carboxylic_acids

Carboxylic_acids - 5 Esterification with diazomethane Formation of methyl esters only R O CH 3 O N 2 R OH O CH 2 N 2 Mechanism R O CH 3 O N 2 R OH

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1 Carboxylic Acids Chap 20 1. Methods to making carboxylic acids- A. Grignrd R X Mg ether R MgX CO 2 R O- O MgX+ H+ R OH O B. Cyano R X R CN H+ R OH O NaCN EX. Br Mg ether CO 2 H+ NaCN H+ OH O 2. Esterification R OH O + R' OH R OR' O + H 2 O A. Acid conditions- R OH O + R' OH R OR' O + H 2 O H+ Mechanism-
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2 R OH O H 3 O+ R OH O H + R OH O H + R O O H + H R OH O H H 2 O R' HO R' O H 3 O+ R O O H R' O H H + R OR' O H + R R' O H + R O O H + R' R OR' O + H 3 O+ Equilibrium is not favored. Can do two things to help equil to the right. 1) Use excess starting materials. 2) Remove the product (H 2 O) by distilling. B. Base conditions hydrolysis of an ester- R OR' O + -OH R O- OR' OH R OH O + -OR" R O- O + HOR' 3. Acid Chlorides- two possible le reagents. R OH O SOCl 2 Cl O Cl O R Cl O Mechanism for thionyl chloride.
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3 R O H O Cl Cl O + R O H O C Cl Cl O- + R O H O C Cl O + Cl- R O O Cl O Cl- R O O- Cl O Cl R Cl O + SO 2 + Cl- 4. Rxns using acid chlorides- R Cl O R'-OH 2R'-NH 2 R O R' O + H 2 O R N H R' O + R'-NH 3 Cl- +
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Unformatted text preview: 5. Esterification with diazomethane. Formation of methyl esters only. R O CH 3 O + N 2 R OH O + CH 2 N 2 Mechanism: R O CH 3 O + N 2 R OH O + H 2 C N N-+ H 2 C N N R O-O H 3 C N N + 4 EX. + N 2 CH 2 N 2 OH O OCH 3 O Not good for industrial use or large scale rxns because it is hazardous. 6. Reduction Rxns of carboxylic acids. R OH O 1) LiAlH 4 2) H 3 0+ R OH Mechanism: R O O H + Al H H H H-Li+ R O-O Al H H H + H 2 + R O-Li+ OAlH 2 H R H O Al H H H H-Li+ R C O-Li+ H H + AlH 3 H 2 O R C OH H H EX. OH O O 1) LiAlH 4 2) H 3 O+ OH OH...
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This note was uploaded on 09/02/2011 for the course CHEM 30b taught by Professor Harrison during the Spring '11 term at West Valley.

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Carboxylic_acids - 5 Esterification with diazomethane Formation of methyl esters only R O CH 3 O N 2 R OH O CH 2 N 2 Mechanism R O CH 3 O N 2 R OH

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