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2 C 6 Cl 2 (CN) 2 O 2 + C 10 H 12 → 2 C 6 Cl 2 (CN) 2 (OH) 2 + C 10 H 8. The resulting hydroquinone is poorly soluble in typical reaction solvents (dioxane, benzene, alkanes), which facilitates workup. Solutions of DDQ in benzene are red, due to the formation of a charge-transfer complex. [9]
The Corey–House synthesis (also called the Corey–Posner–Whitesides–House reaction and other permutations) is an organic reaction that involves the reaction of a lithium diorganylcuprate with an organic halide or pseudohalide (′) to form a new alkane, as well as an ill-defined organocopper species and lithium (pseudo)halide as byproducts.
In this example the organic layer is the product, which is a liquid at room temperature. The bottom aqueous layer is removed with a pipette and discarded. The top layer is transferred to an Erlenmeyer flask where it is treated with anhydrous sodium sulfate to remove any remaining water.
Such reactions usually involve an aqueous acidic workup, though this step is rarely shown in reaction schemes. In cases where the Grignard reagent is adding to an aldehyde or a prochiral ketone, the Felkin-Anh model or Cram's Rule can usually predict which stereoisomer will be formed.
The mechanism of the reaction involves two steps. The first step is a nucleophilic addition to the nitrile with the aid of a polarizing Lewis acid, forming an imine, which is later hydrolyzed during the aqueous workup to yield the final aryl ketone. Hoesch reaction mechanism
Furthermore, specialized synthetic routes include the reaction of dilithiated carboxylic acids with oxygen, followed by aqueous workup. [15] R−CHLiCO 2 Li + O 2 → R−CH(O 2 Li)CO 2 Li R−CH(O 2 Li)CO 2 Li + H + → R−CH(OH)CO 2 H + 2Li + + ... Additionally, α-keto aldehydes can be transformed into α-hydroxy acids through the ...
The McMurry reaction of benzophenone. The McMurry reaction is an organic reaction in which two ketone or aldehyde groups are coupled to form an alkene using a titanium chloride compound such as titanium(III) chloride and a reducing agent.
The Enders SAMP/RAMP hydrazone alkylation begins with the synthesis of the hydrazone from a N,N-dialkylhydrazine and a ketone or aldehyde [14]. The hydrazone is then deprotonated on the α-carbon position by a strong base, such as lithium diisopropylamide (LDA), leading to the formation of a resonance stabilized anion - an azaenolate.