notes_6_week_6_Practice%20Problem_KEY

notes_6_week_6_Practice%20Problem_KEY - 1. In order of...

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Unformatted text preview: 1. In order of increasing reactivity with NaBH4 rank the carbonyl containing molecules shown below. (1 = least reactive, 3 = most reactive) 2. Fill in the box with the appropriate starting material(s), product(s) or reagents. For products draw only the major organic products (unless otherwise specified). Note: H30+ = dilute aqueous acid. I . ' 0504 \ peroxides, NaOH 2. HIO4 —————————> O l. MeMgBr (o) 2. H3O+ /\/OH —-————> 3. Propose a high yield synthesis of compound R using only small alcohols (less than 3 carbons) as starting materials. You may use any additional reagents that are necessary. Show all reagents and the products formed after each step. 4. Starting with the molecule on the left, design an efficient synthesis of the product shown. Show all reagents and the products formed after each step. OH 5. You’ve isolated an unknown compound (A) that contains only Carbon, Hydrogen and Oxygen from a mixture of yeast metabolites. You take an Hl-NMR of A (shown below) and determine the mass (128) with mass spectrometry. Compound A gives product B (NMR shown below, mass = 132) when treated with excess LiAlH4. Upon subjection of product B with anhydrous PCC, product C (NMR shown below, mass = 128) is formed. What is the structure of Compound A? \ - i (D O—Cfir—Cl / N LiAlH 0 III 4 A (excess) B (FCC) . C mass = 128 mass = 132 mass = 128 singlet 6H singlet 2H Product B Singlet 6H singlet 2H Product C singlet 6H triplet 2H PPM 6. Draw the products of the reaction shown below. You are able to separate the three products that are obtained. The H-NMR and C-NMR of one of the products is shown below. Draw the structure of this product. 0 O 1. CH3MgBr (1 equiv) 2. H30+ 3 products 6H (singlet) 1 H(triplet) 2H(doublet) 11H(singlet OH 0‘ é'é‘fil'é'é‘l'rT—l—‘W’PBC‘J‘Q\H do ' 260 ' 1&0 1 1&0 ' 115 10PPM10 so 60 4o 20 ...
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notes_6_week_6_Practice%20Problem_KEY - 1. In order of...

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