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Experiment: Synthesis of Aspirin Title: Adolf von Baeyer's 1893 Synthesis of Aspirin: Acetylation of Salicylic Acid Ref: Hall, S. S. J. Chem. Education, to be

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Experiment: Synthesis of Aspirin Title: Adolf von Baeyer's 1893 Synthesis of Aspirin: Acetylation of Salicylic Acid Ref: Hall, S. S. J. Chem. Education, to be submitted (General reference: Smith, M. J. H.; Smith, P. K. The Salicylates, Interscience, New York, 1966). Purpose: Neat acetylation techniques with acetic anhydride and the phenol, salicylic acid Reagent table: Please write the answers to the questions below directly on your notebook. 1. Draw a detailed mechanism using curved arrow formalism of the synthesis of aspirin from salicylic acid and acetic anhydride. ( 5pts) 2. Hydrochloric acid is about as strong a mineral acid as sulfuric acid, why would HCl not be a satisfactory catalyst in this reaction? Please draw a reaction scheme to support your answer. (2 pts) 3. How is the purity of a crystalized solid assessed? ( 2 pts) 4. Briefly describe the technique for packing a capillary melting point-tube. ( 3 pts)

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