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Periodic Table of the Elements smi75625_endppFRONT.indd 2 Periodic Table of the Elements Group number 1A 8A 1 Key Period 2 number 1 H 1 Hydrogen 67 He 1.0079 Atomic number Symbol Helium 2A Ho 3A 4A 5A 6A 7A 4.0026 3 4 Holmium 5 6 7 8 9 10 Name 164.9303 Atomic weight 2 2 Li Be An element B C N O F Ne Lithium Beryllium Boron Carbon Nitrogen Oxygen Fluorine Neon 6.941 9.0122 10.811 12.011 14.0067 15.9994 18.9984 20.1797 11 12 13 14 15 16 17 18 3 Na Mg Al Si P S Cl Ar 3 Sodium Magnesium Aluminum Silicon Phosphorus Sulfur Chlorine Argon 22.9898 24.3050 3B 4B 5B 6B 7B 8B 8B 8B 1B 2B 26.9815 28.0855 30.9738 32.066 35.4527 39.948 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 4 K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr 4 Potassium Calcium Scandium Titanium Vanadium Chromium Manganese Iron Cobalt Nickel Copper Zinc Gallium Germanium Arsenic Selenium Bromine Krypton 39.0983 40.078 44.9559 47.88 50.9415 51.9961 54.9380 55.845 58.9332 58.693 63.546 65.41 69.723 72.64 74.9216 78.96 79.904 83.80 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 5 Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe 5 Rubidium Strontium Yttrium Zirconium Niobium Molybdenum Technetium Ruthenium Rhodium Palladium Silver Cadmium Indium Tin Antimony Tellurium Iodine Xenon 85.4678 87.62 88.9059 91.224 92.9064 95.94 (98) 101.07 102.9055 106.42 107.8682 112.411 114.82 118.710 121.760 127.60 126.9045 131.29 55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 6 Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn 6 Cesium Barium Lanthanum Hafnium Tantalum Tungsten Rhenium Osmium Iridium Platinum Gold Mercury Thallium Lead Bismuth Polonium Astatine Radon 132.9054 137.327 138.9055 178.49 180.9479 183.84 186.207 190.2 192.22 195.08 196.9665 200.59 204.3833 207.2 208.9804 (209) (210) (222) 87 88 89 104 105 106 107 108 109 110 111 112 113 114 115 116 7 Fr Ra Ac Rf Db Sg Bh Hs Mt Ds Rg – – – – – 7 Francium Radium Actinium Rutherfordium Dubnium Seaborgium Bohrium Hassium Meitnerium Darmstadtium Roentgenium — — — — — (223) (226) (227) (267) (268) (271) (272) (270) (276) (281) (280) (285) (284) (289) (288) (293) 58 59 60 61 62 63 64 65 66 67 68 69 70 71 Lanthanides 6 Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu 6 Cerium Praseodymium Neodymium Promethium Samarium Europium Gadolinium Terbium Dysprosium Holmium Erbium Thulium Ytterbium Lutetium 140.115 140.9076 144.24 (145) 150.36 151.964 157.25 158.9253 162.50 164.9303 167.26 168.9342 173.04 174.967 90 91 92 93 94 95 96 97 98 99 100 101 102 103 Actinides 7 Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr 7 Thorium Protactinium Uranium Neptunium Plutonium Americium Curium Berkelium Californium Einsteinium Fermium Mendelevium Nobelium Lawrencium 232.0381 231.0359 238.0289 (237) (244) (243) (247) (247) (251) (252) (257) (258) (259) (260) 12/2/09 10:14:16 AM smi75625_endppFRONT.indd 3 COMMON FUNCTIONAL GROUPS Type of Compound General Structure Example Functional Group Type of Compound General Structure Example Functional Group O O Acid C C –COCl Aromatic compound phenyl group chloride l RC CH3 Cl –OH O O Alcohol R OH CH3 OH Carboxylic –COOH hydroxy group acid C C carboxy group R OH CH3 OH O O O O Aldehyde C C C O Ester C C –COOR RH CH3 H carbonyl group R OR CH3 OCH3 –OR – – Alkane R HCH3CH3 Ether RRO CH3 O CH3 alkoxy group H H O O C O Alkene C C C C double bond Ketone C C carbonyl group RR CH3 CH3 H H R X –C N Alkyl halide CH3 Br –X Nitrile RCN CH3 CN (X = F, Cl, Br, I) halo group cyano group Alkyne C C HCCH triple bond Sulfide RRS CH3 S CH3 –SR alkylthio group O O –CONH2, C H (or R) – Amide C CONHR, Thiol R SH CH3 SH –SH RN – CH3 NH2 CONR2 mercapto group H (or R) O O Amine R NH2 or CH3 NH2 –NH2 Thioester C C –COSR R SR CH SCH R2NH or R3N amino group 3 3 O O 12/2/09 10:14:16 AM O O O O Anhydride C C C C C C RRO CH3 O CH3 O Organic Chemistry Third Edition Janice Gorzynski Smith University of Hawai’i at Ma-noa TM smi75625_fm_00i-xxxiv.indd i 11/17/09 11:21:07 AM TM ORGANIC CHEMISTRY, THIRD EDITION Published by McGraw-Hill, a business unit of The McGraw-Hill Companies, Inc., 1221 Avenue of the Americas, New York, NY 10020. Copyright © 2011 by The McGraw-Hill Companies, Inc. All rights reserved. Previous editions © 2008 and 2006. No part of this publication may be reproduced or distributed in any form or by any means, or stored in a database or retrieval system, without the prior written consent of The McGraw-Hill Companies, Inc., including, but not limited to, in any network or other electronic storage or transmission, or broadcast for distance learning. Some ancillaries, including electronic and print components, may not be available to customers outside the United States. This book is printed on acid-free paper. 1 2 3 4 5 6 7 8 9 0 DOW/DOW 1 0 9 8 7 6 5 4 3 2 1 0 ISBN 978–0–07–337562–5 MHID 0–07–337562–4 Vice President & Editor-in-Chief: Marty Lange Vice President, EDP: Kimberly Meriwether-David Director of Development: Kristine Tibbetts Publisher: Ryan Blankenship Senior Sponsoring Editor: Tamara L. Hodge Vice President New Product Launches: Michael Lange Senior Developmental Editor: Donna Nemmers Senior Marketing Manager: Todd L. Turner Senior Project Manager: Jayne L. Klein Lead Production Supervisor: Sandy Ludovissy Senior Media Project Manager: Sandra M. Schnee Senior Designer: Laurie B. Janssen (USE) Cover Image: ©Amama Images Inc., Alamy Lead Photo Research Coordinator: Carrie K. Burger Photo Research: Mary Reeg Supplement Producer: Mary Jane Lampe Compositor: Precision Graphics Typeface: 10/12 Times LT Std Printer: R. R. Donnelley All credits appearing on page or at the end of the book are considered to be an extension of the copyright page. Library of Congress Cataloging-in-Publication Data Smith, Janice G. Organic chemistry / Janice Gorzynski Smith. — 3rd ed. p. cm. Includes index. ISBN 978–0–07–337562–5 — ISBN 0–07–337562–4 (hard copy : alk. paper) 1. Chemistry, Organic–Textbooks. I. Title. QD253.2.S65 2011 547—dc22 2009034737 www.mhhe.com smi75625_fm_00i-xxxiv.indd ii 11/17/09 11:21:08 AM For Megan Sarah smi75625_fm_00i-xxxiv.indd iii 11/17/09 11:21:08 AM About the Author Janice Gorzynski Smith was born in Schenectady, New York, and grew up following the Yankees, listening to the Beatles, and water skiing on Sacandaga Reservoir. She became interested in chemistry in high school, and went on to major in chemistry at Cornell University where she received an A.B. degree summa cum laude. Jan earned a Ph.D. in Organic Chemistry from Harvard University under the direction of Nobel Laureate E. J. Corey, and she also spent a year as a National Science Foundation National Needs Postdoctoral Fellow at Harvard. During her tenure with the Corey group she completed the total synthesis of the plant growth hormone gibberellic acid. Following her postdoctoral work, Jan joined the faculty of Mount Holyoke College where she was employed for 21 years. During this time she was active in teaching organic chemis- try lecture and lab courses, conducting a research program in organic synthesis, and serving as department chair. Her organic chemistry class was named one of Mount Holyoke’s “Don’t- miss courses” in a survey by Boston magazine. After spending two sabbaticals amidst the natu- ral beauty and diversity in Hawai‘i in the 1990s, Jan and her family moved there permanently in 2000. She is currently a faculty member at the University of Hawai‘i at Ma-noa, where she teaches the two-semester organic chemistry lecture and lab courses. In 2003, she received the Chancellor’s Citation for Meritorious Teaching. Jan resides in Hawai‘i with her husband Dan, an emergency medicine physician. She has four children: Matthew and Zachary, age 14 (margin photo on page 163); Jenna, a student at Temple University’s Beasley School of Law; and Erin, an emergency medicine physician and co-author of the Student Study Guide/Solutions Manual for this text. When not teaching, writing, or enjoying her family, Jan bikes, hikes, snorkels, and scuba dives in sunny Hawai‘i, and time permitting, enjoys travel and Hawaiian quilting. The author (far right) and her family from the left: husband Dan, and children Zach, Erin, Jenna, and Matt. iv smi75625_fm_00i-xxxiv.indd iv 11/17/09 11:21:09 AM Contents in Brief Prologue 1 1 Structure and Bonding 6 2 Acids and Bases 54 3 Introduction to Organic Molecules and Functional Groups 81 4 Alkanes 113 5 Stereochemistry 159 6 Understanding Organic Reactions 196 7 Alkyl Halides and Nucleophilic Substitution 228 8 Alkyl Halides and Elimination Reactions 278 9 Alcohols, Ethers, and Epoxides 312 10 Alkenes 358 11 Alkynes 399 12 Oxidation and Reduction 426 13 Mass Spectrometry and Infrared Spectroscopy 463 14 Nuclear Magnetic Resonance Spectroscopy 494 15 Radical Reactions 538 16 Conjugation, Resonance, and Dienes 571 17 Benzene and Aromatic Compounds 607 18 Electrophilic Aromatic Substitution 641 19 Carboxylic Acids and the Acidity of the O–H Bond 688 20 Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction 721 21 Aldehydes and Ketones—Nucleophilic Addition 774 22 Carboxylic Acids and Their Derivatives—Nucleophilic Acyl Substitution 825 23 Substitution Reactions of Carbonyl Compounds at the α Carbon 880 24 Carbonyl Condensation Reactions 916 25 Amines 949 26 Carbon–Carbon Bond-Forming Reactions in Organic Synthesis 1002 27 Carbohydrates 1027 28 Amino Acids and Proteins 1074 29 Lipids 1119 30 Synthetic Polymers 1148 Appendices A-1 Glossary G-1 Credits C-1 Index I-1 v smi75625_fm_00i-xxxiv.indd v 11/17/09 11:21:09 AM Contents Preface xviii Acknowledgments xxiii List of How To’s xxv List of Mechanisms xxvii List of Selected
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