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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.
tert-Butyl bromide (also referred to as 2-bromo-2-methylpropane) is an organic compound with the formula Me 3 CBr (Me = methyl). The molecule features a tert-butyl group attached to a bromide substituent. This organobromine compound is used as a standard reagent in synthetic organic chemistry. It is a colorless liquid.
Such reagents are used to attach butyl groups to various substrates. 1-Bromobutane is the precursor to n -butyllithium : [ 4 ] 2 Li + C 4 H 9 X → C 4 H 9 Li + LiX
Relative rates of chemical reactions provide useful insights into the effects of the steric bulk of substituents. Under standard conditions, methyl bromide solvolyzes 10 7 faster than does neopentyl bromide. The difference reflects the inhibition of attack on the compound with the sterically bulky (CH 3) 3 C group. [3]
2-Bromobutane (sec-butyl bromide) 1-Bromo-2-methylpropane (isobutyl bromide) 2-Bromo-2-methylpropane (tert-butyl bromide) This page was last edited on 5 February ...
An example of a reaction taking place with an S N 1 reaction mechanism is the hydrolysis of tert-butyl bromide forming tert-butanol: This S N 1 reaction takes place in three steps: Formation of a tert-butyl carbocation by separation of a leaving group (a bromide anion) from the carbon atom: this step is slow. [5] Recombination of carbocation ...
The reaction is facilitated by electron-releasing substituents (the inductive effect) and in general the observed order (with decreasing reactivity) is tert-butyl > isopropyl > ethyl > methyl. The observed order in this particular reaction however was methyl > ethyl> isopropyl > tert-butyl.
Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C 4 H 9 O H, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; [1] all are a butyl or isobutyl group linked to a hydroxyl group (sometimes represented as BuOH, sec-BuOH, i-BuOH, and t-BuOH).