Hydrolysis Of T-Butyl Chloride Lab Report

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In this experiment, the reaction kinetics of the hydrolysis of t-butyl chloride, (CH3)3CCl, was studied. The experiment was to determine the rate constant of the reaction, as well as the effects of solvent composition on the rate of reaction. A 50/50 V/V isopropanol/water solvent mixture was prepared and 1cm3 of (CH3)3CCl was added. At specific instances, aliquots of the reaction mixture were withdrawn and quenched with acetone. In addition, phenolphthalein was added as an indicator. The aliquots were titrated against sodium hydroxide (NaOH) solution until end point was reached, after which volume of NaOH consumed was recorded. The value of the rate constant, k, obtained was 0.0002 s-1. The experiment was then repeated with 40/60 V/V isopropanol/water mixture and a larger value of k = 0.0007 s-1 was obtained. We concluded that the rate of hydrolysis of (CH3)3CCl is directly proportional to water content in the solvent mixture.

Aims of experiment
• Determine the rate constants for hydrolysis of (CH3)3CCl in solvent mixtures of different composition (50/50 V/V isopropanol/water and 40/60 V/V isopropanol/water)
• Examine the effect of solvent mixture composition on the rate of hydrolysis of (CH3)3CCl

With t-butyl chloride, (CH3)3CCl, being a tertiary halogenoalkane, it is predicted that (CH3)3CCl reacts with water in a nucleophilic substitution reaction (SN1 mechanism), where Step 1 is the rate-determining step. The reaction proceeds in a manner as shown

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