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HWKey (17) - mechanisms for the reactions that you use Use...

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Problem of the Day #16 – Answer Key Deadline : 3:00 p.m., Thursday, 7/3/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. In each part below, propose a sequence of reactions to synthesize the target compound from the indicated starting material(s). You may use any other organic and/or inorganic reagents necessary to complete your synthesis, but all carbon atoms in the target must be derived from the starting material(s) specified in each part. It is only necessary to give overall transformations in answering this question. It is not necessary to provide complete curved arrow
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Unformatted text preview: mechanisms for the reactions that you use. Use the back of the page if you need more space for your answers. (a) (10 points) Prepare from and as only sources of carbon atoms O Br Br CH 3 CH 2 Br (b) (10 points) Prepare from as only source of carbon atoms Br Br ( meso ) (racemic) Br Br O Br Br 1) NaNH 2 (3 equiv.) 2) CH 3 CH 2 Br HgSO 4 , H 2 SO 4 , H 2 O OR 1) (sia) 2 BH or BH 3 2) H 2 O 2 , NaOH, H 2 O 1) NaNH 2 (3 equiv.) 2) H 3 O + 1) NaNH 2 2) CH 3 CH 2 Br Br Br ( meso ) (racemic) Br Br NaNH 2 (2 equiv.) Na or Li (2 equiv.) in NH 3 ( l ) Br 2...
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