Cannizzaro Reaction With 4-Chlorobenzaldehyde

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2.7 – Micro-scale Cannizzaro Reaction with 4-Chlorobenzaldehyde Student ID: ###### Name: Students Name Date: November 8th, 2010 1 - Aim: To prepare and isolate the products of the Cannizzaro reaction of 4-Chlorobenzaldehyde. 2 - Introduction: In the presence of a strong base, an aldehyde with acidic α hydrogens tend to form enolates and undergo Aldol condensation but aldehydes with no α hydrogens such as benzaldehyde, instead undergo a self oxidation/reduction known as the Cannizzaro reaction. 3 – Reaction Scheme: [pic] 4 – Table of Reagents: |Compound |RMM |Wt/g |Mol | |4-Chlorobenzaldehyde |140.57 |0.302 |0.00214 | The limiting reagent was 4-Chlorobenzaldehyde The maximum possible yield was 1.07 mmol. 5 - Procedure: The experimental procedure was followed as detailed on page 75 and 76 of the laboratory manual. An accidental spillage occurred during the recrystallisation of the alcohol product, resulting in a significant loss of product. 6 - Results: 6.1 - Product: Alcohol: Product was obtained as fine white crystals with a melting point range of 71°C-75°C. The substance did not have the same almond smell that was exhibited by the precursor compound. Acid: Product was obtained as coarse, white crystals with a melting point range of 240°C-242°C. 6.2 - Yield: Theoretical yield of alcohol: 0.1526g Theoretical yield of acid: 0.1668g |Compound |RMM |Wt/g |Mol |% Yield | |4-chlorobenzyl alcohol |142.58 |0.05 |0.00036 |32.77 | |4-chlorobenzoic acid |156.57 |0.1259 |0.000804 |75.48 | Discussion: The low yield of the alcohol was

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