8B_quiz8b-key - Chem 8B winter 2008 Quiz#8B Name_KEY(Last...

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Chem 8B, winter 2008 Name: _____ _____ KEY ______________ Quiz #8B (Last, First) ( print clearly) TA name or section #: ______________________________ • DO NOT start the quiz until you are instructed. • You must stop writing and turn in your quiz when time is called. • Ambiguous or incomplete answers will not get full credit. • Please give clear and concise answers – a single sentence or phrase should be sufficient to accurately convey the information required. “Brevity is the soul of wit” – Shakespeare Problem # Score 1. [14] ________ 2. [8] ________ 3. [10] ________ 4. [8] ________ Total [40] ________/40 Bonus [5] _________
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Chem 8B, quiz 8B 1. a) (4 pts) For the molecules shown below, circle the compound that has a more basic nitrogen and provide a brief explanation for your answer. O N H CH 3 N H CH 3 or O N H CH 3 The nitrogen of the amide is less basic because the lone pair is already shared in resonance with the carbonyl (see resonance structure) and so it is not available to grab a proton more basic because the lone pair is not shared in resonance so it is available to grab a proton (there is no carbonyl and the benzene ring is not directly connected) b) (4 pts) For the molecules shown below, circle the compound that is more reactive in a nucleophilic acyl substitution reaction with hydroxide ion ( OH). Provide a brief explanation for your answer. H 3 C O Cl H 3 C O N H CH 3 or the carbonyl of the acid chloride is more reactive (electrophilic) because the Cl is electronegative and pulls electrons away from the electrophilic carbon site, making the carbon more electrophilic H 3 C O N H CH 3
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