JOHN MCMURRY THIRD EDITION Organic Chemistry with Biological Applications
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Structures of Common Coenzymes The reactive parts of the molecules are darkened,while nonreactive parts are ghosted. Adenosine triphosphate-ATP(phosphorylation) OHOH Coenzyme A(acyl transfer) 0 O CH3 HSCH2CH2NHCCH2CH2NHCCHCCH2O HO CH3 O-O- Nicotinamide adenine dinucleotide-NAD(oxidation/reduction) (NADP+) CONH2 OH OH (OPO32) Flavin adenine dinucleotide-FAD(oxidation/reduction) HO OH HO CHCHCHCH OR Ueentdllcnn
Structures of Common Coenzymes The reactive parts of the molecules are darkened, while nonreactive parts are ghosted. + CONH2 N H3C H3C N N N N O O– P –O O O O– P O OCH2 O O– P O OH Flavin adenine dinucleotide—FAD (oxidation/reduction) Nicotinamide adenine dinucleotide—NAD+ (oxidation/reduction) Coenzyme A (acyl transfer) Adenosine triphosphate—ATP (phosphorylation) OH HO CHCHCHCH2OPOPOCH2 O O– OH O O– CH2 HSCH2CH2NHCCH2CH2NHCCHCCH2OPOPOCH2 O O– O O– HO CH3 O O CH3 HO O OH OH (OPO3 2–) (NADP+) CH2OPOPOCH2 O O– O O– O O H 2–O3PO O OH O OH HO O OH OH NH2 N N N N NH2 N N N N NH2 N N N N NH2 N N N N Unless otherwise noted, all content on this page is © Cengage Learning. 42912_33_EP2-EP3.indd 2 1/10/14 1:21 PM Copyright 2015 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it
Tetrahydrofolate(transfer of C units) NHCHCH2CH2C- S-Adenosylmethionine(methyl transfer) CH3 -OCCHCH2CH2-S-CH2 +NH3 Lipoic acid(acyl transfer) CH2OPO32- CH2CH2CH2CH2CO2- CHO HnN人o CHa Biotin (carboxylation HNN一H
S-Adenosylmethionine (methyl transfer) Lipoic acid (acyl transfer) Thiamin diphosphate (decarboxylation) Pyridoxal phosphate (amino acid metabolism) Tetrahydrofolate (transfer of C1 units) CH2 –OCCHCH2CH2 CH2CH2CH2CH2CO2 – S + +NH3 O CH3 O OHOH H2N N N N N H N H H O O H H NHCHCH2CH2C O– 1–5 CO2 O – S S CH2OPO3 2– CH3 CHO OH N H + H CH3 –OPOPOCH2CH2 N + S NH2 CH3 N N O O– O O– Biotin (carboxylation) N N H H O S H H H CH2CH2CH2CH2CO2 – NH2 N N N N Unless otherwise noted, all content on this page is © Cengage Learning. 42912_33_EP2-EP3.indd 3 1/10/14 1:21 PM Copyright 2015 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it
CeingGE ko3g7t6ona 2015,2011 Cengage Learning APpl WCN:02-200-203 John McMurry Product Director:Mary Finch ALL RIGHTS RESERVED.No part of this work covered by the copyright herein Product Manager:Maureen Rosener but not limi to pn otocopying Content Developer:Sandra Kiselica obrm2tonstoaeandrenealetesecetaspemwelOneS」 Section 107or 10 of the 976United States Copyright Act.without the prior written permission of the publisher. Media Developer:Lisa Weber Marketing Manager:lulie Schuster Content Project Manager:Teresa L.Trego Cengage Lea Art Director:Maria Epes Manufacturing Planner:Judy Inouye Rights Acquisitions Specialist:Dean Dauphinais Production Service:Graphic World Inc Library of Congress Control Number:2013956751 Photo Researcher:PreMedia Global 15BN-13:978-1-285-84291-2 Text Researcher:PreMedia Global Copy Editor Graphic 15BN-10:1-285-84291-X llustrator:Graphic World In Text Designer:Parallelogram Graphics Cover Designer:Cheryl Carrington gemu4hie Cer iAmord.Groe9o2 Compositor:Graphic World Inc Cengage Learning is a leading provider of customized learning solutions with We gratefully acknowledge SDBS for providing office locations around the globe,including Singapore,the United Kingdom, data for figureson the fol data for the *404 349g.482i.and 598g(http://.aist go.jp/sdbs/,National Institute of Advanced Cengage Learing products are represented in Canada by Nelson Education,Ltd. olea more about Cengage,visit www.cengage.com Purchase any of our products at your local college store or at our preferred online store www.cengagebrain.com. Printed in the United States of America 12345671817161514
Organic Chemistry with Biological Applications, 3e John McMurry Product Director: Mary Finch Product Manager: Maureen Rosener Content Developer: Sandra Kiselica Content Coordinator: Elizabeth Woods Product Assistant: Karolina Kiwak Media Developer: Lisa Weber Marketing Manager: Julie Schuster Content Project Manager: Teresa L. Trego Art Director: Maria Epes Manufacturing Planner: Judy Inouye Rights Acquisitions Specialist: Dean Dauphinais Production Service: Graphic World Inc. Photo Researcher: PreMedia Global Text Researcher: PreMedia Global Copy Editor: Graphic World Inc. Illustrator: Graphic World Inc. Text Designer: Parallelogram Graphics Cover Designer: Cheryl Carrington Cover Image: Vickie Lewis/National Geographic Creative Compositor: Graphic World Inc. We gratefully acknowledge SDBS for providing data for figures on the following pages: 331, 335, 339, 341, 475, 476, 523, 524, 549, 672; and data for the spectra in problems on pages 349d, 349g, 482i, and 598g (http://riodb01.ibase.aist .go.jp/sdbs/, National Institute of Advanced Industrial Science and Technology, 8/26/05, 2/7/09, 2/13/09, 3/10/09). © 2015, 2011 Cengage Learning ALL RIGHTS RESERVED. No part of this work covered by the copyright herein may be reproduced, transmitted, stored, or used in any form or by any means graphic, electronic, or mechanical, including but not limited to photocopying, recording, scanning, digitizing, taping, Web distribution, information networks, or information storage and retrieval systems, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without the prior written permission of the publisher. Library of Congress Control Number: 2013956751 ISBN-13: 978-1-285-84291-2 ISBN-10: 1-285-84291-X Cengage Learning 200 First Stamford Place, 4th Floor Stamford, CT 06902 USA Cengage Learning is a leading provider of customized learning solutions with office locations around the globe, including Singapore, the United Kingdom, Australia, Mexico, Brazil, and Japan. Locate your local office at www.cengage.com/global. Cengage Learning products are represented in Canada by Nelson Education, Ltd. To learn more about Cengage Learning Solutions, visit www.cengage.com. Purchase any of our products at your local college store or at our preferred online store www.cengagebrain.com. For product information and technology assistance, contact us at Cengage Learning Customer & Sales Support, 1-800-354-9706. For permission to use material from this text or product, submit all requests online at www.cengage.com/permissions. Further permissions questions can be e-mailed to permissionrequest@cengage.com. Printed in the United States of America 1 2 3 4 5 6 7 1 8 1 7 1 6 1 5 1 4 42912_00_FM_i-xxiv.indd 4 1/16/14 3:00 PM Copyright 2015 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it. WCN: 02-200-203
BRIEF CONTENTS 1 Structure and Bonding 1 2 Polar Covalent Bonds;Acids and Bases 28 3 Organic Compounds:Alkanes and Their Stereochemistry 9 4 Organic Compounds:Cycloalkanes and Their Stereochemistry 87 5 Stereochemistry at Tetrahedral Centers 113 6 An Overview of Organic Reactions 146 Alkenes and Alkynes 179 8 Reactions of Alkenes and Alkynes 212 9 Aromatic Compounds 265 10 Structure Determination:Mass Spectrometry,Infrared Spectroscopy,and Ultraviolet Spectroscopy 319 Structure Determination:Nuclear Magnetic Resonance Spectroscopy 350 12 Organohalides:Nucleophilic Substitutions and Eliminations 382 13 Alcohols,Phenols,and Thiols;Ethers and Sulfides 435 A Preview of Carbonyl Chemistry 483 4 Aldehydes and Ketones:Nucleophilic Addition Reactions 492 Carboxylic Acids and Nitriles 530 16 Carboxylic Acid Derivatives:Nucleophilic Acyl Substitution Reactions 555 17 Carbonyl Alpha-Substitution and Condensation Reactions 599 18 Amines and Heterocycles 644 19 Biomolecules:Amino Acids,Peptides,and Proteins 678 20 Amino Acid Metabolism 714 21 Biomolecules:Carbohydrates 738 22 Carbohydrate Metabolism 73 23 Biomolecules:Lipids and Their Metabolism 805 24 Biomolecules:Nucleic Acids and Their Metabolism 852 e25 Secondary Metabolites:An Introduction to Natural Products Chemistry 877 e26 Orbitals and Organic Chemistry:Pericyclic Reactions 905 e27 Synthetic Polymers 925
B r i e f C o n t e n t s 1 structure and Bonding 1 2 polar covalent Bonds; acids and Bases 28 3 organic compounds: alkanes and their stereochemistry 59 4 organic compounds: cycloalkanes and their stereochemistry 87 5 stereochemistry at tetrahedral centers 113 6 an overview of organic Reactions 146 7 alkenes and alkynes 179 8 Reactions of alkenes and alkynes 212 9 aromatic compounds 265 10 structure Determination: Mass spectrometry, infrared spectroscopy, and Ultraviolet spectroscopy 319 11 structure Determination: nuclear Magnetic Resonance spectroscopy 350 12 organohalides: nucleophilic substitutions and Eliminations 382 13 alcohols, phenols, and thiols; Ethers and sulfides 435 ** a preview of carbonyl chemistry 483 14 aldehydes and Ketones: nucleophilic addition Reactions 492 15 carboxylic acids and nitriles 530 16 carboxylic acid Derivatives: nucleophilic acyl substitution Reactions 555 17 carbonyl alpha-substitution and condensation Reactions 599 18 amines and heterocycles 644 19 Biomolecules: amino acids, peptides, and proteins 678 20 amino acid Metabolism 714 21 Biomolecules: carbohydrates 738 22 carbohydrate Metabolism 773 23 Biomolecules: lipids and their Metabolism 805 24 Biomolecules: nucleic acids and their Metabolism 852 To access the following online-only chapters, enter ISBN: 978-1-285-84291-2 at www.cengagebrain.com and visit this book’s companion website. e25 secondary Metabolites: an introduction to natural products chemistry 877 e26 orbitals and organic chemistry: pericyclic Reactions 905 e27 synthetic polymers 925 v 42912_00_FM_i-xxiv.indd 5 1/16/14 3:00 PM Copyright 2015 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s). Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it