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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 class="selected"><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 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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><a 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</div><section id="main-content"><p>This page explains how the nature of the halogen, whether the halogenoalkane is primary, secondary or tertiary and the choice of solvent can all affect the rate of substitution reactions of halogenoalkanes with nucleophiles such as the hydroxide ion. It reinforces chemistry given elsewhere on the site but in particular looks in detail at why protic polar solvents are preferred for S<sub>N</sub>1 reactions whereas aprotic polar solvents are preferred for S<sub>N</sub>2 reactions. </p><hr class="hidden"><div class="blueBg"><h1 class="MsoNormal"><img alt="" height="21" src="../../../img/tib-icons/higher-level-32-1.png" title="" width="21"> The three factors affecting the rate</h1><p class="MsoNormal">Apart from the identity of the nucleophile itself, there are three main factors which affect the rate of nucleophilic substitution of halogenoalkanes.</p><hr class="hidden"><h2 class="MsoNormal">1. The nature of the halogen</h2><p style="text-align: center;">RX + NaOH → ROH + NaX (X = Cl, Br or I)</p><p class="MsoNormal"><span style="mso-spacerun:yes"></span>Iodoalkanes react faster than bromoalkanes which in turn react faster than chloroalkanes. This is due to the strength of the carbon to halogen bond. The C−I bond is the weakest and the C−Cl bond is the strongest so iodine is the better leaving group as less energy is required to break the carbon to halogen bond heterolytically. (Note that the C−F is so strong that fluoroalkanes do not undergo nucleophilic substitution reactions.)</p><p class="MsoNormal" style="text-align: center;"><img alt="" class="noborder" src="../../../ib/chemistry/images/Exams/c-halogen-bond-enthalpies-2.png" style="width: 320px; height: 112px;"><br>(Taken from Section 11 in the IB data booklet)</p><hr class="hidden"><h2 class="MsoNormal">2. Whether the halogenoalkane is primary, secondary or tertiary</h2><p class="MsoNormal"><br>Nucleophilic substitution of tertiary halogenoalkanes proceeds by the S<sub>N</sub>1 mechanism so that the rate equation is rate = <em>k</em>[R−X] and does not involve the concentration of the nucleophile. The first (slow) step involves the breaking of the carbon to halogen bond to leave a carbonium ion (a positive carbon atom bonded to hydrogen atoms or other alkyl groups). The positive inductive effect of the surrounding alkyl groups increases the stability the intermediate carbonium ion making it more likely to form. Hence the order of reaction is:</p><hr class="hidden"><p class="MsoNormal" style="text-align: center;"><span style="mso-spacerun:yes"></span><span style="mso-spacerun:yes"> </span>tertiary halogenoalkane > secondary halogenoalkane > primary halogenoalkane</p><hr class="hidden"><p class="MsoNormal">Note that primary halogenoalkanes proceed by the S<sub>N</sub>2 mechanism and secondary halogenoalkanes can proceed by both mechanisms. S<sub>N</sub>1 reactions are generally faster than S<sub>N</sub>2 reactions.</p><hr class="hidden"><p class="MsoNormal">(See the slide gallery on<span style="mso-spacerun:yes"> <a href="../18762/nucleophilic-substitution--1.html" title="Core & AHL » Teaching each topic & sub-topic » Topics 10 & 20 » Nucleophilic substitution ">Nucleophilic substitution</a> </span>for fuller explanations of the first two factors and to refresh your understanding of the S<sub>N</sub>1 and S<sub>N</sub>2 mechanisms including the evidence for the S<sub>N</sub>2 mechanism from Walden inversion. You may also wish to refresh your understand of the correct use of <a href="../16308/curly-arrows.html" title="Exams » Paper 2 » Areas of difficulty » 'Curly arrows'">'Curly arrows'</a>)</p><hr class="hidden"><h2 class="MsoNormal">3. The choice of solvent</h2><p>This is the factor that students (and teachers) have the most problem with. Partly this is because the IB itself has been inconsistent with the way in which it is detailed in the chemistry guide.</p><p class="MsoNormal">In some ways it is not too easy to explain the choice of solvent at IB level as the only nucleophiles specifically mentioned in the syllabus are the hydroxide ion and water. Other nucleophiles such as cyanide ions, CN<sup>−</sup> and ammonia, NH<sub>3</sub> are not referred to in the guide. Similarly no specific examples of protic and aprotic solvents are given. What students need to know is that both S<sub>N</sub>1 and S<sub>N</sub>2 reactions are best carried out in polar solvents but protic solvents should be used for S<sub>N</sub>1 reactions whereas aprotic solvents should be used for S<sub>N</sub>2 reactions<sup>1</sup>. According to the guide students do not need to be able to explain this as under the ‘Application and skills” part of 20.1 they are only required to be able to outline the difference between protic and aprotic solvents rather than explain why different solvents affect the rate of nucleophilic substitution. However it may well help them in their understanding if an explanation is given.</p><hr class="hidden"><p class="MsoNormal">The reason why polar solvents are required for both S<sub>N</sub>1 and S<sub>N</sub>2 reactions is that they help to stabilises the carbocation intermediate in S<sub>N</sub>1 reactions and the transition state in S<sub>N</sub>2 reactions as both involve ions. They also help to dissolve the nucleophile as nucleophiles either have a negative charge (e.g. OH<sup>­−</sup>) or are polar themselves (e.g. H<sub>2</sub>O or NH<sub>3</sub>). However the more polar the solvent the more it solvates the nucleophile which paradoxically makes the nucleophile less nucleophilic. This is not a problem in S<sub>N</sub>1 reactions as the first step does not involve the nucleophile. The nucleophile is attracted to the carbonium ion intermediate once it has been formed in the first slower step. In S<sub>N</sub>2 reactions though the nucleophile is involved in the first (slow) step where it is attracted to the central carbon atom which only has a small positive charge.</p><hr class="hidden"><p class="MsoNormal">The difference between protic and aprotic is basically the ability of the solvent to form hydrogen bonds. Protic solvents such as water and ethanol contain O−H bonds and the proton develops a significant positive charge due to the much greater electronegativity of the oxygen atom. The protic hydrogen can strongly interact with anions, whereas the non-bonding pair of electrons on the oxygen atom can stabilize cations. Polar aprotic solvents, such as propanone, CH<sub>3</sub>COCH<sub>3</sub>, are still polar enough to dissolve charged species (such as halide and hydroxide ions) but do not form hydrogen bonds as they posess no δ<sup>+</sup> protons. In S<sub>N</sub>1 reactions polar protic solvents can help to stabilise the leaving group so that the nucleophile is able to interact with the intermediate carbocation. Aprotic solvents can still help to dissolve the nucleophile but do not solvate the nucleophile as much as protic solvents so in S<sub>N</sub>2 reactions the nucleophile can be attracted to the central <span style="mso-ascii-font-family:Cambria;mso-hansi-font-family:
Cambria">δ+ </span>carbon atom to form the transition state with five groups surrounding the central carbon atom.</p><hr class="hidden"><p class="MsoNormal"><span style="font-family:Arial"> <sup>1</sup> </span>There is a problem with the current pdf version of the guide (I’m writing this in September 2021) as it actually has the statement wrong. It is written as “S<sub>N</sub>2 reactions are best conducted using aprotic, <b>non-</b>polar solvents and S<sub>N</sub>1reactions are best conducted using protic, polar solvents”, even though the statement is given correctly in the html version. In fact when the guide was first published it did state wrongly that “S<sub>N</sub>2 reactions are best conducted using aprotic, non-polar solvents”. This was then corrected to “S<sub>N</sub>2 reactions are best conducted using aprotic, polar solvents” in revised editions (e.g. in the updated February 2015 version) but the mistake has now crept back in again in the latest pdf version available to download on My IB (updated August 2018).</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="32529" 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=%22Factors+affecting+the+rate+of+nucleophilic+substitution+reactions%22+-+via+%40InThinker+%23chemistry%0A&url=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F32529%2Ffactors-affecting-the-rate-of-nuceophilic-substitution-reactions"><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%2F32529%2Ffactors-affecting-the-rate-of-nuceophilic-substitution-reactions&t=Factors+affecting+the+rate+of+nucleophilic+substitution+reactions"><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%2F32529%2Ffactors-affecting-the-rate-of-nuceophilic-substitution-reactions"><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%2F32529%2Ffactors-affecting-the-rate-of-nuceophilic-substitution-reactions"><i class="fa fa-google-plus-square"></i><span>Google +</span></a></li><li><a class="" href="mailto:?subject=Factors affecting the rate of nucleophilic substitution reactions&body=This page explains how the nature of the halogen, whether the halogenoalkane is primary, secondary or tertiary and the choice of solvent can all affect the rate of substitution reactions of halogenoalkanes with nucleophiles...%0Ahttps%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F32529%2Ffactors-affecting-the-rate-of-nuceophilic-substitution-reactions"><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. Any unauthorised copying or posting of materials on other websites is an infringement of our copyright and could result in your account being blocked and legal action being taken against you.</em></small></div></section><section id="comments"></section></div><!-- /#main-column -->
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