chm2211ps18sol - CHM 2211 Problem Set 18 Solutions Alpha...

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COO + CHI 3 COO + CHI 3 CHM 2211 Problem Set 18 Solutions Alpha Substitution and Aldol Reactions Complete the Reactions. If No Reaction Occurs, Write N.R. 1. 2 . T h i s i s a C a n n i z a r r o reaction. One molecule gets oxidized and the other gets reduced. 3. 4. 5. 6. 7. 8. 9. 10. 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 CH CH 2 CH CH 3 O OH COOH CH 2 OH + CH Br Br Br C CH 3 O O + CH OH CH 2 CHO CH 3 C CH 2 CH 2 O HO O OH -H 2 O O H CH CH C O C CH 2 CO O CH 2 CH 3 O H 3 C
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O OH O C CH CH 2 CH 2 CH 3 OH O CH 2 CH 3 C C CH 2 CH 2 CH 3 OEt O CH 2 CH 3 COOEt C CH 2 CH 2 CH 3 OH O O CH 3 CH 3 OH CH 3 CH 3 Br CH 3 CH 3 O OCH 2 CH 3 O + EtOH CH 3 C CH 3 O 11. 12. 13. 14. 15. 16. 17. 18. C CH CH CH H 2 C H 2 C O CH 3 1. (CH 3 ) 2 CuLi 2. H 2 O NaBH 4 EtOH / H 2 O PBr 3 3,3-dimethylbutanone I 2 / NaOH H 2 O / EtOH / heat 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 CO E t EtO O O C CH 2 E t EtO O O 1. NaOEt 1. NaOEt 2. CH 3 CH 2 Br 2. CH 3 CH 2 CH
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This note was uploaded on 07/26/2009 for the course CHEM 2211 taught by Professor Grow during the Spring '09 term at Pensacola Junior College.

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chm2211ps18sol - CHM 2211 Problem Set 18 Solutions Alpha...

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