CHE 231-Synthesis

Br 2 h 2o 2 naoh oh h 2cro4 o o oh oh h 2so 4 o d cn 1

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Unformatted text preview: O d. CN 1. NaNH 2 2. Na, NH 3 O OH 3. H 2O PBr 3 OH or SOCl2, pyridine or TosCl, pyridine NaCN Br CN 4 2. Joe Bob, an 8th year senior taking CH 231 for the fourth time, has proposed to carry out the following reactions. Most of the reactions will not work as desired, however. If the proposed reaction would work, write “correct” in the box. If the reaction would not give the desired product, draw the product that would form. If no reaction would occur, write NR in the box. Briefly state why the reaction would not work. Actual product NB S H 2O a. OH Br Br OH In this reaction, the OH is added to the more substituted carbon. NaC C CH3 b. Br CH3 Strong base with secondary RX will give E2 product. c. Br NaNH2 NH2 DMF d. 1) BH3 2) NaOH, H2O2 Correct HO H HO H H H H and OH are added cis. Joe Bob has the wrong diastereomer of the product. 5...
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