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<title>DP Chemistry: 20.1(1) 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 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 href="../16314/advice-to-students-paper-3-1.html">Advice to students (Paper 3)</a></li><li><a href="../16342/data-response-questions-1.html">Data response questions</a></li><li><a href="../20054/experimental-work-questions-1.html">Experimental work questions</a></li></ul></li><li><a href="../16324/the-examination-process-1.html" class="father">The examination process</a><ul class="level-2"><li><a href="../16316/setting-the-exam-papers-1.html">Setting the exam papers</a></li><li><a href="../16317/predicted-grades-1.html">Predicted grades</a></li><li><a href="../16318/marking-the-papers-1.html">Marking the papers</a></li><li><a href="../16319/commenting-on-the-exams-1.html">Commenting on the exams</a></li><li><a href="../16320/grade-awarding-1.html">Grade Awarding</a></li><li><a href="../16321/enquiry-upon-results-1.html">Enquiry upon results</a></li><li><a href="../16322/chief-examiners-report-1.html">Chief Examiner's report</a></li><li><a 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 class="level-2"><li><a href="../41171/the-12-tok-concepts-1.html">The 12 TOK concepts</a></li><li><a href="../3507/why-tok-chemistry-1.html">Why TOK & 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 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 class="selected"><a href="../41465/complete-course-for-students--2.html">Complete course for students </a><ul class="level-1"><li 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<nav id="sidemenu" class="side-nav"><div class="header"><span style="color: #fff;"><a href="../41465/complete-course-for-students--2.html">Complete course for students </a></span><span id="sidetreecontrol"><a title="Collapse all" rel="collapse" href="#"><i class="fa fa-minus-circle"></i></a> <a title="Expand all" rel="expand" href="#"><i class="fa fa-plus-circle"></i></a></span></div><ul class="level-0 always-expanded"><li class="ancestor parent" style="padding-left: 0px"><i class="expander fa fa-caret-right fa-rotate-90"></i><a href="../27988/full-coverage-of-each-topic-and-sub-topic-2.html" title="Full coverage of each topic and sub-topic">Full coverage of each topic and sub-topic</a></li><ul class="level-1 expanded"><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../27959/topic-1-stoichiometric-relationships-1.html" title="Topic 1 : Stoichiometric relationships">Topic 1 : Stoichiometric relationships</a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27947/11-particulate-nature-of-matter-and-chemical-change--1.html" title="1.1 Particulate nature of matter and chemical change ">1.1 Particulate nature of matter and chemical change </a></li><li class=" parent" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27954/12-the-mole-concept-1.html" title="1.2 The mole concept">1.2 The mole concept</a></li><ul class="level-3 "><li class="" style="padding-left: 42px"><i class="expander fa fa-caret-right "></i><a href="../41469/comprehending-avogadros-constant-1.html" title="Comprehending Avogadro's constant">Comprehending Avogadro's constant</a></li></ul><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27958/13-reacting-masses-and-volumes--1.html" title="1.3 Reacting masses and volumes ">1.3 Reacting masses and volumes </a></li></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../27960/topics-2-12-atomic-structure-1.html" title="Topics 2 & 12 : Atomic structure">Topics 2 & 12 : Atomic structure</a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27961/21-the-nuclear-atom--1.html" title="2.1 The nuclear atom ">2.1 The nuclear atom </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27962/22-electron-configuration--1.html" title="2.2 Electron configuration ">2.2 Electron configuration </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27963/121-electrons-in-atoms--1.html" title="12.1 Electrons in atoms ">12.1 Electrons in atoms </a></li></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../27965/topics-3-13-periodicity-1.html" title="Topics 3 & 13 : Periodicity">Topics 3 & 13 : Periodicity</a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27966/31-the-periodic-table-1.html" title="3.1 The periodic table">3.1 The periodic table</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27967/32-periodic-trends--1.html" title="3.2 Periodic trends ">3.2 Periodic trends </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27968/131-first-row-d-block-elements-1.html" title="13.1 First-row d-block elements">13.1 First-row d-block elements</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27970/132-coloured-complexes-1.html" title="13.2 Coloured complexes">13.2 Coloured complexes</a></li></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../27971/topics-4-14-chemical-bonding-structure-1.html" title="Topics 4 & 14 : Chemical bonding & structure">Topics 4 & 14 : Chemical bonding & structure</a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27972/41-ionic-bonding-structure--1.html" title="4.1 Ionic bonding & structure ">4.1 Ionic bonding & structure </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27973/42-covalent-bonding-1.html" title="4.2 Covalent bonding">4.2 Covalent bonding</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27974/43-covalent-structures-1--1.html" title="4.3 Covalent structures (1) ">4.3 Covalent structures (1) </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27980/43-covalent-structures-2--1.html" title="4.3 Covalent structures (2) ">4.3 Covalent structures (2) </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27981/44-intermolecular-forces--1.html" title="4.4 Intermolecular forces ">4.4 Intermolecular forces </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27982/45-metallic-bonding--1.html" title="4.5 Metallic bonding ">4.5 Metallic bonding </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27983/141-further-aspects-of-covalent-bonding-1.html" title="14.1 Further aspects of covalent bonding">14.1 Further aspects of covalent bonding</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27985/142-hybridization-1.html" title="14.2 Hybridization">14.2 Hybridization</a></li></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../27987/topics-5-15-energeticsthermochemistry-1.html" title="Topics 5 & 15 : Energetics/thermochemistry">Topics 5 & 15 : Energetics/thermochemistry</a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27989/51-measuring-energy-changes-1.html" title="5.1 Measuring energy changes">5.1 Measuring energy changes</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27991/52-hesss-law-1.html" title="5.2 Hess's Law">5.2 Hess's Law</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27992/53-bond-enthalpies--1.html" title="5.3 Bond enthalpies ">5.3 Bond enthalpies </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27993/151-energy-cycles-1.html" title="15.1 Energy cycles">15.1 Energy cycles</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27994/152-entropy-spontaneity-1.html" title="15.2 Entropy & spontaneity">15.2 Entropy & spontaneity</a></li></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../27995/topics-6-16-chemical-kinetics-1.html" title="Topics 6 & 16 : Chemical kinetics">Topics 6 & 16 : Chemical kinetics</a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27996/61-collision-theory-rates-of-reaction-1.html" title="6.1 Collision theory & rates of reaction">6.1 Collision theory & rates of reaction</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27997/161-rate-expression-reaction-mechanism-1.html" title="16.1 Rate expression & reaction mechanism">16.1 Rate expression & reaction mechanism</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27998/162-activation-energy-1.html" title="16.2 Activation energy">16.2 Activation energy</a></li></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../28001/topics-7-17-equilibrium--1.html" title="Topics 7 & 17 : Equilibrium ">Topics 7 & 17 : Equilibrium </a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../27999/71-equilibrium-1.html" title="7.1 Equilibrium">7.1 Equilibrium</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28000/171-equilibrium-law-1.html" title="17.1 Equilibrium law">17.1 Equilibrium law</a></li></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../28017/topics-8-18-acids-and-bases--1.html" title="Topics 8 & 18 : Acids and bases ">Topics 8 & 18 : Acids and bases </a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28002/81-theories-of-acids-bases-1.html" title="8.1 Theories of acids & bases">8.1 Theories of acids & bases</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28010/82-properties-of-acids-bases-1.html" title="8.2 Properties of acids & bases">8.2 Properties of acids & bases</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28011/83-ph-scale-1.html" title="8.3 pH scale">8.3 pH scale</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28012/84-strong-weak-acids-bases-1.html" title="8.4 Strong & weak acids & bases">8.4 Strong & weak acids & bases</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28013/85-acid-deposition--1.html" title="8.5 Acid deposition ">8.5 Acid deposition </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28014/181-lewis-acids-bases--1.html" title="18.1 Lewis acids & bases ">18.1 Lewis acids & bases </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28015/182-calculations-involving-acids-bases--1.html" title="18.2 Calculations involving acids & bases ">18.2 Calculations involving acids & bases </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28016/183-ph-titration-curves-1.html" title="18.3 pH titration curves">18.3 pH titration curves</a></li></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../28031/topics-9-19-redox-process-1.html" title="Topics 9 & 19 : Redox process">Topics 9 & 19 : Redox process</a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28021/91-oxidation-reduction-1.html" title="9.1 Oxidation & reduction">9.1 Oxidation & reduction</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28022/92-electrochemical-cells-1.html" title="9.2 Electrochemical cells">9.2 Electrochemical cells</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28023/191-electrochemical-cells-ahl-1.html" title="19.1 Electrochemical cells (AHL)">19.1 Electrochemical cells (AHL)</a></li></ul><li class="ancestor parent" style="padding-left: 14px"><i class="expander fa fa-caret-right fa-rotate-90"></i><a href="../28061/topics-10-20-organic-chemistry-1.html" title="Topics 10 & 20 : Organic chemistry">Topics 10 & 20 : Organic chemistry</a></li><ul class="level-2 expanded"><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28042/101-fundamentals-of-organic-chemistry-1.html" title="10.1 Fundamentals of organic chemistry">10.1 Fundamentals of organic chemistry</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28043/1021-alkanes-alkenes-addition-polymers-1.html" title="10.2(1) Alkanes, alkenes & addition polymers">10.2(1) Alkanes, alkenes & addition polymers</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28044/1022-alcohols--1.html" title="10.2(2) Alcohols ">10.2(2) Alcohols </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28047/1023-halogenoalkanes-benzene-1.html" title="10.2(3) Halogenoalkanes & benzene">10.2(3) Halogenoalkanes & benzene</a></li><li class="current" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="2011-nucleophilic-substitution--1.html" title="20.1(1) Nucleophilic substitution ">20.1(1) Nucleophilic substitution </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28051/2012-electrophilic-addition--1.html" title="20.1(2) Electrophilic addition ">20.1(2) Electrophilic addition </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28053/2013-electrophilic-substitution-1.html" title="20.1(3) Electrophilic substitution">20.1(3) Electrophilic substitution</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28054/2014-reduction-reactions--1.html" title="20.1(4) Reduction reactions ">20.1(4) Reduction reactions </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28056/202-synthetic-routes--1.html" title="20.2 Synthetic routes ">20.2 Synthetic routes </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28059/203-stereoisomerism--1.html" title="20.3 Stereoisomerism ">20.3 Stereoisomerism </a></li></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../28038/topics-11-21-measurement-data-processing-analysis-1.html" title="Topics 11 & 21 : Measurement, data processing & analysis">Topics 11 & 21 : Measurement, data processing & analysis</a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28032/111-uncertainty-errors--1.html" title="11.1 Uncertainty & errors ">11.1 Uncertainty & errors </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28033/112-graphical-techniques-1.html" title="11.2 Graphical techniques">11.2 Graphical techniques</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28034/113-spectroscopic-identification-of-organic-compounds-1.html" title="11.3 Spectroscopic identification of organic compounds">11.3 Spectroscopic identification of organic compounds</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28039/211-spectroscopic-identification-of-organic-compounds-ahl-1.html" title="21.1 Spectroscopic identification of organic compounds (AHL)">21.1 Spectroscopic identification of organic compounds (AHL)</a></li></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../28074/option-a-materials--1.html" title="Option A : Materials ">Option A : Materials </a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28062/a1-introduction-to-materials-science--1.html" title="A.1 Introduction to materials science ">A.1 Introduction to materials science </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28063/a2-metals-and-icp-spectroscopy-1.html" title="A.2 Metals and ICP spectroscopy">A.2 Metals and ICP spectroscopy</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28065/a3-catalysts--1.html" title="A.3 Catalysts ">A.3 Catalysts </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28066/a4-liquid-crystals-1.html" title="A.4 Liquid crystals">A.4 Liquid crystals</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28067/a5-polymers-1.html" title="A.5 Polymers">A.5 Polymers</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28069/a6-nanotechnology-1.html" title="A.6 Nanotechnology">A.6 Nanotechnology</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28070/a7-environmental-impact-plastics-1.html" title="A.7 Environmental impact - plastics">A.7 Environmental impact - plastics</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28071/a8-superconducting-metals-x-ray-crystallography--1.html" title="A.8 Superconducting metals & X-ray crystallography ">A.8 Superconducting metals & X-ray crystallography </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28072/a9-condensation-polymers-1.html" title="A.9 Condensation polymers">A.9 Condensation polymers</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28073/a10-environmental-impact-heavy-metals-1.html" title="A.10 Environmental impact - heavy metals">A.10 Environmental impact - heavy metals</a></li></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../28087/option-b-biochemistry-1.html" title="Option B : Biochemistry">Option B : Biochemistry</a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28076/b1-introduction-to-biochemistry--1.html" title="B.1 Introduction to biochemistry ">B.1 Introduction to biochemistry </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28078/b2-proteins-enzymes-1.html" title="B.2 Proteins & enzymes">B.2 Proteins & enzymes</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28079/b3-lipids-1.html" title="B.3 Lipids">B.3 Lipids</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28080/b4-carbohydrates-1.html" title="B.4 Carbohydrates">B.4 Carbohydrates</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28081/b5-vitamins-1.html" title="B.5 Vitamins">B.5 Vitamins</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28082/b6-biochemistry-the-environment-1.html" title="B.6 Biochemistry & the environment">B.6 Biochemistry & the environment</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28083/b7-proteins-enzymes-ahl--1.html" title="B.7 Proteins & enzymes (AHL) ">B.7 Proteins & enzymes (AHL) </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28084/b8-nucleic-acids-1.html" title="B.8 Nucleic acids">B.8 Nucleic acids</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28085/b9-biological-pigments-1.html" title="B.9 Biological pigments">B.9 Biological pigments</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28086/b10-stereochemistry-in-biomolecules-1.html" title="B.10 Stereochemistry in biomolecules">B.10 Stereochemistry in biomolecules</a></li></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../28098/option-c-energy--1.html" title="Option C : Energy ">Option C : Energy </a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28088/c1-energy-sources--1.html" title="C.1 Energy sources ">C.1 Energy sources </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28089/c2-fossil-fuels-1.html" title="C.2 Fossil fuels">C.2 Fossil fuels</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28090/c3-nuclear-fusion-nuclear-fission-reactions-1.html" title="C.3 Nuclear fusion & nuclear fission reactions">C.3 Nuclear fusion & nuclear fission reactions</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28091/c4-solar-energy--1.html" title="C.4 Solar energy ">C.4 Solar energy </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28094/c5-environmental-impact-global-warming--1.html" title="C.5 Environmental impact - global warming ">C.5 Environmental impact - global warming </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28095/c6-electrochemistry-rechargeable-batteries-fuel-cells-1.html" title="C.6 Electrochemistry, rechargeable batteries & fuel cells">C.6 Electrochemistry, rechargeable batteries & fuel cells</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28096/c7-nuclear-fusion-fission-hl--1.html" title="C.7 Nuclear fusion & fission (HL) ">C.7 Nuclear fusion & fission (HL) </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28097/c8-photovoltaic-cells-and-dsscs-1.html" title="C.8 Photovoltaic cells and DSSCs">C.8 Photovoltaic cells and DSSCs</a></li></ul><li class=" parent" style="padding-left: 14px"><i class="expander fa fa-caret-right "></i><a href="../28109/option-d-medicinal-chemistry-1.html" title="Option D : Medicinal chemistry">Option D : Medicinal chemistry</a></li><ul class="level-2 "><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28099/d1-pharmaceutical-products-drug-action--1.html" title="D.1 Pharmaceutical products & drug action ">D.1 Pharmaceutical products & drug action </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28100/d2-aspirin-penicillin-1.html" title="D.2 Aspirin & penicillin">D.2 Aspirin & penicillin</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28101/d3-opiates-1.html" title="D.3 Opiates">D.3 Opiates</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28103/d4-ph-regulation-of-the-stomach-1.html" title="D.4 pH regulation of the stomach">D.4 pH regulation of the stomach</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28102/d5-antiviral-medications-1.html" title="D.5 Antiviral medications">D.5 Antiviral medications</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28104/d6-environmental-impact-of-some-medications-1.html" title="D.6 Environmental impact of some medications">D.6 Environmental impact of some medications</a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28105/d7-taxol-a-chiral-auxiliary-case-study--1.html" title="D.7 Taxol - a chiral auxiliary case study ">D.7 Taxol - a chiral auxiliary case study </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28107/d8-nuclear-medicine--1.html" title="D.8 Nuclear medicine ">D.8 Nuclear medicine </a></li><li class="" style="padding-left: 28px"><i class="expander fa fa-caret-right "></i><a href="../28108/d9-drug-detection-analysis-1.html" title="D.9 Drug detection & analysis">D.9 Drug 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</div><section id="main-content"><div id="toc-1672969268" 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><p>Written specifically for students to provide help and support for the IB Diploma chemistry <span data-scayt-word="programme" data-wsc-lang="en_US">programme</span> this page provides full coverage of nucleophilic substitution, the first part of the syllabus content of Topic 20.1 Types of organic reactions. It encourages you to think critically and provides many questions with full worked answers so that you can monitor and improve your knowledge and understanding.</p><hr class="hidden"><div class="box"><h2><img alt="" src="../../../ib/chemistry/images/student-learning/sn2-sn1(1).png" style="width: 1px; height: 1px;"><img alt="" height="21" src="../../../img/tib-icons/higher-level-32-1.png" title="" width="21"> Learning outcomes</h2><p><img alt="" class="noborder" src="../../../ib/chemistry/images/student-learning/sn2-sn1(1).png" style="float: right; width: 499px; height: 388px;">After studying this sub-topic you 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 your 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><hr class="hidden"><div class="blueBg"><h2>Relationships & vocabulary</h2><h4>Nature of science</h4><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"><h4>International-mindedness</h4><p>How important in the global context is organic chemistry to green and sustainable chemistry?</p><hr class="hidden"><p>For more examples and links to <em>International mindedness, Theory of knowledge, utilization etc. </em>see <a href="../18420/topics-10-20-1.html" title="Core & AHL » Incorporating IM, TOK, 'Utilization' etc. » Topics 4 & 14 ">separate page</a> which covers all of Topics 10 & 20 : Organic chemistry.</p><hr class="hidden"><h4>Vocabulary</h4><table><tbody><tr><td>'curly' arrow</td><td>heterolytic fission</td><td>S<sub>N</sub>1 (unimolecular nucleophilic substitution)</td><td>protic solvent</td></tr><tr><td>carbocation</td><td>transition state</td><td>S<sub>N</sub>2 (bimolecular nucleophilic substitution)</td><td>aprotic solvent</td></tr></tbody></table><hr class="hidden"></div><hr class="hidden"><div class="greenBg"><h2 id="header-6">Learning slides</h2><p>You can use this slide gallery for learning or for reviewing concepts and information. It covers all the key points in the syllabus for this sub-topic.</p><div id="myCarousel-17" 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-17" data-slide="prev">‹</a><a class="carousel-control right" href="#myCarousel-17" 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="pinkBg"><div><h2>Something to think about</h2><p><strong>1. Use of curly arrows</strong></p><p>When 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><hr class="hidden"><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><hr class="hidden"><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><hr class="hidden"><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><hr class="hidden"><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 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><hr class="hidden"><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><hr class="hidden"><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><hr class="hidden"><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><hr class="hidden"><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><hr class="hidden"><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 your own experimental work you should 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><hr class="hidden"><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><hr class="hidden"><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="yellowBg"><h2 id="header-8">Test your understanding of this topic</h2><p><em>(Note that your teacher may have restricted your access to some or all of these questions and worked answers if they are going to use them as a class test or set them as an assignment.)</em></p><hr class="hidden"><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 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"></div><hr class="hidden"><div class="blueBg"><h2><span style="font-weight: bold;">More 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 know that <em>tert-</em>butyl is the old name for the −C(CH<sub>3</sub>)<sub>3</sub> group.)</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"></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="28050" 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=%2220.1%281%29+Nucleophilic+substitution+%22+-+via+%40InThinker+%23chemistry%0A&url=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F28050%2F2011-nucleophilic-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%2F28050%2F2011-nucleophilic-substitution-&t=20.1(1)+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%2F28050%2F2011-nucleophilic-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%2F28050%2F2011-nucleophilic-substitution-"><i class="fa fa-google-plus-square"></i><span>Google +</span></a></li><li><a class="" href="mailto:?subject=20.1(1) Nucleophilic substitution &body=Written specifically for students to provide help and support for the IB Diploma chemistry programme this page provides full coverage of nucleophilic substitution, the first part of the syllabus content of Topic 20.1 Types...%0Ahttps%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F28050%2F2011-nucleophilic-substitution-"><i class="fa fa-envelope"></i><span>Email</span></a></li></ul></li><li><a class="" href="chemistry/teaching-materials"><i class="fa fa-puzzle-piece colored"></i></a></li></ul></div></div><div style="border-top: solid 1px #eee;border-bottom: solid 1px #eee;padding: 4px 0 4px 0;line-height: 1em;color: #666;font-size: .8em"><small><em>All materials on this website are for the exclusive use of teachers and students at subscribing schools for the period of their subscription. 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