lecture 20 - Chapter 20: Carboxylic Acids and Nitriles...

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Chapter 20: Carboxylic Acids and Nitriles Based on McMurry’s Organic Chemistry , 7 th edition
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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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3 Why this Chapter? Carboxylic acids present in many industrial processes and most biological processes They are the starting materials from which other acyl derivatives are made An understanding of their properties and reactions is fundamental to understanding organic chemistry
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4 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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5 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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6 Nitriles, RCN 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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7 20.2 Structure and 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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lecture 20 - Chapter 20: Carboxylic Acids and Nitriles...

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