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Exp 32 - aspirin 4 recrystallization yield 5 color of FeCl...

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TA: HSIEN-PO CHIU OCT 16 & 18, 2007 Exp.32 Synthesis of Aspirin Principle 1. Esterification using acid anhydride R 1 O R 1 O O R 1 O R 2 O + R 2 OH 2. Acylation (Acetylation) of salicylic acid to aspirin OH COOH + O O O O COOH O + O OH salicylic acid acetic anhydride aspirin acetic acid conc H 2 SO 4 3. Rxn mechanism COOH + O O O OH O + O - COOH H O O O + COOH O H O - O + O COOH O + OH O 4. Side rxn in the existence of moist O O O + O H H O O - O + O H H O - O + O + O H H OH O 2 Safety caution Conc H 2 SO 4 is extremely corrosive. Wear goggles and gloves. Procedure : follow procedures on p.143. No spectral analysis Acylation vacuum filtration recrystallization by 95% ethanol/water analysis by FeCl 3 Result 1. Theoretical yield of aspirin 2. Crude yield of aspirin 3. Purified yield of
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Unformatted text preview: aspirin 4. recrystallization yield (%) 5. color of FeCl 3 analysis Q&A 1. H + plays a catalytic role in the synthesis of aspirin from salicylic acid by (A) increasing the nucleophilicity of salicylic acid (B) reducing the nucleophilicity of salicylic acid (C) increasing the electrophilicity of acetic anhydride (D) decreasing the electrophilicity of acetic anhydride 2. What happens when pure acetyl salicylic acid is combined with an aqueous FeCl 3 solution? (A) it turns purple (B) it reacts with the phenol group (C) it turns brown (D) no observable reaction...
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