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fuels</a></li><li><a href="../19411/nuclear-fusion-nuclear-fission-reactions-1.html">Nuclear fusion & nuclear fission reactions</a></li><li><a href="../19429/solar-energy-1.html">Solar energy</a></li><li><a href="../19437/environmental-impact-global-warming-1.html">Environmental impact - global warming</a></li><li><a href="../19453/electrochemistry-rechargeable-batteries-fuel-cells-1.html">Electrochemistry, rechargeable batteries & fuel cells</a></li><li><a href="../19458/nuclear-fusion-fission-hl--1.html">Nuclear fusion & fission (HL) </a></li><li><a href="../19470/photovoltaic-cells-and-dsscs-1.html">Photovoltaic cells and DSSCs</a></li></ul></li><li><a href="../19078/option-d-1.html" class="father">Option D</a><ul class="level-2"><li><a href="../19079/pharmaceutical-products-drug-action--1.html">Pharmaceutical products & drug action </a></li><li><a href="../19158/aspirin-penicillin--1.html">Aspirin & penicillin </a></li><li><a href="../19174/opiates-1.html">Opiates</a></li><li><a href="../19184/ph-regulation-of-the-stomach-1.html">pH regulation of the stomach</a></li><li><a href="../19194/antiviral-medications--1.html">Antiviral medications </a></li><li><a href="../19211/environmental-impact-of-some-medications-1.html">Environmental impact of some medications</a></li><li><a href="../19254/taxol-a-chiral-auxiliary-case-study-1.html">Taxol - a chiral auxiliary case study</a></li><li><a href="../19258/nuclear-medicine--1.html">Nuclear medicine </a></li><li><a href="../19273/drug-detection-analysis--1.html">Drug detection & analysis </a></li></ul></li></ul></li><li><a href="../16592/practical-scheme-of-work-ia--1.html">Practical scheme of work & IA </a><ul class="level-1"><li><a href="../16682/internal-assessment-1.html" class="father">Internal Assessment</a><ul class="level-2"><li><a href="../18892/scaffolding-the-investigation-1.html">'Scaffolding' the investigation</a></li><li><a href="../18896/timing-organisation--1.html">Timing & organisation </a></li><li><a href="../18905/choosing-the-research-question-1.html">Choosing the research question</a></li><li><a href="../18946/personal-engagement-1.html">Personal engagement</a></li><li><a href="../18950/exploration-1.html">Exploration</a></li><li><a href="../18957/analysis-1.html">Analysis</a></li><li><a href="../18965/evaluation-1.html">Evaluation</a></li><li><a href="../18966/communication-1.html">Communication</a></li><li><a href="../19882/internal-standardization-of-the-ia-1.html">Internal standardization of the IA</a></li><li><a href="../19901/submitting-the-samples-for-moderation-2.html">Submitting the samples for moderation</a></li><li><a href="../33754/ten-suggestions-for-ias-using-secondary-data-1.html">Ten suggestions for IAs using secondary data</a></li><li><a href="../37544/gaining-full-marks-for-a-databased-ia--1.html">Gaining full marks for a databased IA </a></li><li><a href="../19506/ia-example-marking-exercise--1.html">IA example & marking exercise </a></li><li><a href="../23929/genuine-examples-of-moderated-ia-reports-1.html">Genuine examples of moderated IA reports</a></li><li><a href="../25234/examples-of-teacher-marked-ia-reports--1.html">Examples of teacher-marked IA reports </a></li><li><a href="../37542/history-of-internal-assessment-1.html">History of Internal Assessment</a></li></ul></li><li><a href="../16598/mandatory-laboratory-components-1.html" class="father">Mandatory laboratory components</a><ul class="level-2"><li><a href="../16613/formula-of-magnesium-oxide--1.html">Formula of magnesium oxide </a></li><li><a href="../16612/determining-the-mr-of-an-unknown-gas-1.html">Determining the <i>M</i><sub>r</sub> of an unknown gas</a></li><li><a href="../16615/acid-base-titrations--1.html">Acid-base titrations </a></li><li><a href="../16616/a-green-acid-base-practical-1.html">A green acid-base practical</a></li><li><a href="../16617/analysis-of-aspirin-tablets-1.html">Analysis of aspirin tablets</a></li><li><a href="../16618/caco3-in-egg-shells-1.html">CaCO<sub>3</sub> in egg shells</a></li><li><a href="../16644/enthalpy-changes-1.html">Enthalpy changes</a></li><li><a href="../16631/reaction-rates-1.html">Reaction rates</a></li><li><a href="../16635/rate-dependent-factors-1.html">Rate-dependent factors</a></li><li><a href="../16636/determining-ea-for-a-reaction-1.html">Determining <i>E</i><sub>a</sub> for a reaction</a></li><li><a href="../16637/iodination-of-propanone-1.html">Iodination of propanone</a></li><li><a href="../18144/titrations-with-a-ph-meter-1.html">Titrations with a pH meter</a></li><li><a href="../18355/redox-titration-with-kmno4--1.html">Redox titration with KMnO<sub>4</sub> </a></li><li><a href="../16640/voltaic-cells-1.html">Voltaic cells</a></li><li><a href="../16659/3-d-molecular-modelling--1.html">3-D molecular modelling </a></li></ul></li><li><a href="../17168/other-good-practicals-1.html" class="father">Other good practicals</a><ul class="level-2"><li><a href="../17196/common-chemical-reactions-1.html">Common chemical reactions</a></li><li><a href="../227/elements-oxides-of-the-third-period--1.html">Elements & oxides of the third period </a></li><li><a href="../17239/the-halogens-1.html">The halogens</a></li><li><a href="../17162/boiling-points-of-mixtures-1.html">Boiling points of mixtures</a></li><li><a href="../17170/polarity-of-molecules-1.html">Polarity of molecules</a></li><li><a href="../18083/le-chateliers-principle--1.html">Le Chatelier's principle </a></li><li><a href="../19582/determining-kc-for-an-esterification-reaction-1.html">Determining <i>K</i><sub>c</sub> for an esterification reaction</a></li><li><a href="../18164/redox-reactions-of-vanadium--1.html">Redox reactions of vanadium </a></li><li><a href="../18351/chlorine-in-swimming-pools--1.html">Chlorine in swimming pools </a></li><li><a href="../18178/analysis-of-cuii-ions-in-solution--1.html">Analysis of Cu(II) ions in solution </a></li><li><a href="../18179/percentage-of-copper-in-brass-1.html">Percentage of copper in brass</a></li><li><a href="../18356/electrolytic-cells--1.html">Electrolytic cells </a></li><li><a href="../18598/reactions-of-organic-compounds-1.html">Reactions of organic compounds</a></li><li><a href="../18752/hydrolysis-of-halogenoalkanes-1.html">Hydrolysis of halogenoalkanes</a></li><li><a href="../18784/preparation-of-13-dinitrobenzene--1.html">Preparation of 1,3-dinitrobenzene </a></li><li><a href="../19022/determination-of-an-organic-structure-1.html">Determination of an organic structure</a></li><li><a href="../19887/preparation-of-nylon-66-1.html">Preparation of nylon 6,6</a></li><li><a href="../19343/determination-of-vitamin-c-content--1.html">Determination of vitamin C content </a></li><li><a href="../19342/hydrolysis-of-starch--1.html">Hydrolysis of starch </a></li><li><a href="../19159/preparation-purification-of-aspirin--1.html">Preparation & purification of aspirin </a></li></ul></li><li><a href="../18851/ict-in-practical-work-1.html" class="father">ICT in practical work</a><ul class="level-2"><li><a href="../18852/data-logging--1.html">Data logging </a></li><li><a href="../18853/software-for-graph-plotting--1.html">Software for graph plotting </a></li><li><a href="../18854/spreadsheets-for-data-processing--1.html">Spreadsheets for data processing </a></li><li><a href="../18855/databases-1.html">Databases</a></li><li><a href="../18856/computer-modelling-simulations--1.html">Computer modelling & simulations </a></li></ul></li><li><a href="../16594/group-4-project-1.html" class="father">Group 4 Project</a><ul class="level-2"><li><a href="../16595/practicalities-1.html">Practicalities</a></li><li><a href="../16596/reflective-statement--2.html">Reflective statement </a></li></ul></li><li><a href="../16666/a-new-laboratory-1.html">A new laboratory?</a></li></ul></li><li><a href="../16284/exams-1.html">Exams</a><ul class="level-1"><li><a href="../16286/essential-facts-1.html" class="father">Essential Facts</a><ul class="level-2"><li><a href="../16287/objectives-command-terms-1.html">Objectives & command terms</a></li><li><a href="../16288/grade-descriptors-1.html">Grade descriptors</a></li><li><a href="../16289/grade-boundaries-1.html">Grade boundaries</a></li></ul></li><li><a href="../16302/paper-1-multiple-choice-1.html" class="father">Paper 1 (Multiple Choice)</a><ul class="level-2"><li><a href="../16303/advice-to-students-paper-1-1.html">Advice to students (Paper 1)</a></li><li><a href="../31515/practice-paper-1-exams-1.html">Practice Paper 1 exams</a></li></ul></li><li><a href="../16305/paper-2-1.html" class="father">Paper 2</a><ul class="level-2"><li><a href="../16306/advice-to-students-paper-2-1.html">Advice to students (Paper 2)</a></li><li><a href="../16307/areas-of-difficulty-1.html">Areas of difficulty</a></li></ul></li><li><a href="../16313/paper-3--1.html" class="father">Paper 3 </a><ul class="level-2"><li><a 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href="../16323/retaking-the-exam-1.html">Retaking the exam</a></li></ul></li><li><a href="../16325/faqs-1.html">FAQs</a></li></ul></li><li><a href="../3147/ib-core-1.html">IB Core</a><ul class="level-1"><li><a href="../3149/learner-profile-1.html">Learner Profile</a></li><li><a href="../21735/extended-essays--1.html" class="father">Extended Essays </a><ul class="level-2"><li><a href="../21736/overview--1.html">Overview </a></li><li><a href="../21780/responsibilities-1.html">Responsibilities</a></li><li><a href="../21790/resources-1.html">Resources</a></li><li><a href="../21800/research-1.html">Research</a></li><li><a href="../21804/writing-the-essay-1.html">Writing the essay</a></li><li><a href="../21810/assessment-1.html">Assessment</a></li><li><a href="../22434/summary-of-advice--1.html">Summary of advice </a></li><li><a href="../25272/faqs--1.html">FAQs </a></li></ul></li><li><a href="../307/theory-of-knowledge-tok-1.html" class="father">Theory of Knowledge (TOK)</a><ul 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options</a></li><li><a href="../24897/sl-quizzes-on-option-sub-topics--1.html">SL Quizzes on option sub-topics </a></li><li><a href="../17785/hl-multiple-choice-tests-on-individual-topics-1.html">HL Multiple choice tests on individual topics</a></li><li><a href="../24352/hl-multiple-choice-quizzes-on-sub-topics-1.html">HL Multiple choice 'quizzes' on sub-topics</a></li><li><a href="../31520/hl-practice-paper-1-exams--1.html">HL Practice Paper 1 exams </a></li><li><a href="../17787/hl-questions-on-each-sub-topic--1.html">HL Questions on each sub-topic </a></li><li><a href="../20428/hl-paper-3-section-a-questions-1.html">HL Paper 3 Section A questions</a></li><li><a href="../17793/hl-questions-on-the-options-1.html">HL Questions on the options</a></li><li><a href="../24973/hl-quizzes-on-option-sub-topics-1.html">HL Quizzes on option sub-topics</a></li><li><a href="../41573/printable-versions-of-written-tasks--1.html">Printable versions of written tasks </a></li></ul></li><li><a 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</div><section id="main-content"><h1>Background</h1><p>Optical isomerism is not on the core part of the programme but is in the AHL under topic <a href="../18844/stereoisomerism--1.html" title="Core & AHL » Teaching each topic & sub-topic » Topics 10 & 20 » Stereoisomerism ">20.3 Stereoisomerism</a>. It also appears in the extension material of Option B under AHL topic <a href="../19366/stereochemistry-in-biomolecules-1.html" title="Options » Option B » Stereochemistry in biomolecules">B.10 Stereochemistry in biomolecules</a> and in Option D under the AHL topic <a href="../19254/taxol-a-chiral-auxiliary-case-study-1.html" title="Options » Option D » Taxol - a chiral auxiliary case study">D.7 Taxol - a chiral auxiliary case study</a>. When covering topic 20 with Higher Level students, teachers need to teach students how to use wedge-dash type representations involving tapered bonds to represent optical isomers. They are also advised to construct real or virtual 3-D models for of a wide range of stereoisomers, although no specific examples are given. Most teachers will probably use simple examples such as butan-2-ol, 2-bromobutane and/or lactic acid (2-hydroxypropanoic acid).<br><br>Personally, I think the use of real models such as <a href="http://www.molymod.com/">molymod </a>are crucial to the understanding of optical isomerism. By using models students can quickly grasp that enantiomers are only possible if there is a chiral carbon atom – i.e. one that has four different groups attached to it. However when I mark examination papers I am surprised how few students can correctly draw the 3-D structures of enantiomers even though they obviously understand the concept.<br> </p><div class="blueBg"><h2>Ways to draw enantiomers correctly</h2><p>There are two ways students can be helped to draw the two enantiomers correctly.<br><br><strong>i. </strong>Draw one of the enantiomers showing the tetrahedral structure of the chiral carbon atom. For the second enantiomer keep two of the groups in exactly the same position and simply interchange the other two. (If more than two of the groups are interchanged it can be very easy to simply draw the same optical isomer twice).<br><br><strong>ii.</strong> Probably the easiest way is to draw one of the enantiomers showing the tetrahedral structure of the chiral atom with the forward and backward groups on the right. Draw an imaginary (or real) mirror then draw the second enantiomer with the same two groups reflecting in the mirror on the left.</p><p style="text-align: center"><img alt="" class="noborder" height="135" src="../../../ib/chemistry/images/Structures/enantiomers1.jpg" width="522"></p></div><p>Once students have grasped the idea of <span data-scayt-word="chirality" data-wsc-lang="en_US">chirality</span> then the data book can be used as a source of many more interesting examples than just <span data-scayt-word="butan-2-ol" data-wsc-lang="en_US">butan-2-ol</span>, <span data-scayt-word="2-bromobutane" data-wsc-lang="en_US">2-bromobutane</span> or <span data-scayt-word="2-hydoxypropanoic" data-wsc-lang="en_US">2-hydoxypropanoic</span> acid. Even if they are not studying options B or D students are familiar with many of the substances contained within them and can relate to them. The following are some of the possibilities:</p><hr class="hidden"><div class="box"><h2>Examples from the data booklet</h2><h3>Example <strong>1. 2-Amino acids</strong></h3><p>Simple condensation reactions between carboxylic acids and alcohols are part of the core content (10.2). Higher Level students studying Option A should know about the condensation reactions of carboxylic acids with amines to form condensation polymers and Standard Level students studying Option B cover the condensation reactions of amino acids to form proteins. Even though amino acids as such do not form part of the core or AHL programme they are important and it is not unreasonable to mention them in passing (particularly if the students are also studying Biology). Ask them to use Section 33 to identify the only amino acid that cannot show optical activity and draw the two enantiomers of alanine.</p><h3><strong>Example 2. Analgesics</strong></h3><p>Probably the one type of drug that all students will have taken is a pain-killer. Either aspirin, paracetamol (known as acetaminophen in the U.S.A.) or ibuprofen. Ask them to use the structures given in Section 37 to determine which one can show optical isomerism.</p><p style="text-align: center"><img alt="" class="noborder" height="255" src="../../../ib/chemistry/images/Structures/ibuprofen.jpg" width="109"></p><p style="text-align: center">Only ibuprofen can exist as enantiomers</p><p style="text-align: center"></p><h3><br><strong>Example 3. Vitamins</strong></h3><p>The structures of three different vitamins are given in Section 35. Ask you students which can show optical isomerism. The prominent black wedge shown on the vitamin C structure will probably give the game away for vitamin C but how many will spot that vitamin D contains five different chiral carbon atoms?</p><p style="text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/2014%20Basic%20information/vitamin-D.png" style="width: 312px; height: 262px;"></p><p style="text-align: center;">Vitamin D has five chiral carbon atoms</p><hr class="hidden"><h3><strong>Example 5. Straight chain sugars</strong></h3><p>Section 34 contains the structures of the open chain forms of both glucose and fructose. Glucose has four chiral centres whereas fructose only has three.</p><p style="text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/2014%20Basic%20information/glucose.png" style="width: 128px; height: 219px;"><span style="color:#0000FF;"> </span>Glucose (four chiral centres)<span style="color:#0000FF;"></span></p><hr class="hidden"><p style="text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/2014%20Basic%20information/Fructose.png" style="width: 120px; height: 223px;"> Fructose (three chiral centres)</p><h3><strong>Example 6. Amphetamines </strong></h3><p>The 2014 data booklet contains the structures of other chiral compounds such as zanamivir and taxol (both in Section 37). Another class of drugs that they may not have taken but they will have heard of are the amphetamines. Amphetamines mimic the action of adrenaline – the flight or fight hormone. The structures of both amphetamine and adrenaline are no longer in the data booklet (they were in Table 20 of the 2009 booklet). They are given in my blog on <a href="chemistry/blog/3151/plant-food-or-drug">Plant food or drug</a> along with the structures of the illegal drugs ecstasy and mephedrone. You could show them the structures and ask the whether they can exist as enantiomers and to label the chiral carbon atom with an asterisk (*).</p><p style="text-align: center"><img alt="" class="noborder" height="132" src="../../../ib/chemistry/images/Structures/adrenaline with chiral.jpg" width="215"> <img alt="" class="noborder" height="131" src="../../../ib/chemistry/images/Structures/amphetamine with chiral.jpg" width="180"></p><p style="text-align: center">Both can exist as optical isomers but the chiral carbon atom is different in the two<br>molecules.</p><p style="text-align: center"></p></div><p style="text-align: center"></p></section></article><section id="media-extras"><div class="page-actions no-print navbar inline hidden-desktop"><div class="navbar-inner"><ul class="nav"><li><a class="presentation" href="#" onclick="return false;"><i class="fa fa-desktop"></i></a></li><li><a class="print-section-blog" href="#" onclick="return false;"><i class="fa fa-print"></i></a></li><li><a class="page-bookmarker" data-ticket="IB Docs (2) Team" data-pid="17347" href="#" onclick="return false;"><i class="fa fa-star"></i></a></li><li><a class="personal-notes" href="#" onclick="return false;"><i class="fa fa-file-text"></i></a></li><li><a class="" data-toggle="modal" href="#modal-feedback" onclick="return false;"><i class="fa fa-envelope-o"></i></a></li><li class="dropdown"><a class="dropdown-toggle" data-toggle="dropdown" data-target="#" href="#"><i class="fa fa-share-alt"></i></a><ul class="dropdown-menu" role="menu"><li><a class="" target="_blank" title="Share on Twitter" href="https://twitter.com/share?text=%22Enantiomers+%22+-+via+%40InThinker+%23chemistry%0A&url=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F17347%2Fenantiomers-"><i class="fa fa-twitter-square"></i><span>Twitter</span></a></li><li><a class="" target="_blank" title="Share on Facebook" href="https://www.facebook.com/sharer.php?u=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F17347%2Fenantiomers-&t=Enantiomers+"><i class="fa fa-facebook-square"></i><span>Facebook</span></a></li><li><a class="" href="http://www.linkedin.com/shareArticle?mini=true&url=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F17347%2Fenantiomers-"><i class="fa fa-linkedin-square"></i><span>LinkedIn</span></a></li><li><a class="" href="https://plus.google.com/share?url=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F17347%2Fenantiomers-"><i class="fa fa-google-plus-square"></i><span>Google +</span></a></li><li><a class="" href="mailto:?subject=Enantiomers &body=Optical isomerism is not on the core part of the programme but is in the AHL under topic 20.3 Stereoisomerism. 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