chm2210ps15sol

chm2210ps15sol - No Reaction 20. 21. No Reaction 22. 23. No...

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Organic Chemistry I Problem Set 15 Answer Key Alcohols and Ethers I. Write structural formulas for important products. 1. 2. 3. 4. No Reaction 5. 6. 7. CH 3 -O-CH 2 -CH 3 conc HI excess reflux CH 2 -O-CH 3 excess conc HI reflux CH 2 CH 3 O HI reflux HI reflux O CH 3 C CH 3 Cl NaNH 2 CH 3 -CH 2 -OH C CH 3 CH 3 CH 3 OH CH 3 -CH 2 -Br CH CH 3 CH 3 OH CrO 3 H + / H 2 O / cool CH 3 -I + I-CH 2 -CH 3 CH 2 I + CH 3 -I OH + CH 3 -CH 2 -I CH 3 -CH 2 -O CH 2 C CH 3 C CH 3 CH 3 CH 3 O CH 3 C CH 3 CH 3 CH 2 CH 3 O CH 3 C CH 3 O + Cr +3 (green)
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8. 9. 10. 11. 12. No Reaction 13. No Reaction 14. 15. 16. 17. O CH H 2 C CH 3 H + / H 2 O O CH H 2 C CH 3 OH - / H 2 O O CH H 2 C CH 3 NaOCH 3 CH 3 OH O CH H 2 C CH 3 H + CH 3 OH CH 3 C CH 3 OH CrO 3 H 3 O + / cool CH 3 -CH 2 -OH LiAlH 4 CH 3 -MgI H + b. a. acetone POCl 3 heat CH 3 -CH 2 -MgBr CH 3 -CH 2 -OH CH 2 CH CH 3 OH OH CH 2 CH CH 3 OH OH CH 2 CH CH 3 OH CH 3 O CH 2 CH CH 3 OH CH 3 O CH CH 3 O NaBH 4 acetic acid H 2 SO 4 , reflux CH 3 -CH 2 -OH C CH 3 O O CH 2 CH 3 C CH 3 CH 3 CH 3 OH CH 2 C CH 3 CH 3 CH 3 -CH 3 + CH 3 -CH 2 -O O NaBH 4 H 2 O / EtOH OH
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18. 19.
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Unformatted text preview: No Reaction 20. 21. No Reaction 22. 23. No Reaction 24. II. Name the following: 1. 2. BIS-chloromethyl ether diphenyl ether 3. 4. 1,4-dioxane methoxybenzene (anisole) 5. 6. furan pyran 7. 1-ethoxycyclopentene O O CH 2 Cl CH 2 Cl CH 3 O O O O O O CH 2 CH 3 CH 3 C CH 3 O a. LiAlH 4 b. H 2 O CH 3-O-CH 3 a. LiAlH 4 b. H 2 O a. LiAlH 4 b. H 2 O O CH H 2 C CH 3 a. LiAlH 4 b. H 2 O C CH 3 CH 3 CH 3 OH a. LiAlH 4 b. H 2 O C CH 3 O O CH 2 CH 3 CH 3 C CH 2 CH 3 O PCC CH 2 CH 2 CH 2 OH Jones Reagent CH CH 3 CH 3 OH CH CH 3 CH 3 OH CH 2 CH 3 OH C CH 2 CH 2 OH O...
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This note was uploaded on 02/23/2010 for the course CHEM 201 taught by Professor Smith during the Spring '10 term at Duke.

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chm2210ps15sol - No Reaction 20. 21. No Reaction 22. 23. No...

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