BENZOIN CONDENSATION Meaning and
Definition
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Benzoin condensation is a chemical reaction that involves the conversion of two molecules of aromatic aldehydes, most commonly benzaldehyde, into a single molecule of a benzoic acid derivative. This reaction typically occurs in the presence of a catalyst, such as a cyanide or a thiazolium salt.
During the benzoin condensation, the aldehyde groups of the aromatic aldehydes undergo a nucleophilic attack by another molecule of the same aromatic aldehyde, resulting in the formation of a nucleophile-stabilized intermediate. This intermediate then reacts with either another molecule of the aromatic aldehyde or the catalyst to form a new carbon-carbon bond, leading to the formation of a cyclic or acyclic dimer.
The benzoin condensation reaction is typically carried out in a solvent under acidic or basic conditions to maximize the yield and selectivity of the desired product. The product of this reaction is often a hydroxy ketone or a derivative of a hydroxy ketone compound.
Benzoin condensation reactions have several applications in organic synthesis, including the formation of carbon-carbon bonds, production of chiral compounds, and synthesis of natural products. It is commonly used as a key step in the synthesis of various pharmaceuticals, fragrances, and fine chemicals.
Overall, the benzoin condensation is a useful synthetic tool that enables the rapid construction of complex organic molecules through the coupling of aromatic aldehydes.
Etymology of BENZOIN CONDENSATION
The term "benzoin" comes from the Arabic word "lubān jāwī" (لبان جاوي) which means "frankincense from Java". It was originally obtained from the resin of certain trees in Southeast Asia, particularly in Java. The word "condensation" in the context of organic chemistry refers to a reaction where two molecules combine to form a larger molecule while simultaneously eliminating a small molecule, usually water. Therefore, the term "benzoin condensation" refers to the reaction in which two molecules of benzaldehyde combine to form benzoin while eliminating a molecule of cyanide or hydrocyanic acid.
