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INVESTIGATIONS HSC CHEMISTRY >Àˆ�Þ˜Ê-V…i��ÊUÊ>À}>ÀiÌÊœ}>˜

All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording or otherwise, without the prior permission of Science Press. ABN 98 000 073 861 © Science Press 2009 First published 2009 Science Press Private Bag 7023 Marrickville NSW 1475 Australia Tel: (02) 9516 1122 Fax: (02) 9550 1915 sales@sciencepress.com.au www.sciencepress.com.au Thanks to Oatley campus of Georges River College for the use of equipment to photograph.

iii Dot Point HSC Chemistry InvestigationsContents Science Press Introduction v Verbs to Watch vi Dot Points Production of Materials vii The Acidic Environment ix Chemical Monitoring and Management xi Industrial Chemistry xiii Shipwrecks, Corrosion and Conservation xv Investigations Production of Materials 1 The Acidic Environment 63 Chemical Monitoring and Management 137 Industrial Chemistry 197 Shipwrecks, Corrosion and Conservation 261 Appendix Answers 312 Data Sheet 318 Periodic Table 319 Contents

iv Dot Point HSC Chemistry Investigations Contents Science Press Notes ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 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v Dot Point HSC Chemistry Investigations Science Press Introduction This book contains all the instructions and other information needed for you to carry out the mandatory first- hand investigations listed in column 3 of the Board of Studies Chemistry syllabus. In some cases more than one experiment has been suggested. The syllabus requires 35 hours of practical work, but this need not all be experimental work. First-hand investigations include research to gather, process and analyse information, the presentation of information in written or spoken format and the solving of problems. In completing the activities in this book, you will have satisfied these aspects of the practical work required by the syllabus as detailed in column 3 of the syllabus document. Note that answers to practical and research exercises have not been provided as this would void the experimentation and research that you need to do in order to get these answers. Additional extension questions have been provided, where applicable, to encourage higher-order thinking and enable deeper understanding of chemistry concepts. Further examples of questions relevant to first- hand investigations in column 3 of the syllabus are included in two other books in this series, Dot Point HSC Chemistry and Dot Point HSC Chemistry Multiple Choice. The dot point numbers allocated to each experiment reflect the numbers allocated to that dot point in the other books in this series. Remember that these numbers are author derived and do not appear in the syllabus. Wherever possible, allowance has been made for variations in experimental method. This is necessary because schools have access to different resources and teachers often wish to design their own activities specific to their resources. Also, you are expected to develop skills in the planning of experiments and if you are always given ‘recipes’ you will never learn to do this. However, as many students struggle when it comes to planning and writing up experiments and research, many hints are provided. Experimental and research work is an integral part of the study of Chemistry. It is not meant to stand alone. You should always look for the relevance of your experimental and research work to the topic being studied. Thus it is recommended that after you carry out these activities, and your teacher has checked your work, the completed sheets should be inserted in the appropriate place in your notes. This book is NOT a series of ‘chemical recipes’ or a ‘how to do it’ manual. It is designed to help you record and evaluate experimental procedures that you will design and carry out during the Chemistry course and to encourage you to see the significance of information obtained from practical activities and research. Before you carry out any experimental procedure it is essential that you consult Safety Data Sheets and information from your teacher and textbooks in order to find out the risks associated with using any chemicals involved and precautions needed to deal with these risks. Before commencing any practical work, you must discuss with your teacher the necessary precautions for dealing with the chemicals and equipment to be used. All aspects of your experimental design must be approved by your teacher. Introduction

vi Dot Point HSC Chemistry Investigations Science Press Verbs to Watch account/account for State reasons for, report on, give an account of, narrate a series of events or transactions. analyse Identify components and the relationships among them, draw out and relate implications. apply Use, utilise, employ in a particular situation. appreciate Make a judgement about the value of something. assess Make a judgement of value, quality, outcomes, results or size. calculate Determine from given facts, figures or information. clarify Make clear or plain. classify Arrange into classes, groups or categories. compare Show how things are similar and different. construct Make, build, put together items or arguments. contrast Show how things are different or opposite. critically (analyse/evaluate) Add a degree or level of accuracy, depth, knowledge and understanding, logic, questioning, reflection and quality to an analysis or evaluation. deduce Draw conclusions. define State the meaning of and identify essential qualities. demonstrate Show by example. describe Provide characteristics and features. discuss Identify issues and provide points for and against.distinguish Recognise or note/indicate as being distinct or different from, note difference between things. evaluate Make a judgement based on criteria. examine Inquire into. explain Relate cause and effect, make the relationship between things evident, provide why and/or how. extract Choose relevant and/or appropriate details. extrapolate Infer from what is known. identify Recognise and name. interpret Draw meaning from. investigate Plan, inquire into and draw conclusions about. justify Support an argument or conclusion. outline Sketch in general terms; indicate the main features. predict Suggest what may happen based on available data. propose Put forward (a point of view, idea, argument, suggestion etc) for consideration or action. recall Present remembered ideas, facts or experiences. recommend Provide reasons in favour. recount Retell a series of events. summarise Express concisely the relevant details. synthesise Put together various elements to make a whole. Verbs to Watch

vii Dot Point HSC Chemistry Investigations Science Press Production of Materials 1. Energy and raw materials from fossil fuels 1.3 First-hand investigation: 3 Alkanes and alkenes with bromine. 1.7 Modelling polymerisation. 9 2. Materials from biomass 2.2 Development and use of a biopolymer. 11 3. Ethanol – use and manufacture 3.3 Modelling the dehydration 15 and hydrolysis of ethylene. 3.4 Industrial production of 19 ethanol from sugar cane. 3.8 First-hand investigation: 23 Molar heats of combustion of alkanols. 3.10 Ethanol as a car fuel. 31 3.12 First-hand investigation: 35 Fermentation of glucose.4. Energy from redox reactions 4.1 First-hand investigation: 41 Galvanic cells. 4.2 First-hand investigation: 45 Potential difference of metals in an electrolyte. 4.9 Calculations using the 49 redox table. 4.10 Chemistry and uses of 53 batteries compared. 5. Nuclear chemistry 5.2 Recent discoveries of elements. 57 5.8 Radioisotopes 59 – benefits and problems. Production of Materials Dot Point Page Dot Point Page

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ix Dot Point HSC Chemistry Investigations Science Press The Acidic Environment The Acidic Environment 1. Indicators 1.1 First-hand investigation: 65 Natural indicators. 1.2 Indicators – colour changes. 71 1.5 Acidic/basicity of 73 household substances. 2. Acidic oxides and the atmosphere 2.7 First-hand investigation: 75 Decarbonation of a soft drink. 2.12 Industrial origins of oxides of sulfur 81 and nitrogen. 3. Acids and pH 3.1 First-hand investigation: 85 Using pH meters or probes 3.4 Naturally occurring acids and bases. 91 3.7 Strong and weak acids. 93 3.8 Ionic equations for acid ionisation. 97 3.9 Modelling acids – molecular 99 nature and ionisation. 3.13 Strong and weak acids 101 – calculating pH. 3.14 Acids as food additives. 1054. Acid/base theories 4.1 Using secondary sources. 107 4.6 First-hand investigation: 109 pH of salt solutions. 4.11 First-hand investigation: Titrations. 113 4.12 First-hand investigation: 125 Titration of a domestic substance using computer-based technology. 4.13 Neutralisation in accidents. 129 5. Esterification 5.7 First-hand investigation: 131 Preparation of an ester by reflux. 5.9 Esters – uses in foods and cosmetics. 135 Dot Point Page Dot Point Page

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xi Dot Point HSC Chemistry Investigations Science Press Chemical Monitoring and Management Chemical Monitoring and Management 1. The work of chemists 1.1 Researching the work of chemists. 139 2. Monitoring in industry – the Haber process 2.9 Development of the Haber 141 process and its significance. 3. Chemical analysis 3.1 First-hand investigation: 143 Flame tests. 3.2 Monitoring ions in substances we use. 157 3.4 First-hand investigation: 161 Sulfate content of lawn fertiliser. 3.5 Analysing reliability of results. 167 3.7 Interpreting data from AAS analysis. 1694. Atmospheric chemistry and ozone 4.9 Modelling haloalkanes. 173 4.12 Destruction of atmospheric ozone. 175 4.14 Replacements for CFCs. 177 5. Monitoring the water supply 5.3 First-hand investigation: Water testing. 179 5.4 Monitoring water for heavy metals 187 and eutrophication. 5.5 The local water supply. 193 Dot Point Page Dot Point Page

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xiii Dot Point HSC Chemistry Investigations Science Press Industrial Chemistry Industrial Chemistry 1. Resources and replacements 1.1 A natural resource (not a fossil fuel). 199 2. Equilibrium and the equilibrium constant 2.1 First-hand investigation: 201 Modelling an equilibrium reaction. 2.2 First-hand investigation: 207 Analysing an equilibrium reaction. 2.5 Calculating the equilibrium constant (K). 213 3. Sulfuric acid 3.4 Transport and storage of sulfuric acid. 219 3.9 Industrial production of H 2SO 4 221 – chemistry and output. 3.10 First-hand investigation: 225 Reactions of H 2SO 4. 4. Sodium hydroxide 4.2 First-hand investigation: 229 Electrolysis of sodium chloride. 4.3 Electrolysis of molten and 233 aqueous sodium chloride.5. Saponification 5.1 First-hand investigation: Saponification. 235 5.2 Saponification. 239 5.5 First-hand investigation: 241 An emulsion, properties and uses. 5.6 First-hand investigation: 245 Soap as an emulsion. 5.11 Environmental impacts of 249 soaps and detergents. 6. The Solvay process 6.5 First-hand investigation: 253 The Solvay process. 6.6 Calculations involving the 257 Solvay process. 6.7 Location of a chemical plant 259 using the Solvay process. Dot Point Page Dot Point Page

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xv Dot Point HSC Chemistry Investigations Science Press Shipwrecks, Corrosion and Conservation Shipwrecks, Corrosion and Conservation 1. The ocean as an electrolyte 1.4 Impact of Galvani, Davy, Faraday 263 and electron transfer reactions. 2. Ships of metal 2.2 Conditions for rusting. 267 2.3 First-hand investigation: 269 Corrosion of iron and steel. 2.4 Composition and properties of steel. 273 3. Electrolytic cells 3.3 First-hand investigation: 275 Rate of electrolysis. 4. Corrosion in a marine environment 4.1 History of ship construction 279 – materials used. 4.2 First-hand investigation: 281 Corrosion rate of metals and alloys. 4.4 First-hand investigation: 285 Prevention of corrosion. 4.8 Applications of cathodic protection. 2895. Corrosion in a sunken ship 5.5 First-hand investigation: 291 Rate of corrosion. 5.6 Predicting corrosion rates at depth. 301 6. Corrosion at depth 6.1 First-hand investigation: 303 Rate of corrosion and acidity. 7. Salvage, conservation and restoration of artefacts 7.6 Restoration techniques used in 307 Australian projects. Dot Point Page Dot Point Page

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Dot Point HSC Chemistry Investigations 1 Production of Materials Science Press DOT POINT *Àœ`ÕV̈œ˜ÊœvÊ>ÌiÀˆ>�Ã

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Dot Point HSC Chemistry Investigations 3 Production of Materials Science Press 1.3 Identify data, plan and perform a first-hand investigation to compare the reactivities of appropriate alkenes with the corresponding alkanes in bromine water. Background information Alkanes and alkenes are homologous groups of hydrocarbon compounds. Homologous series of hydrocarbonsGeneral formulaFunctional groupExample Alkane C nH2n+2 –C–C– Ethane Alkene C nH2n –C=C– Ethylene (ethene) Alkanes undergo substitution reactions, e.g. -H HCCH +F2 light HF -H - -- -H-H -H HCCH + -F - -- - H - H Alkenes undergo addition reactions as they have reactive double bonds, e.g. -H HC CH +F2 -H - -- - -F HCCH -F - -- -H-H Bromine water is a yellow-brown colour. As it reacts with a hydrocarbon the yellow-brown colour disappears leaving a clear solution. You could also confirm your results by testing the alkane and alkene with acidified potassium permanganate solution (KMnO 4). Alkenes will decolourise the purple potassium permanganate but alkanes will not react. Aim: To compare the reactivity of an alkane and an alkene. Materials Hints: Label any photographed equipment that you used and add any other items used to the list below. Four test tubes Bromine water (BrOH) Alkane, e.g. cyclohexane (C 6H12) Alkene, e.g. cyclohexene (C 6H10) Potassium permanganate solution (optional) A fume cupboard

Dot Point HSC Chemistry Investigations 4 Production of Materials Science Press Justify the use of these materials. Hints: Cyclohexane and cyclohexene are both colourless liquids. Is this important here? You could also compare the toxicity and volatility of these cyclic hydrocarbons with similar straight-chain hydrocarbons. Why is bromine water used here? Will it show a different reaction rate for an alkane and an alkene? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Hypothesis: Write an hypothesis for this experiment. Hints: From your theoretical knowledge of alkanes and alkenes, predict which will be more reactive and write this as a statement that can be tested. Your prediction should be an educated guess. For example, would you predict that: Cyclohexene will react faster and more vigorously with bromine water than cyclohexane. Or that: Cyclohexane will react faster and more vigorously with bromine water than cyclohexene? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Variables: Identify the following variables in this experiment. Independent variable Dependent variable Variables that must be controlled Hint: This is the one thing that you change in your experiment. What is different in your test tubes?Hint: This is what you measure or observe to see the effect of the one change. Hint: These are the things that stay the same throughout the experiment. Risk analysis: Before you carry out any activity you must carry out a risk analysis. Complete the table opposite to indicate any risk involved in using the equipment and chemicals involved in this investigation and explain any necessary precaution for this experiment. The table has been started for you. Hints: This should acknowledge risks to people carrying out the experiment and also to the broader environment. Think about what the risks are in this activity and how you can remove or reduce these risks. You will need to look up the relevant Material Safety Data Sheets. Ask your teacher for these if they are not in the laboratory. Are any of the chemicals you will be using toxic or corrosive? Are there regulations for their safe disposal when the experiment is over?

Dot Point HSC Chemistry Investigations 5 Production of Materials Science Press Chemicals and equipmentRisk Describe the precaution Explain the precaution Bromine water Toxic and corrosive Use a fume cupboard, goggles and gloves. Work in a well-ventilated area. Do not discard into the sink. The used bromine water will be mixed with the alkane and alkene, so can be placed in the organic waste disposal. Prevent toxic substances being inhaled, ingested, splashed into the eyes or contacting the skin. Toxic substances would enter environment and could enter the food chain and cause poisoning. Cyclohexane Cyclohexene

Dot Point HSC Chemistry Investigations 6 Production of Materials Science Press Method: Follow the procedure below and note any modifications you make. 1. Carry out this procedure in a fume cupboard and wear gloves and safety goggles. 2. Pour 1 mL cyclohexane into each of 2 test tubes labelled A and B. 3. Pour 1 mL cyclohexene into each of 2 test tubes labelled C and D. 4. Cover test tubes A and C so they are in the dark. 5. Place test tubes B and D in the sunlight. 6. Add 5 drops bromine water to each test tube. 7. Tap the side of the test tube gently to mix the contents. 8. Observe any colour change. If you are going to confirm your results using potassium permanganate, then write the method below. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Results: Record your observations. Hints: Results should be tabulated whenever possible. Describe any colour change observed in each test tube and how long it took for the colour to change. Remember that you must always describe results as changing from one colour to another colour, e.g. from yellow to colourless. Do not use the word ‘clear’ when you mean ‘colourless’. ‘Clear’ means you can see through it so coloured solutions can be clear. Did you observe anything else, e.g. did the chemicals separate into layers? Test tubeInitial colour of hydrocarbonsInitial colour of bromine waterColour after bromine water added to alkane/alkeneTime for change A B C D Use a labelled diagram or photographs to illustrate what you observed. Hints: You should always draw diagrams using a pencil and a ruler and label all diagrams fully.

Dot Point HSC Chemistry Investigations 7 Production of Materials Science Press Write equations in words and symbols. Use structural formulas. Hints: Show what happened when bromine dissolved in water and when the alkane and alkene were added to the bromine water. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Conclusion: Complete the following statements to write a conclusion for this experiment. You must always make sure that your conclusion ‘answers your aim and hypothesis’. The results (support/do not support) the hypothesis. The alkene, cyclohexene, reacted (quickly/slowly) with bromine water, changing colour from ......................................... to ......................................... . This happened even in the (light/dark). The alkane, cyclohexane, reacted (quickly/very slowly) with bromine water in the (dark/light) and did not react at all when in the (light/dark). Discussion: Discuss your results under the following subsections. 1. Account for your results. Hints: Were they what you expected? Did you notice any layers forming in the test tubes and if so, can you account for this? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 2. Comment on the accuracy of your results. Hints: Could the colour change be readily observed? Were the same quantities of chemicals used in each test tube to allow accurate comparison? Was care taken to avoid using excess bromine (which could mask a colour change)? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 3. Comment on the reliability of your results. Hint: Was the experiment carried out more than once to check if the results are reliable? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... .........................................................................................................................................................................................................................................................

Dot Point HSC Chemistry Investigations 8 Production of Materials Science Press 4. Comment on the validity of your investigation. Hints: Did the design of your experiment allow you to test what you set out to test, or could it be improved? Did you have a control? This could be a container of bromine water with no added chemicals – to see if the bromine water would change colour without the addition of cyclohexene. Did you confirm your results by testing the alkane and alkene with acidified potassium permanganate solution (KMnO 4)? Are your conclusions valid? Do they accurately reflect the results you obtained. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 5. Discuss the relevance of this experiment. Hints: Did performing this experiment help you to understand/remember reactions of hydrocarbon groups? Did your results suggest any further experiments that would be interesting to carry out? To make a polymer, would you use an alkane or alkene as the starting point (raw material)? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... .........................................................................................................................................................................................................................................................

Dot Point HSC Chemistry Investigations 9 Production of Materials Science Press Background information Monomer – small molecule, e.g. ethylene – many of which join to form a polymer, e.g. polyethylene. Polymer – large molecule made by many monomers joining together, e.g. plastics, PVC, polystyrene, polyester, rubber, starch, cellulose, protein, DNA. Polymerisation – manufacture of a polymer from monomers using heat, pressure and transition metal catalyst. Stages are initiation, propagation and termination. An example is: (where n is a large number) Describe how you modelled the polymerisation process. Include a diagram or photographs showing the modelling process. If you used a computer simulation, identify its source. Hints: A model shows a representation of reality. It helps you to visualise a structure or process. What did you use to represent the monomers? How did you represent the breaking of the double –C=C– bonds? There are many animations on the internet which model polymerisation. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 1.7 Analyse information from secondary sources such as computer simulations, molecular model kits or multimedia resources to model the polymerisation process.

Dot Point HSC Chemistry Investigations 10 Production of Materials Science Press Discuss advantages of your model of polymerisation. Hints: Do you understand the process better because you can now visualise it? Did making the model help you to summarise or learn about the process? Can the model be used to make predictions and/or design improvements in the process? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Discuss limitations of your model. Hints: Was your model based on complete information? Could it have been improved if you knew more about the chemicals involved or the process itself? If so, make suggestions. Are there any assumptions behind your model? Is your model a simplification of what is really happening and does this matter? Is your model static or dynamic? Did it include the role of the initiator and catalyst? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Risks and safety assessment: Discuss any risks and how these could be reduced. Hints: Are there any risks involved in this process? If so they are probably minimal. It is acceptable to state that there are no risks or only minimal risks involved in carrying out an activity. If you are using model kits then a risk could be people being bruised if they slip on models dropped onto the floor and thus fall over. Models involving a lot of activity may involve the risks of injury during collisions. Note that the risk is the injury that could result from a collision, not the collision itself. For example, small balls used for modelling are not a risk in themselves, even if they fall on the floor. 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Dot Point HSC Chemistry Investigations 11 Production of Materials Science Press Background information Biopolymers occur naturally, e.g. starch, cellulose, cotton, proteins, gluten, PHA, polylactic acid. Biopolymers can be made using renewable resources such as plants and micro-organisms, e.g. Biopol R. Biopolymers are renewable, biodegradable and biocompatible. Biopolymers can be modified, e.g. rayon and cellophane are modified cellulose. Resources and references Use a variety of resources and list the ones you found most useful. Hints: You will need current resources here (within the last couple of years) as this is a developing area of chemistry. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Select one reference that you consulted and decided to ignore. Identify the reference and justify your decision. Hints: When undertaking research it is essential to ensure that all reference material is accurate, reliable and valid. Was the information in this resource inaccurate, unreliable or not valid? Was it just too difficult to understand? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Summary: Use a proforma, such as the ones shown over, to summarise your research findings. You can either write in the information here or type it up on the computer, print it out and add the page(s) here. Hints: Always use your own words. This will increase your understanding and help you to remember the information. Copying information from references without acknowledging the source is called plagiarism and is not acceptable. If you do not understand the information well enough to put it into your own words, then you should get help from your teacher. 2.2 Use available evidence to gather and present data from secondary sources and analyse progress in the recent development and use of a named biopolymer. This analysis should name the specific enzyme(s) used or organism used to synthesise the material and an evaluation of the use or potential use of the polymer produced related to its properties.

Dot Point HSC Chemistry Investigations 12 Production of Materials Science Press Production of the biopolymer: ...................................................................... Formula of biopolymer Organism or enzyme used to produce this biopolymer How is it produced? How has the production process changed over time? Hints: For example, is it now more efficient, does it use new technology such as genetic engineering? Properties and uses of the biopolymer: ................................................................... Use Properties that allow it to be used in this way

Dot Point HSC Chemistry Investigations 13 Production of Materials Science Press Evaluation: Based on the information that you have researched, evaluate the use or potential use of the polymer produced related to its properties. Hints: In an evaluation you should: s .AMETHEBIOPOLYMERANDSTATEITSFORMULA s ,ISTITSPROPERTIESANDUSESTHATDEPENDONTHESEPROPERTIES s 3TATEITSVALUE3AYSOMETHINGLIKE4HEPOLYMERGIVENAME ISEXTREMELYUSEFULVERYUSEFULNOTATALLUSEFULNOTUSEFULNOWBUTWILLBE in the future … Always be specific about what it is useful for. It is useless to just say it is ‘good for people and the environment’, as that is too general. s *USTIFYYOUREVALUATIONANDBACKUPYOURCLAIM&OREXAMPLE4HEBIOPOLYMERSTATENAME ISVERYUSEFULINTHEMANUFACTUREOFSTAPLES for use in surgery because it can be produced inexpensively, it is strong enough to hold tissues together, it is biocompatible so it does not cause allergic reactions in people and it eventually biodegrades so it does not have to be surgically removed later. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 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Dot Point HSC Chemistry Investigations 15 Production of Materials Science Press Background information Dehydration is a chemical reaction involving the removal of water from a molecule. This is also called condensation. -H HCCOH H2SO 4 180°C -H - -- -H-H + C = C H H H H O H H Addition is a chemical reaction that involves the adding of a molecule across a double bond. The addition of water is called hydration. It may also be called hydrolysis because the water molecule is split in the process (to H and OH). -H HCCOH -H - -- -H-H + C = C H H H H O H H dilute acid Dehydration of ethanol 1. What is meant by dehydration? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 2. Write an equation for the dehydration of ethanol. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 3. Describe how you modelled this reaction using diagrams, photographs or videos. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 3.3 Process information from secondary sources such as molecular model kits, digital technologies or computer simulations to model the dehydration of ethanol, and the addition of water to ethylene.

Dot Point HSC Chemistry Investigations 16 Production of Materials Science Press Addition of water to ethylene 1. What is meant by an addition reaction? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 2. Write an equation for the addition of water to ethylene. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 3. Describe how you modelled this reaction. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 4. Include diagrams, photographs and/or videos of your model or simulation. Evaluation: Evaluate your models of dehydration and addition. Hints: Did you successfully illustrate these processes? What difficulties did you encounter? How could you improve this procedure next time? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... .........................................................................................................................................................................................................................................................

Dot Point HSC Chemistry Investigations 17 Production of Materials Science Press Summary: Summarise the advantages and limitations of your models or simulations in the table below: Advantages Limitations Hints: Do you understand the process better because you can visualise it? Does making the model help you to summarise or learn about the process? Can the model be used to make predictions and/or design improvements in the process? Why did you decide to model the reaction in this way?Hints: Was your model: s AVALIDREPRESENTATIONOFTHEPROCESS s BASEDONCOMPLETEINFORMATION s BASEDONASSUMPTIONS s ASIMPLIlCATIONOFWHATISREALLYHAPPENING Could it have been improved if you knew more about the process? Dehydration of ethanol Dehydration of ethanol Addition of water to ethylene Addition of water to ethylene Risks and safety assessment: Discuss any risks involved and how these could be reduced. Hints: Are there any risks involved in this process? If so they are probably minimal. It is acceptable to state that there are no risks or only minimal risks involved in carrying out an activity. If you are using model kits then a risk could be people being bruised or injured if they slip on models dropped onto the floor and thus fall over. Models involving a lot of activity may involve the risk of people being injured during collisions. Note that the risk is the injury, not the collision or fall itself. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... .........................................................................................................................................................................................................................................................

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Dot Point HSC Chemistry Investigations 19 Production of Materials Science Press Background information Ethanol (C 2H5OH) is an alkanol that can be produced by either the hydration (addition of water) of ethylene or the fermentation of sugars and starches. See also Section 3.12 for fermentation of glucose in the laboratory. Resources and references Use resources and references to find out about the industrial production of ethanol by the fermentation of sugar cane. Describe the type of reference you used here. Hints: Did you use journals, websites, school textbooks, information from industries or teacher notes and worksheets? If you used the internet did you use key words with AND, OR and NOT when making your searches? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Explain what is meant by the reliability of a resource document. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Identify a strategy you used to determine the validity of your research data. Hints: If a reference provides the data on which their claims are based, and you would draw the same conclusions from this data, then it is a valid reference. Note that many sources do not provide the original data and we assume the information is valid if it is from an expert or reputable source. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 3.4 Process information from secondary sources to summarise the processes involved in the industrial production of ethanol from sugar cane.

Dot Point HSC Chemistry Investigations 20 Production of Materials Science Press Industrial production of ethanol Use a flow chart to summarise the industrial production of ethanol from sugar cane. Hints: Remember to use arrows (not just lines) to link the steps. And plan it so arrows do not cross over if possible. During the industrial production of ethanol filtering, fermentation and distillation take place. Using your research, complete the following table to compare these three processes. Filtering Fermentation Distillation Physical or chemical reaction involved? Why is this procedure used? Outline the procedure

Dot Point HSC Chemistry Investigations 21 Production of Materials Science Press Discuss technological developments that have improved the industrial production of ethanol. 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Dot Point HSC Chemistry Investigations 22 Production of Materials Science Press Extension activity: Prepare a report for the government informing them of the need for government subsidies to encourage the development of alternative energy sources in Australia. Hints: A report should start with a general statement. This should be followed by a series of paragraphs, each on a different aspect of the issue. The first sentence in each paragraph should summarise what is in that paragraph. Include headings so the reader can see at a glance where the report is ‘going’. You could also include a sentence under each heading that previews what is in the following paragraphs. Technical terms should be used wherever possible. Present tense should be used e.g. ‘Alternative energy sources produce…’ Tables of information can be included if relevant. 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Dot Point HSC Chemistry Investigations 23 Production of Materials Science Press Background information Combustion is a chemical reaction in which oxygen is used and energy is released. Heat of combustion is the amount of heat released during a combustion reaction. Alkanols are an homologous group of carbon compounds containing the hydroxyl (OH) grouping, e.g. methanol, ethanol, propanol. They have the general formula C nH2n+1 OH. This experiment involves the combustion of a measured mass of an alkanol to heat a measured mass of water through a measured temperature rise. It is assumed that the heat released by the combustion reaction will all be absorbed by the water. The heat of combustion can then be calculated using the equation: 'H = –mC'T where: 'H = change in energy content (enthalpy change) m = mass of water being heated by the burning alkanol (kg) C = specific heat of the water being heated (4.18 × 10 3 J kg –1 K–1) 'T = change in temperature of water being heated (K) Note: If the mass used in the equation is in grams, then C must be in J g –1 K–1. The value of C is then 4.18 (not 4.18 × 10 3). Aim: To determine and compare the heats of combustion (per gram and per mole) of three liquid alkanols per gram and per mole. Materials: Label the equipment in the photograph which you will use and list any other materials provided by your teacher. Three alkanols, each in its own spirit burner (state names and formulas): .......................................................................................... , ......................................................................................................................... and ..................................................................................................................... Safety goggles A container, with 100 mL water, suspended above each spirit burner A thermometer to measure the temperature rise of the water (or temperature probe and data logger) A balance to record the mass of each alkanol before and after burning ..................................................................................................... ..................................................................................................... ..................................................................................................... ..................................................................................................... 3.8 Identify data sources, choose resources and perform a first-hand investigation to determine and compare heats of combustion of at least three liquid alkanols per gram and per mole.

Dot Point HSC Chemistry Investigations 24 Production of Materials Science Press Justify the use of these materials and procedures. Hints: Did you need heatproof mats? How did you decide what to use to hold the water? Why is it necessary to weigh the spirit burner both before and after burning the alkanol? Will the alkanols burn readily and safely and release heat to warm the water? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Hypothesis Hints: Make an educated guess about the results – a testable prediction as to which alkanol will release the most or least energy during combustion. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Variables: Identify the following variables in this experiment. Independent variable Dependent variable Variables that must be controlled Hint: What was the one thing you changed each time you burned fuel?Hint: What did you observe or measure to see the effect of changing to another type of fuel?Hint: What do you have to keep the same each time you burn a fuel?

Dot Point HSC Chemistry Investigations 25 Production of Materials Science Press Risk analysis: Use the table below to indicate any risk involved in using the equipment and chemicals involved in this investigation and any necessary precaution for this experiment. Hints: Consult the relevant MSDS. Think carefully about the risks involved in burning fuels. Risk Describe the precaution Explain the precaution Alkanols ................................ ................................ ................................ Equipment Method: Write out the method you will use in procedural text type (‘recipe’ format). Include a labelled diagram (use pencil and ruler as always) or a photograph to illustrate your method. Hints: Put each step on a new line and start each step with a verb. Think about how you will ensure as much heat from the burning alkanol goes into the water as possible. Design your experiment to minimise heat loss to the environment. Remember to stir the water before you measure the temperature rise. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... .........................................................................................................................................................................................................................................................

Dot Point HSC Chemistry Investigations 26 Production of Materials Science Press Results: Complete the following table (or a similar table) to record your results. Add in the names of the alkanols you used. Hints: When tabulating information, always rule lines down between columns and rule across after each section – otherwise it is not a table. Alkanol burningAlkanol 1 .................................................Alkanol 2 .................................................Alkanol 3 ................................................. Initial mass of spirit burner + alkanol (g) Final mass of spirit burner + alkanol (g) Mass of alkanol burnt (initial mass – final mass) Initial temperature of water (before heating) (°C) Final temperature of water (°C) Rise in water temperature (final – initial) (°C) Volume of water being heated (mL) Mass of water being heated (g) Any observations you made, e.g. colour of flame, any soot present

Dot Point HSC Chemistry Investigations 27 Production of Materials Science Press Calculations: Using your results, calculate the heat released by burning the fuel in your experiment and then the heat that would be released if you burnt 1 gram and 1 mole of each fuel. Hints: If you need help, you will find hints and a sample calculation below. Name of alkanol used Heat released by burning fuel ('H = –mC'T) Heat released by burning 1 gram of fuel Formula of fuel Molar mass of fuel(g) Heat released by burning the molar mass of fuel (kJ mol –1) Sample calculation: Ethanol was burned in a spirit burner and used to heat a container of water. The volume of water heated was 100 mL. The mass of the spirit burner and ethanol was 240.0 g before burning and 239.1 g after burning. The temperature of the water rose from 22.0°C to 36.2°C. Hints Sample calculation Mass of alkanol burned (g) Initial mass of spirit burner + alkanol – final mass of spirit burner + alkanol (g)240.0 – 239.1 = 0.9 g Initial temperature (°C) Temperature before heating starts 22.0°C Final temperature (°C)Maximum temperature water reaches due to heating 36.2°C Rise in water temperature (°C) Final – initial temperature 36.2 – 22.0 = 14.2°C Volume of water heated (mL) 100 mL 100 mL Mass of water heated (g) 1 mL water weighs 1 g 100 g Heat released by burning fuel Look at the temperature increase. Use the equation: 'H = –mC'T where: C = 4.18 J g –1 K–1.'H = – 100 × 4.18 × 14.2 = 5935.6 J 5935.6 J has been released by burning 0.9 g of fuel Heat released by burning 1 gram of fuel0.9 g of fuel has released 5935.6 J of heat energy by burning. Formula of fuel Molar mass of fuel (g)Formula of ethanol is C 2H5OH Use Periodic Table to find molar mass = 2 × 12.01 + 6 × 1.008 + 16 = 46.068 g Heat released by burning the molar mass of fuel (molar heat of combustion)1 gram of ethanol will release 6595.1 J heat 46.068 g of ethanol will release 6595.1 × 46.068 J = 303691.7.1 J = 303.6917 kJ = 3.04 × 10 2 kJ The molar heat of combustion of ethanol was found to be: –3.04 × 10 2 kJ mol –1. Note that this value is well below the value for molar heat of combustion of ethanol given in data books. Can you explain this?

Dot Point HSC Chemistry Investigations 28 Production of Materials Science Press Graphs: Graph your results to show the heat of combustion per gram and per mole for each fuel. 1. Graph the heat released by burning 1 gram of fuel for each of the three alkanols. Hints: Place the type of alkanol (the independent variable) along the horizontal axis and the heat of combustion per gram on the vertical axis. Draw a line of best fit and look for any relationship shown by the graph. 2. Graph the molar heat of combustion against molar mass of the alkanols. Hints: Heat of combustion will go on the vertical axis, molar mass on the horizontal axis. Could you use this graph to predict the molar heat of combustion of another fuel, e.g. pentanol? Draw a line of best fit and look for any relationship shown by the graph.

Dot Point HSC Chemistry Investigations 29 Production of Materials Science Press Equations: Write balanced equations, using words and symbols, to show the combustion of each fuel. Hints: Assume the alkanols underwent complete combustion (products will be carbon dioxide and water). If you noticed a yellow (rather than blue) flame and lots of soot being formed for any of the alkanols, this would indicate incomplete combustion (carbon as one of the products and perhaps carbon monoxide as well). ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Conclusion: Write a conclusion for this experiment. Hints: State the heats of combustion determined experimentally. Remember that heat of combustion should always be shown as a negative value as combustion is an exothermic reaction and heat is released. Compare your experimental values to the accepted values. Compare the experimental heats of combustion for the three fuels. Which fuel releases the most or least heat per gram and per mole burned? Did the graphs show a relationship between molar mass of fuels and molar heat of combustion? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... .........................................................................................................................................................................................................................................................

Dot Point HSC Chemistry Investigations 30 Production of Materials Science Press Discussion 1. Comment on the accuracy of your results. Hints: Look up a data book to find the accepted values for heat of combustion of the alkanols you used, e.g. AlkanolHeat of combustion (kJ mol –1) Methanol –727 Ethanol –1367 Propan-1-ol –1367 Propan-2-ol –2021 Butanol –2767 Compare these values with the values that you obtained. Are your experimental values accurate? Can you explain the big differences between your values and those in the data book? Did all of the heat released go into heating the water? Did all the fuels burn ‘cleanly’? Did you stir the water being heated so it would heat evenly? Did you measure the highest water temperature recorded? (It may continue to rise after the spirit burner is extinguished.) Was your balance sensitive enough to measure the small change in mass of the fuel? Explain how using graphs contributes to the accuracy of results. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 2. Does your experiment provide a valid method to determine and compare the heats of combustion of different alkanols? Hints: Did the design of your experiment allow you to test what you set out to test? Did the water container allow all heat from the burning alkanol to pass through to the water or was heat lost to the environment? Could you prevent any heat loss by improving your experiment? Is this a valid method for determining heats of combustion – does it allow you to obtain accurate and reliable measurement of these? Is this a valid method for comparing heats of combustion – does it allow you to make accurate and reliable comparisons between them? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... .........................................................................................................................................................................................................................................................

Dot Point HSC Chemistry Investigations 31 Production of Materials Science Press Background information The development of renewable fuels, such as ethanol, from biomass is an interesting area of research. This has become popular with the realisation that petroleum supplies are dwindling and that fuels such as ethanol, although not carbon neutral, do have a lesser impact on the greenhouse effect and global warming as they are produced from plant material. Resources and references: Use a number of sources to find out about the use of ethanol in car engines. Describe the types of resources you found most useful and identify one website which you felt was presenting a biased view. Hints: Did you use journals, websites, school textbooks, information from industries or teacher notes and worksheets? You will need to be particularly careful that you are using up-to-date information here. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Research report: Write a one-page report on the use of ethanol as an alternative car fuel, evaluating the success of current usage. Hints: You may use point form and tables in your report. Use subheadings and present tense. In your answer you should include the following: s 0ROPERTIESOFETHANOLTHATMAKEITUSEFULASACARFUEL Does it ignite and burn easily? Include equations. Does it mix well with petrol? Can it be safely stored and transported? Is it renewable? s 5SEOFETHANOLASAFUEL Find out where ethanol is used as a fuel supplement and how much it is used in different countries. s !DVANTAGESOFETHANOLASAFUEL Explain at least three advantages of using ethanol as a fuel rather than other fuels. Remember that to explain you must first state, then describe and then explain how this is an advantage. And an explanation, in chemistry, should include an equation whenever possible. s $ISADVANTAGESOFETHANOLASAFUEL Describe and explain at least three disadvantages of using ethanol as a fuel. Use equations. s %VALUATION Make a value judgement about the success (or otherwise) of ethanol as a fuel. Is it being suggested as a replacement – why or why not? Is it being used to supplement petrol supplies. Why or why not? ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... 3.10 Process information from secondary sources to summarise the use of ethanol as an alternative car fuel, evaluating the success of current usage.

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Dot Point HSC Chemistry Investigations 33 Production of Materials Science Press Extension question 1: A lot has been printed in the mass media about the advantages and disadvantages of using ethanol as a fuel. Assess the accuracy of this information by comparing it with similar information presented in scientific journals. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... Extension question 2: Discuss the suggestion that biodiesel made from plants and/or algae may be more useful as a fuel supplement than ethanol. ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... ......................................................................................................................................................................................................................................................... .........................................................................................................................................................................................................................................................

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