Solution

ID: past-exam-of-the-chemistry-course-of-the-year-4-of-the-natural-sciences-course-of-the-university-of-cambridge/2022/paper-2/section-i/34/c/ii/solution

The acidic ethanolic step converts the terminal carboxylic acid to its ethyl ester, leaving the pre-existing thiazole ester. Azide then adds across the alkyne by 1,3-dipolar cycloaddition, followed by protonation at work-up. F contains an NH-1,2,3-triazole replacing the alkyne, with the thiazole and attached to its two carbon atoms. The thiazole's own COEt group remains.
The formula check is decisive:
One can represent the cycloaddition with cyclic movement of the azide resonance-form electrons and the alkyne electrons into the two new C–N bonds. Alkali azide initially gives a triazolide; aqueous work-up provides the NH. Interchanging formal 4/5 labels for the carbon substituents in an N-unsubstituted triazole does not establish a separate permanently fixed N-substituted regioisomer.

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