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Ebook Organic chemistry (6th edition): Part 2

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(BQ) Part 2 book "Organic chemistry" has contents: Functional derivatives of carboxylic acids, enolate anions and enamines; benzene and the concept of aromaticity; reactions of benzene and its derivatives; catalytic carbon carbon bond formation; carbohydrates,.and other contents. | Outline 18.1 Structure and Nomenclature 18.2 Acidity of Amides, Imides, and Sulfonamides 18.3 18.4 Chapter 18 Characteristic Reactions Functional Derivatives of Carboxylic Acids Reaction with Water: Hydrolysis 18.5 18.6 Reaction with Alcohols 18.7 Reaction of Acid Chlorides with Salts of Carboxylic Acids 18.8 Interconversion of Functional Derivatives 18.9 Reactions with Organometallic Compounds Reactions with Ammonia and Amines 18.10 Reduction Colored scanning electron micrograph of Penicillium s. fungus. The stalklike objects are condiophores to which are attached numerous round condia. The condia are the fruiting bodies of the fungus. Inset: a model of amoxicillin. See Chemical Connections: “The Penicillins and Cephalosporins: b-Lactam Antibiotics.” © SCIMAT/Science Source/Photo Researchers, Inc. I n this chapter, we study five classes of organic compounds, each related to the carboxyl group: acid halides, acid anhydrides, esters, amides, and nitriles. Under the general formula of each functional group is an illustration to show you how the group is formally related to a carboxylic acid. Formal loss of !OH from a carboxyl group and H! from H!Cl, for example, gives an acid chloride. Similarly, loss of !OH from a carboxyl group and H! from ammonia gives an amide. For illustrative purposes, we show each of these reactions as a formal loss of water. However, as we will see in this chapter, some actual mechanisms do not involve a step in which an H2O molecule is lost. O O O RCCl RCOCR9 RCOR9 RCNH2 RC # N An acid chloride An acid anhydride An ester An amide A nitrile 2H2O O RC!OH Online homework for this chapter may be assigned in OWL for Organic Chemistry. 2H2O O H!Cl O O 2H2O O RC ! OH H ! OCR9 O RC ! OH H ! OR9 2H2O O RC ! OH H ! NH2 2H2O HO H RC " N The enol of an amide 680 Copyright 2010 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights,