practiceexam4b - epoxide one is intermediate in reactivity...

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2. Consider the following reactions. Please label whether they are oxidations, reductions, or neither. If there is an oxidation or reduction, please indicate the number of electrons involved. Please put your answer in the box provided. A. Br B. HO O O OH + 2CO 2 C. 1 12 pts
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- O O O O - - O O O O - 3. Complete the following equations: (Some may require more than one step.) Include stereochemistry where appropriate. a) HBr (excess) b) HI (Excess) O 2 32 pts
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c) O d) 1) NaOEt 2) aqueous work up O e) 1) NaH 2) CH 3 CH 2 I OH f) 3
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O EtOH H 2 SO 4 H H g) (Make sure to show all organic products.) O CH 2 H 2 Pd/C h) 4. Predict the major product(s) of the reaction shown below. Justify your answer using clear structures to support your hypothesis. 4 10 pts
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O 1) NaOMe 2) aqueous workup 5. Devise a synthesis of the molecule shown below. You may start with any 2- carbon olefins or alkynes, and any necessary reagents (including those used to append protecting groups if you need one). OH HO 5 14 pts
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6. Drawn below are three isomeric halohydrins. One reacts rapidly to form an
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Unformatted text preview: epoxide, one is intermediate in reactivity, and one does not react at all. Identify which halohydrin corresponds to each kind of reactivity and explain why. (Use clear structures to justify your arguments.) (H 3 C) 3 C OH Cl A (H 3 C) 3 C OH Cl B (H 3 C) 3 C OH Cl C 6 10 pts 6. Predict the product of the reaction sequence shown below. You must show stereochemistry. Do not show the product as a Fischer projection. OH Et CH 3 H TsO CH 3 1. NaOH 2. EtOH, H 2 SO 4 7 12 pts 8. Devise a synthesis of the compound shown below. You may use any organic starting materials of 3 carbons or less, but they may not contain deuterium. You may use any reagents you wish. D D 8 15 pts C341 EXAM IV Spring 2009 GRADE SHEET Question Possible Points Actual Points 1 10 _____ 2 12 _____ 3 32 _____ 4 10 _____ 5 14 _____ 6 10 _____ 7 12 _____ 8 extra credit 15 _____ Total 115 _____ 9 10...
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