Iodobutane Lab Report

After deprotonation of 6.8 mmol naphthalen-2-ol by 14.0 mmol NaOH, the resulting anion was placed together with 8.8 mmol 1-iodobutane, and the reaction was performed by reflux in 20 mL of ethanol (EtOH) solvent, and the product was allowed to cool on ice and collected by suction filtration. The final crystals had a very pale amber color and were odorless. The following week, after being allowed to completely dry for a week at room temperature, the IR spectrum of the product in liquid suspension was measured (see attached spectrum), as well as the product’s melting point range and the percent yield of the reaction (The limiting reagent and theoretical yield were determined using the reaction stoichiometry).
Melting Point Range Trial 1: 30.3C …show more content…
In theory, two things are required for an SN2 reaction to proceed: a strong nucleophile (and by extension a good base), and a minimally substituted electrophile with a good leaving group attached. The reaction will proceed as shown in the mechanism below, with the nucleophile (Nu-) performing a backside attack on the minimally substituted electrophile (a generic methyl halide in this case), with the leaving group (halide LG) facing in the opposite direction …show more content…
If all goes as expected, the expected major product to arise from this experiment is 2-butoxynaphthalene. It should also be noted that this product will not occur by way of the unimolecular SN1 reaction, which involves carbocation formation of the electrophile in solution before any nucleophilic attack. As the name suggests, the SN1 reaction’s rate is only dependent on the formation of carbocations. However, if this were to happen with the electrophile 1-iodobutane, it would lead to a primary carbocation, a far too unstable molecule to form that easily in solution. Thus, this lack of carbocation formation bars any sort of product formation arising from the SN1