Question

Experiment You have just started graduate school at a prominent university, and are looking forward to developing new drugs (which as an aside you've decided is easier to explain to your family at holidays when they ask "so what is it that you do?"). As you know by now, many drugs are derived from or inspired by natural products. One such molecule that you keep reading about is curcumin, which is the reason turmeric is yellow, and serves as a staple of alternative medicine. Unfortunately, in the lab results have generally not confirmed that curcumin is in fact particularly useful – it readily decomposes in the body and isn't very bioavailable (meaning it Figure 3. Potential Polyeneone Compounds for Drug Leads isn't absorbed very well), and as a result isn't considered to be a viable scaffold for drug development. However, analogues of curcumin OME Curcumin Оме Dibenzylidene acetone without the second carbonyl, such as dibenzylidene acetone, though not very bioavailable, seem to be much more stable. In fact, research has shown that these compounds, which can be easily prepared by the aldol condensation between ketones and aromatic aldehydes, can have useful cytotoxicity against various cancer cell lines, without significant side effects such as neurotoxicity. As such, your Figure 4. Unknown Aldehydes and Ketones goal will be to prepare analogues of these compounds. CHO CHO CHO Prelab Questions HOY OH үсно Meo 1) Based on the Material Safety Data Sheets (MSDS) for the compounds, which of the compounds in this experiment is the most hazardous, and why? Me Me Me
Answer the second question please

Answer 1

Acid catalyzed aldol condensation of acetophenone and benzaldehyde

- c=0 - Chhe the + H+ > Phc ОН Ph-ch Ht Ph-ch OH -C Acetophenone - CH2 Enol 0 Ph - c H + H+ -H CH OH Ph-c- H Benzaldehyde Protonated Benzaldehyde JOH , Ph-CECH H1 0 + Ph OOH OH Ph-C-Cty - CH-Ph H Enol Protonated Benzaldehyde ой Ph-c-ch-Ct Ph Aldol Dehydration step 0 :0H Ph-c-ch-CH-ph ozo tht - Ph-C-CHACH - Ph 1-H₂O Ph-c-CH=CH-Ph. po 12, ß- unsaturated ketone

All the reactions are fairly reversible with Final (dehydration) step lying more favorable towards products. (P.S. it is also reversible to certain extent, if water remains in the reaction mixture, otherwise it is irreversible)