HW18Key - necessary to provide complete curved arrow...

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Bocknack CH 310M/318M Fall 2009 Graded Homework Problem #18 – Answer Key Deadline : 3:00 p.m., Monday, 11/16/09 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
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Unformatted text preview: necessary to provide complete curved arrow mechanisms for the reactions that you use. Use the back of the page if you need more space for your answers. (a) (8 points) Prepare from as the only source of C atoms in the target ( Hint : Count the number of C atoms in each structure carefully!!!) H O (b) (12 points) Prepare from ethylene and acetylene as the only sources of C atoms in the target OH H 2 /Lindlar cat. 1) O 3 2) (CH 3 ) 2 S O H Ethylene C C H H H H HBr CH 3 CH 2 Br (HCl or HI also OK) C C H H Acetylene 1) NaNH 2 2) CH 3 CH 2 Br H 2 /Lindlar cat. 1) BH 3 2) H 2 O 2 , NaOH, H 2 O OH...
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