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12-11 - Final Exam Thurs Dec 17 8:00-10:45 AM Models and...

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12/11/2009 1 Final Exam Thurs, Dec 17 8:00-10:45 AM Models and one 5” x 8” index card permitted No calculators or other electronic devices R C ID 1 Room Course ID From To Sports Arena 2002 2759 Javits 102 2760 2868 Javits 100 2869 3066 Review Session Day Time From To Echoes will be posted 2 Fri Dec 11 - Javits 100 4:30 pm 6:30 pm Tools for understanding, remembering, and predicting reactions. Synthesis Stereochemistry 3 Addition/Elimination/Substitution Electrophiles/Nucleophiles Lewis Acids/Bases Resonance Induction/Hyperconjugation Electronegativity Structure Addition of NaHCO 3 to both A and B yields CO 2 . One diastereomer forms a compound with a new carbon structure C . One diastereomer does not. B NaHCO 3 /H 2 O CO 2 NaHCO 3 /H 2 O CO 2 + ? + ? 4 A Why is CO 2 formed? a. Deprotonation of the carboxylic acid by HCO 3 - b. Decarboxylation of the norbornene carboxylic acid + HCO 3 - H 2 O + CO 2 + H 2 CO 3 One diastereomer forms a compound with a new carbon structure C . One diastereomer does not. Which atom is the most nucleophilic (Lewis base)? a b c c 5 b a d d a One diastereomer forms a compound with a new carbon structure C . One diastereomer does not. Which atom is the most electrophilic (Lewis acid)? b c c b 6 a d d
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12/11/2009 2 One diastereomer forms a compound with a new carbon structure C . One diastereomer does not. electrophile electrophile 7 Why aren’t we considering the HCO 3 - ? It has approximately the same basicity as the norbornene carboxylate. Intramolecular reaction is faster than intermolecular reaction. nucleophile nucleophile One diastereomer forms a compound with a new carbon structure C . One diastereomer does not.
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