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CHM+112B+Review+KEY - CHM112B FinalReviewSession 1 Me O Br...

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CHM 112B Final Review Session 1. 2. MeO Br O Me O Me H H H MeO plus any other reagent MeO O Me H Answer: O Me MgBr CuBr OLi Me MeO Br MeO O Me H O Me H H H MeO heat heat Justify stereochemistry in this step. heat O O Me MeO O O Me MeO O O Me MeO O O Me MeO O O Answer: MeO O O Me O O Me 4 ! conrotatory 6 ! disrotatory Claisen RAR Me
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3. 4. MeO Me Me CO 2 Me CO 2 Me heat Me Me CO 2 Me CO 2 Me Justify relative stereochemistry of methyl groups MeO Answer: MeO Me Me MeO Me Me MeO Me Me OR CO 2 Me CO 2 Me Me Me CO 2 Me CO 2 Me MeO N N N O N OH O NH 2 O HO H 2 N N OH O NH 2 O HO H 2 N O Cl H 2 N N NH O N N O O N N N O H 2 N Answer:
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5. Cl O O O N O O O 2 N O N H C A B Propose a synthesis for C starting from benzene, using A , B , and any other common organic laboratory chemicals. Bonus: show the mechanism for each step. Cl Cl O 2 N O O 2 N O O O O 2 N O OH O O O 2 N O Cl O O O 2 N O N O O O 2 N O Cl 2 , FeCl 3 HNO 3 , H 2 SO 4 CH 3 O - Cl O O O AlCl 3 NaOH, H 2 O Carbodiimide coupling OR Acid Cl formation N H Solution
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