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The desired product, benzoic acid (3), is obtained by the following work-up: [2] Synthesis of benzoic acid with work-up step in red. The reaction mixture containing the Grignard reagent is allowed to warm to room temperature in a water bath to allow excess dry ice to evaporate. Any remaining Grignard reagent is quenched by the addition of water.
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (or DDQ) is the chemical reagent with formula C 6 Cl 2 (CN) 2 O 2. This oxidant is useful for the dehydrogenation of alcohols, [3] phenols, [4] and steroid ketones. [5] DDQ decomposes in water, but is stable in aqueous mineral acid. [6]
Acid–base extraction is a subclass of liquid–liquid extractions and involves the separation of chemical species from other acidic or basic compounds. [1] It is typically performed during the work-up step following a chemical synthesis to purify crude compounds [2] and results in the product being largely free of acidic or basic impurities.
For example, nonylmagnesium bromide reacts with methyl p-chlorobenzoate to give p-nonylbenzoic acid, in the presence of Tris(acetylacetonato)iron(III) (Fe(acac) 3), after workup with NaOH to hydrolyze the ester, shown as follows. Without the Fe(acac) 3, the Grignard reagent would attack the ester group over the aryl halide. [21]
In another example, the Nicolaou's total synthesis of Taxol uses this reaction, although coupling stops with the formation of a cis-diol, rather than an olefin. Optimized procedures employ the dimethoxyethane complex of TiCl 3 in combination with the Zn(Cu). The first porphyrin isomer, porphycene, was synthesised by McMurry coupling. [8]
Aldol reactions may proceed by two distinct mechanisms. Carbonyl compounds, such as aldehydes and ketones, can be converted to enols or enol ethers. These species, being nucleophilic at the α-carbon, can attack especially reactive protonated carbonyls such as protonated aldehydes. This is the 'enol mechanism'.
A solution of a carbonyl compound is added to a Grignard reagent. (See gallery) An example of a Grignard reaction (R 2 or R 3 could be hydrogen). The Grignard reaction (French:) is an organometallic chemical reaction in which, according to the classical definition, carbon alkyl, allyl, vinyl, or aryl magnesium halides (Grignard reagent) are added to the carbonyl groups of either an aldehyde or ...
Like many other oxidations of alcohols by metal oxides, the reaction proceeds via the formation of a mixed chromate ester: [3] [4] These esters have the formula CrO 3 (OCH 2 R) −. CrO 3 (OH) − + RCH 2 OH → CrO 3 (OCH 2 R) − + H 2 O. Like conventional esters, the formation of this chromate ester is accelerated by the acid.