1. Compound 1 was identified to be Benzoic Acid. The sample’s melting point range (122.5°C -123.2°C) fell within the range of pure Benzoic Acid (121°C – 125°C). The IR spectra also provided key peaks only found in Benzoic Acid compared to the other compounds, such as the carboxylic C=O stretch at 1678.44 cm-1 and the very broad O-H stretch at 2552.89 cm-1 – 3071.13 cm-1. Based on the acid/base chemistry, the reaction between sodium bicarbonate and benzoic acid leads to the products of the sodium salt of benzoic acid and carbonic acid. Compound 2 was identified to be 2-naphthol. The sample’s melting point range (121.3°C – 122.6°C) was slightly below the range of pure 2-naphthol (123°C – 124°C), therefore melting point analysis was not sufficient to determine the identity of the compound. The IR spectra on the other hand provided many key peaks such as a much more narrow...
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...and conversion to an ionic salt. Compound 2 (2-naphthol) would then be extracted with sodium hydroxide.
Based off the reaction, the conjugate acid (pKa = 15.7) is weaker than the starting acid (pKa=14.7), resulting in the formation of products and conversion to an ionic salt. Using the base of sodium hydroxide first results in a failure of separation. Because the conjugate acid of sodium hydroxide is a weaker acid than both the starting acids Benzoic acid and 2-naphthol, both compounds would be extracted together from the mixture. The conjugate acid of sodium bicarbonate on the other hand is a stronger acid than 2-naphthol, therefore products would never form due to equilibrium lying towards the reactants. Sodium bicarbonate assures compound 1 and 2 would be separated from one another due to the strength of acidity, represented by the following reaction.
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