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The effect of the tert-butyl group on the progress of a chemical reaction is called the Thorpe–Ingold effect illustrated in the Diels-Alder reaction below. Compared to a hydrogen substituent, the tert-butyl substituent accelerates the reaction rate by a factor of 240. [2] tert-Butyl effect. The tert-butyl effect is an example of steric hindrance.
Neopentyl alcohol can be prepared from the hydroperoxide of diisobutylene. [3] It can also be prepared by the reduction of trimethylacetic acid with lithium aluminium hydride.
tert-Butyl alcohol is used as a solvent, ethanol denaturant, paint remover ingredient, and gasoline octane booster and oxygenate.It is a chemical intermediate used to produce methyl tert-butyl ether (MTBE) and ethyl tert-butyl ether (ETBE) by reaction with methanol and ethanol, respectively, and tert-butyl hydroperoxide (TBHP) by reaction with hydrogen peroxide.
The terms sec and tert are considered obsolete and should only be used for unsubstituted sec-butoxy, sec-butyl [26] [27] or tert-butyl groups. [ 28 ] [ 27 ] There are various spellings such as "sec-butyl", "s-butyl", "sBu" or "bus" which are also considered obsolete.
For example, the tert-butyl group (A-value=4.9) has a larger A-value than the trimethylsilyl group (A-value=2.5), yet the tert-butyl group actually occupies less space. This difference can be attributed to the longer length of the carbon–silicon bond as compared to the carbon–carbon bond of the tert-butyl group.
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The energy difference between gauche and anti is 0.9 kcal/mol associated with the strain energy of the gauche conformer. The anti conformer is, therefore, the most stable (≈ 0 kcal/mol). The three eclipsed conformations with dihedral angles of 0°, 120°, and 240° are transition states between conformers. [6]
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