Synthesis Of 3-Nitrochalcone Lab Report

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The objective of this experiment was to use an aldol condensation reaction to synthesize 3-nitrochalcone from 3- nitrobenzaldehyde. This was accomplished with a Diels-Alder reaction that utilized 3-nitrobenzaldehyde, acetophenone, ethanol, and sodium hydroxide. The mechanism for the synthesis of 3-nitrochalcone is presented in Figures 1 and 2. The alpha carbon on the acetophenone is deprotonated. This is followed by the attack of the alpha carbon anion on the carbonyl carbon on the 3-nitrobenzaldehyde. Next, the oxygen is protonated from the 3-nitrobenzaldehyde, which is then followed by an elimination reaction where this acts as a leaving group. The product is the trans-alkene present in the product. After the reaction was completed, purification of the product was conducted using semi-microscale recrystallization.…show more content…
The yield of 3-nitrochalcone was 0.786 grams after filtration (percent yield of 62.04%). Multiple peaks were observed in the IR spectrum of 3-nitrochalcone at 1348.14 (N-O bond); 1593.33 (benzene ring); 1658.86 (unsaturated ketone). The carbon-carbon bonds are widely used in the drug industry to manufacture drugs and aldor condensation is used. Figure 1: Synthesis of 3-Nitrochalcone from 3-Nitrobenzaldehyde Source: Figure 2: Mechanism Involved in the Synthesis of 3-Nitrochalcone Source:
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