Exam_3_Chem_35_2005_answers

Exam_3_Chem_35_2005_answers - Chemistry 35 Exam 3 ANSWERS...

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1 Chemistry 35 Exam 3 – ANSWERS April 28, 2005 1) (21 points) Devise a synthesis for each of the transformations shown below using the indicated starting material. Each of the syntheses can be accomplished in 2 steps, although you can use as many steps as you find necessary. Make sure that you indicated stereochemistry where it is required. Your answers should be structured as follows: 6WDUWLQJ 0DWHULDO 5HDJHQWV±² 3URGXFW³² 5HDJHQWV±´ 3URGXFW³´ HWFµ³DV QHFHVVDU\ You do not need to provide mechanisms. A) (3 points) Br 2 Br Br LDA or tBuOK, B) (3 points) O O Br 2 , H 2 O Br OH NaH A one step synthesis using mCPBA is also OK, but this is a reaction from chapter 10. C) (3 points)
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2 OH CN OH CN TsCl pyridine OTs NaCN D) (3 points) Br Br Br Br Br Br Br Br LDA or tBuOK, HBr SiO 2 E) (3 points) O CO 2 H OMe O CO 2 H OMe H 2 SO 4 MeOH OH OMe KMnO 4 , NaOH or Jones oxidation F) (3 points)
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3 Br OPh Br OPh LDA or tBuOK, or DBU H 2 SO 4 PhOH G) (3 points) Br Br O Br Br O LDA or tBuOK, HgSO 4 H 2 SO 4 H 2 O A one step synthesis using water and heat is also acceptable. This reaction would amount to a double S N 1 reaction, followed by a dehydration, all occurring under the same reaction conditions.
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4 2) (18 points) The following reactions provide a reactant, reagents and a product. If the indicated product is correct, write ‘correct’ in the adjacent box. If the indicated product is incorrect, write ‘incorrect’ and provide the correct product in the box.
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This note was uploaded on 05/17/2008 for the course CHEM 0350 taught by Professor Suggs during the Spring '08 term at Brown.

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Exam_3_Chem_35_2005_answers - Chemistry 35 Exam 3 ANSWERS...

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