the grard reaction is quite a useful reaction for forming new carbon carbon bonds the one major downside to the grard reaction is its incredible sensitivity to water presence of even a small amount of water is capable of ruining the reaction this is just a quick list of the chemicals that I use in this reaction I didn't list the quantity of The Ether the hydrochloric acid or the sodium hydroxide because you should have all of these in abundance an oven dried three-necked round bottom flask was charged with 1.5 G of magnesium as well as 15 mlit of dry ether the apparatus is closed from the atmosphere and a drying tube is at the top of the condenser column 5 ml of bromopropane was then injected into the solution the bromopropane was added slowly until the reaction started and then the rest was added at this point the reaction will start to occur and you can see the ether starting to reflux and boil if the reaction does not start adding a couple crystals of iodine almost always gets it to start you can see here that the solution has turned black and a lot of the ether is being lost so you're going to need to add more as the reaction progresses I keep injecting ether in order to try to maintain a constant volume if you use a very cold condens column you probably don't have to do this but since I'm just using tap water a lot of The Ether was lost out the top the reaction between the bromopropane and the Magnesium is shown above the bromopropane reacts with the Magnesium to form the grard reagent this reaction is very exothermic so it causes The Ether to boil and that's why it's very important to have a condenser column once the bubbling stops and The Ether stops boiling the reaction is complete and you can allow it to cool down to room temperature afterwards uh CO2 generator was set up using dry ice as shown because this grard reagent is very sensitive to moisture just for good measure I flushed the flask with nitrogen as well as the feeding tube the needle was then placed into the solution with strong stirring and CO2 was fed in as more and more CO2 is added the solution becomes thicker and thicker the reaction between the CO2 and the grard reagent is shown above as CO2 is bubbled through the solution there will be a loss of ether so you're going to have to replenish it several times bubble the CO2 through the solution for 15 minutes at least the product was transferred to an Erin me flask and washed several times with a total of 60 m L of three molar hydrochloric acid the addition of the hydrochloric acid induces hydrolysis which leads to the formation of our final butyric acid product the reaction that is taking place is shown above I did my best to wash out as much product as possible but there still was some that remained in the three neck round bottom after the addition of the hydrochloric acid the solution will bubble swirl the mixture around around and don't proceed to The Next Step until the bubbling has stopped in the end the solution should be completely transparent with a small ether layer on top and a larger aquous layer on the bottom then I directly vacuum filtered the solution into a separatory funnel this step is necessary to remove any unreacted magnesium metal but you definitely don't need to use the same setup that I did directly vacuum filtering into into the separatory funnel just saves a few steps the vacuum filtration apparatus was then washed with 50 mL of ether the solution was mixed thoroughly with frequent venting the lower aquous layer was drained and discarded and The Ether layer was maintained uyc acid is much more soluble in ether than in water so most of the BC acid should be in The Ether layer but some will be lost in the aquous layer wash The Ether layer with 30 mL of water and Save The Ether layer then wash The Ether layer with 21 mL of 3 molar sodium hydroxide and save the aquous layer this time this neutralizes the butyric acid and brings the sodium butyrate into the aquous layer wash The Ether layer again with 15 mL of 3 molar sodium hydroxide and again save the aquous layer then wash The Ether layer one last time with 15 mL of water and again save the aquous layer the aquous layers are then added back to the separatory funnel and re acidified using 50 mL of 3 molar hydrochloric acid this regenerates the ether soluble butyric acid the IC acid was then extracted using 30 ml of ether three times remember that it's always better to do multiple Washings with a smaller volume than one washing with a large volume the combined ether layers were then washed twice with 50 mL of saturated salt solution to dry it The Ether Washings were then drained into a round bottom flask and dried using sodium sulfate I use a separatory funnel and a small vial to evaporate The Ether I opted to use this method because using a rotor VAP could stink up the lab this way the butyric acid stays in the fume Hood the whole time finally I'm left with my final product which is clearly contaminated with something considering the pink color I'm entirely unsure what the pink color is caused by but I ran an NMR and it came back pretty clean