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2-Butyne

Alkyne with four carbon atoms

Alkyne with four carbon atoms

Crotonylene

2-Butyne (dimethylacetylene, crotonylene or but-2-yne) is an alkyne with chemical formula CH3C≡CCH3. Produced artificially, it is a colorless, volatile, pungent liquid at standard temperature and pressure.

2-Butyne is of interest to physical chemists because of its very low torsional barrier and the problem of determining that barrier using high-resolution infrared spectroscopy. Analysis of its infrared spectrum{{cite journal | last = di Lauro | first = C.|display-authors=etal| year = 1997 | title =The rotation-torsion structure in the ν11/ν15 (Gs) methyl rocking fundamental band in dimethylacetylene leads to a determination that the torsional barrier is only 6 cm−1 (1.2 J or 72 J mol−1). However, it has not been determined whether the equilibrium structure is eclipsed (D3h) or staggered (D3d). Symmetry analysis using the Molecular Symmetry Group{{cite journal | author1=P. R. Bunker | year=1964

2-Butyne (dimethylethyne) forms with 5-decyne (dibutylethyne), 4-octyne (dipropylethyne) and 3-hexyne (diethylethyne) a group of symmetric alkynes.

Synthesis

2-Butyne can be synthesized by the rearrangement reaction of ethylacetylene in a solution of ethanolic potassium hydroxide.

Applications

2-Butyne, along with propyne, is used to synthesize alkylated hydroquinones in the total synthesis of Vitamin E.

References

References

  1. [https://www.sigmaaldrich.com/US/en/product/aldrich/254339] at [[Sigma-Aldrich]]
  2. [http://webbook.nist.gov/cgi/cbook.cgi?ID=C503173 NIST Chemistry WebBook page for 2-butyne]
  3. (1963). "The symmetry groups of non-rigid molecules". Molecular Physics.
  4. (1916). "Organic Chemistry: Chemistry of the aliphatic series Vol. I: Smith's 3rd American Ed.". P. Blakiston's Sons & Co..
  5. (1969). "Cyclization of Acetylenic Compounds". Angewandte Chemie International Edition in English.
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