Picture this. A chemical so powerful it might have been used to push rockets. Born out of secret World War II era labs and now showing real promise for zero emission hydrogen power. Think drones, portable fuel cells, hydrogen storage, all powered by one small but mighty molecule. Wait, one molecule does all that? Sodium borohydide. Today, we're putting that tiny workhorse to work in the lab. Sodium bow. What? Okay, slow down. It was discovered in 1947 in a rocket propulsion lab by Herman Schlesinger and his student Herbert C. Brown, and its crazy reduction power showed up almost by accident. Ooh, accidental science stories are my favorite. What happened? Brown tried to wash sodium borohydide with acetone, and suddenly isopropanol formed really fast. That observation showed it could reduce carbonal compounds, a serendipitous moment that changed organic synthesis forever. And Brown got a Nobel for that, right? Yep. Herbert C. Brown earned the Nobel Prize in chemistry in 1979. But the ripple effects kept going. Some of his students like Akira Suzuki and Aichi Nagishi later won the Nobel in 2010 for palladium catalyzed crossoupling reactions. Those reactions are huge in making complex molecules, drugs, materials, everything. Do our students get to try one of those? They do. Next week in lab, we'll run a Suzuki reaction. But today's focus is a hands-on reduction. We'll reduce benzopenone to benzyrol step by step and show how these Nobel discoveries connect to both pharmaceuticals and modern clean energy ideas. I love that. From a splash of acetone in a propulsion lab to hydrogen storage and drug synthesis, science really is full of plot twists. To the round bottom flask, add stirbar, 0.5 g of benzopenone, and 10 ml of methanol. Allow the reaction to stir for a moment. Lower the labjack and place an ice bath on the stir plate and use the labjack to raise the ice bath around the round bottom flask. Stir for a few minutes and add 0.5 g of sodium borohydide slowly to the reaction mixture. You will see the solution producing bubbles of hydrogen gas from the reaction of sodium borohydide with the methanol solvent. After 2 minutes, remove the ice bath and allow to stir at room temperature for 10 minutes. Again, cool the reaction with an ice bath and quench the reaction with the addition of dilute 3 molar hydrochloric acid and acidify reaction mixture to a pH of 2. Check the pH with the pH test paper until the pH is about 2. This will be evident when the pH paper turns red. If the pH paper turns blue, green or yellow, the solution is still basic and more HCl should be added. Although it was not done here, it is recommended that you add 5 ml of water after adding the acid. This will dissolve the white salts in the solution and make the extraction go smoother. You may ask yourself where these salts came from and what type of salt is it. Using hydrochloric acid to quench sodium borohydide leads to the formation of sodium chloride salt. with the sodium ion coming from the sodium borohydide and the chlorine ion coming from the hydrochloric acid. After quenching the reaction, the water from the quench and acidification must be removed from the mixture so the product can be recovered and analyzed. Here the reaction mixture is being added to the separatory funnel and the round bottom flask is rinsed with ether. Shake the separatory funnel and being sure to vent often and taking care to point the separatory funnel into the hood when venting. Always remove the stopper when you are not actively shaking the separatory funnel as it will become stuck or worse, pressure may build up inside the separatory funnel leading to the stopper popping out or potentially the flask exploding. Drain the water which is the lower layer into a labeled beaker. The top layer is the organic solvent solution containing the product. This layer will be added to a flask labeled organic. After collecting this material, set it aside for a moment. Now take the water solution that you removed from the separatory funnel previously and add it back to the separatory funnel. This will be extracted with another portion of ether. The goal here is to capture all the product molecules that may have escaped into the aquous layer. Extracting three times will remove 99% of the organic material from the water or aqueous layer. With each extraction, you will place the original aqueous layer back into the separatory funnel with fresh, clean organic solvent and shake, followed by removing the bottom aqueous layer. Remembering that this was the aqueous layer was the result of quenching the reaction with hydrochloric acid and water. And this water layer could still possibly contain some product and this is why we are extracting it three times with ether. This is the second extraction. The final step of the extraction starts by adding the same aqueous layer back to the separatory funnel again. We then add clean fresh ether to the separatory funnel. The lower layer containing the water is removed first, followed by removing the organic layer. At this point, you should have two flasks. One with the water layer and one with the organic layer. The organic flask with the organic layer should be a volume of twice or more than that of the water solution in the aquous flask. This flask holds the organic material. And as you can see, there is water in the bottom of the flask forming a white bubble. To remove this water from the organic, we will wash the organic solution with water. To do this, clean out the separatory funnel and add the organic material. To the separatory funnel, add water from the tap about 15 ml. Shake the separatory funnel. The lower water layer will be discarded and the top organic layer will be dried with sodium sulfate. Dry the organic solution with sodium sulfate. Then remove the solid sodium sulfate with a Buckner funnel. Be sure to add ether to the funnel before adding the solution with the sodium sulfate. This will ensure the filter paper is adhered to the funnel and not allowing any solid to pass by the filter paper. And finally, use a steam bath to remove the organic solvent from the product. Obtain NMR and IR data.