0127-Ch17 - Chapter 17 Carboxylic Acids Ch-15- 1 Structure...

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Chapter 17 Carboxylic Acids Ch-15- 1
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The functional group of a carboxylic acid is a carboxyl group. Structure COOH CO 2 H O O H C O O H Alternative representations for a carboxyl group General formula for an aliphatic carboxylic acid: RCOOH or RCO 2 H. General formula for an aromatic carboxylic acid: ArCOOH or ArCO 2 H. 2 Ch-17
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IUPAC Nomenclature IUPAC names: drop the -e from the parent alkane and add the suffix -oic acid . 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 3 Ch-17 If the compound contains a carbon-carbon double bond, change the infix -an- to -en- .
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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 4 Ch-17 IUPAC Nomenclature
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5 Ch-17 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 Dicarboxylic acids: add the suffix -dioic acid to the name of the parent alkane containing both carboxyl groups. IUPAC Nomenclature
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If the carboxyl group is bonded to a ring , name the ring compound and add the suffix -carboxylic acid . 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) 6 Ch-17 IUPAC Nomenclature Benzoic acid is the simplest aromatic carboxylic acid. Use numbers to show the location of substituents.
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When common names are used, the Greek letters α, β, γ , δ, etc. are often used to locate substituents relative to a functional group. Most often, the position with a Greek letter will be numbered differently ( α ≠ 1) to indicate the absolute position in a chain or in a ring. Also, the functional group may be numbered differently ( α ≠ 1) within the carbon chain or ring. L -alanine] [( S )- α-Αμ ινοπροπιονιχ αχιδ; (γ-Αμ ινοβυτψριχαχιδ, Γ ΑΒΑ29 29 -2-Αμ ινοπροπανοιχαχιδ 4-Αμ ινοβυτανοιχαχιδ 4 3 2 5 H 2 N OH O OH O NH 2 OH O a b g d 1 7 Ch-17 Nomenclature: Common Names
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8 Ch-17 Nomenclature: Common Names
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9 Ch-17 Nomenclature: Common Names The functional group of a ketone carbonyl group in a carboxylic acid is indicated by the prefex keto-, e.g., β -ketobutyric acid.
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0127-Ch17 - Chapter 17 Carboxylic Acids Ch-15- 1 Structure...

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