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tert-Butyl chloride is the organochloride with the formula (CH 3) 3 CCl. It is a colorless, flammable liquid. It is sparingly soluble in water, with a tendency to undergo hydrolysis to the corresponding tert-butyl alcohol. It is produced industrially as a precursor to other organic compounds. [1]
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.
The tert-butoxide is a strong, non-nucleophilic base in organic chemistry. It readily abstracts acidic protons from substrates, but its steric bulk inhibits the group from participating in nucleophilic substitution, such as in a Williamson ether synthesis or an S N 2 reaction. tert-Butyl alcohol reacts with hydrogen chloride to form tert-butyl ...
P 4-t-Bu is a readily accessible chemical from the group of neutral, peralkylated sterically hindered polyaminophosphazenes, which are extremely strong bases but very weak nucleophiles, with the formula (CH 3) 3 C−N=P(−N=P(−N(CH 3) 2) 3) 3. "t-Bu" stands for tert-butyl (CH 3) 3 C –. "P 4" stands for the fact that this molecule has 4 ...
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 ...
It was originally prepared by the oxidation of pinacolone with chromic acid [2] and by the hydrolysis of tert-butyl cyanide. [3] Convenient laboratory routes proceed via carbonation of the Grignard reagent formed from tert-butyl chloride [4] and by oxidation of pinacolone. [5] Pinacol rearrangement
N-tert-Butylbenzenesulfinimidoyl chloride is a useful oxidant for organic synthesis reactions. [1] It is a good electrophile, and the sulfimide S=N bond can be attacked by nucleophiles, such as alkoxides, enolates, and amide ions. The nitrogen atom in the resulting intermediate is basic, and can abstract an α-hydrogen to create a new double bond.
As such it is more bulky that trimethylsilyl chloride. It is a colorless or white solid that is soluble in many organic solvents but reacts with water and alcohols. The compound is used to protect alcohols in organic synthesis. [1] tert-Butyldimethylsilyl chloride reacts with alcohols in the presence of base to give tert-butyldimethylsilyl ...