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222_Aldol_Report.doc

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Department
Chemistry
Course
CHEM 203
Professor
David Harpp
Semester
Fall

Description
Chemistry 222 Fall 2012 1 By: Krishnaa Siva Date: November 28, 2012, Thursday 1:30-5:30 PM Lab Group TA: Mathieu Bedard Experiment 5 (Part 1): Aldol 1. Objective: 1 mark What is the purpose of this experiment? The objective of this lab is to produce a product through an aldol condensation reaction between a substituted benzaldehyde and a substituted acetophenone and then identify the product. Use the melting point analysis, IR, NMR and mass spectroscopy to identify the product that was formed. 2. Introduction: 1 marks Brief description of the concept/reaction studied – aldol reaction The Aldol Condensation reaction is another useful way to make a carbon- carbon bond. This reaction is generally used in organic chemistry to create bigger molecules as it involves two aldehydes or ketones reacting in the presence of a dilute base (McHale, 2007). In the case where two aldehydes are used, a molecule with both an aldehyde and alcohol functional groups and this is where this reaction gets its name. 3. Reaction Equation: 1 marks Include proper structures and data for reactants and products [molar mass, concentration, density, volume, mass, moles, etc – including theoretical yield] Chemistry 222 Fall 2012 2 Molar Boilin Densit mass g y (g/mol Melting Point (g·cm− Volume/ ) Point (C) (̊ ) 3) Mass Moles Acetophenone 0.005 (Unknown D) 120.15 19-20 202 1.028 0.58 mL substituted benzaldehyde (4- Chlorobenzaldehyde)= 213- (Unknown 3) 140.57 45-50 214 1.196 0.7012g 0.005 NaOH 39.997 318 1388 2.13 0.2060g 0.00515 Ethanol 460.07 -114 78.37 0.789 - - Theoretic Theoretical: al: 0.005 113.0 C - 117.0 C 1.2135 g Crude product: 0.00601 1.46 g 5 Experiment Pure al: 111.C ̊ product: 0.00263 4-Chlorochalcone 242.70 - 114.0 C 0.64 g 7 4. Procedure: 1 marks Summary of lab procedure – what YOU did, third person, past tense – be concise! 0.7012g (5 mmol) of Unknown 3 was mixed with 0.58 mL (5mmol) of Unknown D and 2 pellets ( 0.2060g) of NaOH in a mortar and pestle. This mixture was ground for 5 minutes. Next, 10 mL of water was added to the mortar and pestle containing the mixture. After scraping the sides, the suspension was filtered using vacuum filtration. The melting point and weight of the crude product was taken. This crude product was then put in a beaker of hot ethanol (placed on a hot plate) and it was left for some time for the product to dissolve. The beaker was then put in an ice bath in order to get the product recrystallized and the product was vacuum filtrated. The IR and melting point of the pure product was taken. To take the NMR, a small amount of the product was added to the NMR tube along with deuterated chloroform (until half way of the tube). This tube was then placed in the NMR machine. 5. Results: 2 marks a. Table 1: Yield and Physical Properties Chemistry 222 Fall 2012 3 Crude Aldol Product Purified Aldol Product Yield (g) 1.46 0.64g Yield (%) 120% 53% Yellow solid/crystals Appearance
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