Multistep Synthesis of Tetraphenylcyclopentadienone
Multistep Synthesis of Tetraphenylcyclopentadienone
Author:
Instructor:
Date work performed: 10.18.2012--10.25.2012
Date work submitted: 11.01.2012
Abstract:
The aim of this experiment was to perform a multistep synthesis to form tetraphenylcyclopentadienone. The first step of the reactions was to synthesize benzoin from the condensation of benzaldehyde. A yield of 28.91% benzoin was obtained. The MP of benzoin was 127O-130O C and the IR spectra displayed a carbonyl peak at 3415 cm-1 ,,which represents and OH functional group. The second step of the reaction was to oxidize benzoin to form benzil; this reaction yielded 27.04% benzil. The MP of the benzil was 91O-93O C and the IR spectra revealed no OH functional groups. The last step of the synthesis was a double aldol condensation reaction to form tetraphenylcyclopentadienone; this reaction had a yield of 76.56% and a melting point of 222O-225O C. The IR spectra revealed a ketone carbonyl peak at 1700 cm-1.
Introduction:
In this experiment a multistep reaction will be performed in order to synthesize tetraphenycyclopentadienone. The product will be synthesized in three steps, but in the industrial world companies often produce compounds that involve up to twenty steps. Tetraphenycyclopentadienone is produced by synthesizing benzoin through the condensation of benzaldehyde and thiamine being used as a catalyst. In the second step of the reaction, benzoin is oxidized to benzil; nitric acid is used as the oxidizing agent in this step. In the last step of the reaction, a mixture of benzil and 1,3-diphenylacetone undergo a double aldol condensation reaction then a dehydration reaction in order to form tetraphenycyclopentadienone.
Experimental:
Materials
* Thermometer * Round bottom flask (RBF) * Reflux condenser * Hot plate * Hirsh Funnel * Melttemp 2, to measure melting point * Microlet IR 100, to measure IR
Benzoin Condensation of Benzaldehyde
First 1.20
Author:
Instructor:
Date work performed: 10.18.2012--10.25.2012
Date work submitted: 11.01.2012
Abstract:
The aim of this experiment was to perform a multistep synthesis to form tetraphenylcyclopentadienone. The first step of the reactions was to synthesize benzoin from the condensation of benzaldehyde. A yield of 28.91% benzoin was obtained. The MP of benzoin was 127O-130O C and the IR spectra displayed a carbonyl peak at 3415 cm-1 ,,which represents and OH functional group. The second step of the reaction was to oxidize benzoin to form benzil; this reaction yielded 27.04% benzil. The MP of the benzil was 91O-93O C and the IR spectra revealed no OH functional groups. The last step of the synthesis was a double aldol condensation reaction to form tetraphenylcyclopentadienone; this reaction had a yield of 76.56% and a melting point of 222O-225O C. The IR spectra revealed a ketone carbonyl peak at 1700 cm-1.
Introduction:
In this experiment a multistep reaction will be performed in order to synthesize tetraphenycyclopentadienone. The product will be synthesized in three steps, but in the industrial world companies often produce compounds that involve up to twenty steps. Tetraphenycyclopentadienone is produced by synthesizing benzoin through the condensation of benzaldehyde and thiamine being used as a catalyst. In the second step of the reaction, benzoin is oxidized to benzil; nitric acid is used as the oxidizing agent in this step. In the last step of the reaction, a mixture of benzil and 1,3-diphenylacetone undergo a double aldol condensation reaction then a dehydration reaction in order to form tetraphenycyclopentadienone.
Experimental:
Materials
* Thermometer * Round bottom flask (RBF) * Reflux condenser * Hot plate * Hirsh Funnel * Melttemp 2, to measure melting point * Microlet IR 100, to measure IR
Benzoin Condensation of Benzaldehyde
First 1.20