Gringard Reactions are part of ochem known as organometallics.

Carbon attached to other atoms like oxygen hat are more electronegative than carbon makes it a electrophilic carbon. Metals make the carbons nucleophile. Can use the nucleophilic carbon to attack electrophilic carbons to make carboncarbon bonds. Victor Gringnard discovered the C-Mg reaction. Carbon Magnesium complex (gringard reagent) are commercially available, but are expensive and are reactive (Bad shelf life), so generally arent so great to purchase. To make them ,start iwht a halide typicallybromide but chloride (And rarely iodide) can be used. Attacking the R-X with Mg, makes a Gringard reagent, which is a nicleophile, base. Have to be careful of a protic environments. If there is a proton source, Gringard reagent will react with it. In a reaction, largest proton source usually the solvent so for Gringard, solvent needs ot be apriotic. If the only consideration was that the solvent needed to be aprotic (and the other job of the solvent is that everything has to be soluble), there would be many possible solvents used for gringards. But in literature, generally always use Diethyl ether (also tetra?). So if only has to be aprotic and everything has to be soluble, why use diethyl ether instead of others like hexane? It is because the lonepair of electrons in the ether being able to complex the Gringard reagent, makes it a much better solvent. 3 main side reactions reactions Gringard reagent reacting with oxygen. 2nd most electronegative element. Gringard is a strong nuclephile and reacts with oxygen to form peroxides. Gingard +CO2 Carbon dioxide readily attacks carbon dioxide to form carboxylates. Concentration of carbon dioxide that dissovles in the solvent is very small even though it is everywhere in the air. Usually forms very little product as a result. Bt even small amounts of product can be problematic in the case of peroxides. This can be eliminated by completely taking out the air from the reaction. Gringard + H-X: Gringard attacking the original halide source because halide is an electron source(?). Makes a R-R + MgX2. The halide has to be in solution for the reaction to occur. Cant completely eliminate it. If you cant completely eliminate it, minimize it. STatstics if we can Stoichiometrically, have to have comparable concentrations of . During the experiment, need to have R-X more likely to run into the Magnesium. Keep ___ concentration of ___ relative to ____ small. Start the experiment with small volumes so that statistically, keeps concentration of free halide small during the ocurse of the reaction. Stastically, it will be morelikely to run into a magnesium than anything else. As the experiment proceeds, the girngard reagent concentration increase so side reaction will start to happen more and more often. By the time it starts to become a siginificatn problem though, we will be finished. So we add halide slowly, keeping concenraino of halide small relative to magnesium. We will be performing a classic gringard reaction bromobenzene will be reacted in the presence of magnesium to produce the gringard reagent and then add dry ice to make carboxylate salt. Protonate with acid and then make the final product of benzylic acid. Water isvery bad for gringard reagetns. There are usually _ sources of water in a ny reaction. Largest source of water is the solvent. As long as the solvent is taken care of, takes care of most of the problem. Gringard reagent however is very sensitive so two other sare important. Air itself has humidity and need to dry the air before it enters the reaction. Need ot use drying tubes to eliminate air water.

Glassware itself has water and sometimes can be enough to hinder start of the gringard reaction. Best way is to flame dry it. Other way is drying oven for extended period of time. Not really practical in terms of time. We dry our glassware for 15 minutes. This si sufficient if you follow the directions in the syllabus. Make sure to explain glassware setup. 50 mL attached to calsen. On the straight arm instead of separator funnel, us e a rubber septa and syringe. Wire arm, place the reflux condnesor and on top, the drying tube is attached. Do not put the reflux condenser in oven. Only clasen and round bottom go in. Only glass goes in the drying oven. Adding the bromine with a syringe. IF there is any difficulty with the plunger pullin it out or pushing it in. Discard it immediately. All needles go in the sharps container. Do not recap the needle. Also, the joints must be greased, esp when using ether as solvent and environemtn is caustic. Ether gets into the airpockets between and causes a frozen joint. Grease fills those airpockets so ether cant get in. The most difficult part of the reaction si the first step. There is a progression that shows it is working. Burbles, cloudy, reflux, then gets darker in color slowly progresses. To speed up the reaction and make sure it worksh, add iodine ( a crystal or two) at the beginning of the reaction. Can also add gringard reagent to primer the pump. If all doesnt work, test tube reaction works for 80% people. The source f magnesium. There are 3 main sources mg strips and mg phylenes ( these are much more expensive) and magnesium powder (much cheaper). No magnesium powder in the oven. Put mg powder in the round bottom flast BEFORE adding the mg powder. The benzylic acid at the end will be a solid that is a sludgy mess at the bottom of the round bottom. At the beginning ,have benzylic acid and biphenyl (from side reaction). Do a solid-liquid extraction. Diethyl ether used to extract the benzylic acid. Biphenyl howver is also soluble in diethylether. Have to separate benzylic acid from biphenyl using liquid-liquid extraction by adding sodium hydroxide that moves the benzylic acid to the NAOH and then NaOH is neutralized and filtered to isolate benzylic acid. REcrsyatllize with water. Percent Yield, Melting Point, IR. Looking for aromatic ring, carbonyl peak of carboxylic acid. Good % yield is 60%.\