W03 problems6c key

W03 problems6c key - CH 3 OH H + O OH H O CO 2 H O OH CO 2...

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CO 2 H OH O CO 2 H O Ph OH O H 2 CrO 4 Ph H O Br 2 O O OCH 3 HO OH O OCH 3 O O O - O O LiAlH 4 H 3 O + O OH O OH O CO 2 H H 2 N Ph CO 2 - Ph OH O O OH COOH Na + HO O O O O - K + O CO 2 H O SH Problem Set-6/Chapter 17 Carboxylic Acids (page 1) Chem 30B-Winter 2003 TA: Chris Mortko, cmortko@chem.ucla.edu D i s c u s s i o n S e c t i o n s Wednesdays: 8-9am (MS 3915H), 9-10am (Boelter 5273) O f f i c e H o u r Wednesday 10-11am (Young 1379) P r o v i d e t h e r e a g e n t s o r p r e d i c t p r o d u c t ( s ) n e c e s s a r y t o c o m p l e t e t h e f o l l o w i n g s y n t h e s e s . 4( R )-Amino-2-oxo-cyclohexane -1( R )-carboxylic acid 2( S ),5-Dimethyl-hex-4-enoic acid Benzoic acid or Benzenecarboxylic acid 2-Methyl-5-oxo-hept-6-enoic acid 1( R ),3,3-Trimethyl-2-oxo-cyclo hexanecarboxylic acid 6( R )-Mercapto-hept-1-yn-3-one D r a w t h e s t r u c t u r e f o r e a c h o f t h e f o l l o w i n g c o m p o u n d s . ANSWER KEY 1. via NaOH, H 2 O 1. O 3, -78°C 2. H 2 O 2 Na 2 Cr 2 O 7, H 2 CrO 4 or 1. Ag 2 O, NH 3 2. H + , H 2 O + Ag metallic silver KOH (excess) or I 2 or Cl 2 2. 3.
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O OH OH O O O O H O O H H O HO H H O HO H H O HO H + H 2 O H + H + O OH O OH O H H OH
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Unformatted text preview: CH 3 OH H + O OH H O CO 2 H O OH CO 2 H O HO OH O OH HO H O OCH 3 O HO OH H O OH 2 O O O CH 3 H CH 3 OH Problem Set-6/Chapter 17 Carboxylic Acids (page 2) ANSWER KEY + + + + + + S h o w t h e m e c h a n i s m s f o r t h e f o l l o w i n g r e a c t i o n s . A) + + + + + + B) 1. Cl 2 , KOH 2. HCl, H 2 O C o m p l e t e t h e f o l l o w i n g s y n t h e s e s i n t h e n u m b e r o f s t e p s s h o w n . K 2 Cr 2 O 7, H 2 SO 4 2 steps 1 step 1. H 2 SO 4 (conc.) 2. BH 3 THF 3) H 2 O 2 , NaOH 4) K 2 Cr 2 O 7 , H 2 SO 4 4 steps...
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W03 problems6c key - CH 3 OH H + O OH H O CO 2 H O OH CO 2...

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