Organic Chemistry PDF
Preview Organic Chemistry
1 2 3 4 5 6 7 m 8A(18) 2HeHelium4.0026 10NeNeon20.1797 18ArArgon39.948 36KrKrypton83.80 54XeXenon131.29 86RnRadon(222) 118UuoUnunoctiu 6 7 m 7A(17) 9FFluorine18.9984 17ClChlorine35.4527 35BrBromine79.904 53IIodine126.9045 85AtAstatine(210) 117UusUnunseptiu 70YbYtterbium173.04 102NoNobelium(259) m m 6A(16) 8OOxygen15.9994 16SSulfur32.066 34SeSelenium78.96 52TeTellurium127.60 84PoPolonium(209) 116LvLivermoriu(292) 69TmThulium168.9342 101MdMendeleviu(258) 5A(15) 7NNitrogen14.0067 15PPhosphorus30.9738 33AsArsenic74.9216 51SbAntimony121.757 83BiBismuth208.9804 115UupUnunpentium 68ErErbium167.26 100FmFermium(257) 4A(14) 6CCarbon12.011 14SiSilicon28.0855 32GeGermanium72.61 50SnTin118.710 82PbLead207.2 114FlFlerovium(289) 67HoHolmium164.9303 99EsEinsteinium(252) 3A(13) 5BBoron10.811 13AlAluminum26.9815 31GaGallium69.723 49InIndium114.82 81TlThallium204.3833 113UutUnuntrium 66DyDysprosium162.50 98CfCalifornium(251) Metals Semimetals Nonmetals 1B2B(11)(12) 2930CuZnCopperZinc63.54665.39 4748AgCdSilverCadmium107.8682112.411 7980AuHgGoldMercury196.9665200.59 112111CnRgCoperniciumRoentgenium(285)(280) 6564TbGdTerbiumGadolium158.9253157.25 9796BkCmBerkeliumCurium(247)(247) er 8B(10) 28NiNickel58.693 46PdPalladium106.42 78PtPlatinum195.08 110DsDarmstadtium(281) 63EuEuropium151.965 95AmAmericium(243) Atomic numbSymbolNameAtomic mass 8B8B(8)(9) 2726FeCoIronCobalt55.84758.9332 4445RuRhRutheniumRhodium101.07 102.9055 7677OsIrOsmiumIridium190.2192.22 109108MtHsMeitneriumHassium(276)(270) 6261SmPmSamariumPromethium150.36(145) 9394NpPuNeptuniumPlutonium(237) (244) Key 79AuGold196.9665 An element 6B7B(6)(7) 2425CrMnChromiumManganese51.996154.9380 4243MoTcMolybdenumTechnetium95.94(98) 7475WReTungstenRhenium183.85186.207 106107SgBhSeaborgiumBohrium(271)(272) 5960PrNdNeodymiumPraseodymium140.9076144.24 9192PaUProtactiniumUranium231.0359238.00289 5B(5) 23VVanadium50.9415 41NbNiobium92.9064 73TaTantalum180.9479 105DbDubnium(268) 58CeCerium140.115 90ThThorium232.0381 ents 4B(4) 22TiTitanium47.88 40ZrZirconium91.224 72HfHafnium178.49 104RfRutherfordium(267) 57LaLanthanum 138.9055 89Ac Actinium (227) Elem 3B(3) 21ScScandium44.9559 39YYttrium88.9059 71LuLutetium174.967 103LrLawrencium(260) anides6 des7 the 2A(2) 4BeBeryllium9.0122 12MgMagnesium24.3050 20CaCalcium40.078 38SrStrontium87.62 56BaBarium137.327 88RaRadium227.0278 Lanth Actini f es riodic Table o Group number,U.S. systemIUPAC system1A(1) 1HPeriod 1Hydrogennumber1.0079 3Li2Lithium6.941 11Na3Sodium22.9898 19K4Potassium39.0983 37Rb5Rubidium85.4678 55Cs6Cesium132.9054 87Fr7Francium(223) Numbers in parenthesare mass numbers ofradioactive isotopes. e P Copyright 2016 Cengage Learning. 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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. Organic Chemistry Copyright 2016 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. Copyright 2016 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. Ninth Edition Organic Chemistry John McMurry COrNEll UNivErsity Australia • Brazil • Mexico • Singapore • United Kingdom • United States Copyright 2016 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. This is an electronic version of the print textbook. Due to electronic rights restrictions, some third party content may be suppressed. 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Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it. Organic Chemistry, Ninth Edition © 2016, 2012, Cengage Learning John McMurry WCN: 02-200-203 Product Director: Mary Finch ALL RIGHTS RESERVED. No part of this work covered by the copyright herein Product Manager: Maureen Rosener may be reproduced, transmitted, stored, or used in any form or by any means graphic, electronic, or mechanical, including but not limited to photocopying, Content Developers: Nat Chen, Lisa Weber recording, scanning, digitizing, taping, Web distribution, information networks, Product Assistant: Morgan Carney or information storage and retrieval systems, except as permitted under Marketing Manager: Julie Schuster Section 107 or 108 of the 1976 United States Copyright Act, without the prior Content Project Manager: Teresa Trego written permission of the publisher. 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Loose-leaf Edition: ISBN: 978-1-305-63871-6 Cengage Learning 20 Channel Center Street Boston, MA 02210 USA Cengage Learning is a leading provider of customized learning solutions with oice locations around the globe, including Singapore, the United Kingdom, Australia, Mexico, Brazil, and Japan. Locate your local oice 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. Printed in the United States of America Print Number: 01 Print Year: 2015 Copyright 2016 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). 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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 60 4 Organic Compounds: Cycloalkanes and Their Stereochemistry 89 5 Stereochemistry at Tetrahedral Centers 115 6 An Overview of Organic Reactions 149 Practice Your scientific Analysis and reasoning i: the Chiral Drug thalidomide 182 7 Alkenes: Structure and Reactivity 185 8 Alkenes: Reactions and Synthesis 220 9 Alkynes: An Introduction to Organic Synthesis 263 10 Organohalides 287 11 Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations 309 Practice Your scientific Analysis and reasoning ii: from Mustard Gas to Alkylating Anticancer Drugs 351 12 Structure Determination: Mass Spectrometry and Infrared Spectroscopy 354 13 Structure Determination: Nuclear Magnetic Resonance Spectroscopy 386 14 Conjugated Compounds and Ultraviolet Spectroscopy 420 Practice Your scientific Analysis and reasoning iii: Photodynamic therapy (PDt) 448 15 Benzene and Aromaticity 451 16 Chemistry of Benzene: Electrophilic Aromatic Substitution 478 17 Alcohols and Phenols 525 18 Ethers and Epoxides; Thiols and Sulfides 568 • Preview of Carbonyl Chemistry 595 19 Aldehydes and Ketones: Nucleophilic Addition Reactions 604 Practice Your scientific Analysis and reasoning iV: selective serotonin reuptake inhibitors (ssris) 649 20 Carboxylic Acids and Nitriles 653 21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 679 22 Carbonyl Alpha-Substitution Reactions 727 v Copyright 2016 Cengage Learning. 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B r i e f C o n t e n t s 23 Carbonyl Condensation Reactions 753 Practice Your scientific Analysis and reasoning V: thymine in DnA 784 24 Amines and Heterocycles 787 25 Biomolecules: Carbohydrates 832 26 Biomolecules: Amino Acids, Peptides, and Proteins 870 27 Biomolecules: Lipids 907 Practice Your scientific Analysis and reasoning Vi: Melatonin and serotonin 939 28 Biomolecules: Nucleic Acids 942 29 The Organic Chemistry of Metabolic Pathways 964 30 Orbitals and Organic Chemistry: Pericyclic Reactions 1013 Practice Your scientific Analysis and reasoning Vii: the Potent Antibiotic traits of endiandric Acid C 1034 31 Synthetic Polymers 1037 Appendix A: Nomenclature of Polyfunctional Organic Compounds A-1 Appendix B: Acidity Constants for Some Organic Compounds A-9 Appendix C: Glossary A-11 Appendix D: Answers to In-Text Problems A-31 Index i-1 vi Copyright 2016 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.
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