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14 Cards in this Set
- Front
- Back
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List:
11 reactions involving Carboxylic Acids |
1. Side-chain oxidation of alkyl groups attached to phenyl groups
2. Oxidation of 1* Alcohols to form carboxylic acids 3. Oxidation of Aldehydes 4. Carboxylation of Grignard's 5. Hydrolysis of Nitriles 6. Acid-Catalyzed Esterification 7. Formation of Acyl Chlorides 8. Reduction of Carboxylic Acids 9. Intramolecular Ester Formation via Hydroxyacid 10. Hell-Volhard-Zelinsky reaction 11. Decarboxylation |
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PROPERTIES/REAGENTS OF:
Side-chain oxidation of alkyl groups attached to phenyl groups |
Side chain is cleaved at benzyllic carbon and is oxidized to give carboxyl group -COOH
Reagents: - KMnO4 or K2Cr2O7 - H2SO4 - H2O |
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PROPERTIES/REAGENTS OF:
Oxidation of 1* Alcohols |
1* carbon bearing the alcohol group is oxidized to a carboxylic acid
R-CH2OH ------> R-COOH Reagents: - KMnO4 or K2Cr2O7 or H2CrO4 - H2SO4 - H2O |
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PROPERTIES/REAGENTS OF:
Oxidation of Aldehydes |
Aldehyde carbon is oxidized to a carboxylic acid
Reagents: - KMnO4 or K2Cr2O7 or H2CrO4 - H2SO4 - H2O |
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PROPERTIES/PRODUCTS/REAGENTS OF:
Carboxylation of Grignard Reagents |
Grignard reagents react with CO2 and worked up with acid to form..
Product: carboxylic acids. Reagent: 1. Alkyl halide, Mg, diethyl ether 2. Carbon dioxide CO2 3. Acid (workup) |
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PROPERTIES/PRODUCTS/REAGENTS OF:
Hydrolysis of Nitriles |
Sn2 reaction (CN- and alkyl halide) to form nitrile. Nitrile reaction with water, heat, and acid gives Carboxylic acid on the nitrile C (ammonium ion byproduct)
Product: Nitrile Reagents: 1. CN- salt, DMSO 2. water, H2SO4, heat |
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What is Acid-Catalyzed Esterification
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Fischer Esterification
Acid catalyzed reaction of carboxylic acid and an alcohol (Ch. 15) |
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PROPERTIES/REAGENTS OF:
Formation of Acyl Chlorides |
-OH group of carboxylic acid (-COOH) is replaced by a Chlorine
Reagents: - Thionyl Chloride - heat |
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PROPERTIES/PRODUCTS/REAGENTS OF:
Reduction of carboxylic acids |
Carboxylic acids are reduced to primary alcohols
Product: 1* Alcohol Reagents: 1. LiAlH4, diethyl ether 2. H2O |
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What is a hydroxy acid?
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A compound that contains both an OH (alcohol) group and a COOH (carboxyl) group
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PROPERTIES OF:
Intramolecular Ester Formation |
Hydroxyacid reacts intramolecularly to form cyclic ester
Reagents: none |
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If given a molecule with a carboxylic acid and a ketone/aldehyde, how can we prep it for Intramolecular Ester Formation?
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1. NaBH4
------------------> 2. H3O+ |
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PROPERTIES/REAGENTS OF:
Hell-Volhard-Zelinsky reaction |
Substitutes hydrogen beta to carbonyl carbon with a halogen
Reagents: - Br2 or Cl2 - P (elemental) or P-X3 |
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PROPERTIES OF:
Decarboxylation |
Dicarboxylic acid and 150 degrees celcius removes a CO2, leaving a single carboxylic acid.
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