Final Exam-2009

Final Exam-2009 - Name _ 1. (24 pts)...

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Name __________________________ page 1 1. (24 pts) Draw each of the molecules specified below. a. An aromatic heterocycle of molecular formula C 3 H 3 NO. b. 2-Benzylpyridine c. p -Vinylphenol d. γ -Aminobutyric acid e. N -allylpentanamide f. 3-Hydroxy-2-hexanone g. Ethyl 2-methylbutanoate h. Succinic anhydride (C 4 H 4 O 3 ). N O N O or N HO H 2 N OH O N H O O OH O O O O O
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page 2 Name __________________________ 2. (12 pts) Each set of compounds in parts a.-c. share common features. These features may include aspects of structure, physical properties, biological origin, etc. For each set, using appropriate terminology, describe the features that are common to all compounds in the set. a) O OH b) N N O N c) O HO HO HO HO O O HO HO OH HO O O HO OH OH HO O The compounds are all terpenes constructed of isoprene subunits and biosynthesized from dimethylallyl- and isopentenyl- pyrophosphates. The compounds are all aromatic with common structural features that include 4n + 2 π electrons, planarity, complete conjugation, cyclic. The compounds are all α -glycosides derived from aldohexoses and phenols. These three compounds occur naturally in plants OCH 3 OCH 3 OCH 3
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3. (12 pts) For each of the molecules shown in parts a.-d. draw an alternative resonance structure that would contribute more to the overall resonance hybrid than the structure shown. Use curved arrow notation to show electron movement from one structure to the next. c. Name __________________________ b. O page 3 a. d. N O O O N O O N H O O O N H O
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value in the space below each compound. pKa Draw the stuctures of the conjugated bases of each phenol and use resonance theory to explain why one of the phenols is more acidic than the other. Name __________________________ page 4 OH O OH 7.95 9.95 O O O O O O Additional resonance stabilization of phenoxide through resonance with the formyl group decreases basicity, which is seen as increased acidty of the phenol. O
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This note was uploaded on 03/30/2011 for the course MCMP 205 taught by Professor Staff during the Spring '08 term at Purdue University-West Lafayette.

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Final Exam-2009 - Name _ 1. (24 pts)...

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