0131-Ch17-updated - Chapter 17 Carboxylic Acids Ch-15- 1...

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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 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 (common names in parentheses) 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. 4 Ch-17 IUPAC Nomenclature
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5 Ch-17 Dicarboxylic acids: add the suffix -dioic acid to the name of the parent alkane containing both carboxyl groups (Remember: “di” for two functional 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. 6 Ch-17 IUPAC Nomenclature Benzoic acid is the simplest aromatic carboxylic acid. Use numbers to show the location of substituents on the ring.
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When common names are used, the Greek letters α, β, γ , δ, etc. are often used to indicate a position relative to another functional group. Numbered positions are different and are used to indicate the absolute position of a functional group in a chain or in a ring. 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 ketone carbonyl group in a carboxylic acid is indicated by the prefex keto-, e.g., β -ketobutyric acid. If the keto group is the acetyl group , CH 3 CO–, it is often named the aceto group in common naming .
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Physical Properties In the liquid and solid states, two carboxylic acids are associated by hydrogen bonding forming dimeric structures. 10 Ch-17
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Carboxylic acids have significantly higher boiling points than other types of organic compounds of comparable molecular weight. Carboxylic acids 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. Carboxylic acids form hydrogen bonds with water molecules through both their C=O and OH groups. 11 Ch-17 Physical Properties
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Table 17.2 12 Ch-17 Physical Properties CH 3 COOH CH 3 CH 2 CH 2 OH CH 3 CH 2 CHO CH 3 ( CH 2 ) 2 COOH CH 3 (CH 2 ) 3 CH 2 OH CH 3 ( CH 2 ) 3 CHO CH 3 ( CH 2 ) 4 COOH CH 3 (CH 2 ) 5 CH 2 OH CH 3 ( CH 2 ) 5 CHO Acetic acid 1-Propanol Propanal 60.1 60.1 58.1 118 97 48 163 88.1 Butanoic acid 1-Pentanol 88.1 137 103 Pentanal 86.1 Heptanal 153 176 116.2 1-Heptanol Hexanoic acid 116.2 205 114.1 Structure Name M olecular Weight (g/mol) Boiling Point (°C) Solubility (g/100 g H 2 O) Infinite Infinite 16 Infinite 2.3 Slight 1.0 0.2 0.1 Table 17.2
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hydrophobic portion (= lipophilic portion) of the molecule increases. 13
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This note was uploaded on 02/15/2012 for the course CHM 2211 taught by Professor Castalleano during the Spring '06 term at University of Florida.

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0131-Ch17-updated - Chapter 17 Carboxylic Acids Ch-15- 1...

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