"In a 125-mL Erlenmeyer flask containing a magnetic stirring bar, mix 0.05 mol of benzaldehyde with the theoretical quantity of acetone, and add one-half the mixture to a solution of 5 g of sodium hydroxide dissolved in 50 mL of water and 40 mL of ethanol at room temperature (Cleaning Up: Dilute the filtrate from the reaction mixture with water and neutralize it with dilute hydrochloric acid before flushing down the drain."
Using the above procedure answer the below question. Please explain your answer through illustration if necessary. Always make your explanation detailed.
1) p. 525 #5 How would you change the procedures if you wanted to synthesize benzalacetone (C6H5CH=CHCOCH3)?
2) How would you change the procedures if you wanted to synthesize benzalacetophenone (C6H5CH=CHCOC6H5)?
3) Draw the three geometric isomers of dibenzalacetone. Which do you expect as the product of the reaction of 2 Benzaldehyde + acetone dibenzalacetone and why?
4) Show a step-by-step mechanism of 2 Benzaldehyde + acetone dibenzalacetone?
5) Calculate a theoretical yield using the above procedure.
6) Show a step-by-step mechanism to make the Benzalacetone?
7) Show a step-by-step mechanism to make benzalacetophenone?
8) Why is it import to maintain the specified proportions of organic reagents 2 Benzaldehyde + acetone dibenzalacetone reaction?
9) Why is the condensation product, dibenzalacetone, formed in this reaction and not the aldol addition product, 1,5-dihydroxy-1,5-diphenylpentane-3-one?
10) Show the complete mechanism (step-by-step) for the formation of dibenzalacetone from benzaldehyde and benzalacetoone?
11) The normal characteristics stretching frequency of the carbonyl group of a ketone in the IR spectrum is about 1720 cm-1. Pick out the carbonyl stretching frequency of dibenzalacetone in Fig.37.6. Why is it so much lower than expected?
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