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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.
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]
An electron donating group (EDG) or electron releasing group (ERG, Z in structural formulas) is an atom or functional group that donates some of its electron density into a conjugated π system via resonance (mesomerism) or inductive effects (or induction)—called +M or +I effects, respectively—thus making the π system more nucleophilic.
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 ...
As an example, self-exchange describes the degenerate reaction between permanganate and its one-electron reduced relative manganate: [MnO 4] − + [Mn*O 4] 2− → [MnO 4] 2− + [Mn*O 4] −. In general, if electron transfer is faster than ligand substitution, the reaction will follow the outer-sphere electron transfer route.
It is a colorless liquid with a pleasant odor. Because the carbon atom connected to the bromine is connected to two other carbons the molecule is referred to as a secondary alkyl halide. 2-Bromobutane is chiral and thus can be obtained as either of two enantiomers designated as (R)-(−)-2-bromobutane and (S)-(+)-2-bromobutane.
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.