that result from the neutralization reaction of an acid and a base. They are composed of cations and anions so that the product is electrically neutral...

 on the addition of ammoniacal silver nitrate
Silver nitrate
Silver nitrate is an inorganic compound with chemical formula . This compound is a versatile precursor to many other silver compounds, such as those used in photography. It is far less sensitive to light than the halides...

 to its aqueous solution
Aqueous solution
An aqueous solution is a solution in which the solvent is water. It is usually shown in chemical equations by appending aq to the relevant formula, such as NaCl. The word aqueous means pertaining to, related to, similar to, or dissolved in water...

, and an amorphous precipitate which explodes on warming with ammoniacal cuprous chloride. Its ethyl ester condenses with hydrazine
Hydrazine
Hydrazine is an inorganic compound with the formula N2H4. It is a colourless flammable liquid with an ammonia-like odor. Hydrazine is highly toxic and dangerously unstable unless handled in solution. Approximately 260,000 tons are manufactured annually...

 to form pyrazolone
Pyrazolone
Pyrazolone, a five-membered-ring lactam, is a derivative of pyrazole that has an additional keto group.It has a molecular formula of C3H4N2O.Examples of derivatives include:* Ampyrone* Metamizole* Phenazone-External links:* *...

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