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W03 problems7b

W03 problems7b - A a Ag 2 O b excess LiAlH 4 followed by...

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O OH O O HO O O O OH OH Cl O O OH OH COOH COOH N H Br OH O O Problem Set 7 (Chapter 17 Carboxylic Acids) TA: Danny Ng 2/24/2003 2. Provide the r e a g e n t s or p r o d u c t s for the following reactions. Pay attention to stereochemistry if applicable. 1. Provide the structures for the following compounds. Pay attention to stereochemistry if applicable. a) 1,1,3-cyclobutanetricarboxylic acid b) formic acid c) 4-hydroxy-2-methylheptanoic acid d) cis -3-pentenoic acid a) warm b) c) d) e) H + cat. (excess)
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TA: Danny Ng 2/24/2003 Problem Set 7 3. Draw the structures for the products you would obtain if you treat the following compound A with: a) Draw the structure of Compound B. O O H O OH Compound
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Unformatted text preview: A a) Ag 2 O b) excess LiAlH 4 , followed by workup c) 1 equiv. LDA d) excess NaBH 4 , followed by workup e) Pt, H 2 (1 atm) f) Pt, H 2 (300 atm!) g) CH 2 N 2 4. For the following reaction: O O H + cat. Compound B b) Provide the reaction mechanism. h) SOCl 2 (excess) OH Na H PCC OTf OH HO OH PPh 3 H + cat. O H H PCC CuLi TA: Danny Ng 2/24/2003 Problem Set 7 5. R E V I E W : Draw the structures for the missing products below. 1. NaNH 2 2. m-CPBA 1. 2. workup 1. LDA 2. 3. H 3 O + , H 2 O (excess) 1. H 2 NNH 2 2. KOH 1. Sia 2 BH 2. H 2 O 2 , NaOH 1.O 3 2. H 2 O 2...
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