Crotonic acid
Encyclopedia
Crotonic acid, or trans-2-butenoic acid, is a short-chain unsaturated
Unsaturated compound
In organic chemistry, a saturated compound is a chemical compound that has of a chain of carbon atoms linked together by single bonds and has hydrogen atoms filling all of the other bonding orbitals of the carbon atoms. Alkanes are an example of saturated compounds...

 carboxylic acid
Carboxylic acid
Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...

, described by the formula CH3CH=CHCO2H. Crotonic acid is so named because it was erroneously thought to be a saponification
Saponification
Saponification is a process that produces soap, usually from fats and lye. In technical terms, saponification involves base hydrolysis of triglycerides, which are esters of fatty acids, to form the sodium salt of a carboxylate. In addition to soap, such traditional saponification processes...

 product of croton oil
Croton oil
Croton oil is an oil prepared from the seeds of Croton tiglium, a tree belonging to the natural order Euphorbiales and family Euphorbiaceae, and native or cultivated in India and the Malay Archipelago. Small doses taken internally cause diarrhea. Externally, the oil can cause irritation and swelling...

. It crystallizes as needles from hot water.

Racemic
Racemic
In chemistry, a racemic mixture, or racemate , is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule. The first known racemic mixture was "racemic acid", which Louis Pasteur found to be a mixture of the two enantiomeric isomers of tartaric acid.- Nomenclature :A...

 threonine
Threonine
Threonine is an α-amino acid with the chemical formula HO2CCHCHCH3. Its codons are ACU, ACA, ACC, and ACG. This essential amino acid is classified as polar...

 can be prepared from crotonic acid by alpha-functionalization using mercury(II) acetate
Mercury(II) acetate
Mercury acetate is the chemical compound with the formula Hg2. Commonly abbreviated Hg2, this compound is employed as a reagent to generate organomercury compounds from unsaturated organic precursors.-Structure:...

.

See also

  • Crotyl
    Crotyl
    A crotyl group is an organic functional group with the formula RCH2CH=CHCH3. Systematically, it is called a but-2-en-1-yl group and exhibits geometric isomerism, being either cis or trans...

  • Crotonaldehyde
    Crotonaldehyde
    Crotonaldehyde is a chemical compound with the formula CH3CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common...

  • Crotyl alcohol
  • Isocrotonic acid
    Isocrotonic acid
    Isocrotonic acid is the cis analogue of crotonic acid. It is an oil, possessing a smell similar to that of brown sugar. It boils at 171.9 °C, concomitant with conversion into crotonic acid. Isomerizaton is complete when the cis acid is heated to 170–180 °C in a sealed tube....

  • Methacrylic acid
    Methacrylic acid
    Methacrylic acid, abbreviated MAA, is an organic compound. This colourless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its...

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