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272_quiz2_solutions - thus more'tightly held(another way of...

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Chain Chem 272 Quiz 2 1. Citric acid and zingerone are two naturally occuring compounds. What orbitals are used to form each indicated bond? 2. What is the hybridization of the N atom in each compound? Rank the basicity of these compounds (1 = most basic, 3 = least basic). Name: HO O O CO 2 H CO 2 H H citric acid HO O CH 3 H CH 3 O zingerone H 3 C C H 2 C N CH 3 H 3 C H N CH 3 N Hybridization Basicity Answer Key sp sp 2 sp 3 3 2 1 Recall, more 's-character' means a lone pair is closer to the nucleus and
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Unformatted text preview: thus more 'tightly held' (another way of saying they are lower energy and more stable). Therefore, lone pairs in orbitals with more 's-character' are less basic (their conjugate acids are more acidic). (O) sp 3 + (H) s (O) sp 2 + (C) sp 2 and (O) p + (C) p (C) sp 2 + (C) sp 3 (C) sp 3 + (C) sp 3 (C) sp 3 + (O) sp 2 ( think resonance ) (C) sp 2 + (H) s (C) sp 2 + (C) sp 3 (C) sp 3 + (C) sp 3...
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