PS_10 - Br OH 1. Mg (ether) 2. H 2 O PCC OH 5 5. Provide a...

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1 Problem Set #10 Swager 5.12 (Practice Only) 1. Suggest reagents and other organic intermediates (4 Cs or less) to carry out the following transformations. H O O Br CH 3 O CH 3 H 3 C CH 3 Br H O OH OH OH O
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2 2. Show all of the reagents and intermediates needed to carry out the following transformations. OH
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3 3. (30 points) Devise a synthesis for each compound shown. You may use any non-carbon reagents, TsCl, acids, or bases. OH CH(CH 2 CH 3 ) 2 (CH 2 ) 5 H O H(H 2 C) 5 From any fragments 5 carbons or less From and any other fragments Br OH OH From bromocyclohexane and any other fragments
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4 4. Give the major product(s) of the following reactions.
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Unformatted text preview: Br OH 1. Mg (ether) 2. H 2 O PCC OH 5 5. Provide a mechanism for the following reaction. H OCH 3 OCH 3 OCH 3 Et-O-Et (solvent) + O O TsOH (catalytic amount) O H 3 CO OCH 3 O H OCH 3 + 6. Cyclopropanone exists dominantly as a hydrate although acetone exists as only 0.1% in the hydrated form. Explain this observation. O H 2 O HO OH 6 7. Trichloroethanol can be readily prepared by reduction of chloral hydrate (shown) with sodium borohydride. Suggest a mechanism. Cl 3 C H OH OH NaBH 4 THF Cl 3 C OH...
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PS_10 - Br OH 1. Mg (ether) 2. H 2 O PCC OH 5 5. Provide a...

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