Chem 317 - Set 2 extra problems

Chem 317 - Set 2 extra problems - OH 1 b. Make compound 2...

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PROBLEM SET 2: ALCOHOLS CHEM 317 1. Name the following: a) OH b) OH Cl 2. Predict the more acidic compound for each pair below (explain your choice): a) Cl HO OH b) OH OH 3. Complete the following: O 1) CH 3 MgI 2) H 3 O + C 6 H 12 O A H 2 SO 4 heat C6H10 B H 2 Pt H 2 SO 4 heat C 6 H 12 O D KMnO 4 warm, conc. C 10 H 16 G H 2 SO 4 heat C 10 H 18 O F 1) Mg, diethyl ether 2) O 3) H 3 O + C 5 H 9 Br E HBr mCPBA C 5 H 8 O C 1) CH 3 MgI 2) H 3 O + 4. Complete the following reactions or reaction sequences: A, B MgBr O H 2 O C a. b. HO OH OH PCC CrO 3 /H + A B c. OH O 18 OH H 2 SO 4 + A d. A,B,C OH Br D e. O O O NaBH 4 LAH A B OH H 3 CO OCH 3 Fremy's salt A NaBH 4 B e. f. OH A O - Na + OTs B
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PROBLEM SET 2: ALCOHOLS CHEM 317 6. Synthesis a. make compound 1 starting from 1,4-butadiene and any other reagents you need.
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Unformatted text preview: OH 1 b. Make compound 2 starting from alcohols or hydrocarbons with 4 carbons or fewer O O c. Make compounds 3 and 4 starting with compound containing 4 carbons or fewer ( 3 and 4 are unrelated). Watch out for stereochemistry! HO Cl Cl 3 EtO 2 C CO 2 Et CHO OHC 4 5. What's wrong with the following reactions? How can you fix them so they'll work? 2 Br OH Mg ether O OH OH OH 1.NaOH 2. CH 3 I OCH 3 a. b. OH HCl 25 C c. Cl d. O 1. CH 3 MgBr CHO CH 3 HO CHO 2. H 2 O...
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Chem 317 - Set 2 extra problems - OH 1 b. Make compound 2...

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