Testing Your Organic Chemistry Knowledge to Reinforce ...

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Testing Your Organic Chemistry Knowledge to Reinforce Comprehension and Understanding using Web-based Multiple Choice Questions 333. Strongest Base Pick out the strongest base: a. A *b. B c. C d. D e. E Andrew Boa and Jason Eames* Department of Chemistry, University of Hull a.n.boa@hull.ac.uk; j.eames@hull.ac.uk Correct Answer Reply: In these examples, the strongest base can be identified by considering the delocalization, or not, of the nitrogen lone pair of the amino group. In all examples, except for the B, the lone pair is stabilized by conjugation with an unsaturated system - the aromatic rings in molecules C, D and E, and the carbonyl group in A. KEYWORD: RESONANCE
Testing Your Organic Chemistry Knowledge to Reinforce Comprehension and Understanding using Web-based Multiple Choice Questions 334. Strongest Base 2 Pick out the strongest base: a. A *b. B c. C d. D e. E Andrew Boa and Jason Eames* Department of Chemistry, University of Hull a.n.boa@hull.ac.uk; j.eames@hull.ac.uk Correct Answer Reply: Compound B is the strongest base due to the charged hydroxide counter anion. All other compounds A, C and D are neutral amine bases, except for amide E, which is not basic as the lone pair is conjugated to the carbonyl group. KEYWORD: HETEROATOM
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