exam4_f00 - O O 1 LiALH 4 2 H 2 O 1 K 2 CH 3 CH 2 Br f OH...

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Chem 12A EXAM #4 Name __________________ Dr. Harrison 1. (16 pts) a) Write the products of the reaction below when R = -OCH 3 , R = -CN, R = - CH 2 CH 3 , and R = -Cl. R HNO 3 H 2 SO 4 b) Predict the order of reactivity for the above reaction according to the following substituents. Place a 1,2,3, or 4 by the substituents with 1 being the fastest and 4 the slowest. Explain your reasoning. R = -OCH 3 R = -CN R = -CH 2 CH 3 R = -Cl 2. (12 pts) Suggest a mechanism for the following reaction. OH OH O H 2 SO 4
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3. (20 pts) Propose a synthesis to accomplish the following transformations. a) Br OH b) OH c) O d) CH 3 CH 3 e) CH 2 Br 2
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4. (20 pts) Write the major product for the following reactions. a) CH 3 HF HBr b) N H C O FeBr 3 AlCl 3 Cl Br 2 c) Br NaNH 2 NH 3 , -33 C d) OH + Cl O
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Unformatted text preview: O O 1) LiALH 4 2) H 2 O 1) K 2) CH 3 CH 2 Br f) OH OH PCC Na 2 Cr 2 O 7 H 2 SO 4 Acetone g) O O MgBr Ether H 3 O + 1) 2) 5. (12 pts) Cirlce the aromatic compound(s), but a box around the anti-aromatic compound(s), and underline the non-aromatic compounds. +-N N H H 3 C O O N N CH 3 caffeine 6. (16 pts) Write in the appropriate reagents to carry out the following reactions. Comment on the optical rotation results of each product. H HO H H 3 CS H Cl Cl racemic mixture optically active (-)-rotation SCH 3 H 7. (12 pts) Explain the differences in basicity for following amines. N N N conjugate acid 5.20 7.79 10.58...
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