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Compound 1 undergoes a thermal elimination of nitrogen at C to form nitrile 4 (Org. Lett. 1999, 1, 537–539). One proposed subsequently refuted) mechanism for this transformation involves intermediates 2 and 3:
(b) To determine whether or not the proposed mechanism operates, one of the nitrogen atoms was isotopically labeled as 15N, and its location in the product was determined. The absence of 4b in the product mixture demonstrates that the proposed mechanism is not operating. Using resonance structures, explain why the proposed mechanism predicts that 4b should be formed.
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Based on our data, we think this problem is relevant for Professor Winter's class at ISU.
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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Klein 2nd Edition. You can also practice Organic Chemistry - Klein 2nd Edition practice problems.