Pb85an-0243-09 - (c Hydrogenation leads to cyclononane B(d...

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Answers to Problem 85, Chemistry 0243 - 2009 Compound X must be 1,4,7-cyclononatriene, or if you want to be picky, cis,cis,cis -1,4,7-cyclononatriene. (a) Ozonolysis gives only Y . (b) The 1 H NMR spectrum shows a methylene group between two double bonds, and a set of simple olefinic hydrogens. Coupling leads to triplets in each case, as there are two equivalent adjacent hydrogens in each case.
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Unformatted text preview: (c) Hydrogenation leads to cyclononane B . (d) Photolysis of diazomethane gives methylene (:CH 2 ), which adds three times to the available double bonds. There are two possible triple adducts, the all-cis and trans versions. C 9 H 12 1. ozone 2. H 2 /Pd/C X Y O O H H 9 H 2 /Pd/C h ! CH 2 N 2 B C and D...
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This note was uploaded on 03/02/2010 for the course CHEM orgo taught by Professor Jones during the Fall '10 term at NYU.

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