Naphthalen 2-Ol Lab Report

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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 – 31.1C
Melting Point Range Trial 2: 30.1C – 31.0C
Actual Yield of 2-butoxynaphthalene = 0.34g product x 1 mol 2-butoxy = 0.001698 moles 200.281g 2-butoxy

Limiting Reagent: naphthalen-2-ol (0.006 moles)
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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

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