Question

propose a mechanism for the synthesis of 4-hexyn-3-ol from acetylene and propanal.

propose a mechanism for the synthesis of 4-hexyn-3-ol from acetylene and propanal.
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Answer:-

Mechanism:-

Step 1, is the oxidation of propanol to propanal by using PCC as an oxidizing agent. The propanal formed in the step 5, of this mechanism.

Step 2, is deprotonation of acetylene using one equivalent of NaNH2 (base).

Step 3, is the methylation of anion.

Step 4, is another deprotonation.

Step 5, is the nucleophilic addition reaction.

Step 6, is protonation.

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