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/35/c/i/solution

K is ethyl 4-(4-methylbenzoyl)-1H-pyrrole-2-carboxylate. AlCl activates the aroyl chloride to an acylium-like electrophile. Pyrrole attacks through C4, forming a sigma complex; deprotonation restores aromaticity and work-up releases the ketone from its Lewis-acid complex.
Unsubstituted pyrrole normally favours an position, but the ester at C2 changes the regioselectivity. Attack at C5, or at C3, permits important sigma-complex contributors with positive charge at the ester-bearing C2, which is strongly destabilized by the electron-withdrawing ester. C4 substitution avoids that particularly unfavourable contributor. The C2 ester therefore directs the acylation towards C4, overriding the simple unsubstituted-pyrrole rule. Combining the starting ester with a p-toluoyl group while replacing a ring hydrogen gives , as required.

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