Penguinone

Penguinone
Names
IUPAC name
3,4,4,5-Tetramethylcyclohexa-2,5-dienone
Properties
Molecular formula
C10H14O
Molar mass 150.22 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Penguinone is an organic compound with the molecular formula C
10
H
14
O
. Its name comes from the fact that its 2-dimensional molecular structure resembles a penguin.[1][2]

The suffix "-one" indicates that it is a ketone, that is, an acid with double bond between an oxygen and a carbon atom.[3] The systematic name of the molecule is 3,4,4,5-tetramethylcyclohexa-2,5-dienone.[4][5]

Although it is a dienone and thus has the necessary structure for dienone phenol rearrangement, the methyl groups in positions 3 and 5 of the ring block the movement of the group at position 4, so even the action of trifluoroacetic acid will not cause transformation to a phenol.[6]

See also

References

  1. May, Paul (2008). Molecules with Silly or Unusual Names. Imperial College London. p. 35. ISBN 1848162073.
  2. May, Paul (23 October 2014). "Molecules with Silly or Unusual names". University of Bristol. Retrieved 1 December 2014.
  3. Laszlo, Pierre (2004). "Science as Play". American Scientist 92 (5): 398. doi:10.1511/2004.5.398.
  4. "Chemical structures beginning with P". about.com. Retrieved 1 December 2014.
  5. Parkvall, Mikael (2006). Limits of Language. London: Battlebridge. p. 176. ISBN 1903292042.
  6. Hagenbruch, Bernd; Hünig, Siegfried (1983). "Ein Beitrag zur Dienon-Phenol-Umlagerung". Chemische Berichte (in German) 116: 3884–3894. doi:10.1002/cber.19831161212.