Lecture 4AB - Carboxylic Acid Family Introduction, Physical...

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Carboxylic Acid Family Introduction, Physical Properties, Chemistry 1 Lecture 4
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40 Functional Groups Carbon-carbon double bond Conjugated Diene Cyclopropane Carbon-carbon triple bond Halide (Primary,Secondary, Tertiary halide ) Aromatic halide Hydroxyl (Primary, Secondary, Tertiary 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 Carbon monoxide Ester Am ide (Primary, Secondary, Tertiary), Nitrile 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 carbon to a heteroatom Alcohols: ____ bonds from carbon to a heteroatom Aldehydes: ____ bonds from carbon to a heteroatom 3 C O H O H [O] [O] Carboxylic Acids: ____ bonds from carbon to a heteroatom Carbon dioxide family: ____ bonds from carbon to a heteroatom
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Biofuels and CO 2 Capture O O H C O O Photosynthesis 4 Algae, plants C O O + Combustion C O O ? Is this reaction oxidation or reduction or….
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The Carboxylic Acid Family O O O O Thioester Imide 5 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 usually the high value 6 synthetic targets. Carboxylic acids are produced by hydrolysis of other members of the carboxylic acid family and are the thermodynamic resting place for all carboxylic acid derivatives.
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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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A Branched Carboxylic Acid: Valproic Acid ( Depakote ) is an Antiepileptic Drug 9 (Chiral?)
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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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Aromatic Acids Benzoic acid Phthalic acid 11 Acetyl salicylic acid (Aspirin) Salicylic acid (skin creams) Bismuth subsalicylate (Pepto Bismol)
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12 Circle and name the functional groups! Oops!
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Esters as Odorants Jasmine 13 Circle and name the functional groups! Which molecules are chiral?
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Cyclic esters are called Lact ones O O O O δ -lactone α γ -lactone β -lactone Acyclic ester δ γ β
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γ City of Ottawa inspectors have discovered toxic giant hogweed in a city park and on private property. July 14, 2010
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Lecture 4AB - Carboxylic Acid Family Introduction, Physical...

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