Tetramethylbutane

Tetramethylbutane[1]
IUPAC name

2,2,3,3-Tetramethylbutane
Other names

Hexamethylethane
Identifiers
CAS number 594-82-1 Y
PubChem 11675
Jmol-3D images Image 1
Properties
Molecular formula C8H18
Molar mass 114.23 g mol−1
Melting point

100.8 °C[2]
Boiling point

107 °C (1020 mbar)[2]
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Tetramethylbutane, sometimes called hexamethylethane, is a hydrocarbon with formula C8H18 or (H3C-)3C-C(-CH3)3. It is the most heavily branched and most compact of the many octane isomers, the only one with a butane (C4) backbone.

The compound can be obtained by reaction of Grignard reagent tert-butylmagnesium bromide with ethyl bromide, or of ethylmagnesium bromide with tert-butyl bromide in the presence of manganese(II) ions.[3] This transformation is believed to go through the dimerization of two tert-butyl radicals, which are generated by decomposition of the organomanganese compounds generated in situ.

The full IUPAC name of the compound is 2,2,3,3-tetramethylbutane, but the numbers are superfluous in this case because there is no other possible arrangement of "tetramethylbutane".

See also

References

  1. ^ 2,2,3,3-Tetramethylbutane at Sigma-Aldrich
  2. ^ a b Scott, D.W.; Douslin, D.R.; Gross, M.E.; Oliver, G.D.; Huffman, H.M.: 2,2,3,3-Tetramethylbutane: Heat capacity, heats of transition, fusion and sublimation, vapor pressure, entropy and thermodynamic functions in J. Am. Chem. Soc. 74 (1952) 883-887.
  3. ^ M. S. KHARASCH, J. W. HANCOCK, W. NUDENBERG, P. O. TAWNEY (1956). "Factors Influencing the Course and Mechanism of Grignard Reactions. XXII. The Reaction of Grignard Reagents with Alkyl Halides and Ketones in the Presence of Manganous Salts". Journal of Organic Chemistry 21 (3): 322–327. doi:10.1021/jo01109a016.