Chapter20 - Chapter 20: Carboxylic Acids and Nitriles Based...

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Chapter 20: Carboxylic Acids and Nitriles Based on McMurry’s Organic Chemistry , 6 th edition ©2003 Ronald Kluger Department of Chemistry University of Toronto
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Based on McMurry, Organic Chemistry, Chapter 20, 6th 2 The Importance of Carboxylic Acids (RCO 2 H) Starting materials for acyl derivatives (esters, amides, and acid chlorides) Abundant in nature from oxidation of aldehydes and alcohols in metabolism Acetic acid, CH 3 CO 2 H, - vinegar Butanoic acid, CH 3 CH 2 CH 2 CO 2 H (rancid butter) Long-chain aliphatic acids from the breakdown of fats
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Based on McMurry, Organic Chemistry, Chapter 20, 6th 3 20.1 Naming Carboxylic Acids and Nitriles Carboxylic Acids, RCO 2 H If derived from open-chain alkanes, replace the terminal -e of the alkane name with -oic acid The carboxyl carbon atom is C1
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Based on McMurry, Organic Chemistry, Chapter 20, 6th 4 Alternative Names Compounds with CO 2 H bonded to a ring are named using the suffix - carboxylic acid The CO 2 H carbon is not itself numbered in this system Use common names for formic acid (HCOOH) and acetic acid (CH 3 COOH) – see Table 20.1
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Based on McMurry, Organic Chemistry, Chapter 20, 6th 5 Nitriles, RC N Closely related to carboxylic acids named by adding - nitrile as a suffix to the alkane name, with the nitrile carbon numbered C1 Complex nitriles are named as derivatives of carboxylic acids. Replace - ic acid or - oic acid ending with - onitrile
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Based on McMurry, Organic Chemistry, Chapter 20, 6th 6 20.2 Structure and Physical Properties of Carboxylic Acids Carboxyl carbon sp 2 hybridized: carboxylic acid groups are planar with C–C=O and O=C–O bond angles of approximately 120° Carboxylic acids form hydrogen bonds, existing as cyclic dimers held together by two hydrogen bonds Strong hydrogen bonding causes much higher boiling points than the corresponding alcohols
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Based on McMurry, Organic Chemistry, Chapter 20, 6th 7 20.3 Dissociation of Carboxylic Acids Carboxylic acids are proton donors toward weak and strong bases, producing metal carboxylate salts, RCO 2 - + M Carboxylic acids with more than six carbons are only slightly soluble in water, but their conjugate base salts are water-soluble
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Based on McMurry, Organic Chemistry, Chapter 20, 6th 8 Acidity Constant and p K a Carboxylic acids transfer a proton to water to give H 3 O + and carboxylate anions, RCO 2 - , but H 3 O + is a much stronger acid The acidity constant, K a, , is about 10 -5 for a typical carboxylic acid (p K a ~ 5)
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Chapter20 - Chapter 20: Carboxylic Acids and Nitriles Based...

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