Preparation of Benzoic Acid by a Grignard Reaction 05singhe
Which of the two reagents should be used depends on the other compounds present in the mixture. Sodium hydroxide is usually easier to handle because it does not evolve carbon dioxide as a byproduct. In addition, the concentration can be increased significantly if is needed. However, if compounds were present that are sensitive towards strong bases or nucleophiles (i.e., esters, ketones, aldehydes, etc.), sodium bicarbonate should be used. It does not react with these compounds because it is a weaker base and a weak nucleophile (due to its resonance stabilization). Note that the formation of carbon dioxide as a byproduct causes a pressure build-up in the separatory funnel, the centrifuge tube or the conical vial. Thus, additional precautions (i.e., frequent venting) have to be taken to prevent any accidents resulting from the pressure build up in the extraction vessel. The target compound can subsequently be recovered by adding a mineral acid to the basic extract i.e., benzoic acid in the Grignard experiment in Chem 30CL.
CARBONATION OF A GRIGNARDPREPARATION OF BENZOIC ACID
After separation of the organic and the aqueous layer, the amine can be recovered by addition of a strong base like NaOH or KOH to the acidic extract i.e., lidocaine synthesis. Note that amides are usually not basic enough to undergo the same protonation (pKa of conjugate acid: ~ -0.5).
Most neutral compounds cannot be converted into salts without changing their chemical nature. Many of these neutral compounds tend to react in undesired ways i.e., esters undergo hydrolysis upon contact with strong bases or strong acids. One has to keep this in mind as well when other compounds are removed. For instance, epoxides hydrolyze to form diols catalyzed by acids and bases. Ketones and aldehydes undergo condensation reactions catalyzed by both, acids and bases. Esters also hydrolyze to form carboxylic acids (or their salts) and the corresponding alcohol. In order to separate these compounds from each other, chromatographic techniques are often used, where the compounds are separated based on their different polarities (see Chromatography chapter).
Based on the discussion above the following overall separation scheme can be outlined. Which sequence is the most efficient highly depends on the target molecule. There is obviously no reason to go through the entire procedure if the compound sought after can be isolated in the first step already. Note that many of these steps are interchangeable in simple separation problems.
Despite all the limitations in preparing Grignard Reagent, it is still the most convenient way to synthesize certain alcohols and large molecules.
Grignard Reaction Preparation Of Benzoic Acid Lab Report
your synthesis based upon the amount of starting benzoic acid used, and another percent yield.
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Grignard Synthesis of Benzoic Acid
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