Preview Chemistry human activity, chemical reactivity, Second Canadian edition by Bucat, R. B. Kotz, John C. Mahaffy, Peter G. McMurry, John Tasker, Roy Treichel, Paul Weaver, Gabriela C (2015) Preview Chemistry human activity, chemical reactivity, Second Canadian edition by Bucat, R. B. Kotz, John C. Mahaffy, Peter G. McMurry, John Tasker, Roy Treichel, Paul Weaver, Gabriela C (2015) Preview Chemistry human activity, chemical reactivity, Second Canadian edition by Bucat, R. B. Kotz, John C. Mahaffy, Peter G. McMurry, John Tasker, Roy Treichel, Paul Weaver, Gabriela C (2015) Preview Chemistry human activity, chemical reactivity, Second Canadian edition by Bucat, R. B. Kotz, John C. Mahaffy, Peter G. McMurry, John Tasker, Roy Treichel, Paul Weaver, Gabriela C (2015) Preview Chemistry human activity, chemical reactivity, Second Canadian edition by Bucat, R. B. Kotz, John C. Mahaffy, Peter G. McMurry, John Tasker, Roy Treichel, Paul Weaver, Gabriela C (2015)
Copyright 2015 Nelson Education Ltd 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) Radium 88 Francium 87 Fr Ra Ba Barium 56 Cesium 55 Cs Sr Rb Ac Actinides Lanthanides Rf Hf Bh Re Rhenium 75 Tc Hs Mt Ir Iridium 77 Rh Ds Pt Platinum 78 Pd Ni Nickel 28 10 Th Rg Au Gold 79 Ag Silver 47 Cu Copper 29 11 Cn Hg Mercury 80 Cd Cadmium 48 Zn Zinc 30 12 Uut Tl Thallium 81 In Indium 49 Ga Gallium 31 Al Hassium Meitnerium Darmstadtium Roentgenium Copernicium Ununtrium 108 109 110 111 112 113 Os Osmium 76 Ru Co Cobalt 27 Aluminum 13 Fl 114 Flerovium Pb Lead 82 Sn Tin 50 Ge Germanium 32 Si Silicon 14 C Carbon Boron B 14 13 Pr Nd Pm Sm Eu Pa U Np Pu Am Cm Curium 96 Gd Bk Cf Dy Es Ho Po At I Polonium Astatine 85 84 Te Iodine 53 Br Bromine 35 Cl Chlorine 17 F Fluorine 17 Rn Radon 86 Xe Xenon 54 Kr Krypton 36 Ar Argon 18 Ne Neon 10 He Fm Er Erbium 68 115 Uup Md Tm No Yb 117 Uus Lr Lu 118 Uuo Thulium Ytterbium Lutetium 70 69 71 Lv 116 Ununpentium Livermorium Ununseptium Ununoctium Bi Bismuth 83 Sb Se Selenium 34 S Sulfur 16 Antimony Tellurium 51 52 As Arsenic 33 P Phosphorus 15 O Oxygen Nitrogen N 16 15 Helium 18 Berkelium Californium Einsteinium Fermium Mendelevium Nobelium Lawrencium 98 99 101 103 97 100 102 Tb Praseodymium Neodymium Promethium Samarium Europium Gadolinium Terbium Dysprosium Holmium 62 63 59 60 61 64 65 67 66 Sg W Tungsten 74 Mo Fe Iron 26 Symbol Atomic number Thorium Protactinium Uranium Neptunium Plutonium Americium 92 93 94 90 95 91 Ce Cerium 58 Db Ta Tantalum 73 Nb Mn Actinium Rutherfordium Dubnium Seaborgium Bohrium 89 105 107 104 106 La Zr Lanthanum Hafnium 72 57 Y Cr U Uranium 92 Zirconium Niobium Molybdenum Technetium Ruthenium Rhodium Palladium 40 44 46 41 45 42 43 V Yttrium 39 Ca Ti Rubidium Strontium 37 38 K Sc Scandium Titanium Vanadium Chromium Manganese 21 22 24 23 25 Mg PROPERTIES UNKNOWN NON-METALS METALLOIDS TRANSITION METALS MAIN GROUP METALS Potassium Calcium 19 20 Na Sodium Magnesium 11 12 Be Beryllium Lithium Li H At the date of publication, elements 113, 115, 117 and 118 had not been named and have been given temporary names Hydrogen Periodic Table of the Elements STANDARD ATOMIC WEIGHTS OF THE ELEMENTS (IUPAC 2013) Element Actinium* Aluminum Americium* Antimony Argon Arsenic Astatine* Barium Berkelium* Beryllium Bismuth Bohrium Boron Bromine Cadmium Calcium Californium* Carbon Cerium Cesium Chlorine Chromium Cobalt Copernicium* Copper Curium* Darmstadtium* Dubnium* Dysprosium Einsteinium* Erbium Europium Fermium* Flerovium* Fluorine Francium* Gadolinium Gallium Germanium Gold Hafnium Hassium* Helium Holmium Hydrogen Indium Iodine Iridium Iron Krypton Lanthanum Lawrencium* Lead Lithium Livermorium* Lutetium Magnesium Manganese Meitnerium* Symbol Z Ac Al Am Sb Ar As At Ba Bk Be Bi Bh B Br Cd Ca Cf C Ce Cs Cl Cr Co Cn Cu Cm Ds Db Dy Es Er Eu Fm Fl F Fr Gd Ga Ge Au Hf Hs He Ho H In I Ir Fe Kr La Lr Pb Li Lv Lu Mg Mn Mt 89 13 95 51 18 33 85 56 97 83 107 35 48 20 98 58 55 17 24 27 112 29 96 110 105 66 99 68 63 100 114 87 64 31 32 79 72 108 67 49 53 77 26 36 57 103 82 116 71 12 25 109 Standard Atomic Weight** 26.981 5385(7) Working Values†† 26.98 121.760(1) 39.948(1) 74.921 595(6) 121.8 39.95 74.92 137.327(7) 137.3 9.012 1831(5) 208.980 40(1) 9.012 209.0 † [10.806, 10.821] [79.901, 79.907]† 112.414(4) 40.078(4) 10.81 79.90 112.4 40.08 [12.0096, 12.0116]† 140.116(1) 132.905 451 96(6) [35.446, 35.457]† 51.9961(6) 58.933 194(4) 12.01 140.1 132.9 35.45 52.00 58.93 63.546(3) 63.55 162.500(1) 162.5 167.259(3) 151.964(1) 167.3 152.0 18.998 403 163(6) 19.00 157.25(3) 69.723(1) 72.630(8) 196.966 569(5) 178.49(2) 157.3 69.72 72.63 197.0 178.5 4.002 602(2) 164.930 33(2) [1.007 84, 1.008 11]† 114.818(1) 126.904 47(3) 192.217(3) 55.845(2) 83.798(2) 138.905 47(7) 4.003 164.9 1.008 114.8 126.9 192.2 55.85 83.80 138.9 207.2(1) [6.938, 6.997]† 207.2 6.94 174.9668(1) [24.304, 24.307]† 54.938 044(3) 175.0 24.31 54.94 *These elements have no stable isotopes and standard atomic weights are not listed, except for four of them (Bi, Th, Pa and U), which have characteristic terrestrial isotopic compositions with standard atomic weights given **These are the current best estimates decided by IUPAC The number in parentheses after each value indicates the uncertainty of estimation of the last digit † The variation in the atomic weights of these elements, depending on the origin and treatment of the sample, is greater than the uncertainty of their measurement In these cases, the atomic weights are Element Mendelevium* Mercury Molybdenum Neodymium Neon Neptunium* Nickel Niobium Nitrogen Nobelium* Osmium Oxygen Palladium Phosphorus Platinum Plutonium* Polonium* Potassium Praseodymium Promethium* Protactinium* Radium* Radon* Rhenium Rhodium Roentgenium* Rubidium Ruthenium Rutherfordium* Samarium Scandium Seaborgium* Selenium Silicon Silver Sodium Strontium Sulfur Tantalum Technetium* Tellurium Terbium Thallium Thorium* Thulium Tin Titanium Tungsten Ununoctium* Ununpentium* Ununseptium* Ununtrium* Uranium* Vanadium Xenon Ytterbium Yttrium Zinc Zirconium Symbol Z Md Hg Mo Nd Ne Np Ni Nb N No Os O Pd P Pt Pu Po K Pr Pm Pa Ra Rn Re Rh Rg Rb Ru Rf Sm Sc Sg Se Si Ag Na Sr S Ta Tc Te Tb Tl Th Tm Sn Ti W Uuo Uup Uus Uut U V Xe Yb Y Zn Zr 101 80 42 60 10 93 28 41 102 76 46 15 78 94 84 19 59 61 91 88 86 75 45 111 37 44 104 62 21 106 34 14 47 11 38 16 73 43 52 65 81 90 69 50 22 74 118 115 117 113 92 23 54 70 39 30 40 Standard Atomic Weight** 200.592(3) 95.95(1) 144.242(3) 20.1797(6) Working Values†† 200.6 95.95 144.2 20.18 58.6934(4) 92.906 37(2) [14.006 43, 14.007 28]† 58.69 92.91 14.01 190.23(3) [15.999 03, 15.999 77]† 106.42(1) 30.973 761 998(5) 195.084(9) 190.2 16.00 106.4 30.97 195.1 39.0983(1) 140.907 66(2) 39.10 140.9 231.035 88(2) 231.0 186.207(1) 102.905 50(2) 186.2 102.9 85.4678(3) 101.07(2) 85.47 101.1 150.36(2) 44.955 908(5) 150.4 44.96 78.971(8) [28.084, 28.086]† 107.8682(2) 22.989 769 28(2) 87.62(1) [32.059, 32.076]† 180.947 88(2) 78.97 28.09 107.9 22.99 87.62 32.06 180.9 127.60(3) 158.925 35(2) [204.382, 204.385]† 232.0377(4) 168.934 22(2) 118.710(7) 47.867(1) 183.84(1) 127.6 158.9 204.4 232.0 168.9 118.7 47.87 183.8 238.028 91(3) 50.9415(1) 131.293(6) 173.054(5) 88.905 84(2) 65.38(2) 91.224(2) 238.0 50.94 131.3 173.1 88.91 65.38 91.22 listed by IUPAC as an interval; the two values listed are the upper and lower limits of the range of values †† Where calculations of extremely high accuracy are not required, these working values (the standard atomic weights abridged to four significant figures) can be used For those elements whose standard atomic weights are expressed as intervals, these are not abridged values, but working values selected by IUPAC from “conventional atomic weights." See Section 2.15 Copyright 2015 Nelson Education Ltd 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) CHEMISTRY Transforming Learning Transforming Lives Discover OWLv2! The Chemist’s Choice The Student’s Solution Created by teaching chemists, OWL, the #1 online solution for chemistry, now offers even more robust features! With OWL, you’ll save time and help your students improve their grades With OWLv2, you can address your students’ different learning styles through a wide range of assignment types, including tutorials, visualization exercises, and algorithmically generated homework questions with instant answer-specific feedback OWLv2 is the only system designed to support mastery learning, allowing students to work at their own pace until they understand each concept and skill Student Features Snapshot: OWLv2 features the MindTap Reader™ Personalized Study Plans (PSPs) lead students through the learning exercise Students first complete a pre-test, and the results determine which learning activities are recommended After completing the learning activities, students take a post-test that measures their improvement If a student’s first answer submission is incorrect, the program will alert the student OWLv2 allows students to draw chemical structures directly in their assignment using ChemDoodle Sketcher MindTap Reader™ in OWLv2 courses brings content to life for better engagement This easy-to-use digital reader embeds video, audio, annotations, activities, apps, and instructor source materials right into the text for a more seamless learning experience Students can personalize the content, access readings and notes from any computer or tablet device, and print chapters Notes, Highlights, Bookmarks, and Search In a traditional textbook, you can bookmark a page, mark up text, and write comments in the margin or in a notebook, and flip through printed pages to find a term or page number MindTap Reader takes this process to new levels of ease: • Highlight and take quick notes using a separate Notebook app, which you can sync with an Evernote account • Click the bookmark icon in a Reading Activity Bookmarks display in the Bookmarks App (under My Notes), organized by location A click takes you to the original location of a bookmark • Skim through the MindTap Reader using right and left arrows or use the Skimmer at the bottom of each page to leap to a section and track your place in the chapter • Search for terms or page numbers to immediately access relevant content MindApp Study Tools The Apps Dock on the right side of the MindTap Reader screen offers useful tools, including: • Merriam-Webster Dictionary • Glossary of key terms from the text • Flashcards of key terms from the text; students can also create their own View full features list online Explore more at: www.cengage.com/owlv2 Copyright 2015 Nelson Education Ltd 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) Correlation of 13C Chemical Shift with Environment CH3 CH2 CH C C C C Intensity C Hal N O C N Aromatic C C 220 C O 200 180 160 140 120 100 80 Chemical shift ( ) 60 40 20 ppm Correlation of 1H Chemical Shift with Environment H H C Aromatic Y C Vinylic Y C H H H C C C C O, N, Halogen Allylic Saturated C C H Alkyne Chemical shift ( ) Chemical S hift ( ) Type of Hydrogen Reference (C H )4 Si CH 0.7–1.3 Saturated secondary CH 1.2–1.6 H C C Aromatic methyl Alkynyl Alkyl halide X Cl, Br, I C Alcohol C Alcohol, ether O 2.5 –4.0 O H 2.5 –5.0 (Variable) C H Aldehyde 2.5–3.0 H 3.3 –4.5 H Ar C 4.5 –6.5 H 6.5 –8.0 O 2.0–2.4 2.4–2.7 CH C C Vinylic Aromatic CH C H H 1.6–2.2 C C Ar Chemical S hift ( ) X H O Methyl ketone 1.4–1.8 C Allylic Type of Hydrogen Saturated primary Saturated tertiary C O Carboxylic acid C 9.7 –10.0 H O H 11.0 –12.0 Copyright 2015 Nelson Education Ltd 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) Copyright 2015 Nelson Education Ltd 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) Copyright 2015 Nelson Education Ltd 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) This is an electronic version of the print textbook Due to electronic rights restrictions, some third party content may be suppressed 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.nelson.com to search by ISBN#, author, title, or keyword for materials in your areas of interest Copyright 2015 Nelson Education Ltd 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) Chemistry, Second Canadian Edition by Peter G Mahaffy, Robert Bucat, Roy Tasker, John C Kotz, Paul M Treichel, Gabriela C Weaver, and John McMurry Vice President, Editorial Higher Education: Anne Williams Senior Production Project Manager: Imoinda Romain Publisher: Paul Fam Production Service: Integra Software Services Marketing Manager: Leanne Newell Copy Editor: Wendy Yano Technical Reviewer: Rabin Bissessur Proofreader: Erin Moore Cover Image: CLAUDIO SANTANA/AFP/Getty Images Managing Developmental Editor: Mark Grzeskowiak Indexer: Stephanie Bilodeau Compositor: Integra software Services Photo Researcher/Permissions Coordinator: Julie Pratt Design Director: Ken Phipps COPYRIGHT © 2015, 2011 by Nelson Education Ltd ALL RIGHTS RESERVED No part of this work covered by the copyright herein may be reproduced, transcribed, or used in any form or by any means—graphic, electronic, or mechanical, including photocopying, recording, taping, Web distribution, or information storage and retrieval systems— without the written permission of the publisher WCN: 02-200-201 Adapted from Chemistry and Chemical Reactivity, Seventh Edition, by John C Kotz, Paul M Treichel, and John Townsend, published by Thomson Brooks/Cole Copyright © 2009 by Thomson Brooks/Cole; and Fundamentals of Organic Chemistry, Sixth Edition, by John E McMurry and Eric E Simanek, published by Thomson Brooks/Cole Copyright © 2007 by Thomson Brooks/Cole Printed and bound in the United States of America 17 16 15 14 For more information contact Nelson Education Ltd., 1120 Birchmount Road, Toronto, Ontario, M1K 5G4 Or you can visit our Internet site at http://www.nelson.com For permission to use material from this text or product, submit all requests online at www.cengage.com/permissions Further questions about permissions can be emailed to permissionrequest@cengage.com Every effort has been made to trace ownership of all copyrighted material and to secure permission from copyright holders In the event of any question arising as to the use of any material, we will be pleased to make the necessary corrections in future printings Managing Designer: Franca Amore Interior Design: Liz Harasymczuk Cover Design: Courtney Hellam Library and Archives Canada Cataloguing in Publication Mahaffy, Peter G., author Chemistry : human activity, chemical reactivity / Peter G Mahaffy, King’s University College, Bob Bucat, University of Western Australia, Roy Tasker, University of Western Sydney, John C Kotz, State University of New York, Paul M Treichel, University of Wisconsin-Madison, Gabriela C Weaver, Purdue University, John McMurry, Cornell University — Second Canadian edition Includes index ISBN 978-0-17-666088-8 (bound) Chemistry—Textbooks Chemical reactions—Textbooks I Bucat, R B., author II Tasker, Roy, author III Kotz, John C., author IV Treichel, Paul, author V Weaver, Gabriela C., author VI McMurry, John, author VII Title QD31.3.C43 2014 540 C2014-900168-1 PKG ISBN-13: 978-0-17-666088-8 PKG ISBN-10: 0-17-666088-7 Copyright 2015 Nelson Education Ltd 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) B R I E F C O N T E N T S Preface xvii Part 1: Chemistry: A Human Activity CHAPTER 1: Human Activity, Chemical Reactivity Part 2: An Overview of Materials and Reactions CHAPTER 2: Building Blocks of Materials 17 CHAPTER 3: Models of Structure to Explain Properties 49 CHAPTER 4: Carbon Compounds 89 CHAPTER 5: Chemical Reaction, Chemical Equations 125 CHAPTER 6: Chemistry of Water, Chemistry in Water 157 CHAPTER 7: Chemical Reactions and Energy Flows 213 Part 3: Relating the Structure and Behaviour of Substances CHAPTER 8: Modelling Atoms and Their Electrons 253 CHAPTER 9: Molecular Structures, Shapes, and Stereochemistry—Our Evidence 303 CHAPTER 10: Modelling Bonding in Molecules 357 CHAPTER 11: States of Matter 413 CHAPTER 12: Solutions and Their Behaviour 457 Part 4: Competing Influences on Chemical Reactions CHAPTER 13: Dynamic Chemical Equilibrium 487 CHAPTER 14: Acid-Base Equilibria in Aqueous Solution 523 CHAPTER 15: Solubility, Precipitation, and Complexation 591 CHAPTER 16: Electron Transfer Reactions and Electrochemistry 619 CHAPTER 17: Spontaneous Change: How Far? 667 CHAPTER 18: Spontaneous Change: How Fast? 719 Part 5: Carbon Compounds: Patterns of Structure and Reactivity CHAPTER 19: Understanding Structure, Understanding Reactivity: Alkenes, Alkynes, and Aromatics 773 CHAPTER 20: Understanding Structure, Understanding Reactivity: Alcohols, Amines, and Alkyl Halides 851 NEL Copyright 2015 Nelson Education Ltd 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) iii ... third party content may be suppressed from the eBook and/or eChapter(s) Chemistry, Second Canadian Edition by Peter G Mahaffy, Robert Bucat, Roy Tasker, John C Kotz, Paul M Treichel, Gabriela C. .. Astatine* Barium Berkelium* Beryllium Bismuth Bohrium Boron Bromine Cadmium Calcium Californium* Carbon Cerium Cesium Chlorine Chromium Cobalt Copernicium* Copper Curium* Darmstadtium* Dubnium* Dysprosium... Bonnie Bassler 914 21.2 Structure and Reactivity of Carboxylic Acids and Derivatives 938 Electronic Structure and Reactivity: Carboxylic Acids 939 Electronic Structure and Reactivity: Carboxylic Acid