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ch12B_slides_problemsets - B.Problemsession...

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Ch. 12 - B. Problem session 12.5-12.8 Problems 12.19b,c,e  What is the major product of each of the  following reactions? Br 1. Mg 2. H H O 3. H 3 O + (a) (b) OH 1. PBr 3 2. Mg 3. H 3 O + (c) 1. EtMgBr 2. H 3 O + 3. NaH 4. CH 3 Br O H (a) Br Mg MgBr H H O O H H MgBr H 3 O + OH H H (b) OH PBr 3 Br Mg MgBr H O H H Grignard reagent is a strong base (c) O H EtMgBr O Et H MgBr H 3 O + OH Et H NaH O Et H Na CH 3 Br OCH 3 Et H
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Ch. 12 - B. Problem session 12.5-12.8 Problem 12.22  Draw a stepwise mechanism of the following  reaction. O O (1) MgBr (excess) (2) H 3 O + HO OH O O MgBr O O MgBr O O MgBr MgBr O O MgBr MgBr H 3 O + OH OH same HO OH
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Ch. 12 - B. Problem session 12.5-12.8  Propose a synthesis of each of  the target molecules (TMs) from the  designated starting materials (SMs) and  any necessary reagents. CHO (a) TM from OH SM COOH (b) TM from OH SM (c) TM from SM (d) TM from SM OH O O HO HO OH OH CHO TM OH oxidation MgBr O + Grignard on epoxide Br Grignard reagent OH SM ROH to RBr OH PBr 3 Br Mg MgBr O OH (1) (2) H 3 O +
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