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Most famously, at least in the classroom, pinacolone arises by the pinacol rearrangement, which occurs by protonation of pinacol (2,3-dimethylbutane-2,3-diol). [4] Industrially pinacolone is made by the hydrolysis of 4,4,5-trimethyl-1,3-dioxane, which is the product of isoprene and formaldehyde via the Prins reaction.
Pinacol is a branched alcohol which finds use in organic syntheses. It is a diol that has hydroxyl groups on vicinal carbon atoms. A white solid that melts just above room temperature, pinacol is notable for undergoing the pinacol rearrangement in the presence of acid and for being the namesake of the pinacol coupling reaction.
2,3-Dimethylbutane is an isomer of hexane. It has the chemical formula (CH 3) 2 CHCH(CH 3) 2. It is a colorless liquid which boils at 57.9 °C. References
In 1967 the group of George A. Olah obtained NMR spectra of tetramethylethylenebromonium ions by dissolving 2,3-dibromo-2,3-dimethylbutane in magic acid at −60 °C. [5] The spectrum for the corresponding fluorine compound on the other hand was consistent with a rapidly equilibrating pair of β-fluorocarbocations.
[2] [5] The compound is used as a reactant in the synthesis of a number of compounds. Notably it is used to synthesize 2,3-dimethylbut-2-ene, and is then converted to 2,3-dimethylbutane-2,3-diol and methyl tert-butyl ketone, better known as pinacolone. Pinacolone itself is then used in synthesis for number of pesticides.
The gauche effect is very sensitive to solvent effects, due to the large difference in polarity between the two conformers.For example, 2,3-dinitro-2,3-dimethylbutane, which in the solid state exists only in the gauche conformation, prefers the gauche conformer in benzene solution by a ratio of 79:21, but in carbon tetrachloride, it prefers the anti conformer by a ratio of 58:42. [9]
2,2-Dimethylbutane; 2,3-Dimethylbutane; See also. Dimethylbutanol This page was last edited on 1 April 2021, at 21:29 (UTC). Text is available under the ...
Pinacolyl alcohol (also known as 3,3-dimethylbutan-2-ol and as pine alcohol) is one of the isomeric hexanols and a secondary alcohol. Pinacolyl alcohol appears on the List of Schedule 2 substances of the Chemical Weapons Convention as a precursor for the nerve agent soman .