Question
Discuss the oxidation of monoalkylacetylenes using thalium nitrate. Also give the mechanism of the reaction.
Answer :
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The oxidation of monoalkylacetylenes using thallium nitrate is an important reaction in Organic Chemistry-II for the conversion of alkynes into carbonyl compounds. When a monoalkylacetylene reacts with thallium nitrate in an aqueous medium, the triple bond undergoes oxidative cleavage to produce a carboxylic acid or an α-ketoaldehyde, depending on the substitution pattern. Thallium nitrate acts as a mild oxidizing agent and selectively attacks the π-electrons of the triple bond, facilitating the addition of oxygen. The mechanism begins with the coordination of the thallium ion to the triple bond of the monoalkylacetylene, which increases the electrophilicity of the
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