Orgo8 - Experiment title: Solvolysis of...

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Unformatted text preview: Experiment title: Solvolysis of 2-chloro-2-methylbutane Introduction/Purpose of experiment: The main purpose of this experiment was to investigate the effect of various factors on the rates of S N 1 reactions. Specifically, we demonstrated the effects of structure on reactivity and the methods of studying chemical kinetics by way of solvolysis of tertiary alkyl halides. Solvolysis refers to a substitution reaction in which the solvent, HOS, functions as the nucleophile. In principle, solvolyses may be performed in any nucleophilic solvent such as water (hydrolysis). However, a limitation in choosing a solvent is the solubility of the substrate in the solvent because the reaction mixture must be homogenous. If it is not, then surface effects at the interface of the phases will make the kinetic results difficult to interpret. Therefore, for this experiment we explored solvolysis using 2-propanol and water. We monitored the progress of this reaction by determining the concentration of hydrogen ion [H + ] as a function of time. The value of [H + ] t was determined by withdrawing an accurately measured sample, called an aliquot, from the reaction mixture and quenching it with a quantity of 98% 2-propanol that was sufficient to prevent further solvolysis, as the solvolysis does not proceed at a measurable rate with so little water present. The elapsed time t In this experiment, 2-chloro-2-methylbutane is formed by way of S N 1 (unimolecular) mechanism. Mechanistically, there are two steps in the S N 1 reaction. The first step of the process involves the protonation of the hydroxyl group of the alcohol, which is also known as a Lewis acid-base reaction. Next, ionization occurs in the 2 nd step, where a molecule of water is lost. The ionization is the slow, rate-determining step (rds), while in the final step of the process, the chloride ion attacks the intermediate carbocation to give...
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This note was uploaded on 02/16/2010 for the course CHEMISTRY V25.0246 taught by Professor Callahan during the Spring '08 term at NYU.

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Orgo8 - Experiment title: Solvolysis of...

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