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Advanced Chemistry
Formation of t-Butyl Chloride Lab1
Advanced Chemistry students explored the nucleophilic substitution reaction of converting t-butyl alcohol to t-butyl chloride. This reaction proceeds via an SN1 reaction mechanism. In the first step, the hydroxyl group is protonated by an acid which leaves as a neutral water forming a carbocation intermediate. The nucleophilic chloride ion attacks the positive charge from either side of the planar carbocation producing a new bond (coordinate covalent bond). The product now has a chlorine where the hydroxyl once resided.
Evidence for the production is the formation of two distinct layers, t-butyl alcohol is water soluble (polar) and t-butyl chloride is water insoluble (nonpolar). The students predicted the existence of the t-butyl chloride when the reaction vial contained two distinct layers.
1.. Russo, T. & Meszaros, M.W. Formation of t-Butyl Chloride. Vial Organic Chemistry. Flinn Scientific, Inc. 1996
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