n contrast to alcohols with their rich chemical reactivity, ethers (compounds contain- ing a C-0-C unit) undergo relatively few chemical reactions. As you saw wher we discussed Grignard reagents in Chapter 14 and lithium aluminum hydride reduc- tions in Chapter 15, this lack of reactivity of ethers makes them valuable as solvents in a number of synthetically important transformatio. In the present chapter you will learn

the preceding chapter you learned that nucleophilic addition to the carbonyl group is one of the fundamental reaction types of organic chemistry. In addition to its own reactivity, a carbonyl group can affect the chemical properties of aldehydes and ketones in other ways. Aldehydes and ketones are in equilibrium with their enol isomers

arboxylic acids, compounds of the type RCOH, constitute one of the most fre- quently encountered classes of organic compounds Countless natural products are carboxylic acids or are derived from them. Some carboxylic acids, such as acetic acid, have been known for centuries. Others, such as the prostaglandins, which are pow erful regulators of numerous biological processes remained unknown until relatively

ou have already had considerable experience with carbanionic compounds and rgani their applications in synthetic organic chemistry. The first was acetylide ion in Chapter 9, followed in Chapter 14 by organometallic compounds-Grignard reagents, for example-that act as sources of negatively polarized carbon. In Chapter 18 you learned that enolate ions-reactive

he value of alkyl halides as starting materials for the preparation of variety of organic functional groups has been stressed many times. In our earlier discussions, we noted that aryl halides are normally much less reactive than alkyl halides in reactions that involve carbon-halogen bond cleavage. In the present chapter you will see that aryl halides can exhibit their own patterns of chemical reactivity, and that these reac

he major classes of organic compounds common to living systems are lipids, pro- teins, nucleic acids, and carbohydrates. Carbohydrates are very familiar to us- we call many of them\sugars.\ They make up a substantial portion of the food we eat and provide most of the energy that keeps the human engine running. Carbohy- drates are structural components of the walls of plant cells and the wood of trees. Genetic

he relationship between structure and function reaches its ultimate expression in the chemistry of amino acids, peptides, and protein Amino acids are carboxylic acids that contain an amine function. Under cer- tain conditions the amine group of one molecule and the carboxyl group of a second can react, uniting the two amino acids by an amide bond. Amide(peptide)bond

Absolute configuration(Section 7.5): The three-dimensional Activating substituent (Sections 12.10 and 12.12): A group rrangement of atoms or groups at a stereogenic center. that when present in place of a hydrogen causes a particular Acetal(Section 17.8): Product of the reaction of an aldehyde or reaction to occur faster. Term is most often applied to a ketone with two moles of an alcohol according to the substituents that increase the rate of electrophilic aromatic

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McGraw-Hill Higher Education A Division of The McGrawp-Hill Companies ORGANIC CHEMISTRY, FOURTH EDITION Copyright 2000, 1996, 1992, 1987 by The McGraw-Hill Companies, Inc. All rights reserved. Printed in the United States of America. Except as permitted under the United States Copyright Act of 1976, no part of this publication may be reproduced or distributed in any form or by any means, or stored in a data base or retrieva