Experiment 4 Preparation of Benzil from Benzoin: Nitric Acid Oxidation of Benzoin Benzoin Benzil | MW 212.24, mp 135°C MW 210.23, mp 995°C | Part 1- Nitric Acid Oxidation of Benzoin 1, Heat a mixture of 4 g of benzoin and 14 ml of concentrated nitric acid on a steam bath for 11 minutes. Carry out the reaction under the hood. v Once the reaction is complete add 75 ml of water to the reaction mixture, cool to room temperature, and swirl for a minute or two to coagulate the precipitated product. 3. Collect the product on a Buchner funnel. Press the product well to remove the moisture 4. Recrystallize the product from 10 ml of ethanol. Once the product is dissolved add water dropwise to reach the cloud point. Allow the product to recrystallize. wa Once the product has recrystallized collect it on a Buchner funnel and dry it. What is the appearance of the purified benzil? 6. Determine the melting point and theoretical yield of the product. Part 2- Testing for the Presence of Unoxidized Benzoin 7. Dissolve about 5 mg of the purified benzil in 0.5 ml of 95% ethanol and add 1 drop of 10% sodium hydroxide, If benzoin is present the solution will acquire a purplish color 8. If no color appears in 2-3 minutes, an indication that the sample is free of benzoin, add a small amount of benzoin and observe the color that develops. 9. Did your product contain unoxidized benzoin? 10. Dispose of the waste in the organic waste container. The Chemistry of Vision Why are some organic compounds colored but other aren’t? Ordinary “white” light, from the sun or from a lamp, consists of all wavelengths in the visible region. When white light strikes a highly conjugated compound, such as p- carotene, the wavelength from 400-500 nm (blue) are absorbed, while all other wavelength are transmitted and can reach the eyes. We therefore see the white light with the blue subtracted out, and we perceive a yellow-orange color for f-carotene. What is true for B-carotene is true for all other colored organic compounds: All have an extended system of x electron conjugation that give rise to an absorption in the visible region.An orbital examination of the x-bonding network of benzil reveals that each carbon atom. possesses a p orbital that can overlap with the p orbitals of the neighboring carbon atoms on both sides. This orbital arrangement leads to an extended conjugation system involving all 14 carbon atoms, and makes it possible for a wavelength of visible light to effect a n-n* electronic transition in the conjugated molecule. Such molecular interaction with electromagnetic radiation remove one or more wavelength components from the light reflected to our eye. We interpret this wavelength absence as color. O20) ‘The structure of Benzil and its conjugation system. Observed Physical Properties Melting point: 94-95 °C. Yellow Color power. Answer the following questions on your notebook. 1. The balanced equation for the oxidation of benzoin with nitric acid requires how many moles of nitric acid per mole of benzoin? In the balanced equation for the oxidation of benzoin with nitric acid, what compound is the oxidizing agent? 3. How many steps are involved in the mechanism? 4. Step two involves what types of reaction? 5. What is an extended conjugation system? 6. The extended conjugation system in benzil involves how many carbons? N