Propiolaldehyde is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
with
molecular formula
In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...
HC
2CHO. It is the simplest chemical compound containing both
alkyne and
aldehyde
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...
functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the re ...
s. It is a colorless liquid with
explosive properties.
Reactions
The compound exhibits reactions expected for an electrophilic alkynyl aldehyde. It is a dienophile and a good
Michael acceptor
In organic chemistry, the Michael reaction or Michael addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbo ...
. Grignard reagents add to the carbonyl center.
[ Its explosive properties are attributed to the exothermicity of its polymerization.][
]
Preparation
Its acetal can be prepared from acrolein.
Occurrence in interstellar medium
Propynal has been observed in the interstellar medium. It is hypothesized to be formed from a carbon monoxide
Carbon monoxide (chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simple ...
- acetylene complex. Another possible pathway is through the reaction of propynylidyne (C3H) with water.
Hazards
The compound is explosive, possibly because it tends to polymerize.[
]
See also
* Acrolein
* Propiolic acid
References
{{Authority control
Aldehydes
Alkyne derivatives