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chm2211ps18 - CHM 2211 Problem Set 18 Alpha Substitution...

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CHM 2211 Problem Set 18 Alpha Substitution and Aldol Reactions Complete the Reactions. If No Reaction Occurs, Write N.R. 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. CH CH 3 O OH - warm OH - warm CHO 2 OH - Br 2 CH 3 C CH 3 O C O CH 3 I 2 NaOH / H 2 O / heat CH O + CH CH 3 O OH - CH OH CH 3 I 2 NaOH / H 2 O / heat H 2 C O CH 3 C CH 3 O + OH - OH - CH CH 2 CH 2 CH 2 CH 2 C CH 3 O O OH - CH O C CH 3 O + C CH 3 O O CH 2 CH 3 NaOEt 3,3-dimethylbutanone I 2 / NaOH H 2 O / EtOH / heat
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12. 13. 14. 15. 16. 17. 18. 19. C CH 3 O O CH 2 CH 3 NaOEt OH - / H 2 O / reflux H + heat C CH 2 C CH 3 O O O CH 2 CH 3 1 mole NaOEt 1 mole CH 3 CH 2 Cl 1. OH - / H 2 O / reflux 2. H + 3. heat NaOEt 1. OH - / H 2 O / reflux 2. H + 3. heat C CH 2 CH 2 CH 2 CH 2 C OEt EtO O O C CH 2 C OEt EtO O O 1. NaOEt 1. NaOEt 2. CH 3 CH 2 Br 2. CH 3 CH 2 CH 2 Br 1. OH- / H 2 O / reflux
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