2009 7 Carboxylic acids I - Carboxylic Acid Family...

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Carboxylic Acid Family Introduction, Properties, Reactions art 1 hapters 20 1 1 Part 1-Chapters 20-21 http://http-server.carleton.ca/~pbuist/
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List of 32 Functional Groups Carbon-carbon double bond Conjugated Diene Cyclopropane Carbon-carbon triple bond Halide (alkyl halide ) Aromatic halide Hydroxyl (alcohol) Phenol (Aromatic alcohol ) Ether Epoxide Thiol Disulfide Thioether Sulfoxide Sulfone Sulfonic Acid Amine (Primary, Secondary, Tertiary) Ammonium Aromatic Amine, Nitro Aldehyde Ketone Carboxylic Acid Ester Am ide (Primary, Secondary, Tertiary) Acid Anhydride Acid halide Carbon dioxide 2
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5 Oxidation states of carbon CH 4 C H 2 O [O] [O] Alkanes: ____ bonds from arbon to a heteroatom 3 C O H O H [O] [O] Carboxylic Acids: ____ bonds from carbon to a heteroatom carbon to a heteroatom
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The Carboxylic Acid Family O O O O Thioester Imide 4 R C N R X R O R O R O R R N H R R O O H Acid chloride Acid anhydride Ester Nitrile Amide
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Overview Acid Chlorides, Acid anhydrides, Nitriles are typically synthetic intermediates. Amides and Esters are the high value synthetic 5 targets. Carboxylic acids are produced by hydrolysis of other members of the carboxylic acid family and are the thermodynamic resting place. Often used as starting materials to make esters and amides
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Assignment 3 McMurry 6 th (7th) edition Topic Chapter Section Problems Nomenclature 20.1 20.1 a-d, 20.2 a-f Physical properties acidity 20.2-20.4 20.5 ( 20.9 ) a,b 6 Carboxylic acid derivatives 21.1, Table 21.1 21.2 a-h IR spectroscopy 21.10 21.26 Nucleophilic Acyl Substitution reactions Relative reactivity 21.2 21.4 a, 21.5
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C1 Formic acid C2 Acetic acid Some Natural Occuring Alkyl Carboxylic Acids ( Meth anoic acid) ( _______oic acid) 7 C8 Caprylic acid C4 Butryic acid C6 Caproic acid ( _______oic acid) ( _______oic acid) ( _______oic acid)
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C10 Capric acid C12 Lauric acid Even numbered Fatty Acids are the most common in Biology ( _______oic acid) ( _______ oic acid) 8 C14 Myristic acid C18 Stearic acid C16 Palmitic acid Cell Membrane components ( _______ oic acid) ( _______ oic acid) ( _______ oic acid)
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Fatty Acid Surfactants: Reducing Surface Tension H 2 O H 2 O 9
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Oxalic acid (ethanedioic acid) DiAcids A TriAcid 10 Malonic acid Succinic acid Citric acid (______anedioic acid) (______anedioic acid) (Chiral?) Ogston was the first to recognize that enzymes could distinguish between the two “identical” groups of a prochiral compound
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Valproic Acid (Depakote): Antiepileptic Drug 11 (Chiral?)
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Aromatic Acids Benzoic acid Phthalic acid 12 Acetyl salicylic acid (Aspirin) Salicylic acid (skin creams) Bismuth subsalicylate (Pepto Bismol)
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Circle and name the functional groups! Oops!
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2009 7 Carboxylic acids I - Carboxylic Acid Family...

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