STUDENT SUPPLEMENT MAY 2008 • VOLUME 45 • NUMBER 3 Cosmetics, naturally Chemicals from plant biomass ISSN 0013-1350 Comparability studies Alternative A-levels STEM qualifications – harder than all the rest? Cambridge Pre-U chemistry set to challenge students ISSUE MAY BRIAN GADSBY/SCIENCE PHOTO LIBRARY BIRD BRAINS KNOW BEST Fruit and vegetables are rich in antioxidants – chemicals thought to play an important role in protecting us from illnesses such as heart disease and certain cancers. Such chemicals react with free radicals in the body – for example hydroxyl radicals, which attack proteins, lipids and even DNA within our cells – rendering them harmless. While people deliberate whether or not they believe this ‘antioxidant’ theory and the need to eat food rich in antioxidants, it seems our feathered friends don’t suffer the same misgivings. Fruiteating birds – specifically the European blackcap, Sylvia atricapilla, known affectionately as the Northern Nightingale because of its tuneful chirp – go out of their way to select berries with the highest concentrations of flavonoids. These polyphenolic compounds, which contain at least one phenol group (C6H5OH), are among the commonest antioxidants found in Nature. In a study of blackcaps, Dr Carlo Catoni and his colleagues at the University of Freiburg and at the Vogelwarte Radolfzell Max Plank Institute for Ornithology in Germany first established, by using HPLC (high-pressure liquid chromatography) and mass spectrometry, that two specific flavonoids found in blackberry extracts are absorbed in the birds’ Black caps favour fruity flavonoids blood. They then investigated whether the birds preferred food enriched with these flavonoids, and finally if they gained any health benefits from ingesting flavonoids. According to the researchers, the blackcaps actively selected food with added flavonoids, as evident by its darker colour. Flavonoids such as anthocyanins are responsible for much of the dark colours found in blackberries, bilberries and elderberries. Previous studies by the researchers had shown that blackcaps do not show colour preference on nutritionally identical food. By measuring the amounts of antibodies in the birds’ blood, the researchers found that those fed on a flavonoid-rich diet produced more antibodies than birds fed on a diet with no berry flavonoids. These results, the researchers say, imply that flavonoids can boost the immune system in a living organism. They hypothesise that their results may support other research that points to flavonoids having beneficial health effects on people. Did you know? The bright red sap from Chinese plants such as Dracaena cochinchinensis is called ‘Dragon’s blood’. This mixture of sugars, salts and minerals has been used for thousands of years in traditional Chinese medicine mainly for treating wounds, stomach and circulatory problems. Recently, Chinese chemists identified several flavonoids (polyphenol compounds) in Dragon’s blood. In an article published in the Journal of Natural Products, the researchers explain that their results suggest that these newly identified compounds show promise as antibacterial agents, and for treating stomach ulcers, cancer, thrombosis (blood clots) and stroke. It’s worth noting that ca 70 per cent of all new medicines discovered in the past 25 years have come from plants and natural products. Download a pdf of this issue at: www.rsc.org/EiC InfoChem_May.indd 1 IN THIS ISSUE Dissolving plastics When the fashion designer met the chemist… A day in the life of… David Henderson, accountant On-screen chemistry Sand dunes pose challenge for heroes Plus… That’s chemistry! Organic prize quiz Webwatch Chemical Futoshiki Editor Kathryn Roberts Assistant editor James Berressem Design and layout Dale Dawson Infochem is a supplement to Education in Chemistry and is published bi-monthly by the Royal Society of Chemistry, Burlington House, Piccadilly, London W1J 0BA, UK. 020-7437 8656, e-mail: [email protected] www.rsc.org/Education/EiC/index.asp © The Royal Society of Chemistry, 2008 Published in January and alternate months. ISSN: 1752-0533 1 14/04/2008 11:29:56 C ISSUE MAY This year saw the launch of a fashion show with a difference. Wonderland, which opened at the London School of Fashion in January for two weeks, exhibited beautiful dresses that disappeared in a giant bowl of water before the public’s eyes, setting off underwater fireworks as they dissolved. Does such imagery merely reflect a division between the worlds of art and science, or is there another more poignant message? W e live in a throwaway society. We use myriad materials every day in all sorts of ways, giving little thought to where these materials came from or where they will end up. Plastics and increasingly cheap clothing, in particular, are BARRY EVANS/UNIVERSITY OF SHEFFIELD Plastics – going out of fashion 2 InfoChem_May.indd 2 metaphors for waste. With landfill sites reaching crisis point and oil resources dwindling, few people would argue that we all need to become more responsible in the way we use and dispose of such materials. But how do we get people to think differently about materials, to think in terms of sustainability and recycling? T A chance encounter between fashion icon Helen Storey and Tony Ryan, ICI professor of physical chemistry at Sheffield University, led to a solution that exploits the glamorous world of fashion with the equally creative world of chemistry. Twenty years ago Helen Storey was designing clothes for Cher and Madonna, but is now more interested in finding solutions to problems such as plastics pollution and world water shortages. Recently she was working with a packaging company, trying to come up with some radical ideas for plastic packaging that would address plastics waste. ‘Why can’t a plastic bottle know when its contents have disappeared and signal the time for the bottle to disappear?’, she asked herself. Later, listening to the radio 4 programme, Material World, she heard Tony Ryan talking about smart polymers, so she contacted him to find out whether he could shed any light on the problem. He invited her to the department of chemistry at Sheffield and an alliance formed that, with funding from the Engineering and Physical Sciences Research Council’s (EPSRC) public engagement of science programme, has recently culminated in Wonderland. The exhibition of dissolvable textiles has an underlying message on sustainable materials, and has seen the chemist and the fashion designer go on to develop a water purification system for people in the developing world. You may copy this issue for use within schools 14/04/2008 11:30:25 Ryan told Infochem, ‘We are both keen to get people to think about the way they use materials and to use them more responsibly. But rather than preach about it, we realised we could reach a wider group of people by using fashion and glamour’. ALEX MAGUIRE B Ryan knew of a polymer that was dry to touch, making it suitable to work up into dresses, and would dissolve in water. ‘Helen would be able to make beautiful gowns in which we could embed all sorts of chemistry, and they would obey the second law of thermodynamics and dissolve’. This polymer, he explained, is used to form the clear pouches that hold laundry and dishwashing liquids, and dissolves in water. Detergents comprise salts which are attracted to water more than the polymer is – the water in the liquid detergent is bound so strongly by the salt ions that only when the polymer is in large amounts of water, as is the case in a washing machine or dishwasher, will it dissolve. The polymer is polyvinyl alcohol (PVA), but because the monomer, vinyl alcohol (ethenol, CH2=CH(OH)), doesn’t exist on its own (it coexists in equilibrium with its isomeric ketone, CH3CHO), PVA is made by polymerising vinyl acetate (ethenyl ethanoate), followed by a saponification reaction. The latter step cleaves the ester, via hydrolysis, to form the alcohol. The result is a copolymer of vinyl alcohol and vinyl acetate, the relative amounts of which can be varied by controlling the saponification reaction. The more acetate, the less soluble in water is the copolymer; the more alcohol, the more soluble in water is the copolymer. The temperature at which the copolymer dissolves can thus be controlled by changing the relative amounts of acetate and alcohol. So the polymer, explained Ryan, could be used to make a bottle that when empty could be filled with boiling water, which would dissolve the polymer and on cooling would form a gel if a crosslinking molecule, such as borax (disodium tetraborate(III)-10water), was added. If the cap of the bottle were designed like a pepper pot and contained flowering or herb seeds and rooting compound, then where once you had a plastic bottle which you would have thrown away, you could have flowers or herbs growing instead. To add to the artistic effect of the dissolving dresses at the exhibition, Ryan provided the You may copy this issue for use within schools InfoChem_May.indd 3 Plastics at an exhibition… Designer plastics… designers with ‘underwater fireworks’, which could be incorporated in the buttons. Small pouches, made of the same copolymer are filled with equal amounts of bicarbonate of soda (sodium hydrogen carbonate) and sodium citrate (the sodium salt of citric acid, 2-hydroxypropane-1,2,3-tricarboxylic acid), and a solid dye. As water leaks into the pouch, the bicarbonate of soda and sodium citrate react, producing carbon dioxide gas, which fires the dye into solution, producing coloured streamers in the water as it sinks. A giant magnifying glass bowl to hold the water adds to the effect. Ryan comments, ‘People will ask, “why are you destroying those beautiful gowns?” and we will say: “to make you think about how you are slowly destroying the planet by throwing away materials”. And because we want them to think in new ways about materials, plants are seen growing from the gooey gel that the dresses have changed into’. Storey designed the dresses and her team made up the garments using lasers to cut the ‘fabric’ and specially designed heat sealers – essentially a wheel on the end of a soldering iron – to bond seams together. Intricate patterns, similar in appearance to lace, could be cut out using the lasers. T - Tony Ryan is well known in the chemistry community for his work on polymers. The focus of his recent research has been in the development of nanoscale (10–9 m), synthetic muscle, which has the potential to be used as molecular motors for the electronics industry, in robotics for example. For this he uses a polymer with ionic side groups, the ionic 3 14/04/2008 11:31:03 “… … .” ISSUE MAY nature of which can be switched ‘on’ or ‘off ’ by changing the pH of its environment. In its ionic state, at pH 4–6 (in a weak acid), the polymer attracts water and swells up, and in its non-ionic state (at low pH) the polymer loses water and collapses. ‘By separating the weakly and strongly acidic solutions with a membrane (thus creating an osmotic pressure between the two solutions) we can change the pH of the environment of the polymer’, explains Ryan, ‘and get the synthetic muscle to change shape and thus do work’. While talking to the artists about his work, Ryan tells them how, in a similar system, the osmotic pressure between two liquids can be exploited to provide clean drinking water for soldiers in Iraq and Afghanistan. ‘The soldiers have a bag made of regenerated cellulose (the membrane) containing salts and sugar’, he says. ‘When they come across a stream or a pool of dirty water, the soldiers fill up their bags, and the osmotic pressure created by the salt/sugar solution pulls clean water through the membrane. Intrigued, the artists ask, ‘could you use the same materials that you use for your synthetic muscles in a water purification system?.’ In collaboration with the artists, Ryan and his team at Sheffield have developed a water purification ‘pillow’ based on ‘synthetic muscle’, that could be used by the military and people in developing countries. In dirty, contaminated water, the polymer electrolyte absorbs pure water across a membrane and swells up. To release the water, simply apply a pressure that is bigger than the osmotic Seams easy… pressure and the water comes out – take the membrane away and squeeze the gel. The portable system has been awarded a patent and Ryan is currently seeking venture capital to develop the prototype for the market. The Wonderland exhibition will be in Sheffield in a city-wide event at Meadowhall, the University of Sheffield, the Botanical Gardens, and the Millennium Galleries between 18 June and 13 July; and in Belfast at the Ormeau Baths Gallery, 7 October to 9 November. Kathryn Roberts that’s chemistry! Simon Cotton, chemistry teacher at Uppingham School, looks at the molecules in our lives. In this issue: Food is chemistry Why do you say that? We eat, smell and taste molecules. ALEX MAGUIRE Don’t we eat food to give us energy? That is an important function of food, but it also supplies protein to provide us with amino acids. Our bodies use these to make other proteins. What are amino acids and proteins? Most amino acids, such as alanine (1), contain just carbon, hydrogen, oxygen and nitrogen atoms. They have an amine (–NH2) and a carboxylic acid (–CO2H) group, hence the name amino acid. An amino acid can join – at either end – with another amino acid to form a dipeptide (2), linked by a peptide bond. This bond is formed by a condensation reaction involving the removal of a H2O molecule. Because amino acids can react at either end, they can form long chain molecules. A molecule with 4 InfoChem_May.indd 4 Peptide bond lots of peptide bonds is called a polypeptide. If the molecular weight of a polypeptide is more than 6000, it is known as a protein. There are 20 different amino acids that are used in different combinations to make the proteins in our bodies. The body is unable to make 10 of these amino acids, which means we have to get them through our diet. H O H2N C H O H H O C OH H2N C CH3 CH3 (1) Alanine H3C H3C CH3 (3) Heptan-2-one Why does food have a taste and smell? Life would be boring otherwise. Food is more attractive because of molecules which impart flavour and odour. These traits also give us clues about what we are eating, eg heptan-2-one (3) is C OH CH3 (2) Dipeptide O What happens to protein we eat? Our bodies take in food proteins, break them down into their amino acid constituents and then reassemble them in different sequences and combinations to make different proteins. C N C N CH3 CH3 (4) Trimethylamine a characteristic flavour compound of blue cheese. When food goes bad, proteins break down into smaller molecules with higher vapour pressures, which we detect as a smell. These act as a warning. For example, when fish protein is attacked by enzymes and bacteria the noxious chemical trimethylamine (4) is formed which we recognise as the odour of rotting fish. ■ You may copy this issue for use within schools 14/04/2008 11:31:27 Jonathan Hare asks… SAND DUNES: can you crank an ambulance up a sand dune? Ice cold in Alex is a classic black and white film starring Sylvia Syms, John Mills and Anthony Quayle. In 1942 in the Libyan war zone, the three find themselves crossing a mined desert in an army ambulance trying to get back to the safety of Alexandria. Nearing the end of their journey they are forced to attempt to drive up a massive sand dune to escape the desert. Realising that the engine will simply burn out in the intense heat, they do a clever thing. They remove the spark plugs from the engine so that the pistons no longer limit the motion of the engine, put the engine in lowest gear and use the crank handle to crank the ambulance up the dune. After several tries they succeed, allowing them to drive back to Alex. There is a classic scene towards the end of the film where they toast their safe arrival, downing several glasses of beer – hence ‘Ice cold in Alex’! But can it be done? In our Hollywood science TV series Robert Llewellyn and I cranked a car up a steep hill to test this stunt. The ambulance would have been much heavier but it would have had a greater gear ratio and so we felt confident that they could have done it – providing the slope of the dune was not too great. So how steep is a sand dune? You might think that a sand dune could be any steepness, from almost flat to a vertical cliff but this is not so. It’s true that sandstone or chalk can produce near vertical cliffs as you can see in quarries or on the south coast such as Beachy Head and the White cliffs of Dover. But this is because they are solid; sand is more fluid. Bright spark has the answer true for many different types of small particles, including sand. Our model gives us some insight into the maximum steepness of a sand dune – about 30–40 degrees. Since we know that there is a maximum angle beyond which the grains can’t go it An experiment means we can be much more confident that Try this experiment. Take a salt cellar and pour our heroes could have cranked the salt onto a flat table top. A little mound of salt ambulance up the sand dune. It would have will build-up and it looks like it will grow ever been a lot of hard work though! steeper to make a pile. All of a sudden you (If you want to find out more about the notice that the grains slip and the pile loses science of flowing particles go to http:// height to form a mound with a larger area www.seed.slb.com/en/scictr/lab/heleshaw/ base. As you continue to add more salt the index.htm.) mound grows higher and steeper but at a Dr Jonathan Hare, The CSC, Chemistry Department, University maximum angle we see our ‘salt dune’ slips. of Sussex, Brighton BN1 9ET (www.creative-science.org.uk/TV. What is true of our salt crystal model is also html). webwatch ASSOCIATED BRITISH/THE KOBAL COLLECTION Emma Woodley, RSC assistant education manager, takes a look at some websites of interest to students Earth – our world in motion http://www.amnh.org/ology/ earth/ This website, from the American Museum of Natural History, is packed with fascinating facts about the structure of the Earth, covering rocks, volcanoes, earthquakes, and plate tectonics. It has good animations and illustrations, and is interactive. There are also interviews with Earth scientists and many experiments for you to try at home. You may copy this issue for use within schools InfoChem_May.indd 5 Plate tectonics earthquakes. The mechanisms that cause the plates of the crust to move are described in detail, and This website describes how the there are clear animations showing theories of the development of the you how we believe the surface of Earth evolved – its mountain ranges, the Earth has changed over the past the causes of volcanoes and 750 million years. http://www.ucmp.berkeley.edu/ geology/tectonics.htlm 5 14/04/2008 11:31:50 Z I U Q E Z I R P C I ORGAN £50 OF HMV TOKENS TO BE WON! If you are studying AS/A2 chemistry, have a go at Infochem’s latest quiz and maybe your revision might pay for some new DVDs, CDs, books or computer games. The questions, contributed by chemistry teacher Simon Cotton of Uppingham School, are based on organic chemistry covered in the current A-level specifications. ISSUE MAY Use the letters a–q to answer the questions (apart from question 1). 1. Name each compound. Which compound(s) are: 2. Alkanes? 3. Alkenes? 4. Arenes? 5. Cyclic hydrocarbons? Which compound(s): 6. Decolourise bromine water in the dark? 7. Only react with Cl2 in the dark in the presence of a Lewis acid such as AlCl3? 8. Undergo addition with HBr? 9. Can be oxidised to benzoic acid on boiling with KMnO4 solution? 10. Undergo side chain substitution with Cl2 in the presence of uv light? 11. Do not occur in Nature but are made by cracking? 12. Can be catalytically hydrated to make alcohols? 13. Undergo electrophilic substitution to make a nitro compound? 14. Are three isomers? 15. Are two more pairs of isomers? 16. Add HCl to form a tertiary halide? 17. Add HCl to form a secondary halide? 18. Add HCl to form a primary halide? 19. Exist as geometric isomers? 20. Have a chiral carbon? 21. Result from an elimination reaction of 2-chlorobutane? 22. Can be made by an isomerisation reaction of E? 23. Could be made industrially by reforming reactions of O? 24. Are planar? 25. Can be polymerised to make polystyrene? 26. Are used to make ethylbenzene industrially? 27. Only have bond angles at carbon ca 109½°? 28. Only have bond angles at carbon ca 120°? 29. Have bond angles at carbon both ca 109½° and ca 120°? 6 InfoChem_May.indd 6 CH2 H3C (a) H3C CH2 CH3 CH3 (b) (c) CH3 H3C H3C CH2 (e) (d) CH3 H3C (f) CH3 (h) (g) CH3 (i) CH2 H3C H2C (k) CH2 (l) (j) CH2 CH3 CH3 H3C (o) (n) (m) CH3 CH3 H3C CH3 H3C (p) (q) SEND YOU ANSWERS TO: The Editor, Education in Chemistry, the Royal Society of Chemistry, Burlington House, Piccadilly, London W1J 0BA (email: [email protected]), to arrive no later than Friday 6 June. First entry out of the editor’s hat with correct answers to all 29 questions will receive a £50 HMV token. You may copy this issue for use within schools 14/04/2008 11:32:14 A … ACCOUNTANT: David Henderson David is in the final year of a three-year contract with BDO Stoy Hayward to qualify as an accountant. He talks to James Berressem about his typical day. BDO Stoy Hayward is the UK member firm of accountancy network BDO International. Based in London, David joined the firm on its graduate training programme (GTP) in 2005 along with some 40 other graduates. He is currently a senior on the GTP, studying towards an ACA accountancy qualification and works in the audit and business assurance department. As part of his contract, David shares his time between work and periods of up to three weeks’ paid study/exam leave at a financial training college. At the end of this year, after 450 days’ work experience and, importantly, nine exams passed, he will qualify as a chartered accountant. A Audit and assurance services offered by accountancy firms provide an independent opinion on information published by client companies. A financial audit aims to ensure that the financial statements released by a company are accurate, prepared correctly, and provide a fair representation of the organisation’s position and performance to interested parties, eg shareholders. David specialises in audits for businesses in the property and professional services sectors – his clients range from large, listed property companies with over £2 billion assets to growing architect firms with turnovers of £1–6 million. Each audit lasts on average PATHWAY TO SUCCESS ● ● 2005–present, qualifying accountant, BDO Stoy Hayward, London 2004–05, analytical researcher, Health and Beauty Care R&D, Procter & Gamble, Egham 2000–04, BSc chemistry with year in industry (2.i), University of Nottingham 1998–2000, chemistry, physics and maths A-levels, Lymm High School, Cheshire ● ● You may copy this issue for use within schools InfoChem_May.indd 7 three weeks and involves obtaining an in-depth understanding of the client’s operations, the industry in which the company operates and the commercial and financial issues it faces. For most of the project David spends each day visiting the client’s premises with his audit team, which comprises a junior and a semisenior (roles he has progressed through while on the GTP). The team collect evidence to support their assessment of the company’s financial statements. As the senior on the audit team David meets with the client’s managing or financial directors – his experience in industry has helped prepare him for dealing with such high-level staff. David is responsible for organising and monitoring the audit team’s work. He delegates many of the repetitive tasks involved in auditing, such as checking invoices and bank statements, to his junior while his semi-senior colleague might work on the audit of stock/work in progress, which can be governed by complex accounting standards. This frees up his time to discuss with the client the business strategy and advise on how to manage potential risks. However, on the rare occasion, some jobs can involve completing the accounts for the clients, which requires David to use accounting skills such as double entry book-keeping. Back at BDO’s office David finalises the audit file, chasing up the client for outstanding documents and explanations. When all the required evidence has been analysed and signed off, David compiles a report detailing the findings of the audit. A BDO partner reviews this at a final meeting with the client’s managing director to discuss any issues prior to signing off the accounts. David Henderson Q Although the pressure to pass exams makes this qualifying period stressful, David enjoys the varied nature of his work and the challenges this brings – he is constantly working with new people in different environments during audits. The ACA qualification will give him a good grounding in business knowledge, which David hopes will unlock many new career opportunities. ■ 7 14/04/2008 11:32:43 £50 OF HMV TOKENS TO BE WON! ISSUE MAY PRIZE WORDSEARCH No. 39 Students are invited to find the 34 words/expressions associated with spices hidden in this grid. Words read in any direction, but are always in a straight line. Some letters may be used more than once. When all the words are found, the unused letters, read in order, will spell a further five-letter word. Please send your answers to the Editor at the usual address to arrive no later than Friday 6 June. First correct answer out of the editor’s hat will receive a £20 HMV token. A T H E R M A L S T I M U L U S I L C P S E V O L C F O S D U B N N K I I T U R M E R I C O O K D S I Y N P E C O R I A N D E R I E C A L N E N I R E G N I G C A V E H H A A R I N S A F F R O N O L G I C M M L R N P R H O T L L L U I L N I A O O A I O C R O C E T I N L O D L N T M C M E N Z Y M E S G I B E D G I O E A G E M T U N R E P R F E U L N S P I P E R I N E R E A A H M L Z E A X A N T H I N O P C M Y I E P B A Y L E A V E S L P O I D N P S A F R A N A L E A T E R L E E E R S E D Y H E D L A E R D Y R E N I C O R C O R C I P I S Y S D B L A C K P E P P E R S D Y H ALKYLAMIDE FAMILY ALDEHYDES AROMA BAY LEAVES BLACK PEPPERS BUDS OF CLOVES CELL CHILLI PEPPERS CINNAMALDEHYDE CINNAMON CLOVES COOK CORIANDER CROCETIN DIET EAT ENZYMES GINGER GINGEROL HOT HYDROCARBON CHAIN INDIAN LONG PEPPERS NUTMEG PELLITORINE PICROCROCIN PIPERINE PIPERLONGUMINE SAFRANAL SAFFRON SEED SPICES THERMAL STIMULUS TURMERIC ZEAXANTHIN FUTOSHIKI CHEMICAL ELEMENTS No. 1 Contributed by education consultant John Payne, this is Benchtalk’s chemical take on the Japanese number puzzle Futoshiki. Students are invited to solve the puzzle by completing the grid using the symbols of the Group 18 elements helium, neon, argon, krypton and xenon. The objective is the same as for numbers in Futoshiki: each of the five elements must appear only once in each row and each column. The ‘greater than’ or ‘less than’ signs between some of the squares indicate where an element must have an atomic number larger or smaller than its neighbour. Please send you answers to: the Editor, Education in Chemistry, the Royal Society of Chemistry, Burlington House, Piccadilly, London W1J 0BA, to arrive no later than Friday 6 June. First out of the editor’s hat to have correctly completed the grid will receive a £30 HMV token. Kr The winner was Paige Johnson of Biddulph High School, Biddulph, Stoke-on-Trent The seven-letter word was DEGRADE. 8 InfoChem_May.indd 8 Ar 1 i u m u r a g z i n c o p p e s t i c h r o m i u l i t h i u m c a l c 10 2 3 4 5 6 7 March PRIZE WORDSEARCH No. 38 winner Xe 8 9 7 n i u m o l d c r o d i u m n m Find the element no. 2 solutions and winner The winner was Fatima Khalil of Claremont High School, Harrow. Download a pdf of this issue at: www.rsc.org/EiC 14/04/2008 13:08:55
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