Dibenzal Acetone

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Medaille College *

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301

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Chemistry

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Feb 20, 2024

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docx

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5

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1 . CHEMICAL EQUATIONS, MECHANISM. 2. DATA Mass of acetone: 1.451g Moles of acetone: 1.451g x (1mol/ 58.08g/mol) = 0.025g (MW = 58.08 g/mol) Mass of benzaldehyde: 5.3g Moles of benzaldehyde: 5.3g x (1mol/ 106.13g/mol) = 0.050moles (MW = 106.13 g/mol) (Density = 1.044 g/mL) M.P. of crude product: Fast: 107 to 111°C Slow: 107 to 110°C Mass of recrystallized product: 5.19g M.P. of recrystallized product: Fast: 108 to 111°C Slow: 109 to 111°C FTIR of final product–attach spectrum: Dibenzalacetone
3. RESULTS 1 mol rxn = 1 mol acetone = 2 mol benzaldehyde = 1 mol dibenzalacetone 0.05 mol benzaldehyde x (2 mol acetone/ 1 mol benzaldehyde) = 0.10 mol 0.05 mol benzaldehyde x (1 mol rxn / 2 mol benzaldehyde) = 0.025 rxn 0.10 mol acetone x (1 mol rxn/ 1 mol acetone) = 0.10 rxn Calculate the theoretical yield of dibenzalacetone: (MW of dibenzalacetone: 234.30 g/mol) Theoretical Yield: 0.025 mol dibenzalacetone x 234. 30g/mol = 5.9g Calculate the % yield of purified dibenzalacetone: Actual Yield: 5.19g (5.19g/ 5.9g) x 100 = 88% 4. DISCUSSION/QUESTIONS (FTIR) o There are three possible geometric isomers of dibenzalacetone. Draw their structures.
o Which is the major product? What is the IUPAC name for the major product? What is its melting point? The trans – trans (E, E) isomer is the major product. (1E,4E)-1,5-Diphenylpenta-1,4-dien- 3-one. The melting point is 104 - 110 °C. o List and discuss at least 3 important bands from your FTIR and compare your spectrum to a known spectrum of the product. The bands in the fingerprint area (labeled A) could be the C=O group, and where it is around 980-960cm-1, label B, indicates a strong C=C bending trans – 1,2 disubstituted. And the C-H peaks above the 3000cm-1, circled, presents that it has double bonds. Our spectrum compared to the known spectrum is pretty accurate. The only difference is that in the known spectrum, there is a slight peak indicating an -OH group, which wasn’t transfer in our product. ^ (Known Spectrum of Dibenzalacetone from google) ^ o Did you produce the correct product? How do you know?
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Yes, we produced the correct product. We could tell by comparing our spectrum with the known FTIR, which resulted in similar property with slight variations. We could identify the product and check its impurity by determining the GC-MS and NMR. The melting point for my product (108 to 111°C) was closely accurate to the actual melting point (110 °C ~ 111 °C). o Is there any evidence of benzaldehyde, water, other isomers, or any other impurity in your purified product in the IR or from the M.P.? There are some evidence of impurities in the fingerprint area. Small peaks present in the IR (circled) also show some evidence of impurities. Also, there is evidence of some benzaldehyde. o What more could you do to identify the product and check its purity? By examining the melting or boiling points of our product, we can determine its purity. The melting and boiling points of a substance will alter if it is impure because it will contain residues of other substances. We could also use MS to check for its purity. o Were there any problems encountered that might explain lower than expected yields or impure product? If so, discuss what happened. The percent yield seems to be accurate. Though it might be low, the product of the experiment was achieved because dibenzalacetone was obtained. Some of the product might have been lost during the process of recrystallization. We can also tell by comparing our melting point to the actual melting point (110 °C ~ 111 °C). This is due to some impurities that might still exist in the particular compound which can lower the melting point.
o Discuss and assign the peaks from the NMR spectrum of the student product. There are multiplets in the region 7.35 - 7.65ppm relate to the different protons contained on the phenyl groups of the compound, which represents the meta- and para- protons on the benzene rings. The peaks around 7.7-7.8 ppm represent the protons nearest the carbonyl. The peaks around 7.0-7.1 ppm represent the protons between the carbonyl and benzene rings (NMR spectrum) o Describe how the procedure would change to produce benzalacetone (C 6 H 5 CHCHCOCH 3 ) or benzalacetophenone (C 6 H 5 CHCHCOC 6 H 5 ). To produce benzalacetone, instead of using two equivalents of benzaldehyde, we could just use one equivalent, and we can condense benzaldehyde and acetone by means of dilute alkali and from benzaldehyde and diketene. And to produce benzalacetophenone, we would use one equivalent of benzaldehyde and replace acetone with a compound that resembles it but has a phenyl group (ex., acetophenone)