Chem210-1 F05 Ex3 p04a

Chem210-1 F05 Ex3 p04a - with aqueous acid a Provide...

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4. Compound 'D' has formula C 7 H 12 . When 'D' was treated with hydrogen gas in the presence of a Pt catalyst, it reacted to give compound 'E', in the process using two moles of H 2 for every mole of compound 'D' initially present. When compound 'D' was ozonolyzed, using an oxidative work-up, only two products (compounds 'F' and 'G') could be identified as products; the relative amounts of 'F' and 'G' were not determined. Compound 'F' was found to be the same material formed when cyclopentene is oxidatively cleaved using warm, basic permanganate (MnO 4 ), assuming subsequent neutralization
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Unformatted text preview: with aqueous acid. a) Provide structures for compounds 'D', 'E', 'F', and 'G' (9 points total) b) Indicate the reagent(s) needed for an oxidative work-up in the ozonolysis procedure. (3 points) c) Compound 'X', an isomer of 'D', was found to react with only one mole of H 2 per mole of 'X, when treated with H 2 and Pt. What structural feature is present in compound 'X' which is NOT present in compound 'D'? (3 points). 'D' H 2 C=CH-CH 2-CH 2-CH 2-CH=CH 2 'E' 'F' 'G' CH 3-CH 2-CH 2-CH 2-CH 2-CH 2-CH 3 HO 2 C-CH 2-CH 2-CH 2-CO 2 H HCO 2 H H 2 O 2 'X' must possess a ring in its structure...
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