Self-condensation of acetone is a possible side reaction for the aldol condensation (Reaction 1). Draw the structure of this side product. How is this side reaction minimized in our procedure written below? Reaction 1 - Experimental Procedure: In a clean, small Erlenmeyer flask, combine your unknown aromatic aldehyde (350 μL (400 mg if it is a solid)), 95% ethanol (2.0 mL), and 5 N aqueous sodium hydroxide (0.6 mL). Swirl to mix, and then add acetone (100 μL). Stir/swirl vigorously for 30 minutes, until precipitation is complete. If no precipitate forms after 15 minutes, heat the Erlenmeyer flask gently in on the sand bath in the hood for 15 minutes, and then allow it to cool to room temperature. Whether heated or not, cool your Erlenmeyer flask in an ice bath for 10 minutes to ensure complete crystallization. Collect the product by vacuum filtration. (If you do not have any solid at this point, evaporate all solvent in the sand bath. Recrystallize if solid residue is obtained; otherwise stop here and analyze the liquid residue.) Wash the crude product consecutively with ice-cold 95% ethanol (1 mL), 10% acetic acid (1 mL), and again with ice-cold 95% ethanol (1 mL). Air dry your sample.

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Self-condensation of acetone is a possible side reaction for the aldol condensation
(Reaction 1). Draw the structure of this side product. How is this side reaction minimized
in our procedure written below?

Reaction 1 - Experimental Procedure: In a clean, small Erlenmeyer flask, combine your unknown
aromatic aldehyde (350 μL (400 mg if it is a solid)), 95% ethanol (2.0 mL), and 5 N aqueous
sodium hydroxide (0.6 mL). Swirl to mix, and then add acetone (100 μL). Stir/swirl vigorously for
30 minutes, until precipitation is complete. If no precipitate forms after 15 minutes, heat the
Erlenmeyer flask gently in on the sand bath in the hood for 15 minutes, and then allow it to cool
to room temperature. Whether heated or not, cool your Erlenmeyer flask in an ice bath for 10
minutes to ensure complete crystallization. Collect the product by vacuum filtration. (If you do
not have any solid at this point, evaporate all solvent in the sand bath. Recrystallize if solid
residue is obtained; otherwise stop here and analyze the liquid residue.) Wash the crude product
consecutively with ice-cold 95% ethanol (1 mL), 10% acetic acid (1 mL), and again with ice-cold
95% ethanol (1 mL). Air dry your sample.

Reaction 1:
2
unknown aromatic
aldehyde
H
+
H3C
acetone
CH3
5 N NaOH
EtOH
+ 2 H₂O
Transcribed Image Text:Reaction 1: 2 unknown aromatic aldehyde H + H3C acetone CH3 5 N NaOH EtOH + 2 H₂O
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