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<title>DP Chemistry: Nucleophilic substitution </title>
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href="../19287/proteins-enzymes--1.html">Proteins & enzymes </a></li><li><a href="../19291/lipids-1.html">Lipids</a></li><li><a href="../19299/carbohydrates--1.html">Carbohydrates </a></li><li><a href="../19305/vitamins--1.html">Vitamins </a></li><li><a href="../19313/biochemistry-the-environment--1.html">Biochemistry & the environment </a></li><li><a href="../19336/proteins-enzymes-ahl--1.html">Proteins & enzymes (AHL) </a></li><li><a href="../19347/nucleic-acids--1.html">Nucleic acids </a></li><li><a href="../19361/biological-pigments--1.html">Biological pigments </a></li><li><a href="../19366/stereochemistry-in-biomolecules-1.html">Stereochemistry in biomolecules</a></li></ul></li><li><a href="../19390/option-c--1.html" class="father">Option C </a><ul class="level-2"><li><a href="../19391/energy-sources-1.html">Energy sources</a></li><li><a href="../19407/fossil-fuels-1.html">Fossil 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 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Chemistry?</a></li><li><a href="../3505/a-modern-paradigm-1.html">A modern paradigm</a></li></ul></li></ul></li><li><a href="../17783/fast-track-to-tests-questions-1.html">Fast track to tests & questions</a><ul class="level-1"><li><a href="../17784/sl-multiple-choice-tests-on-individual-topics-1.html">SL Multiple choice tests on individual topics</a></li><li><a href="../24351/sl-multiple-choice-quizzes-on-sub-topics-1.html">SL Multiple choice 'quizzes' on sub-topics</a></li><li><a href="../31519/sl-practice-paper-1-exams-1.html">SL Practice Paper 1 exams</a></li><li><a href="../17786/sl-questions-on-each-sub-topic-1.html">SL Questions on each sub-topic</a></li><li><a href="../20431/sl-paper-3-section-a-questions-1.html">SL Paper 3 Section A questions</a></li><li><a href="../17792/sl-questions-on-the-options-1.html">SL Questions on the 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 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class="expander fa fa-caret-right "></i><a href="../24660/mc-test-the-equilibrium-law-1.html" title="MC test: The equilibrium law">MC test: The equilibrium law</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../40961/equilibrium-law-questions-1.html" title="Equilibrium law questions">Equilibrium law questions</a></li></ul></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../18120/topics-8-18--1.html" title="Topics 8 & 18 ">Topics 8 & 18 </a></li><ul class="level-2 "><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18124/theories-of-acids-bases--1.html" title="Theories of acids & bases ">Theories of acids & bases </a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24662/mc-test-theories-of-acids-bases-1.html" title="MC test: Theories of acids & bases">MC test: Theories of acids & bases</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../40963/theories-of-acids-bases-questions-1.html" title="Theories of acids & bases questions">Theories of acids & bases questions</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18126/properties-of-acids-bases-1.html" title="Properties of acids & bases">Properties of acids & bases</a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24663/mc-test-properties-of-acids-bases--1.html" title="MC test: Properties of acids & bases ">MC test: Properties of acids & bases </a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../40964/properties-of-acids-bases-questions-1.html" title="Properties of acids & bases questions">Properties of acids & bases questions</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18140/ph-scale-1.html" title="pH scale">pH scale</a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24668/mc-test-the-ph-scale-1.html" title="MC test: The pH scale">MC test: The pH scale</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../40971/ph-scale-questions-1.html" title="pH scale questions">pH scale questions</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18152/strong-weak-acids-bases-1.html" title="Strong & weak acids & bases">Strong & weak acids & bases</a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24670/mc-test-strong-weak-acids-bases-1.html" title="MC test: Strong & weak acids & bases">MC test: Strong & weak acids & bases</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../40972/strong-weak-acid-bases-questions-1.html" title="Strong & weak acid & bases questions">Strong & weak acid & bases questions</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18156/acid-deposition-1.html" title="Acid deposition">Acid deposition</a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24674/mc-test-acid-deposition-1.html" title="MC test: Acid deposition">MC test: Acid deposition</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../40983/acid-deposition-questions-1.html" title="Acid deposition questions">Acid deposition questions</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18160/lewis-acids-bases-1.html" title="Lewis acids & bases">Lewis acids & bases</a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24710/mc-test-lewis-acids-bases-1.html" title="MC test: Lewis acids & bases">MC test: Lewis acids & bases</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../40986/lewis-acids-bases-questions-1.html" title="Lewis acids & bases questions">Lewis acids & bases questions</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18250/acid-base-calculations-1.html" title="Acid base calculations">Acid base calculations</a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24714/mc-test-calculations-involving-acids-bases--1.html" title="MC test: Calculations involving acids & bases ">MC test: Calculations involving acids & bases </a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../40988/acid-base-calculations-questions--1.html" title="Acid-base calculations questions ">Acid-base calculations questions </a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../26161/ph-titration-curves-1.html" title="pH titration curves">pH titration curves</a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../26158/mc-test-ph-curves-1.html" title="MC test: pH curves">MC test: pH curves</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41000/ph-curves-questions--1.html" title="pH curves questions ">pH curves questions </a></li></ul></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../18350/topics-9-19-1.html" title="Topics 9 & 19">Topics 9 & 19</a></li><ul class="level-2 "><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18365/oxidation-reduction-1.html" title="Oxidation & reduction">Oxidation & reduction</a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24725/mc-test-oxidation-reduction-1.html" title="MC test: Oxidation & reduction">MC test: Oxidation & reduction</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41033/oxidation-reduction-questions-1--1.html" title="Oxidation & reduction questions (1) ">Oxidation & reduction questions (1) </a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41034/oxidation-reduction-questions-2-1.html" title="Oxidation & reduction questions (2)">Oxidation & reduction questions (2)</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41035/oxidation-reduction-questions-3-1.html" title="Oxidation & reduction questions (3)">Oxidation & reduction questions (3)</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18383/electrochemical-cells-1.html" title="Electrochemical cells">Electrochemical cells</a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24740/mc-test-electrochemical-cells-1.html" title="MC test: Electrochemical cells">MC test: Electrochemical cells</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41072/electrochemical-cells-questions--1.html" title="Electrochemical cells questions ">Electrochemical cells questions </a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18401/electrochemical-cells-ahl--1.html" title="Electrochemical cells (AHL) ">Electrochemical cells (AHL) </a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24742/mc-test-electrochemical-cells-ahl-1.html" title="MC test: Electrochemical cells (AHL)">MC test: Electrochemical cells (AHL)</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41098/electrochemical-cells-1-ahl-questions-1.html" title="Electrochemical cells (1) (AHL) questions">Electrochemical cells (1) (AHL) questions</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41099/electrochemical-cells-2-ahl-questions-1.html" title="Electrochemical cells (2) (AHL) questions">Electrochemical cells (2) (AHL) questions</a></li></ul></ul><li class="ancestor parent" style="padding-left: 14px"><i class="expander fa fa-caret-right fa-rotate-90"></i><a href="../18475/topics-10-20--1.html" title="Topics 10 & 20 ">Topics 10 & 20 </a></li><ul class="level-2 expanded"><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18497/fundamentals-of-organic-chemistry--1.html" title="Fundamentals of organic chemistry ">Fundamentals of organic chemistry </a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24749/mc-test-fundamentals-of-organic-chemistry-1.html" title="MC test: Fundamentals of organic chemistry">MC test: Fundamentals of organic chemistry</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41111/fundamentals-of-organic-chemistry-1-questions-1.html" title="Fundamentals of organic chemistry (1) questions">Fundamentals of organic chemistry (1) questions</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41112/fundamentals-of-organic-chemistry-2-questions-1.html" title="Fundamentals of organic chemistry (2) questions">Fundamentals of organic chemistry (2) questions</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18597/alkanes-alkenes-addition-polymers-1.html" title="Alkanes, alkenes & addition polymers">Alkanes, alkenes & addition polymers</a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24750/mc-test-alkanes-alkenes-addition-polymers-1.html" title="MC test: Alkanes, alkenes & addition polymers">MC test: Alkanes, alkenes & addition polymers</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41121/alkanes-questions-1.html" title="Alkanes questions">Alkanes questions</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41124/alkenes-questions-1.html" title="Alkenes questions">Alkenes questions</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18741/alcohols--1.html" title="Alcohols ">Alcohols </a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24772/mc-test-alcohols-1.html" title="MC test: Alcohols">MC test: Alcohols</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41125/alcohols-questions-1.html" title="Alcohols questions">Alcohols questions</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18742/halogenoalkanes-benzene--1.html" title="Halogenoalkanes & benzene ">Halogenoalkanes & benzene </a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24797/mc-test-halogenoalkanes-benzene-1.html" title="MC test: Halogenoalkanes & benzene">MC test: Halogenoalkanes & benzene</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41130/halogenoalkanes-benzene-questions-1.html" title="Halogenoalkanes & benzene questions">Halogenoalkanes & benzene questions</a></li></ul><li class="current parent" style="padding-left: 28px"><i class="expander fa fa-caret-right fa-rotate-90"></i><a href="nucleophilic-substitution--1.html" title="Nucleophilic substitution ">Nucleophilic substitution </a></li><ul class="level-3 expanded"><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24757/mc-test-nucleophilic-substitution-1.html" title="MC test: Nucleophilic substitution">MC test: Nucleophilic substitution</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41138/nucleophilic-substitution-questions-1.html" title="Nucleophilic substitution questions">Nucleophilic substitution questions</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18766/electrophilic-addition--1.html" title="Electrophilic addition ">Electrophilic addition </a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24805/mc-test-electrophilic-addition-electrophilic-substitution-reacti-2.html" title="MC test: Electrophilic addition & electrophilic substitution reactions">MC test: Electrophilic addition & electrophilic substitution reactions</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41148/electrophilic-addition-questions-1.html" title="Electrophilic addition questions">Electrophilic addition questions</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18780/electrophilic-substitution--2.html" title="Electrophilic substitution ">Electrophilic substitution </a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41149/electrophilic-substitution-questions-1.html" title="Electrophilic substitution questions">Electrophilic substitution questions</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18793/reduction-reactions--1.html" title="Reduction reactions ">Reduction reactions </a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24811/mc-test-reduction-reactions-1.html" title="MC test: Reduction reactions">MC test: Reduction reactions</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41150/reduction-reactions-questions-1.html" title="Reduction reactions questions">Reduction reactions questions</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18797/synthetic-routes--1.html" title="Synthetic routes ">Synthetic routes </a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24822/mc-test-synthetic-routes-1.html" title="MC test: Synthetic routes">MC test: Synthetic routes</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41152/synthetic-routes-questions--1.html" title="Synthetic routes questions ">Synthetic routes questions </a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18844/stereoisomerism--1.html" title="Stereoisomerism ">Stereoisomerism </a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24817/mc-test-stereoisomerism-1.html" title="MC test: Stereoisomerism">MC test: Stereoisomerism</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41166/stereoisomerism-questions-1.html" title="Stereoisomerism questions">Stereoisomerism questions</a></li></ul></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../17285/topics-11-21--1.html" title="Topics 11 & 21 ">Topics 11 & 21 </a></li><ul class="level-2 "><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../17276/uncertainty-errors--1.html" title="Uncertainty & errors ">Uncertainty & errors </a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24818/mc-test-uncertainties-errors-1.html" title="MC test: Uncertainties & errors">MC test: Uncertainties & errors</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../38869/uncertainty-error-questions--1.html" title="Uncertainty & error questions ">Uncertainty & error questions </a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../15014/graphical-techniques-1.html" title="Graphical techniques">Graphical techniques</a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24819/mc-test-graphical-techniques-1.html" title="MC test: Graphical techniques">MC test: Graphical techniques</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39387/graphical-techniques-questions--1.html" title="Graphical techniques questions ">Graphical techniques questions </a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../18968/spectroscopic-identification-of-organic-compounds-1.html" title="Spectroscopic identification of organic compounds">Spectroscopic identification of organic compounds</a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24820/mc-test-spectroscopic-identification-of-organic-compounds--1.html" title="MC test: Spectroscopic identification of organic compounds ">MC test: Spectroscopic identification of organic compounds </a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39388/index-of-hydrogen-deficiency-questions-1.html" title="Index of hydrogen deficiency questions">Index of hydrogen deficiency questions</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39351/identification-from-spectra-question-1-1.html" title="Identification from spectra - Question 1">Identification from spectra - Question 1</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39353/identification-from-spectra-question-2-1.html" title="Identification from spectra - Question 2">Identification from spectra - Question 2</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39354/identification-from-spectra-question-3-1.html" title="Identification from spectra - Question 3">Identification from spectra - Question 3</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39355/identification-from-spectra-question-4-1.html" title="Identification from spectra - Question 4">Identification from spectra - Question 4</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39356/identification-from-spectra-question-5-1.html" title="Identification from spectra - Question 5">Identification from spectra - Question 5</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39357/identification-from-spectra-question-6-1.html" title="Identification from spectra - Question 6">Identification from spectra - Question 6</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39358/identification-from-spectra-question-7-1.html" title="Identification from spectra - Question 7">Identification from spectra - Question 7</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39359/identification-from-spectra-question-8-1.html" title="Identification from spectra - Question 8">Identification from spectra - Question 8</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39360/identification-from-spectra-question-9-1.html" title="Identification from spectra - Question 9">Identification from spectra - Question 9</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39361/identification-from-spectra-question-10-1.html" title="Identification from spectra - Question 10">Identification from spectra - Question 10</a></li></ul><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../19027/spectroscopic-identification-of-organic-compounds-ahl--1.html" title="Spectroscopic identification of organic compounds (AHL) ">Spectroscopic identification of organic compounds (AHL) </a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../24821/mc-test-spectroscopic-identification-of-organic-compounds-ahl-1.html" title="MC test: Spectroscopic identification of organic compounds (AHL)">MC test: Spectroscopic identification of organic compounds (AHL)</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39375/identification-from-spectra-question-11-1.html" title="Identification from spectra - Question 11">Identification from spectra - Question 11</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39376/identification-from-spectra-question-12-1.html" title="Identification from spectra - Question 12">Identification from spectra - Question 12</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39377/identification-from-spectra-question-13-1.html" title="Identification from spectra - Question 13">Identification from spectra - Question 13</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39378/identification-from-spectra-question-14-1.html" title="Identification from spectra - Question 14">Identification from spectra - Question 14</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39379/identification-from-spectra-question-15-1.html" title="Identification from spectra - Question 15">Identification from spectra - Question 15</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39380/identification-from-spectra-question-16-1.html" title="Identification from spectra - Question 16">Identification from spectra - Question 16</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39381/identification-from-spectra-question-17-1.html" title="Identification from spectra - Question 17">Identification from spectra - Question 17</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39382/identification-from-spectra-question-18-1.html" title="Identification from spectra - Question 18">Identification from spectra - Question 18</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39383/identification-from-spectra-question-19-1.html" title="Identification from spectra - Question 19">Identification from spectra - Question 19</a></li><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../39385/identification-from-spectra-question-20-1.html" title="Identification from spectra - Question 20">Identification from spectra - Question 20</a></li></ul></ul></ul><li class=" parent" style="padding-left: 0px"><i class="expander fa fa-caret-right "></i><a href="../16441/the-nature-of-science-1.html" title="The Nature of Science">The Nature of Science</a></li><ul class="level-1 "><li class="" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../16450/key-terms-concepts-1.html" title="Key terms & concepts">Key terms & concepts</a></li><li class="" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../34566/nos-critical-thinking-1.html" title="NOS & Critical Thinking">NOS & Critical Thinking</a></li><li class="" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../32100/how-the-elements-were-named-1.html" title="How the elements were named">How the elements were named</a></li><li class="" 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</div><section id="main-content"><div id="toc-1672972938" class="toc"><a href="#" class="toc-switcher" title="Show table of contents"><small><i class="fa fa-reorder"></i> Table of contents <span class="pull-right"><i class="fa fa-chevron-down"></i></span></small></a></div><h1><img class="ico" src="../../../img/icons/higher-1.png"> 20.1 Types of organic reactions (7 hours)</h1><h1>1. Nucleophilic substitution reactions (Estimated 2 hours)</h1><div class="pinkBg"><div><h2>Pause for thought</h2><p><strong>1. Use of curly arrows</strong></p><p>When teaching and describing organic mechanisms involving the use of curly arrows it is much clearer to use 3-D diagrams rather than 2-D diagrams. A curly arrow represents the movement of a pair of electrons from where they start to where they end up. If you only use a 2-D diagram this can cause considerable confusion. Consider the substitution of the bromine atom in bromoethane by the hydroxide nucleophile. Firstly the curly arrow should start from a lone pair on the oxygen atom of the hydroxide ion not from the hydrogen atom - but where should the arrowhead go? Some books show it going to the carbon atom but the pair of electrons ends up forming the bond <strong>between</strong> the carbon atom and the oxygen atom of the -OH group so the arrowhead should really be going there. In 2-D this is exactly where the electron pair between the carbon atom and the bromine atom is already located. So the diagram will look like this:</p><p style="text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/2014%20Core%20%26%20AHL/Topics-10---20/Sn2.jpeg" style="width: 574px; height: 150px;"></p><p>Although 'correct' in 2-D there are two big problems. The first is that the existing electron pair forming the C-Br bond will repel the incoming electrons and the second is that the angle between the C<sup>….</sup>OH and C<sup>....</sup>Br bonds in the transition state looks to be 90<sup>o</sup> or even less. In reality the hydroxide nucleophile will approach the δ+ carbon atom of the polar C—Br bond from the opposite side. This means that the bond angle between the C<sup>....</sup>OH and the C<sup>....</sup>Br bonds in the transition state will be 180<sup>o</sup>. This can easily be shown using a 3-D representation and avoids all the problems caused by a 2-D diagram.</p><p style="text-align: center;"><img alt="" class="noborder" height="125" src="../../../ib/chemistry/images/Exams/Curly%20arrow%20%285%29.jpg" title="The correct way to show the use of curly arrows. Diagram taken from the 2nd edition of my Chemistry Course Companion. " width="537"></p><p>Full details about using curly arrows correctly (and the common errors that students make) can be found on the page <a href="../16308/curly-arrows.html" title="New 2014 programme (First exams 2016) » Exams » Paper 2 » Areas of difficulty » 'Curly arrows'">'Curly arrows'</a> in <a href="../16307/areas-of-difficulty-1.html" title="New 2014 programme (First exams 2016) » Exams » Paper 2 » Areas of difficulty">Areas of difficulty</a>. It is worth talking about the work of Paul Walden (1863 - 1957), a Latvian chemist, who provided strong evidence for the S<sub>N</sub>2 mechanism using secondary halogenoalkanes. If an optically active halogenoalkane is used and the nucleophile does 'attack' from the other side then the product should rotate the plane of plane-polarized light in the opposite direction, which is indeed the case. This is known as <a href="../18420/topics-10-20-1.html" title="Core & AHL » Incorporating IM, TOK, 'Utilization' etc. » Topics 10 & 20">Walden inversion </a>and is a good way to bring some TOK into the lesson and also cover this part of the syllabus.</p><p style="text-align: center;"><img alt="" class="noborder" height="126" src="../../../ib/chemistry/images/Core%20and%20AHL/Walden%20inversion.jpg" title="Walden inversion" width="519"></p><hr class="hidden"><p><strong>2. How important are electron deficient carbon atoms?</strong></p><p>Chemistry is not always as simple and obvious as it would appear to be. When describing the mechanism for nucleophilic substitution it is usual to state that the nucleophile, which contains a non-bonding pair of electrons, is attracted to a carbon atom deficient in electrons in some way. This electron deficient carbon atom may be an actual positive ion as it is in the case of S<sub>N</sub>1 where the first step is the breaking of the carbon-halogen bond to form an intermediate carbocation. Alternatively it may be the carbon atom in the halogenoalkane which is electron deficient due to the more electronegative halogen atom and hence attracts the nucleophile as in the S<sub>N</sub>2 mechanism.</p><p>This is normally shown by using δ<sup>+</sup> and δ<sup>–</sup> with the nucleophile being attracted to the δ<sup>+</sup> on the carbon atom.</p><p style="text-align: center;"><img alt="" class="noborder" height="149" src="../../../ib/chemistry/images/Core and AHL/Organic/nucelophilic attack.jpg" title="Attack by a nucleophile on the polar C-Br bond" width="200"></p><p>It would seem logical that the stronger the polarity of the carbon-halogen bond the more the nucleophile will be attracted to the δ<sup>+</sup> carbon atom. The strength of the polarity will depend on the electronegativity of the halogen compared to the carbon atom. By far the most polar bond is the carbon to fluorine bond.</p><p style="text-align: center;">Difference in electronegativity values for the carbon-halogen bond</p><p style="text-align: center;"><img alt="" class="noborder" height="156" src="../../../ib/chemistry/images/Core and AHL/Organic/C-X electronegativities table.jpg" width="640"></p><p>On this logic alone one would expect nucleophiles to react most readily with fluoroalkanes and least readily with iodoalkanes. In fact exactly the reverse is the case. Fluoroalkanes are generally so unreactive that one of their main uses is as fire extinguishers and they are not even included in this sub-topic. From their own experimental work students will be able to see that 1-iodobutane, for example, reacts much faster with nucleophiles than 1-brombutane which in turn reacts much faster than 1-chlorobutane. This suggests that the polarity of the carbon atom is relatively insignificant and that some other factor must be dictating the ease of the reaction.<br><br>Even though the 'Application and skills' section uses the words 'Explanation of how the rate depends on the identity of the<br>halogen (i.e. the leaving group)', there is no mention in the 'Guidance' as to exactly what explanation is required. The syllabus and some books talk about the halogen being a 'leaving group' and it is the ease with which this group leaves that is the important factor, not the polarity of the bond. The ease with which the halogen leaves is, of course related to the strength of the carbon-halogen bond. Iodo- compounds are the most reactive because the carbon-iodine bond is very weak compared to the other carbon-halogen bonds. The fact that the carbon to fluorine bond is so strong accounts for the inertness of fluorocarbons even though they have high polarity.</p><p style="text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/2014%20Core%20%26%20AHL/Topics-10---20/C-X-bond-energies.jpg" style="width: 400px; height: 99px;"></p><p>One other interesting aside concerns the first 'Understandings' statement. It is easy to explain why the hydroxide ion is a better nucleophile than water but for reactions following the S<sub>N</sub>1 pathway the concentration of the nucleophile does not appear in the rate equation. It could be asked how important is the nature of the nucleophile in the substitution of tertiary halogenoalkanes?</p><hr class="hidden"></div></div><hr class="hidden"><div class="box"><div><div><h2 id="anchor-3">Nature of Science</h2><p>Organic reactions fall into a number of different categories. By understanding different types of organic reactions and their mechanisms, it is possible to synthesize new compounds with novel properties for use in diverse applications.<br>Collaboration between scientists on investigating the synthesis of organic compounds using new green chemistry pathways involves ethical and environmental implications.</p><hr class="hidden"></div></div></div><hr class="hidden"><div class="box"><table align="left" border="0" cellpadding="10" cellspacing="0"><tbody><tr><td style="width: 50%;" valign="top"><div class="yellowBg"><div><h2 id="anchor-4"><strong>Learning outcomes</strong></h2><p>After studying this sub-topic students should be able to:</p><p><strong>Understand:</strong></p><ul><li>Nucleophilic unimolecular substitution reactions are represented by S<sub>N</sub>1 and nucleophilic bimolecular substitution reactions are represented by S<sub>N</sub>2.</li><li>Carbocation intermediates are formed in S<sub>N</sub>1 reactions whereas S<sub>N</sub>2 reactions involve a concerted reaction with a transition state.</li><li>The predominant mechanism for tertiary halogenoalkanes is S<sub>N</sub>1 and for primary halogenoalkanes it is S<sub>N</sub>2. Secondary halogenoalkanes react by both mechanisms.</li><li>The rate determining step (slow step) for S<sub>N</sub>1 reactions depends only on the concentration of the halogenoalkane, rate = <em>k</em>[R−X]. For S<sub>N</sub>2 reactions, rate = k[R−X][Nu]. S<sub>N</sub>2 is stereospecific and involves inversion of configuration at the carbon atom.</li><li>S<sub>N</sub>2 reactions are favoured by aprotic, polar solvents and S<sub>N</sub>1 reactions are favoured by protic, polar solvents.</li></ul><p><strong>Apply their knowledge to:</strong></p><ul><li>Explain why a hydroxide ion is a better nucleophile than a water molecule.</li><li>Deduce the mechanism of the nucleophilic substitution reactions of halogenoalkanes with aqueous sodium hydroxide in terms of S<sub>N</sub>1 and S<sub>N</sub>2 reaction mechanisms.</li><li>Explain how the rate depends upon the identity of the leaving group (i.e. the halogen), whether the halogenoalkane is primary, secondary or tertiary and on the choice of solvent.</li><li>Outline the difference between protic and aprotic solvents.</li></ul></div></div></td><td style="width: 50%;" valign="top"><h4 id="anchor-5"><b><span style="font-weight: normal;"></span></b></h4><div class="yellowBg"><div><h4 id="anchor-5"><b><span style="font-weight: normal;"><strong>Clarification notes</strong></span></b></h4><p>Students should know the difference between homolytic and heterolytic fission and appreciate that S<sub>N</sub>1 reactions involve heterolytic fission.</p><hr class="hidden"><p>Emphasise the difference between the use of curly arrows and fish-hooks in reaction mechanisms.</p><hr class="hidden"><p>The use of partial charges (δ<sup>+</sup> and δ<sup>-</sup>) and 3-D (wedge-dash) representations should be used where appropriate in explaining reaction mechanisms.</p><hr class="hidden">Although typical conditions and reagents for all reactions should be known (e.g. catalysts, reducing agents, reflux etc.); more precise details, such as specific temperatures, do not need to be included.<hr class="hidden"><hr class="hidden"><h4>International-mindedness</h4><p>How important in the global context is organic chemistry to green and sustainable chemistry?</p></div></div></td></tr></tbody></table></div><hr class="hidden"><div class="box"><table align="left" border="0" cellpadding="10" cellspacing="0"><tbody><tr><td style="width: 50%;" valign="top"><h2><span style=""><b><span style="font-weight: normal;"><strong>Teaching tips</strong></span></b></span></h2><p><span style=""><span style="font-weight: normal;">If you have the luxury of being able to teach Higher Level students on their own rather than together with Standard Level students then it makes sense to cover all of nucleophilic substitution (sub-topics 10.2 and 20.1) in one go.</span></span></p><p>If you have already taught sub-topic 16.1 then it fits in well with rate equations, order of reaction and rate determining steps. Students need to grasp that S<sub>N</sub>1 depends only on the concentration of the halogenoalkane as the slow step is the breaking of the carbon to halogen bond to form a carbocation. With the S<sub>N</sub>2 mechanism both the halogenoalkane and the hydroxide ion are involved in the one step mechanism to form a transition state so the rate depends on the concentration of both of them.</p><p>Impress upon them the difference between a transition state (make sure they include the negative charge outside the square brackets when the hydroxide ion is the nucleophile) and a carbocation intermediate. It can be useful to get them to suggest why primary alcohols go via S<sub>N</sub>2 (room to get five groups around the central carbon atom) and tertiary halogenoalkanes go via S<sub>N</sub>1 (stability of the tertiary carbocation). Protic, polar solvents such as water or ethanol, favour S<sub>N</sub>1 as they support the formation of carbocations and halide ions whereas aprotic, polar solvents, such as propanone, favour the formation of the transition state formed during S<sub>N</sub>2 reactions. The chemistry guide has been inconsistent in how it has stated this which has caused problems so I have written more about this on the page <a href="../32529/factors-affecting-the-rate-of-nucleophilic-substitution-reaction.html" title="Exams » Paper 2 » Areas of difficulty » Factors affecting the rate of nucleophilic substitution reactions">Factors affecting the rate of nucleophilic substitution reactions</a> in <a href="../16307/areas-of-difficulty-1.html" title="Exams » Paper 2 » Areas of difficulty">Areas of difficulty.</a></p><p>There is no mention of other nucleophiles such as ammonia or cyanide ions on the syllabus. However I would include them and mention that substitution with ammonia can proceed further as the amines produced still contain a non-bonding pair of electrons so can continue to act as nucleophiles. It is also worth pointing out that using the cyanide ion as a nucleophile is a good way to increase the number of carbon atoms in the chain by one. The nitrile produced can then be hydrolysed by dilute hydrochloric acid to a carboxylic acid. Mention too that all nucleophiles act as Lewis bases.</p><p>Although arguably not on the syllabus you could also discuss why chlorobenzene is very unreactive towards nucleophiles.</p><hr class="hidden"></td><td style="width: 50%;" valign="top"><h4><b><span style="font-weight: normal; "><strong>Study guide</strong></span></b></h4><p style="margin: 0px 0px 1em; padding: 0px; color: rgb(0, 0, 0); font-size: 1em;"><img alt="" src="../../../ib/chemistry/images/2014%20Basic%20information/New%20cover.jpg" style="width: 67px; height: 96px;"></p><p style="margin: 0px 0px 1em; padding: 0px; color: rgb(0, 0, 0); font-size: 1em;"><b><span style="font-weight: normal;">Page </span></b><span style="font-weight: normal;">89 </span></p><hr class="hidden"><h2>Questions</h2><p>For ten 'quiz' multiple choice questions with the answers explained see <a href="../24757/mc-test-nucleophilic-substitution-1.html" title="Core & AHL » Teaching each topic & sub-topic » Topics 10 & 20 » Nucleophilic substitution » MC test: Nucleophilic substitution">MC test: Nucleophilic substitution</a>.</p><p style="margin: 0px 0px 1em; padding: 0px; color: rgb(0, 0, 0); font-size: 1em;">For short-answer questions which can be set as an assignment for a test, homework or given for self study together with model answers see <a href="../41138/nucleophilic-substitution-questions-1.html" title="Core & AHL » Teaching each topic & sub-topic » Topics 10 & 20 » Nucleophilic substitution » Nucleophilic substitution questions">Nucleophilic substitution questions</a>.</p><hr class="hidden"><h4><span style=""><b><span style="font-weight: normal;"><strong>Vocabulary list</strong></span></b></span></h4><p>'curly' arrow<br>heterolytic fission<br>S<sub>N</sub>1 (unimolecular nucleophilic substitution)<br>S<sub>N</sub>2 (bimolecular nucleophilic substitution)<br>carbocation<br>transition state<br>protic solvent<br>aprotic solvent</p><hr class="hidden"><h4 id="anchor-11"><strong><strong>IM, TOK, Utilization etc.</strong></strong></h4><p>See <a href="../18420/topics-10-20-1.html" title="New 2014 programme (First exams 2016) » Core & AHL » Incorporating IM, TOK, 'Utilization' etc. » Topics 10 & 20">separate page </a>which covers all of Topics 10 & 20.</p><hr class="hidden"><h2><strong>Practical work</strong></h2><p><a href="../18752/hydrolysis-of-halogenoalkanes-1.html"><img class="ico" src="../../../img/icons/lab-1.png"> Hydrolysis of halogenoalkanes</a></p></td></tr></tbody></table></div><hr class="hidden"><div class="greenBg"><h2 id="header-14">Teaching slides</h2><p>Teachers may wish to share these slides with students for learning or for reviewing key concepts.</p><div id="myCarousel-15" class="carousel slide" data-id="318"><!-- Carousel items --><div class="carousel-inner"><div class="active item"><a class="fancy" href="/files/tib-galleries/3-318/1.png" rel="gallery-318" title=""><img alt="" src="/files/tib-galleries/3-318/1.png"></a><div class="carousel-caption"><p>Nucleophilic substitution reactions: </p></div></div><div class="item"><a class="fancy" href="/files/tib-galleries/3-318/2.png" rel="gallery-318" title=""><img alt="" src="/files/tib-galleries/3-318/2.png"></a><div class="carousel-caption"><p>Nucleophilic substitution reactions: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-318/2013.png" rel="gallery-318" title=""><img alt="" src="files/tib-galleries/3-318/2013.png"></a><div class="carousel-caption"><p>Nucleophilic substitution reactions: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-318/2014.png" rel="gallery-318" title=""><img alt="" src="files/tib-galleries/3-318/2014.png"></a><div class="carousel-caption"><p>Nucleophilic substitution reactions: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-318/2015.png" rel="gallery-318" title=""><img alt="" src="files/tib-galleries/3-318/2015.png"></a><div class="carousel-caption"><p>Nucleophilic substitution reactions: </p></div></div><div class="item"><a class="fancy" href="/files/tib-galleries/3-318/6.png" rel="gallery-318" title=""><img alt="" src="/files/tib-galleries/3-318/6.png"></a><div class="carousel-caption"><p>Nucleophilic substitution reactions: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-318/2017.png" rel="gallery-318" title=""><img alt="" src="files/tib-galleries/3-318/2017.png"></a><div class="carousel-caption"><p>Nucleophilic substitution reactions: </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-318/2018.png" rel="gallery-318" title=""><img alt="" src="files/tib-galleries/3-318/2018.png"></a><div class="carousel-caption"><p>Nucleophilic substitution reactions: </p></div></div><div class="item"><a class="fancy" href="/files/tib-galleries/3-318/9.png" rel="gallery-318" title=""><img alt="" src="/files/tib-galleries/3-318/9.png"></a><div class="carousel-caption"><p>Nucleophilic substitution reactions: </p></div></div></div><!-- Carousel nav --><a class="carousel-control left" href="#myCarousel-15" data-slide="prev">‹</a><a class="carousel-control right" href="#myCarousel-15" data-slide="next">›</a><div class="tib-indicators"><img class="" title="Click to view" style="margin: 10px 4px; width: 48px; height: 48px;" alt="" src="/files/tib-galleries/3-318/1-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="/files/tib-galleries/3-318/2-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-318/2013-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-318/2014-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-318/2015-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="/files/tib-galleries/3-318/6-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-318/2017-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-318/2018-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="/files/tib-galleries/3-318/9-thumb128.jpg"></div></div><p> </p></div><hr class="hidden"><div class="blueBg"><h2><span style="font-weight: bold;">Other resources</span></h2><p><strong>1.</strong> I've made a small slideshow on<a href="/media/ib/chemistry/files/Powerpoints/Problems%20with%20Curly%20arrows.ppsx"> </a>Problems with using 'curly arrows'.</p><div id="myCarousel-16" class="carousel slide" data-id="317"><!-- Carousel items --><div class="carousel-inner"><div class="active item"><a class="fancy" href="../../../tib-galleries/3-317/ca1.png" rel="gallery-317" title=""><img alt="" src="files/tib-galleries/3-317/ca1.png"></a><div class="carousel-caption"><p>Problems using 'curly arrows': </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-317/ca2.png" rel="gallery-317" title=""><img alt="" src="files/tib-galleries/3-317/ca2.png"></a><div class="carousel-caption"><p>Problems using 'curly arrows': </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-317/ca3.png" rel="gallery-317" title=""><img alt="" src="files/tib-galleries/3-317/ca3.png"></a><div class="carousel-caption"><p>Problems using 'curly arrows': </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-317/ca4.png" rel="gallery-317" title=""><img alt="" src="files/tib-galleries/3-317/ca4.png"></a><div class="carousel-caption"><p>Problems using 'curly arrows': </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-317/ca5.png" rel="gallery-317" title=""><img alt="" src="files/tib-galleries/3-317/ca5.png"></a><div class="carousel-caption"><p>Problems using 'curly arrows': </p></div></div><div class="item"><a class="fancy" href="../../../tib-galleries/3-317/ca6.png" rel="gallery-317" title=""><img alt="" src="files/tib-galleries/3-317/ca6.png"></a><div class="carousel-caption"><p>Problems using 'curly arrows': </p></div></div></div><!-- Carousel nav --><a class="carousel-control left" href="#myCarousel-16" data-slide="prev">‹</a><a class="carousel-control right" href="#myCarousel-16" data-slide="next">›</a><div class="tib-indicators"><img class="" title="Click to view" style="margin: 10px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-317/ca1-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-317/ca2-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-317/ca3-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-317/ca4-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-317/ca5-thumb128.jpg"><img class="" title="Click to view" style="margin: 5px 4px; width: 48px; height: 48px;" alt="" src="files/tib-galleries/3-317/ca6-thumb128.jpg"></div></div><p> </p><hr class="hidden"><p><strong>2.</strong> A rather long (13 minutes) but quite thorough account of S<sub>N</sub>1 and S<sub>N</sub>2 and the factors affecting their rate from ChemSurvival. (You will need to explain what <em>tert-</em>butyl means.)</p><p style="text-align: center;"><iframe allowfullscreen="" frameborder="0" height="280" src="https://www.youtube.com/embed/QAyriElN-30?rel=0" width="360"><br></iframe></p><p style="text-align: center;"><a href="http://youtu.be/QAyriElN-30">S<sub>N</sub>1 and S<sub>N</sub>2 reactions <img class="ico" src="../../../img/icons/video-1.png"><span class="anchor" id="video-1" name="video-1"> </span></a></p><p style="text-align: center;"></p><hr class="hidden"><p><strong>3.</strong> S<sub>N</sub>1 reactions are actually explained (rather than just described) in this good video by Surrey University.</p><hr class="hidden"><p style="text-align: center"><iframe allowfullscreen="" frameborder="0" height="280" src="https://www.youtube.com/embed/JmcVgE2WKBE" width="360"></iframe></p><p style="text-align: center;"><a href="http://youtu.be/JmcVgE2WKBE" target="_blank" title="Videos"><img class="ico" src="../../../img/icons/video-1.png"><span class="anchor" id="video-2" name="video-2"> </span> S<sub>N</sub>1 mechanism </a></p><hr class="hidden"><p><strong>4. </strong>A similarly good explanation by Surrey University of the S<sub>N</sub>2 reaction mechanism.</p><p style="text-align: center"><iframe allowfullscreen="" frameborder="0" height="280" src="https://www.youtube.com/embed/h5xvaP6bIZI" width="360"></iframe></p><p style="text-align: center;"><a href="http://youtu.be/h5xvaP6bIZI" target="_blank" title="Videos"><img class="ico" src="../../../img/icons/video-1.png"><span class="anchor" id="video-3" name="video-3"> </span> S<sub>N</sub>2 mechanism </a></p><hr class="hidden"><p>5. Richard Thornley shows how ammonia can act as a nucleophile and how the product in turn can act as a nucleophile to form primary, secondary, tertiary and quaternary amines.</p><p style="text-align: center;"><iframe allowfullscreen="" frameborder="0" height="280" src="https://www.youtube.com/embed/z0ryePkDfrg?rel=0" width="360"><br></iframe></p><p style="text-align: center;"><a href="http://youtu.be/z0ryePkDfrg">Ammonia as a nucleophile <img class="ico" src="../../../img/icons/video-1.png"><span class="anchor" id="video-4" name="video-4"> </span></a></p><hr class="hidden"><p style="text-align: center;"></p><p style="text-align: center; "></p></div></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="18762" 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=%22Nucleophilic+substitution+%22+-+via+%40InThinker+%23chemistry%0A&url=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F18762%2Fnucleophilic-substitution-"><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%2F18762%2Fnucleophilic-substitution-&t=Nucleophilic+substitution+"><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%2F18762%2Fnucleophilic-substitution-"><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%2F18762%2Fnucleophilic-substitution-"><i class="fa fa-google-plus-square"></i><span>Google +</span></a></li><li><a class="" href="mailto:?subject=Nucleophilic substitution &body=1. 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