4. (a) A WileyPlus problem from the (now defunct) Ch. 21 assignment I used to give asked about the product formed from the aromatic nitrile below upon reaction with amide. Their product was actua...
4. (a) A WileyPlus problem from the (now defunct) Ch. 21 assignment I used to give asked about the product formed from the aromatic nitrile below upon reaction with amide. Their product was actually quite different than mine... That said, both have plausible mechanisms to support their formation. Propose two different mechanisms to explain the formation of the two different products (don't bother drawing the mechanism of the acidic workup that's Ch. 16). (9 points) WP answer 2 equiv KNH2 liquid NH My answer: 1. 2 eq. KNH2/NH 2. HOH 0 workup NH O (b) It tuns out, WP was right and I was wrong (doggone it!). The product formed depends on what happens as the very first reaction between NH2 and the reactant. What likely occurs first, in the WP mech, which cannot occur first if my mechanism was to occur? And why should I (having scads of pKa's memorized) have known there was a potential problem with my proposed mechanism? (NH2 is similar in basicity to LDA.) (4 points)
4. (a) A WileyPlus problem from the (now defunct) Ch. 21 assignment I used to give asked about the product formed from the aromatic nitrile below upon reaction with amide. Their product was actually quite different than mine... That said, both have plausible mechanisms to support their formation. Propose two different mechanisms to explain the formation of the two different products (don't bother drawing the mechanism of the acidic workup that's Ch. 16). (9 points) WP answer 2 equiv KNH2 liquid NH My answer: 1. 2 eq. KNH2/NH 2. HOH 0 workup NH O (b) It tuns out, WP was right and I was wrong (doggone it!). The product formed depends on what happens as the very first reaction between NH2 and the reactant. What likely occurs first, in the WP mech, which cannot occur first if my mechanism was to occur? And why should I (having scads of pKa's memorized) have known there was a potential problem with my proposed mechanism? (NH2 is similar in basicity to LDA.) (4 points)