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O X F O R D I B D I P L O M A P R O G R A M M E 2014 EDITION CHEMISTRY COURSE COMPANION Sergey Bylikin Gary Horner Brian Murphy David Tarcy 3 Library; p310: Patrick Aventurier/Getty Images; p315: Valua Vitaly/ Shutterstock; p317: Sheila Terry/Science Photo Library; p332: Chemical Education Digital Library; p346: Bob Adelman/Corbis; p352: Andrew Great Clarendon Street, Oxford, OX2 6DP, United Kingdom Lambert Photography/Science Photo Library; p353: Laguna Design/Science Photo Library; p365: Andrew Lambert Photography/Science Photo Library; Oxford University Press is a department of the University of Oxford. It p366: AdStock/Universal Image Group/Getty Images; p368: Gabriel furthers the University’s objective of excellence in research, scholarship, Sperandio/Getty Images; p378: Sam Ogden/Science Photo Library; p391: and education by publishing worldwide. Oxford is a registered trade mark Getty Images; p398: Patrick Landmann/Science Photo Library; p404: of Oxford University Press in the UK and in certain other countries Marytn F Chillmaid/Science Photo Library; p409: Andrew Lambert © Oxford University Press 2014 Photography/Science Photo Library; p414: Dr Morley Read/Science Photo Library; p415: Photostock-Israel/Science Photo Library; p462: Du Cane The moral rights of the authors have been asserted Medical Imaging Ltd/Science Photo Library; p464: Jon Wilson/Science Photo First published in 2014 Library; p472: NASA/Science Photo Library; p482a: Brian Young/Virginia All rights reserved. No part of this publication may be reproduced, stored Tech Chemistry Department; P482b: Science Photo Library; p487: Biosym in a retrieval system, or transmitted, in any form or by any means, without Technologies Inc/Science Photo Library; p488a: Kletr/Shutterstock; p488b: the prior permission in writing of Oxford University Press, or as expressly Clive Freeman/Biosym Technologies/Science Photo Library; p491: Martyn F permitted by law, by licence or under terms agreed with the appropriate Chillmaid/Science Photo Library; p495: Andrew Lambert Photography/ reprographics rights organization. Enquiries concerning reproduction Science Photo Library; p497: Martyn F Chillmaid/Science Photo Library; outside the scope of the above should be sent to the Rights Department, p503: Victor Habbick Visions/Science Photo Library; p506: Digital Oxford University Press, at the address above. Instruments/Vecco/Science Photo Library; p517: David Parker/IMI/ University of Birmingham High TC Consortium/Science Photo Library; You must not circulate this work in any other form and you must impose p519: Stefano Torrione/Hemis/Alamy; p530: Laguna Design/Science Photo this same condition on any acquirer Library; p544a: Microeld Scientic Ltd/Science Photo Library; p544b: British Library Cataloguing in Publication Data Herve Conge, ISM/Science Photo Library; p551a: Pascal Goetgheluck/ Data available Science Photo Library; p551b: Gusto Images/Science Photo Library; p557: 978-0-19-839212-5 Pasieka/Science Photo Library; p559a: Laguna Design/Science Photo Library; p559b: Laguna Design/Science Photo Library; p559c: Laguna 1 3 5 7 9 10 8 6 4 2 Design/Science Photo Library; p559d: Laguna Design/Science Photo Library; Paper used in the production of this book is a natural, recyclable product p559e: Steve Gschmeissner/Science Photo Library; p559f: Fotoedgaras/ made from wood grown in sustainable forests. 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p6c: Geoff Tompkinson/Science Photo Library; p10: Getty Images; p658a: Frank Khramer/Getty Images; p658b: E.O/Shutterstock; Images; p13: AFP/Stringer/Getty Images; p17: Laguna Design/Science Photo p662: Paul Rapson/Science Photo Library; p664: Ashley Cooper/Visuals Library; p19: Science Photo Library; p23: Science Photo Library; p25: Unlimited Inc/Getty Images; p666a: Science Museum/Science and Society Science Photo Library; p28: Charles D Winters/Science Photo Library; p41: Picture Library; p666b: Maximilian Stock Ltd/Science Photo Library; p668: One-Image Photography/Alamy; p42: A Barrington Brown/Science Photo Vaughn Melzer/JVZ/Science Photo Library; p672a: Karen Kasmauski/Science Library; p46: Gianni Tortoli/Science Photo Library; p51b: Giphostock/ Faction/SuperStock; p672b: Sheila Terry/Science Photo Library; p672c: Rev Science Photo Library; p52: Physics Department, Imperial College/Science Ronald Royer/Science Photo Library; p675: OUP; p677a: Cate Gillon/Getty Photo Library; p69a: Science Photo Library; 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p180c: Charles D Winters/Science Photo Library; p746b: Library of Congress/Science Photo Library; p748a: Photo Library; p185: Andrew Lambert Photography/Science Photo Library; Thomas Deerinck, NCMIR/Science Photo Library; p748b: Jacopin/Science p192: Charles D Winters/Science Photo Library; p196a: Charles D Winters/ Photo Library; p754: Patrick Landmann/Science Photo Library; p758: David Science Photo Library; p196b: Charles D Winters/Science Photo Library; Nunuk/Science Photo Library; p762: Phillipe Benoist/Look at Sciences/ p197: Andrew Lambert Photography/Science Photo Library; p200: Andrew Science Photo Library; p765: CNRI/Science Photo Library; p769: Astier- Lambert Photography/Science Photo Library; p202: Charles D Winters/ Chru Lille/Science Photo Library; p778: Science Photo Library; p780: Getty Images; p203a: Andrew Lambert Photography/Getty Images; p203b: Science Photo Library Andrew Lambert Photography/Getty Images; p211: AJP/Shutterstock; p212: Realimage/Alamy; p220: Tyler Olson/Shutterstock; p223: Richard Wareham Artwork by Six Red Marbles and OUP Fotograe/Alamy; p228: Andrew Lambert Photography/Science Picture Library; p230a: Jaxa; p230b: Martin Bond/Science Photo Library; p231: Tim Graham/Getty Images; p242a: Kenneth Eward/Biografx/Science Photo Library; p242b: Professor K Seddon and Doctor T Evans, Queen’s University, Belfast/Science Photo Library; p247: Science Photo Library; p252: Andrew Lambert Photography/Science Photo Library; p255: Andrew Lambert Photography/Getty Images; p257: Science Photo Library; p262a: Martyn F Chillmaid/Science Photo Library; p262b: Charles D Winters/Science Photo Library; p285a: National Institute of Advanced Industrial Science and Technology; p360: Charles D Winters/ Science Photo Library; p285b: Dennis Schroeder, NREL/US Department of Energy/ Science Photo Library; p285c: National Institute of Advanced Industrial Science and Technology; p306a: Royal Society of Chemistry; p306b: Royal Society of Chemistry; p307: Science Photo Library; p308: Charles D Winters/Science Photo Contents 1 Stoichiometric relationships 12 Atomic structure (AHL) Condensation polymers 528 Introduction to the particulate nature Electrons in atoms 291 Environmental impact— of matter and chemical change 1 heavy metals 534 The mole concept 12 13 The periodic table—the Reacting masses and volumes 20 transition metals (AHL) B Biochemistry Introduction to biochemistry 539 First-row d-block elements 301 2 Atomic structure Proteins and enzymes 547 Coloured complexes 319 The nuclear atom 37 Lipids 565 Electron conguration 50 14 Chemical bonding and Carbohydrates 580 Vitamins 590 structure (AHL) 3 Periodicity Biochemistry and the Further aspects of covalent environment 597 Periodic table 67 bonding and structure 329 Proteins and enzymes 606 Periodic trends 75 Hybridization 345 Nucleic acids 619 4 Chemical bonding and Biological pigments 629 15 Energetics/thermochemistry Stereochemistry in biomolecules 641 structure (AHL) Ionic bonding and structure 93 Energy cycles 357 C Energy Covalent bonding 97 Entropy and spontaneity 364 Energy sources 653 Covalent structures 104 Fossil fuels 657 Intermolecular forces 122 16 Chemical kinetics (AHL) Nuclear fusion and ssion 665 Metallic bonding 133 Rate expression and reaction Solar energy 674 mechanism 375 Environmental impact—global 5 Energetics/thermochemistry Activation energy 384 warming 679 Measuring energy changes 139 Electrochemistry, rechargeable Hess’s Law 148 17 Equilibrium (AHL) batteries and fuel cells 687 Bond enthalpies 152 The equilibrium law 389 Nuclear fusion and nuclear ssion 702 Photovoltaic and dye-sensitized 6 Chemical kinetics 18 Acids and bases (AHL) solar cells 710 Collision theory and rates Lewis acids and bases 395 of reaction 161 D Medicinal chemistry Calculations involving acids and bases 397 Pharmaceutical products and 7 Equilibrium pH curves 403 drug action 717 Equilibrium 179 Aspirin and penicillin 725 19 Redox processes (AHL) Opiates 732 8 Acids and bases pH regulation of the stomach 737 Electrochemical cells 413 Theories of acids and bases 191 Anti-viral medications 745 Properties of acids and bases 195 20 Organic chemistry (AHL) Environmental impact of some The pH scale 197 medications 751 Types of organic reactions 437 Strong and weak acids and bases 200 Taxol—a chiral auxiliary Synthetic routes 448 Acid deposition 204 case study 758 Stereoisomerism 451 Nuclear medicine 765 9 Redox processes Drug detection and analysis 775 21 Measurement and analysis Oxidation and reduction 209 (AHL) Internal Assessment Electrochemical cells 226 Spectroscopic identication of (with thanks to Mark Headlee for his 10 Organic chemistry organic compounds 461 assistance with this chapter) 785 Fundamentals of organic chemistry 235 A Materials Index 791 Functional group chemistry 248 Materials science introduction 471 Metals and inductively coupled 11 Measurement and data plasma (ICP) spectroscopy 475 Catalysts 484 processing Liquid crystals 489 Uncertainties and errors in Polymers 494 measurement and results 261 Nanotechnology 501 Graphical techniques 272 Environmental impact—plastics 509 Spectroscopic identication of Superconducting metals and X-ray organic compounds 277 crystallography 516 iii Course book denition The IB Learner Prole The IB Diploma Programme course books are The aim of all IB programmes to develop resource materials designed to support students internationally minded people who work to create throughout their two-year Diploma Programme a better and more peaceful world. The aim of the course of study in a particular subject. They will programme is to develop this person through ten help students gain an understanding of what learner attributes, as described below. is expected from the study of an IB Diploma Inquirers: They develop their natural curiosity. Programme subject while presenting content in a They acquire the skills necessary to conduct way that illustrates the purpose and aims of the IB. inquiry and research and snow independence in They reect the philosophy and approach of the learning. They actively enjoy learning and this love IB and encourage a deep understanding of each of learning will be sustained throughout their lives. subject by making connections to wider issues and providing opportunities for critical thinking. Knowledgeable: They explore concepts, ideas, and issues that have local and global signicance. The books mirror the IB philosophy of viewing the In so doing, they acquire in-depth knowledge and curriculum in terms of a whole-course approach; develop understanding across a broad and balanced the use of a wide range of resources, international range of disciplines. mindedness, the IB learner prole and the IB Diploma Programme core requirements, theory Thinkers: They exercise initiative in applying of knowledge, the extended essay, and creativity, thinking skills critically and creatively to recognize action, service (CAS). and approach complex problems, and make reasoned, ethical decisions. Each book can be used in conjunction with other materials and indeed, students of the IB are Communicators: They understand and express required and encouraged to draw conclusions from ideas and information condently and creatively in a variety of resources. Suggestions for additional more than one language and in a variety of modes and further reading are given in each book of communication. They work effectively and and suggestions for how to extend research are willingly in collaboration with others. provided. Principled: They act with integrity and honesty, In addition, the course books provide advice with a strong sense of fairness, justice and respect and guidance on the specic course assessment for the dignity of the individual, groups and requirements and on academic honesty protocol. communities. They take responsibility for their They are distinctive and authoritative without own action and the consequences that accompany being prescriptive. them. IB mission statement Open-minded: They understand and appreciate their own cultures and personal histories, and are The International Baccalaureate aims to develop open to the perspectives, values and traditions inquiring, knowledgeable and caring young people of other individuals and communities. They are who help to create a better and more peaceful accustomed to seeking and evaluating a range of world through intercultural understanding and points of view, and are willing to grow from the respect. experience. To this end the organization works with schools, Caring: They show empathy, compassion and governments and international organizations to respect towards the needs and feelings of others. develop challenging programmes of international They have a personal commitment to service, and education and rigorous assessment. to act to make a positive difference to the lives of others and to the environment. These programmes encourage students across the world to become active, compassionate and lifelong Risk-takers: They approach unfamiliar situations learners who understand that other people, with and uncertainty with courage and forethought, their differences, can also be right. and have the independence of spirit to explore new roles, ideas, and strategies. They are brave and articulate in defending their beliefs. iv Balanced: They understand the importance of What constitutes malpractice? intellectual, physical and emotional balance to Malpractice is behaviour that results in, or may achieve personal well-being for themselves and result in, you or any student gaining an unfair others. advantage in one or more assessment component. Malpractice includes plagiarism and collusion. Reective: They give thoughtful consideration to their own learning and experience. They are Plagiarism is dened as the representation of the able to assess and understand their strengths and ideas or work of another person as your own. The limitations in order to support their learning and following are some of the ways to avoid plagiarism: personal development. words and ideas of another person to support ● A note on academic honesty one’s arguments must be acknowledged It is of vital importance to acknowledge and ● passages that are quoted verbatim must appropriately credit the owners of information be enclosed within quotation marks and when that information is used in your work. acknowledged After all, owners of ideas (intellectual property) CD-Roms, email messages, web sites on the ● have property rights. To have an authentic piece Internet and any other electronic media must of work, it must be based on your individual be treated in the same way as books and and original ideas with the work of others fully journals acknowledged. Therefore, all assignments, written the sources of all photographs, maps, or oral, completed for assessment must use your ● illustrations, computer programs, data, graphs, own language and expression. Where sources are audio-visual and similar material must be used or referred to, whether in the form of direct acknowledged if they are not your own work quotation or paraphrase, such sources must be appropriately acknowledged. works of art, whether music, lm dance, ● How do I acknowledge the work of others? theatre arts or visual arts and where the creative use of a part of a work takes place, the The way that you acknowledge that you have used original artist must be acknowledged. the ideas of other people is through the use of footnotes and bibliographies. Collusion is dened as supporting malpractice by another student. This includes: Footnotes (placed at the bottom of a page) or endnotes (placed at the end of a document) are allowing your work to be copied or submitted ● to be provided when you quote or paraphrase for assessment by another student from another document, or closely summarize the duplicating work for different assessment information provided in another document. You ● components and/or diploma requirements. do not need to provide a footnote for information that is part of a ‘body of knowledge’. That is, Other forms of malpractice include any action denitions do not need to be footnoted as they are that gives you an unfair advantage or affects the part of the assumed knowledge. results of another student. Examples include, taking unauthorized material into an examination Bibliographies should include a formal list of the room, misconduct during an examination and resources that you used in your work. ‘Formal’ falsifying a CAS record. means that you should use one of the several accepted forms of presentation. This usually involves separating the resources that you use into different categories (e.g. books, magazines, newspaper articles, internet-based resources, CDs and works of art) and providing full information as to how a reader or viewer of your work can nd the same information. A bibliography is compulsory in the Extended Essay. v Using your IB Chemistry Online Resources What is Kerboodle? Kerboodle is an online learning platform. If your school has a subscription to IB Chemistry Kerboodle Online Resources you will be able to access a huge bank of resources, assessments, and presentations to guide you through this course. What is in your Kerboodle Online Resources? There are three main areas for students on the IB Chemistry Kerboodle: planning, resources, and assessment. Resources There a hundreds of extra resources available on the IB Chemistry Kerboodle Online. You can use these at home or in the classroom to develop your skills and knowledge as you progress through the course. Watch videos and animations of experiments, dif cult concepts, and science in action. Hundreds of worksheets – read articles, perform experiments and simulations, practice your skills, or use your knowledge to answer questions. Look at galleries of images from the book and see their details close up. Find out more by looking at recommended sites on the Internet, answer questions, or do more research. Planning Be prepared for the practical work and your internal assessment with extra resources on the IB Chemistry Kerboodle online. Learn about the different skills that you need to perform an investigation. Plan and prepare experiments of your own. Learn how to analyse data and draw conclusions successfully and accurately. vi Assessment Click on the assessment tab to check your knowledge or revise for your examinations. Here you will  nd lots of interactive quizzes and exam- style practice questions. Formative tests: use these to check your comprehension, there’s one auto-marked quiz for every sub-topic. Evaluate how con dent you feel about a sub-topic, then complete the test. You will have two attempts at each question and get feedback after every question. The marks are automatically reported in the markbook, so you can see how you progress throughout the year. Summative tests: use these to practice for your exams or as revision, there’s one auto-marked quiz for every topic. Work through the test as if it were an examination – go back and change any questions you aren’t sure about until you are happy, then submit the test for a  nal mark. The marks are automatically reported in the markbook, so you can see where you may need more practice. Assessment practice: use these to practice answering the longer written questions you will come across when you are examined. These worksheets can be printed out and performed as a timed test. Don't forget! You can also  nd extra resources on our free website www.oxfordsecondary.co.uk/ib-chemistry Here you can  nd answers to questions in the book. vii Introduction This book is a companion for students of Chemistry in the International Baccalaureate Diploma Programme. Chemistry is one of the pivotal science subjects of the IB Diploma Programme. It is an experimental science that combines academic study with the acquisition of laboratory and investigational skills. Chemistry is often called the central science, as chemical principles underpin both the physical environment in which we live and all biological systems. Apart from being a subject worthy of study in its own right, chemistry is also a prerequisite for many other disciplines such as medicine, biological and environmental sciences, materials and engineering. A study of chemistry invariably involves fostering of a wide range of additional generic, transferable skills, such as analytical skills, problem-solving, data-handling, IT and communication skills, critical-thinking, numeracy and scientic literacy skills. During the two years of an IB Diploma Programme Chemistry Course, students are encouraged to develop knowledge of chemistry and an understanding of the nature of scientic inquiry. With its focus on understanding the nature of science (NOS), IB Chemistry learners will develop a level of scientic literacy that will better prepare them to act on issues of local and global concern, with a full understanding of the scientic perspective. The structure of this book closely follows the chemistry programme in the Subject Guide. Topics 1 - 11 explain in detail the core material that is common to both SL and HL courses. Topics 12 - 21 explain the AHL (additional higher level material). Topics A, B, C and D cover the content of the options. The optional topics cover four of the major domains in Applied Chemistry: Materials, Biochemistry, Energy and Medicinal Chemistry. Each option has a number of common strands – quantitative aspects, analytical techniques, environmental perspectives and integrated organic chemistry linkages. All topics in the book include the following elements: Understandings The specics of the content requirements for each sub-topic are covered in detail. Concepts are presented in ways that promote enduring understanding. Applications and skills These sections help you to develop your understanding by considering a specic illustrative example, often following a step-by-step working method approach or by considering a particular chemical experiment, involving key laboratory techniques. Nature of science Here you can explore the methods of science and some of the knowledge issues, theories, hypotheses and laws that are associated with scientic endeavour. This is done using carefully selected examples, including chemical research that led to paradigm shifts in our understanding of the world. NOS underpins each topic presented and throughout the book viii there are a wide range of NOS based questions and exercises to challenge your chemical understanding and draw on your scientic perspectives. NOS is an assessable component of the programme and sample NOS style questions are integrated throughout the book. Theory of Knowledge These short sections have headings that are equivocal 'knowledge questions'. The text that follows often details one possible answer to the knowledge question. We encourage you to draw on these examples of knowledge issues in your TOK essays. Of course, much of the material elsewhere in the book, particularly in the NOS sections, can be used to prompt TOK discussions. TOK provides a space for you to engage in stimulating wider discussions about questions such as whether there should be ethical constraints on the pursuit of scientic knowledge. It also provides an opportunity for you to reect on scientic methodologies, and how these compare to the methodologies of other areas of knowledge. TOK is not formally assessed in the IB Chemistry programme, but it plays a pivotal role in the teaching of IB science. Activities and quick questions A variety of short topics or challenging questions are included with a focus on active learning. We encourage you to research these topics or problems yourselves using information readily available in textbooks or from the Internet. The aim is to promote an independent approach to learning. End -of-topic questions At the end of each topic you will nd a wide range of questions (multiple-choice, data-base exercises, extended response, NOS style problems and hypothesis style questions). Answers can be found at www.oxfordsecondary.co.uk/ib-chemistry ix Meet the authors Sergey Bylikin was awarded a PhD in Chemistry from Moscow State University in 1998 and, one year later, received the State Prize of the Russian Federation in Chemistry. Until 2009, he was assistant professor at Russian State Medical University, after which point he took up a role at the Open University in the UK. Sergey is an author of several textbooks. He has been associated with the IB since 2007 and was involved in the latest IB Chemistry curriculum review. Gary Horner, a graduate of the University of Queensland, has taught Chemistry since 1986 in Australia, Switzerland and Hong Kong. In his International School career Gary has held various leadership positions, including that of CAS coordinator and Head of Science. Since 2000, he has had signicant involvement with the IBO, attending workshops across Europe and Canada and leading workshops in India, Hong Kong and Japan. In 2010, he began advising on the IB Chemistry curriculum review and is a member of the team developing the latest DP science course. Gary is currently teaching at King George V School in Hong Kong. Brian Murphy graduated with a PhD in Inorganic Chemistry from University College Cork. Following postdoctoral and teaching posts in the UK and Ireland, he moved to the United Arab Emirates to take up a position at UAE University, where he became Head of the Department of Chemistry and associate professor of Inorganic Chemistry. After 8 years he moved back to Ireland to take up a post at Athlone Institute of Technology, where he is currently a senior lecturer. Brian has been associated with the IB since 1998 and was involved in the design of the latest IB Chemistry curriculum. David Tarcy graduated cum laude with a degree in Science Education from Whitworth College and has done graduate work in sciences and information technology in the Northwest USA and Queensland, Australia. He has taught in the USA, Australia, Europe, and Southeast Asia and has been involved in curriculum writing, moderation, and question setting for various exam boards and institutions. David is active in many chemistry education discussion boards, is an IB Diploma Programme Chemistry Workshop Leader and Field Representative and was involved in the design of the latest IB Chemistry curriculum. A project of this size would not have been possible without support and encouragement. To the greatest extent, the authors would like to thank their families for their love and patience. In particular, special appreciation goes to: Brian Murphy - to my wife Mary, for all her love, understanding and unremitting support (míle buíochas!), parents, Teresa and Joe (RIP) who instilled in me an appreciation of internationalisation from an earlier age, sister, Lorraine and her family; Gary Horner - to my parents Dennis and Myrtle for their devotion, vision and unwavering support of their children's happiness, my sister Susan for her eternal friendship, selessness and professional expertise; David Tarcy - to Tina Walton, my brothers Gary and Brian, for their input and support, as well as the many friends and professional colleagues I have met through my teaching career for their support, advice, and friendship; Sergey Bylikin - to Natasha for her patience, support and invaluable comments. x

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