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Unformatted text preview: Experiment 20B: Synthesis of trans-Cinnamic Acid: Perkin Condensation 1) Compound Amount needed for Experiment Molecular Mass (g/mol) Boiling Point Melting Point Density g/mL Solubility Toxictiy/Hazards. Benzaldehyde 9.81 mmoles 106.12 178.1 C 26 C 1.0415 0.6 g/100 ml Skin Irritation Acetic Anhydride 14.83 mmoles 102.09 139.8 C 73.1 C 1.082 2.6 g/100 ml Severe Health/Moderate Flammability Potassium Acetate 6.11 mmoles 98.15- 292 C 1.57 Soluble in ethanol Slight Health/ None Flammable Trans- Cinnamic Acid Product (See Percent Yield) 148.16 300 C 133 C 1.2475 0.4 g/L Irritant 2) Chemical Reaction It is formed through the attack of the enolate anion of the acid anhydride (The enolate anion of acetic anhydride is formed when the catalyst attacks the acetic anhydride) on the aromatic aldehyde. A series of rearrangement follows, with an overall effect forming a carbon-carbon double bond (loss of water) hydrolyzing the anhydride group. Potassium acetate is used as a catalyst. The enolate anion of acetic anhydride is the nucleophile....
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- Winter '09