Investigation Of The Hydrolysis Of T Butyl Chloride

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Introduction Learning Outcome This experiment was aimed to determine the order of the hydrolysis reaction and to determine the effect of water:acetone ratio on the rate constant. Theory The hydrolysis of t-butyl chloride can be presented as the following equation: (CH3)3CCl + H2O (CH3)3COH + HCl NaOH is added to neutralise the HCl produced. NaOH + HCl NaCl + H2O (CH3)3CCl is a tertiary haloalkane in which the C atom is bonded to 3 methyl groups and a Cl group. A partial positive charge is formed on the carbon atom due to the electron-withdrawing effect of the electronegative Cl atom, causing carbon to be susceptible to be attacked by a nucleophile. The hydrolysis of t-butyl chloride is a nucleophilic substitution SN1 reaction which involves 3 steps. The reaction mechanism can be portrayed as such: 1st step involves the spontaneous dissociation of the (CH3)3CCl to form carbocation intermediate and chloride ion. This is the slow step which determines the rate of reaction. 2nd step involves the carbocation intermediate being attacked by water that acts as a nucleophile to form protonated alcohol intermediate. This is the fast step and does not determine rate of reaction. 3rd step involves the proton being donated to the Cl- ion to form final products, HCl and (CH3)3COH. Since the first step is the rate-determining step and it is a pseudo first order reaction, thus the rate equation can be derived as Rate= k[(CH3)3CCl] (1) (d[(CH_3 )_3

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