Test 3 Carbonyls Mechanisms Practice-Compressed

Test 3 Carbonyls Mechanisms Practice-Compressed - Some...

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1 Some Practice Problems for the Carbonyls Test 3 Draw the Products and Mechanisms for the following Reactions 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. O 1. PhMgBr 2. H 3 O + H O 1. 2. H 3 O + MgBr Ph Ph Aldehyde "enol" OH O OH, H 2 O Ph Ph OH O Ketone "enol" H + , H 2 O OH OH O + H 2 O Hydrate H + OMe OH O Hemiacetal + MeOH H + NHMe OH O + MeNH 2 H + Aminol OH NHMe NMe + H 2 O H + Aminol Imine H O OH OH H H 2 O, H H O OMe OH H MeOH, H OMe OMe H MeOH, H H O MeOH, H
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2 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. O HO OH H H O OH H + O OH H + O OH MeOH O OMe OMe OH H HOH, H OMe OMe H HOH, H H O H + O OMe H 2 O O OH H O OH H + O OH H 2 O, H MeO Ph OMe H 2 O, H O O Ph H O aminol Phase 1: Aminol Formation (an addition reaction) Phase 2: Aminol to Imine (an elimination reaction) H 2 NMe, H Ph NHMe OH H - H 2 O, H Ph H NMe Ph H O + H 2 NNH 2 H H O NH 2 H + HN OH
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3 23. 24. 25. 26. 27. 28. 29. 30. 31. 32. H + HN OH N Ph H NMe aminol Phase 1: Aminol Formation (an addition reaction) Phase 2: Aminol to Imine (an elimination reaction) H 2 O, H Ph OH NHMe H - MeNH 2 , H Ph H O H + N H 2 O HN OH H O NH 2 H + HN OH Ph O 2 Br 2 , 2NaOH H
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