Problem: 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. 

FREE Expert Solution
92% (428 ratings)
Problem Details

Compound undergoes a thermal elimination of nitrogen at C to form nitrile  (Org. Lett. 19991, 537–539). One proposed subsequently refuted) mechanism for this transformation involves intermediates 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. 

Frequently Asked Questions

What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Reaction Mechanism concept. You can view video lessons to learn Reaction Mechanism. Or if you need more Reaction Mechanism practice, you can also practice Reaction Mechanism practice problems.

What is the difficulty of this problem?

Our tutors rated the difficulty ofCompound 1 undergoes a thermal elimination of nitrogen at C ...as high difficulty.

What professor is this problem relevant for?

Based on our data, we think this problem is relevant for Professor Winter's class at ISU.

What textbook is this problem found in?

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.