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EFS08 - CHE 322 Spring 2008 Final Exam Form 3 Page 1 1...

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CHE 322 Spring 2008 Final Exam Form 3: Page 1 1. Predict the major product of the following reaction sequence. Cl AlCl 3 Cl 2 FeCl 3 Cl Cl Cl Cl Cl (a) (b) (c) (d) (e) 2. Predict the product of the following Diels Alder reaction. O + H 3 C CH 3 CH 3 O H H 3 C CH 3 CH 3 O H H 3 C CH 3 CH 3 O H H 3 C CH 3 CH 3 O H H 3 C CH 3 CH 3 O H (a) (b) (c) (d) (e) 3. Consider the four π molecular orbitals of butadiene. Which of the following drawings does not properly represent one of the four π orbitals of butadiene? 4. Which of the following compounds is not aromatic? N O N H N H N N
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CHE 322 Spring 2008 Final Exam Form 3: Page 2 5. Predict the major product of the following reaction. Br 1. P(C 6 H 5 ) 3 2. LiC 6 H 5 H O O O Br 6. Predict the major product of the following reaction. H + (a) (b) (c) (d) (e) 7. Predict the formula of the major product of the following reaction. H 3 C O D + D 2 O 8. Which of the following compounds most readily forms a hydrate? In other words, which hydration reaction has the highest equilibrium constant? H H O H CH 3 O H 3 C CH 3 O H 3 C O O CH 3 H 3 C N H O CH 3 R R' O + H 2 O R R' HO OH K eq
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CHE 322 Spring 2008 Final Exam Form 3: Page 3 . 9. Predict the major product of the following aldol condensation. H O H O H O O H O H O 2 HO 10. Predict the major product of the following reaction. O CH 3 LDA Br O CH 3 O HO O O (a) (b) (c) (d) (e) 11. A student was asked to draw a mechanism for the acid catalyzed formation of a lactone. Which intermediate would not be found along a correct mechanistic pathway ? O O H O H H + H 2 O O O H O H H O O H H O H O O H O H H O O H O O O H H O O
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