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・ Tert-Amyl alcohol
・ Tert-Amyl chloride
・ Tert-Amyl methyl ether
・ Tert-Butanesulfinamide
・ Tert-Butyl acetate
・ Tert-Butyl alcohol
・ Tert-Butyl bromide
Tert-Butyl chloride
・ Tert-Butyl formate
・ Tert-Butyl hydroperoxide
・ Tert-Butyl isocyanide
・ Tert-Butylamine
・ Tert-Butyldiphenylsilyl
・ Tert-Butylhydroquinone
・ Tert-Butyllithium
・ Tert-Butyloxycarbonyl protecting group
・ Tert-Butylphosphaacetylene
・ Tert-Butylthiol
・ Tert.am
・ Tertali
・ Tertangala
・ Tertatolol


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Tert-Butyl chloride : ウィキペディア英語版
Tert-Butyl chloride

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''tert''-Butyl chloride is a colorless, liquid organic compound at room temperature. It is sparingly soluble in water, with a tendency to undergo spontaneous solvolysis when dissolved into it. The compound is flammable and volatile, and its main use is as a starting molecule to carry out nucleophilic substitution reactions, to produce different substances, ranging from alcohols to alkoxide salts.
When ''tert''-butyl chloride is dissolved in a polar and protic solvent, like water, it undergoes a solvolysis reaction. The chloride groups leaves, causing an heterolytic rupture of the compound, giving rise to a carbocation which eventually becomes a tertiary alcohol after a water molecule reacts with it, releasing hydrochloric acid as the final product. If a different, stronger nucleophilic agent is present at the moment of reaction, reaction product may not be an alcohol, but a tertiary carbon with the nucleophile as a substituent. Because of the steric hindrance of the ''tert''-butyl group the solvolysis reaction follows the SN1 mechanism and not the SN2 mechanism.
== Synthesis ==
''tert''-Butyl chloride can be synthesized in the laboratory by the SN1 reaction of ''tert''-Butanol with concentrated hydrochloric acid, as shown below.
The overall reaction, therefore, is:
Because ''tert''-butanol is a tertiary alcohol, the relative stability of the ''tert''-butyl carbocation in the Step 2 allows the SN1 mechanism to be followed, whereas a primary alcohol would follow an SN2 mechanism.

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