Project Description: • To reduce benzil to hydrobenzoin (phase one) and analyze/verify the product; then synthesize stilbenediol

acetonide from that hydrobenzoin (phase two) and analyze/verify that product. Synthesis Plan: • Phase One: Benzil to Hydrobenzoin (1,2-diphenylethane-1,2-diol) *We will reduce benzil (in ethanol) with sodium borohydride, to produce hydrobenzoin (1,2-diphenylethane-1,2-diol). The solution will be filtered (if necessary), then set aside to crystallize. Phase Two: Hydrobenzoin to Stilbenediol acetonide (2,2-dimethyl-1,5-dioxolane) *We will take the hydrobenzoin produced in phase one, dissolve it in acetone (acetone is solvent and reactant) and add iron (III) chloride as a catalyst. We will heat the solution to form the stilbenediol acetonide. The solution will be poured into water (that contains a base that will react with the acid) and the product will be extracted with dichloromethane. The product will be crystallized in hexane and cooled, collected, and dried.

Purification Determination (for phase one-- benzil to hydrobenzoin step): • Melting Point Determination—the MP of hydrobenzoin should be 136137 degrees Celsius • Thin-layer chromatography—our Rf value should be between .3 and .7; our pure product should only make one spot (not multiple spots) Verification (for phase one-- benzil to hydrobenzoin step): • IR Spectroscopy—looking especially the for spectra show absorptions for O-H, the benzene ring/aromatic carbons, and the C-O bond *O-H bond: 3400-3650 cm-1 *Benzene Ring/Aromatic Carbons: 3030 cm-1 and 1660-2000 cm-1 (both weak)/ 1450-1600 cm-1 (medium) *C-O stretch: 1050-1150 cm-1 (strong) • Mass Spectroscopy—the molecular weight of hydrobenzoin should be 214.25; if different ion fragments are shown on the spectra, we can determine the structure of the compound (and confirm that we have hydrobenzoin) by observing how it fragments Purification Determination (for phase two-- hydrobenzoin to stilbenediol acetonide step): • Thin-layer chromatography—our Rf value should be between .3 and .7; our pure product should only make one spot (not multiple spots) when viewed under UV light

Gas chromatography—our product should show only one peak (with maybe a small peak for air); we should have only one isomer of stilbenediol acetonide present (making only one peak)

Verification (for phase two-- hydrobenzoin to stilbenediol acetonide step): • IR Spectroscopy—looking especially the for spectra show absorptions for the benzene ring/aromatic carbons, the C-O bond *Benzene Ring/Aromatic Carbons: 3030 cm-1 and 1660-2000 cm-1 (both weak)/ 1450-1600 cm-1 (medium) *C-O stretch: 1050-1150 cm-1 (strong) • Mass Spectroscopy—the molecular weight of stilbenediol acetonide should be approximately 254.3; if different ion fragments are shown on the spectra, we can determine the structure of the compound (and confirm that we have stilbenediol acetonide) by observing how it fragments Chemicals: • Benzil • 95% Ethanol • Sodium Borohydride • Solid Sodium Chloride • Acetone • Anhydrous Iron (III) Chloride • 3M Potassium Carbonate • Granular Anhydrous Calcium Chloride • Dichloromethane • Hexane Special Materials: • Wilfilter • Small separatory funnel • Viton connector • Pipe cleaner • Air condenser