lecture 17 - Carboxylic Acids Chapter 17 Active ingredient...

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Carboxylic Carboxylic Acids Acids Chapter 17 Chapter 17 Active ingredient is a derivative of arylpropanoic acid ± The functional group of a carboxylic acid is a carboxyl group the general formula for an aliphatic carboxylic acid is RCOOH; that for an aromatic carboxylic acid is ArCOOH Structure Nomenclature Nomenclature - IUPAC IUPAC ± IUPAC names: drop the - e from the parent alkane and add the suffix - oic oic acid acid HCOOH CH 3 COOH 3-Methylbutanoic acid (Isovaleric acid) Ethanoic acid (Acetic acid) Methanoic acid (Formic acid) OH O Nomenclature - IUPAC IUPAC ± IUPAC names: drop the - e from the parent alkane and add the suffix - oic oic acid if the compound contains a carbon-carbon double bond, change the infix - an an- to - en en- Propenoic acid (Acrylic acid) trans- 3-Phenylpropenoic acid (Cinnamic acid) 2-Butenoic acid (Crotonic acid) OH O OH O OH O Formic Acid
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Nomenclature Nomenclature - IUPAC IUPAC ± The carboxyl group takes precedence over most other functional groups 4-Aminobutanoic acid H 2 N OH O ( R )-5-Hydroxyhexanoic acid OH OH O 5-Oxohexanoic acid O OH O an amino group an oxo group a hydroxyl group Nomenclature Nomenclature - IUPAC IUPAC dicarboxylic acids: add the suffix - dioic acid acid to the name of the parent alkane containing both carboxyl groups HO OH O Propanedioic acid (Malonic acid) Ethanedioic acid (Oxalic acid) O HO O O Hexanedioic acid (Adipic acid) Pentanedioic acid (Glutaric acid) Butanedioic acid (Succinic acid) O O HO O HO O HO O O Nomenclature - IUPAC IUPAC if the carboxyl group is bonded to a ring, name the ring compound and add the suffix - carboxylic acid COOH HOOC 3 2 1 2-Cyclohexenecarboxylic acid trans- 1,3-Cyclopentanedicarboxylic acid Nomenclature Nomenclature - IUPAC IUPAC benzoic acid is the simplest aromatic carboxylic acid use numbers to show the location of substituents COOH COOH 1,4-Benzenedicarboxylic acid (Terephthalic acid) Benzoic acid COOH OH 2-Hydroxybenzoic acid (Salicylic acid) 1,2-Benzenedicarboxylic acid (Phthalic acid) Common Aliphatic Carboxylic Acids Z-9-Octadecenoic acid trans-2- Hydroxycyclohexanecarboxylic acid
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(R)-2-Hydroxypropanoic acid Physical Properties Physical Properties ± In the liquid and solid states, carboxylic acids are associated by hydrogen bonding into dimeric structures Physical Properties ± Carboxylic acids have significantly higher boiling points than other types of organic compounds of comparable molecular weight they are polar compounds and form very strong intermolecular hydrogen bonds Physical Properties Physical Properties ± Carboxylic acids are more soluble in water than alcohols, ethers, aldehydes, and ketones of comparable molecular weight they form hydrogen bonds with water molecules through their C=O and OH groups
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Physical Properties Physical Properties water solubility decreases as the relative size of the hydrophobic portion of the molecule increases Acidity Acidity ± Carboxylic acids are weak acids values of p K a
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lecture 17 - Carboxylic Acids Chapter 17 Active ingredient...

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