Nucleophilic Substitution Reaction Lab Report

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In order to synthesize p-chlorophenoxyacetic acid, a nucleophilic substitution reaction was used as a reaction mechanism between the 4-chlorophenolate ion and the chloroacetate anion (Preparation of a Synthetic Plant Hormone Print Out). This specific type of reaction will yield a hydrogen ion and a deprotonated carboxylic tail that will participate in an acid treatment in order to produce the final compound, p-chlorophenoxyacetic acid. This specific mechanism involves the displacement of a leaving group. In order for the nucleophile to be able to leave, it had to be on a primary carbon. According to Mastering Organic Chemistry, this is necessary because the reaction is concerted, meaning that both the leaving group and substrate is key in determining…show more content…
According to Rhett Smith’s Organic Chemistry II Lecture Guide, the more groups that are around the leaving group, the less likely the reaction is going to occur. Therefore, if a leaving group is on a primary carbon, the reaction rate will be fastest. In this case, the chloride ion is attached to a primary carbon, allowing for the electrons to be pushed onto the chloride ion after the substrate (the oxygen on the 4-chlorophenolate anion) attacks the primary carbon. This allows for the easy removal of the chloride ion. The stability of the chlorine on the benzene of the 4-chlorophenolate anion does not allow for that particular chlorine to be used as a leaving group in this…show more content…
If the HCl were to be added to the solution too fast, then splattering would result which could potentially cause harm. Also, an exothermic reaction results when acid is being added to the solution because it is very reactive. The slow addition allows for there to be control over the reaction. The swirling action during the small additions of acid is needed in order to ensure a complete reaction with the mixture to produce a higher yield of p-chlorophenoxyacetic acid. During the vacuum filtration process, many techniques were used in order to ensure complete filtration of precipitate. Filtration allows for separation of impurities from pure compound. When setting up the apparatus, the filter paper was wet with a couple drops of water for a variety of reasons. Primarily, the water droplets hold the filter paper in place. Secondly, making sure to add the proper solvent to the filter paper before vacuum filtration causes the filter paper to have a similar polarity allowing for the easier separation of precipitate from
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