Chem 109 Lab 611

Linda Tran Nov. 27

The Synthesis and Analysis of Aspirin

Objective: To synthesize aspirin from salicylic acid and acetic anhydride, determine the amount of salicylate ion found in the filtrate, and to use the titration method on the aspirin made to determine the purity of it. Experimental Reactions: Synthesis of Aspirin Equation: Salicylic acid + acetic anhydride -> aspirin + acetic acid C7H6O3 + C4H6O3 -> C9H8O4 + C2H4O2 USP Test for Salicylate: (Fe+3) + 3 salicylate ion -> Fe(salicylate ion)3 NaOH (aq) + KHP (s) -> Na+ (aq) + K- (aq) + H2O (l) NaOH + acetylsalicylic acid -> NaOH (aq) + C9H8O4 (s) -> Na+(C9H7O4)-(aq) + H2O (l) Results and Discussion: Calculations: Theoretical Yield: 0.016moles Aspirin (180.154 aspirin / 1 mole aspirin) = 2.88g Aspirin Percent of Theoretical Yield: (1.254g Aspirin synthesized / 2.8g aspirin) * 100 = 43.5% NaOH Morality for each Titration: 0.614g KHP (1 mol KHP / 204.179g KHP) (1 mol NaOH / 1 mol KHP) (1 / 0.0248L) = 0.121M NaOH 0.626g KHP (1 mol KHP / 204.179g KHP) (1 mol NaOH / 1 mol KHP) (1 / 0.0248L) = 0.114M NaOH 0.693g KHP (1 mol KHP / 204.179g KHP) (1 mol NaOH / 1 mol KHP) (1 / 0.0248L) = 0.119M NaOH Mass Percent of Synthesized Aspirin: 0.0181L NaOH (0.128M NaOH) (1 mole aspirin / 1 mole NaOH) (0.310g aspirin / 1 mole aspirin) = (7.18*10^-4g aspirin / (0.310g)) * 100 = 0.23% 0.0156L NaOH (0.128M NaOH) (1 mole aspirin / 1 mole NaOH) (0.336g aspirin / 1 mole aspirin) = (6.17*10^-4g aspirin / (0.336g)) * 100 = 0.20% 0.0156L NaOH (0.128M NaOH) (1 mole aspirin / 1 mole NaOH) (0.330g aspirin / 1 mole aspirin) = (6.59*10^-4g aspirin / (0.330g)) * 100 = 0.20% Percent Aspirin in the Commercial Tablet: 0.0256L NaOH (0.128M NaOH) (1 mole aspirin / 1 mole NaOH) (0.597g aspirin / 1 mole aspirin) = (1.9*10^-3g aspirin / (0.597g)) * 100 = 0.32%

Spectrophotometer Analysis: Graph:

Concentration of Salicylate in Filtrate: 0.00015M salicylate in filtrate with the absorbance of 0.143 Discussion: The structural formulas of acetaminophen, Naprosyn, and dextropropoxyphene are different types of pain relievers. Acetaminophen is C8H9NO2, Naprosyn is C14H13NaO3, and dextropropoxyphene is C22HNO2. When comparing these different pain relievers we see that Naprosyn has Na instead of N, each formula has different ratios of elements. Aspirin contains 325mg of 5 grain, Molecules of Acetaminophen: (325mg) (1g 5 grain / 1000mg) (1mol 5 grain / 1g 5 grain) (1mol ace / 1 mol 5 grain) (150.154g ace / 1 mol ace) (6.022*10^23 molecules / 1 mole ace) = 2.94*10^25 molecules Molecules of Naprosyn: (325mg) (1g 5 grain / 1000mg) (1mol 5 grain / 1g 5 grain) (1mol ace / 1 mol 5 grain) (252.094g nP / 1 mol nap) (6.022*10^23 molecules / 1 mole ace) = 4.93*10^25 molecules Molecules of Dextropropoxyphene: (325mg) (1g 5 grain / 1000mg) (1mol 5 grain / 1g 5 grain) (1mol ace / 1 mol 5 grain) (311.231g Dex / 1 mol Dex) (6.022*10^23 molecules / 1 mole ace) = 6.09*10^23 molecules Sources: http://chemistry.about.com/od/demonstrationsexperiments/ss/aspirin.htm http://dailymed.nlm.nih.gov/dailymed/ http://en.wikipedia.org/wiki/Paracetamol http://en.wikipedia.org/wiki/Naprosyn http://en.wikipedia.org/wiki/Dextropropoxyphene