ORGO midterm

ORGO midterm - CHM 2210 Problem Set 6 Due: October 20, 2008...

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1a. HBr adds to an alkene X to give compound 1 . CH 3 Br 1 HBr X Give us three (3) structures for an X that would give 1 as a major product. Explain with a mechanism how each structure for X could give 1 . Put the three structures in the boxes. OVER for part (b)
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1b. Ozonolysis of X followed by oxidative workup , gives formic acid (HCOOH) and cyclopentanone. Which of the three possibilities of part (a) is X ? Explain how you made your choice. X 1. O 3 2. HOOH O + H OH O
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2. Treatment of 1,5-cyclooctadiene ( 2 ) with one equivalent of Hg(OAc) 2 /H 2 O, followed by NaBH 4 , gives 3 , C 8 H 14 O (IR 3430 cm –1 ). Further treatment with Hg(OAc) 2 /H 2 O, followed by NaBH 4 leads to both 4 and 5 . Give a structure for 3 and explain the formations of 3 , 4 and 5 mechanistically. 1. Hg(OAc) 2 /H 2 O 2. NaBH 4 3 1. Hg(OAc) 2 /H 2 O 2. NaBH 4 O O 4 5
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2 adds to compound 6 to give only the trans product ( 7 ), whereas the product of syn addition ( 8 ) predominates in addition of Br 2 to alkene 9. Br
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ORGO midterm - CHM 2210 Problem Set 6 Due: October 20, 2008...

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