Hydrolysis and Elimination of tert-Butyl Chloride
This is a demonstration of the hydrolysis of tertiary butyl chloride. The mechanism of this reaction depends on the pH of the solution. Under basic conditions, elimination predominates and the major product is the alkene. Under neutral or acidic conditions, hydrolysis occurs and the major product is the alcohol.
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0.1 molar hydrochloric acid is added to a solution of isopropyl alcohol, water and universal indicator. The solution is made basic with one molar sodium hydroxide. This is shown by the blue color of the indicator. Tertiary butyl chloride is added. As the slow hydrolysis of the chloride proceeds, the acidity of the solution increases, as eventually shown by the color of the indicator.
If more sodium hydroxide is added, the solution turns blue again.
These ChemEd DL Resource Groups Include This Video
Nucleophilic Substitution Reactions
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