Discussion: Nucleophilic displacement - Formation of an ether by an SN2 reaction

In this experiment, 2-naphthol, sodium hydroxide, and ethanol were reacted via SN2 reaction and butyl naphthyl ether was obtained in 13.6% yield.  The product was identified to be ether via melting point which was measured at 32-34°C. TLC analysis was then performed to determine which components dominate the solvent mixture. For the 95:5 hexane:EtOAC mixture, the Rf value of 2-naphthol was 0.723 and the Rf value of the product was 0.702. For the 95:5 EtOAC:hexane mixture, the Rf value of 2-naphthol was 0.879 and the Rf value of the product was 0.914. For the 60:40 EtOAC:hexane mixture, the Rf value of 2-naphthol was 0.808 and the Rf value of the product was 0.787.