PPS 15 solutions - Br Page 3 of 4 7 H C H H O H H O H H H O H H O H H C H O H H O H H O H O 8 H H H H H H Na NH 3(l H H H H H H H H 2 Equiv KMnO 4

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C357 PPS#15 Solutions Page 1 of 4 1) a) 3-heptyne b) (2E) 3-bromo-7,7,10-trimethylundeca-2,9-dien-5-yne c) (6E) dec-8-en-2-yne d) hepta-1,6-diyne 2) C C H 3 C H H C + H O + H H H O S O O O H O H H H H O H H H O H H H O S O O O H C + O H O + H O H H O 3) C C H 3 C H Br Br C + H Br Br H Br Br-
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Page 2 of 4 4) Compound A Compound B Compound C Compound D H 2 /Pt H 2 /Ni 2 B Na, NH 3(l) 5) A and C are believed to involve carbocation intermediates. 6) Br Br C + Br- Br Br
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Unformatted text preview: Br Page 3 of 4 7) H + C + H H O H H O + H H H O H H O H H + C + H O H H O + H H O H O 8) H H H H H H Na NH 3(l) H H H H H H H H 2 Equiv KMnO 4 O HO O OH H H Page 4 of 4 9) Dr. Who: H 1) BH 3 2) H 2 O 2 , NaOH H 2 O Major Product Dr. Strangelove: H Major Product Alkene 1 Alkene 2 H 2 SO 4 H 2 O O H O H H...
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This note was uploaded on 03/31/2008 for the course CHEM 3570 taught by Professor Ganem, b during the Fall '06 term at Cornell University (Engineering School).

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PPS 15 solutions - Br Page 3 of 4 7 H C H H O H H O H H H O H H O H H C H O H H O H H O H O 8 H H H H H H Na NH 3(l H H H H H H H H 2 Equiv KMnO 4

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