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Ch 13 Carboxylic Acids Carboxylic Acids • Functional Group: Carboxyl Group (Carbonyl and Hydroxyl at the same carbon has a new name!) • • • • Condensed writing: COOH Carboxyl Carbon is C#1 Alkane name, drop e replace with -oic acid 2 word name: Methanoic acid Benzoic Acid • Carboxyl on a benzene • Carboxyl is attached to C#1 • List all substituent alpha and Number either cw or ccw so you get lowest numbers! 4-bromo-2-methylbenzoic acid Naming Practice • Parent alkane has to include carboxylic acid, which is THE highest oxidized functional group Drawing Practice Draw: a) 2-methyl-3-phenyl pentanoic acid b) 4- Iodo-2-isopropyl benzoic acid Common Names of Carboxylic Acids Fatty Acids • Very long carboxylic acids AHA: Alpha Hydroxy Acids • Hydroxyl groups on the α Carbon: Carbon # 2 • Super polarity on this end!!! • Natural occurring acids in sour milk and fruits Part of many skin care products to exfoliate and smooth skin Properties of Carboxylic Acids Acid Behavior • Acids are H+ Donors • Carboxylic Acids dissociate in water and lower the pH COOH + H2O → COO- + H3O+ carboxylate ion and hydronium ion Intermolecular Forces Molecule class Van de Waals alkanes Ethers, aldehydes, ketones alcohols Carboxylic acids Dipoles H-Bonds Intermolecular Forces Molecule class Van de Waals Dipoles H-Bonds alkanes Ethers, aldehydes, ketones yes yes no yes no no alcohols Carboxylic acids yes yes yes (1) Yes (2) yes (1) yes (2) H-bonds between Carboxyls Boiling Point • Carboxylic Acids have the highest boiling point of organic molecules • More partial charges (4) than alcohols (3) Solubility • Carboxylic Acids dissolve very well in water • form H-bonds with water molecules • But the longer the C-chain, the less soluble! Solubility Rx of Carboxylic Acids Dissociation Rx • when carboxylic acids dissociate they form a carboxylate ion Example: HCOOH → HCOO- + H+ Methanoic Acid Methanoate Ion Naming of Ion: Acid name: Methano-ic replace by –ate ion Condensed structure: CH3-CH2-COO- Neutralization Rx • Acid + Base → Salt + water • Carboxylate anions can react with metal cations to form carboxylic acid salts: • CH3COOH + NaOH → CH3COO-Na+ + H2O Sodium ethanoate • Draw in stick… Esterification Rx • Carboxylic Acid + Alcohol → Ester + H2O H 2O Ethanoic Acid Methanol Methyl ethanoate Name of Ion and Salt Name: a) Potassium ethanoate Or Potassium acetate b) Pentanoate Ion CA in Nature • Flavor enhancer: Sodium glutamate Benzoic Acid • Common Preservative Aspirin • Common analgesic
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