Ch 17 - Structure The functional group of a carboxylic acid...

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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 COOH CO 2 H O O H C O O H Alternative representations for a carboxyl group 1
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Nomenclature - IUPAC IUPAC names: drop the -e from the parent alkane and add the suffix -oic acid if the compound contains a carbon-carbon double bond, change the infix -an- to -en- HCOOH CH 3 COOH 3-Methylbutanoic acid (Isovaleric acid) Ethanoic acid (Acetic acid) Methanoic acid (Formic acid) OH O Propenoic acid (Acrylic acid) trans- 3-Phenylpropenoic acid (Cinnamic acid) trans- 2-Butenoic acid (Crotonic acid) OH O OH O OH O 2
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Nomenclature - IUPAC dicarboxylic acids: add the suffix -dioic acid to the name of the parent alkane containing two carboxyl groups HO OH O Propanedioic acid (Malonic acid) Ethanedioic acid (Oxalic acid) O HO OH O O Hexanedioic acid (Adipic acid) Pentanedioic acid (Glutaric acid) Butanedioic acid (Succinic acid) O OH O HO OH O HO O HO OH O O 3
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Nomenclature - IUPAC if the carboxyl group is bonded to a ring, name the ring compound and add the suffix -carboxylic acid Use numbers to show the location of substituents on aromatic carboxylic acids COOH COOH HOOC 3 2 1 2-Cyclohexenecarboxylic acid trans- 1,3-Cyclopentanedicarboxylic acid COOH COOH OH COOH COOH COOH COOH Benzoic acid 2-Hydroxybenzoic  acid (Salicylic acid) 1,2-Benzenedicarboxylic  acid (Phthalic acid) 1,4-Benzenedicarboxylic  acid (Terephthalic acid) 4
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Nomenclature when common names are used, the letters α, β, γ , δ, etc. are often used to locate substituents L -alanine] [( S )- α -Aminopropionic acid; ( γ -Aminobutyric acid, GABA) ( S )-2-Aminopropanoic acid 4-Aminobutanoic acid 4 3 2 5 H 2 N OH O OH O NH 2 OH O α β γ δ 1 The carboxyl group takes precedence over most other functional groups 5-Oxohexanoic acid 4-Aminobutanoic acid ( R )-5-Hydroxyhexanoic acid OH O OH O OH O H 2 N OH O 5
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Physical Properties In the liquid and solid states, carboxylic acids are associated by hydrogen bonding into dimeric structures 6
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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 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 7
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Ch 17 - Structure The functional group of a carboxylic acid...

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