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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 water, a polar and protic solvent, the bulky chloride substituent is carried away by it, and isolated from the aliphatic chain, causing an heterolitic 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.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Tert-Butyl_chloride". A list of authors is available in Wikipedia.|