Chem 317 - Set 6 extra problem solutions

Chem 317 - Set 6 extra problem solutions - 2 O O N HO OH O...

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Problem Set 6. Solutions Carboxylic Acids and Derivatives Chem 317 1. a) OH O H + OH O H CH 3 OH OCH 3 OH OH H OCH 3 OH OH H + OCH 3 OH O H H OCH 3 O H OCH 3 O b) Cl O + OH O Cl O H O O H O O 2. a) O OH + CH 3 Li O O + CH 3 Li b) OH leaving group (-OCH3) present here allows further reaction to tertiary alcohol O OCH 3 O CH 3 Li O H + O O O - Li + CH 3 Li O - Li + O - Li + stable intermediate H + /H 2 O OH OH -H 2 O
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OH OH O OH O F F OH O F OH O F OH O OH O OH O F OH O NO 2 OH O OH O I OH O OH OH O OH NO 2 O - + Na OH O OH O NO 2 O - + Na O O Cl 3. Rank the following from most to least acidic: A. O - + Na O B. C. 4. Complete the following reactions and determine the direction of the equilibrium: N H O + a. O - + Na b. + c. O O + + H N d. + e. Problem Set 7. Solutions Carboxylic Acids and Derivatives Chem 317 1 2 4 3 5 1 2 3 4 5 1 2 3 4 5 OH O - + Na O + O - + Na O NO 2 OH O + O O O + NaCl O O + NaNHCH 3 N O + CH 3 OH
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Problem Set 7. Solutions Carboxylic Acids and Derivatives Chem 317 5. Complete each of the following: a) COOH 1) LAH 2) H + b) Br O O 1) Mg, ether 2) CO 2 3) H + c) Cl O + O O O d) OH + O O e) O O + NH 2 f) O O NaOH g) O O O + OH h) Br O Cl OH CO 2 H O OH O O Cl H N H O + CH 3 CH 2 OH O O CH 3 OH Na OH O H O O 1) Mg 2) CO 2 3) H + SOCl
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Unformatted text preview: 2 O O N HO OH O N O O O O O O 6. Propose syntheses for the following products. Remember that the double arrow means retrosynthesis: the product is on the left and the starting materials are on the right! a. b. Br c. O + d. (CH 3 ) 2 NH N HO O 1. LAH 2. H + /H 2 O 1. LAH 2. H + /H 2 O OH PCC O CH 3 NH 2 1. NaOH/H 2 O 2. H + OH O Li 1. 2. H 2 O Problem Set 7. Solutions Carboxylic Acids and Derivatives Chem 317 O O O Br O d. 6, continued Mg/ether MgBr O O OH HO OH H + 1 eq O O O O H + /H 2 O should simultaneously cleave acetal and do elimination, since the elimination is so easy. Problem Set 7. Solutions Carboxylic Acids and Derivatives Chem 317...
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This homework help was uploaded on 04/09/2008 for the course CHEM 317 taught by Professor Kantorowski during the Fall '08 term at Cal Poly.

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Chem 317 - Set 6 extra problem solutions - 2 O O N HO OH O...

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