INTRO TO SPECTROSCOPY FIFTH EDITION SUMMARY OF CHANGES. The order of the chapters was rearranged Introduction to Organic Laboratory Techniques: A Small.
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INTRODUCTION TO SPECTROSCOPYDonald L. PaviaGary M. Lampman George S. Kriz James R. Vyvyan Department of ChemistryWestern WashingtonUniversity Bellingham,Washington FIFTH EDITIONAustralia • Brazil • Mexico • Singapore • United Kingdom • United Statesiranchembook.ir/edu
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This is an electronic version of the print textbook. Due to electronic rights restrictions, some third party content may be suppressed. Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. The publisher reserves the right to remove content from this title at any time if subsequent rights restrictions require it. For valuable information on pricing, previous editions, changes to current editions, and alternate formats, please visit www.cengage.com/highered to search byISBN#, author, title, or keyword for materials in your areas of interest. iranchembook.ir/edu
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© 2015, 2009Cengage Learning ALL RIGHTS RESERVED. No part of this work covered by the copyright herein may be reproduced, transmitted, stored, or used in any form orby any means graphic, electronic, or mechanical, including but not limited to photocopying, recording, scanning, digitizing, taping, Web distribution, information networks, or inf ormation storage and retrievalsystems, except as permitted under Section 107or 108of the 1976United States Copyright Act, without the prior written permission of the publisher. Library of Congress Control Number: 2013950396ISBN-13: 978-1-285-46012-3ISBN-10: 1-285-46012-XCengage Learning 200First Stamford Place, 4th Floor Stamford, CT 06902USA 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 .Introduction to Spectroscopy, Fifth Edition Donald L. Pavia, Gary M. Lampman, George S. Kriz, and James R. Vyvyan Product Director: Mary Finch Product Manager: Maureen Rosener Content Developer: Alyssa White Content Coordinator: Karolina Kiwak Product Development Manager: Rebecca Berardy-Schwartz Media Developer: Lisa Weber Marketing Director: Jason Sakos Marketing Development Manager: Julie ShusterContent Project Manager: Teresa L. Trego Art Director: Maria Epes Manufacturing Planner: Judy Inouye Rights Acquisitions Specialist: Thomas McDonoughProduction Service: MPS Limited Photo Researcher: PreMedia Global Text Researcher: PreMedia Global Copy Editor: MPS Limited Illustrator: MPS Limited Cover Designer: Bartay Studio Cover Image: Expansion of the C- 4methine proton of ethyl 2-methyl-4-pentenoate acquired at 500MHz. Data acquired and processed by James Vyvyan. Compositor: MPS Limited For product information and technology assistance, contact us at Cengage Learning Customer & Sales Support, 1-800-354-9706For permission to use material from this text or product, submit all requests online at www ww w. .c ce en ng ga ag ge e. .c co om m/ /p pe er rm mi is ss si io on ns sFurther permissions questions can be e-mailed to permissionrequest@cengage.com Printed in the United States of America 1 2 3 4 5 6 7 17 16 15 14 13 iranchembook.ir/edu
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ADVICE FOR STUDENTSSuccess in working out the solutions to spectroscopy problems comes more easily and is more en- joyable by following some simple suggestions: 1.Carefully study the solved examples that may be found at the end of each chapter. Do not attempt to work on additional problems until you are comfortable with the approach that is being demonstrated with the solved examples. 2.There is great value to be gained in working collaboratively to solve spectroscopy problems. Try standing around a blackboard to exchange ideas. You will find it to be fun,and you will learn more!3.DonÕt be afraid to struggle. It is too easy to look up the answer to a difficult problem,and you wonÕt learn much. You need to train your brain to think like a scientist,and there is no substitute for hard work. 4.Work problems concurrently as you study each chapter. That will solidify the concepts in your mind.Although this book concentrates on organic chemistry examples,be aware that the study of spec- troscopy crosses over into many areas,including biochemistry,inorganic chemistry,physical chemistry,materials chemistry,and analytical chemistry. Spectroscopy is an indispensible tool to support all forms of laboratory research.ACKNOWLEDGMENTSThe authors are very grateful to Mr. Charles Wandler,without whose expert help this project could not have been accomplished. We also acknowledge numerous contributions made by our students, who use the textbook and who provide us careful and thoughtful feedback. Finally,once again we must thank our wives,Neva-Jean Pavia,Marian Lampman,and Cathy Vyvyan,for their support and patience. They endure a great deal in order to support us as we write, and they deserve to be part of the celebration when the textbook is completed! We honor the memory of Carolyn Kriz; we miss her and the love and encouragement that she provided. Donald L. Pavia Gary M. Lampman George S. Kriz James R. Vyvyan viPreface iranchembook.ir/edu
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Preface viiFourth edition chapternumber/titleFifth edition chapter number/titleNotes 1 Molecular Formulas and What Can Be Learned from Them1 Molecular Formulas and What Can Be Learned from Them Section 1.6,A Quick Look Ahead to Simple Uses of Mass Spectra,was deleted. (Mass Spectra were moved earlier into Chapters 3 and 4.)A new Section 1.6 is now titled:ÒThe Nitrogen Rule.ÓReferences were revised/updated. 2 Infrared Spectroscopy 2 Infrared Spectroscopy Section 2.6,the solid samples subsection was updated to include ATR techniques. Several figures were revised/updated. Section 2.21,Alkyl and Aryl Halides,was revised. Section 2.23,How to Solve Infrared Spectral Problems,is a new section. The sections that followed were renumbered. Problems were revised. References were revised/ updated.3 Nuclear MagneticResonance Spectroscopy Part One:Basic Concepts. 5 Nuclear Magnetic Res-onance Spectroscopy Part One:Basic Concepts.New Section 5.20 References were revised/updated. New online resources were referenced and/or updated.4 Nuclear MagneticResonance Spectroscopy Part Two:Carbon-13 etc. 6 Nuclear Magnetic Reso-nance Spectroscopy Part Two:Carbon-13 etc.Section 6.4 introduces a new decoupling notation. New Section 6.12. Sections following 6.12 are renumbered. Several new problems were added. Some spectra replaced/improved. References were revised/updated. New online resources referenced and/or updated.5 Nuclear MagneticResonance Spectroscopy Part Three:Spin-Spin Cou- pling7Nuclear Magnetic Res-onance Spectroscopy Part Three:Spin-Spin CouplingNew discussion of splitting in diastereotopic systems.New discussion of heteronuclear splitting between 1HÐ19F and SÐ31PAddition of solved example problems. New and revised end-of-chapter problems using cou- pling constant information and chemical shift calcu- lations.References were revised/updated. 6 Nuclear MagneticResonance Spectroscopy Part Four:Other Topics in One-Dimensional NMR8Nuclear Magnetic Res-onance Spectroscopy Part Four:Other Topics in One-Dimensional NMRNew discussion and examples of solvent effects. Addition of solved example problems. New and revised end-of-chapter problems. References were revised/updated. INTRO TO SPECTROSCOPY FIFTH EDITION SUMMARY OF CHANGES The order of the chapters was rearranged to better reflect the requests and practices of our users. Mass Spectroscopy was moved to an earlier position,causing the renumbering. (Continued )iranchembook.ir/edu
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viiiPreface Fourth edition chapternumber/titleFifth edition chapter number/titleNotes7Ultraviolet Spectroscopy 10 Ultraviolet Spectroscopy Few changes. 8 Mass Spectrometry (first half) Chapter was split. 3 Mass Spectrometry Part One:Basic Theory, Instrumentation,and Sampling Techniques To highlight the continued development and importance of mass spectrometry (MS) methods, we have moved this material to the early part of the text and split it into two chapters,one on theory and instrumentation (Chapter 3) and the other on detailed structural analysis using characteristic fragmentation patterns of common functional groups (Chapter 4).Expanded and refined discussion of sampling and ionization methods,including atmospheric pressure chemical ionization techniques.Examples of applications for different MS techniques and instrumentation,including pros and cons of different methods. 8 Mass Spectrometry (second half)4Mass Spectrometry Part Two:Fragmentation and Structural Analysis Refined discussion of fragmentations in EI-MS for common functional groups.New examples of use of MS in structure determination.Additional solved example problems. New and revised end-of-chapter problems. 9Combined Structure Problems11Combined Structure Prob-lemsSeveral new problems were introduced. Two-dimensional spectra were replaced with new, improved ones. References were revised/updated. Online resources were updated.10Nuclear MagneticResonance Spectroscopy Part Five:Advanced NMR Techniques. 9Nuclear Magnetic Reso-nance Spectroscopy Part Five:Advanced NMR Techniques Sections 9.4 and 9.7 were extensively revised. Many of the two-dimensional spectra were replaced with new,improved ones. AppendicesAppendicesOld Appendix 11 was removed. Values in some of the tables were updated or revised. iranchembook.ir/edu
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CHAPTER 1MOLECULAR FORMULAS AND WHAT CAN BE LEARNED FROM THEM1 1.1 Elemental Analysis and Calculations1 1.2 Determination of Molecular Mass5 1.3 Molecular Formulas5 1.4 Index of Hydrogen Deficiency6 1.5 The Rule of Thirteen9 1.6 The Nitrogen Rule12 Problems12 References13 CHAPTER 2INFRARED SPECTROSCOPY14 2.1 The Infrared Absorption Process15 2.2 Uses of the Infrared Spectrum16 2.3 The Modes of Stretching and Bending17 2.4 Bond Properties and Absorption Trends19 2.5 The Infrared Spectrometer22 A.Dispersive Infrared Spectrometers22 B.Fourier Transform Spectrometers24 2.6 Preparation of Samples for Infrared Spectroscopy25 2.7 What to Look for When Examining Infrared Spectra26 2.8 Correlation Charts and Tables28 2.9 How to Approach the Analysis of a Spectrum (Or What You Can Tell at a Glance)30 ixCONTENTSiranchembook.ir/edu
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