One of the experiments we carry out in our first semester organic chemistry laboratory course is a substitution reaction to synthesize an alkyl halide.  Subsequently, the alkyl halide product is used as the starting material for an elimination reaction.  Our lab schedule is such that we synthesize a compound one week and then analyze it the following week.  Initially, we used an experiment involving the synthesis of 2-chloro-2-methylbutane from 2-methyl-2-butanol.  However, the products of the subsequent elimination reaction, 2-methyl-1-butene and 2-methyl-2-butene, were produced in such small amounts and were volatile enough that many of the students’ products evaporated before analysis, even when stored at 4<sup>o</sup>C.  Therefore, we have undertaken modification of the experiment to use 3-methyl-3-pentanol in synthesizing 3-chloro-3-methylpentane, and subsequently performing the dehydrohalogenation reaction to produce 2-ethyl-1-butene and 3-methyl-2-pentene.  We have tested the feasibility of this change and are working to optimize the modified procedures.  We will present the results of our studies.

Adapting a set of organic chemistry experiments for delayed analysis time

249th National Meeting (2015)

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