Enolate Formation Lab - Name Joseph Youkhanna CHM2230...

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Name: Joseph Youkhanna CHM2230 : Section 11 Title: Enolate Formation – Aldol Reactions Date: February 21 st , 2007 Purpose: The purpose of this experiment is to carry out two Aldol reactions; this experience will highlight principles of reaction stoichiometry, and will also provide exposure to widely used carbon-carbon bonding forming reaction. Table of Reagents: Reagent Name Molecular Weight Mol used Part A 2 mL p-anisaldehyde 136.15 g/mol .016 mol 2 mL of acetophenone 120.15 g/mol .018 mol 6 mL of ethanol 46.06 g/mol .103 mol 10 drops of 50% aq. NaOH 39.99 g/mol NA 20 drops of ice-cold 95% ethanol 46.06 g/mol NA Minimum amount of hot methanol 32.02 g/mol NA Part B 50 mL of 2M NaOH 39.99 g/mol 2.66 mol 40 mL of ethyl alcohol 46.06 g/mol .685 mol 5.2 mL of Bezaldehyde * 147.0 g/mol .0512 mol 1.88 mL of acetone * 58.08 g/mol .0256 mol 5 mL ethanol 46.06 g/mol .085 mol 200 mL of H20 18.02 g/mol 11.05 mol 95% ethanol 46.06 g/mol NA * = Stoichiometry of starting material Benzaldehyde 0.0253 mol X 2 (ratio) = 0.0512 mol Density – 1.044 Molecular Weight – 106 g/mol (0.0512 mol Bezaldehyde) X (106 g/mol Bezaldehyde) X (1 mL/ 1.044g of Bezaldehyde) = 5.2 mL of Bezaldehyde Acetone 0.0253 mol X 1 (ratio) = 0.0253 mol Density – 0.791 Molecular Weight – 58.078 g/mol (0.0253 mol acetone) X (58.078 g/mol of Acetone) X (1mL/ 0.791g of Acetone) = 1.88 mL Acetone
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Product Data: Trans-anisalacetophenone 1-5-Diphenyl-1,4-pentadine-3-one Melting Point – 77-78°C Melting Point – 110-111°C Molecular Weight – 238.3 g/mol Molecular Weight – 234.31 g/mol Theoretical Yield – 3.8g Theoretical Yield – 6.0g (Calculation located in Stoichiometry and (From product literature) Percent Yield areas of lab report) Balanced Equation(s): Mechanisms (Reaction Scheme):
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Procedure: As per lab manual Results and Observations: Part A →I added 2 mL of p-anisaldehyde, 2 mL of acetophenone, 6 mL of ethanol, and 10 drops of 50% aq. NaOH into a flask →I proceeded to stir the mixture manually for 15 minutes →After a couple minutes, fog started to appear at the top of the flask →After the 15 minute mark passed, a yellowish crystal slushy formation was left in the flask →I put the mixture in a ice bath for 5 minutes to cool the reaction
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