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	<title>DP Chemistry: Hydrolysis of halogenoalkanes</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 class="selected"><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">&#039;Scaffolding&#039; 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 class="selected"><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&#039;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 class="selected"><a href="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&#039;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 &#039;quizzes&#039; 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 &#039;quizzes&#039; 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 href="../41465/complete-course-for-students--2.html">Complete course for students </a><ul class="level-1"><li><a href="../27988/full-coverage-of-each-topic-and-sub-topic-2.html" class="father">Full coverage of each topic and sub-topic</a><ul class="level-2"><li><a href="../27959/topic-1-stoichiometric-relationships-1.html">Topic 1 : Stoichiometric relationships</a></li><li><a href="../27960/topics-2-12-atomic-structure-1.html">Topics 2 & 12 : Atomic structure</a></li><li><a href="../27965/topics-3-13-periodicity-1.html">Topics 3 & 13 : Periodicity</a></li><li><a href="../27971/topics-4-14-chemical-bonding-structure-1.html">Topics 4 & 14 : Chemical bonding & structure</a></li><li><a href="../27987/topics-5-15-energeticsthermochemistry-1.html">Topics 5 & 15 : Energetics/thermochemistry</a></li><li><a href="../27995/topics-6-16-chemical-kinetics-1.html">Topics 6 & 16 : Chemical kinetics</a></li><li><a href="../28001/topics-7-17-equilibrium--1.html">Topics 7 & 17 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</div><section id="main-content"><div class="blueBg"><h1><img alt="" height="21" src="../../../img/tib-icons/standard-level-32-1.png" title="" width="21"> <img alt="" height="21" src="../../../img/tib-icons/higher-level-32-1.png" title="" width="21"> Introduction</h1><p>The study of the <span data-scayt-word="nucleophilic" data-wsc-lang="en_US">nucleophilic</span> substitution reactions of <span data-scayt-word="halogenoalkanes" data-wsc-lang="en_US">halogenoalkanes</span> cuts right across the Core and the Additional Higher Level material on the syllabus. In sub-topic 10.2 Standard Level students need to be able to describe with equations the substitution reactions of <span data-scayt-word="halogenoalkanes" data-wsc-lang="en_US">halogenoalkanes</span> with aqueous sodium hydroxide and they also need to understand what a <span data-scayt-word="nucleophile" data-wsc-lang="en_US">nucleophile</span> is and the concept of <span data-scayt-word="nucleophilic" data-wsc-lang="en_US">nucleophilic</span> substitution. In sub-topic 20.1 Higher Level students need to be able to explain these substitution reactions in terms of S<sub>N</sub>1 and S<sub>N</sub>2 mechanisms. This means that HL students need to understand the concept of &lsquo;curly arrows&rsquo;. Higher Level students also need to be able to explain the effect of changing the <span data-scayt-word="nucleophile" data-wsc-lang="en_US">nucleophile</span><sup>1</sup>, changing the alcohol from primary to secondary to tertiary and changing the halogen from chlorine to bromine to iodine on the rate of <span data-scayt-word="nucleophilic" data-wsc-lang="en_US">nucleophilic</span> substitution. Through this practical students investigate all these effects; it therefore covers almost all the HL material as well as the SL. However, SL students should be able to understand much of the HL material especially the use of bond enthalpies to explain why <span data-scayt-word="iodoalkanes" data-wsc-lang="en_US">iodoalkanes</span> react faster than <span data-scayt-word="chloroalkanes" data-wsc-lang="en_US">chloroalkanes</span>. In fact this theory can then be extended to explain why <span data-scayt-word="fluorohydrocarbons" data-wsc-lang="en_US">fluorohydrocarbons</span> make good fire extinguishers. All the explanations and mechanisms for these reactions can be found in Chapter 10 of the<a href="http://global.oup.com/education/product/9780198393535/?region=uk"> IB Study Guide</a>.</p><hr class="hidden"><h4>Footnote</h4><p><sup>1</sup> <em>A student once said to me that she understood why the hydroxide ion is a better nucleophile than water as it is a negative ion and much more highly charged. She then went on to comment that she could not see that the nature of the nucleophile would make any difference with tertiary halogenoalkanes as these proceed by an S<sub>N</sub>1 mechanism. In other words, the nature of the nucleophile should have no effect on the rate of the reaction as the nucleophile does not appear in the rate equation. What would your response be to this?</em></p><hr class="hidden"></div><hr class="hidden"><div class="greenBg"><h1 class="MsoNormal">Teacher&#39;s notes</h1><p>The first set of experiments are actually a revision (UK) review (USA) of the reactions of halide ions with silver nitrate which students have already seen in the <a href="../17239/the-halogens-1.html">practical on Group 17</a>. This is to <span data-scayt-word="emphasise" data-wsc-lang="en_US">emphasise</span> that silver ions only form a precipitate with halide ions. When the halogen atom is covalently bonded to a carbon atom then no precipitation with silver ions will occur.</p><p>In one sense this practical does not fit sub-topic 10.2 as the <span data-scayt-word="nucleophile" data-wsc-lang="en_US">nucleophile</span> is not sodium hydroxide. The hydroxide ion is too good a <span data-scayt-word="nucleophile" data-wsc-lang="en_US">nucleophile</span> for this reaction and no obvious difference would be observed between <span data-scayt-word="1-chlorobutane" data-wsc-lang="en_US">1-chlorobutane</span> and <span data-scayt-word="1-iodobutane" data-wsc-lang="en_US">1-iodobutane</span> as they would both react very fast. For this reason a deliberately poor <span data-scayt-word="nucleophile" data-wsc-lang="en_US">nucleophile</span> is used so that the changes can easily be seen. In fact the <span data-scayt-word="iodoalkane" data-wsc-lang="en_US">iodoalkane</span> will react immediately, the <span data-scayt-word="bromoalkane" data-wsc-lang="en_US">bromoalkane</span> will form a precipitate within five minutes and the <span data-scayt-word="chloroalkane" data-wsc-lang="en_US">chloroalkane</span> will still not have reacted by the end of the five minute period. It will also be seen that the tertiary <span data-scayt-word="bromoalkane" data-wsc-lang="en_US">bromoalkane</span> reacts much faster than the primary <span data-scayt-word="bromoalkane" data-wsc-lang="en_US">bromoalkane</span> with the secondary <span data-scayt-word="bromoalkane" data-wsc-lang="en_US">bromoalkane</span> intermediate.</p><hr class="hidden"><p class="MsoNormal">There are two good explanations as to why <span data-scayt-word="bromobenzene" data-wsc-lang="en_US">bromobenzene</span> is so unreactive towards <span data-scayt-word="nucleophilic" data-wsc-lang="en_US">nucleophilic</span> attack. One is that the <span data-scayt-word="delocalised" data-wsc-lang="en_US">delocalised</span> pi electrons in the benzene ring repel the <span data-scayt-word="nucleophile" data-wsc-lang="en_US">nucleophile</span> and the other is that the pi electrons in the ring <span data-scayt-word="delocalise" data-wsc-lang="en_US">delocalise</span> with a non-bonding pair of electrons on the bromine atom making the carbon to bromine bond (C&minus;Br) much stronger and therefore more difficult to break.</p><hr class="hidden"><p class="MsoNormal"><img alt="" class="right" height="275" src="../../../ib/chemistry/images/Practicals/dioxins%20in%20Vietnam.jpg" title="Dioxins used during the Vietnam War" width="448">This set of reactions has been designed to work well. It perhaps typifies a really good Chemistry experiment which demonstrates the theory and asks students searching questions to ensure that they fully understand the underlying Chemistry. It can also be used to exemplify some social and ethical issues as one famous <span data-scayt-word="chloro-organic" data-wsc-lang="en_US">chloro-organic</span> compound is dioxin. Many students will have heard of dioxin. It was infamously used in the Vietnam War during the 1960 and <span data-scayt-word="1970s" data-wsc-lang="en_US">1970s</span>. The Americans used it in a compound called &lsquo;Agent Orange&rsquo;. It was not chemical warfare as such because it was used as a defoliant rather than specifically targeted against people but it had the unfortunate affect of causing many birth deformities. I took the photograph when I visited the War Remnant Museum in Ho Chi Minh City (formerly known as Saigon).</p><hr class="hidden"></div><hr class="hidden"><div class="box"><h2 class="MsoNormal"><img alt="Standard Level" class="ico" src="../../../img/icons/standard-1.png" title="Standard Level"> <img alt="Higher Level" class="ico" src="../../../img/icons/higher-1.png" title="Higher Level"> Student worksheet</h2><hr class="hidden"><p align="center"><strong>HYDROLYSIS OF </strong><strong>HALOGENOALKANES</strong></p><hr class="hidden"><p>Halogenoalkanes react with an aqueous solution of hydroxide ions according to the equation:</p><p>RX + OH<sup>&minus;</sup> &rarr; ROH + X<sup>&minus; </sup>( X = Cl, Br or I)</p>The following experiments examine the effect on the rate of hydrolysis when (a) the halogen is changed and (b) primary, secondary and tertiary <span data-scayt-word="halogenoalkanes" data-wsc-lang="en_US">halogenoalkanes</span> and a <span data-scayt-word="halogenoarene" data-wsc-lang="en_US">halogenoarene</span> are used. Ethanol is used both as a good solvent and as a rather poor hydrolysis agent in place of hydroxide ions which tend to react too quickly for comparisons to be made.<hr class="hidden"><p><strong>ENVIRONMENTAL CARE:</strong></p><p>The aqueous residues will contain the heavy metal ions of Ag<sup>+</sup> and the organic residues will contain halogenated hydrocarbons so it important not to dispose of any waste down the sink. Place all residues in the marked beaker in the fume cupboard. At the end of the practical the two immiscible layers in the combined waste can be separated and the aqueous layer transferred to the &#39;heavy metals waste&#39; container and the remainder to the &#39;Organic Waste&#39; container.</p><hr class="hidden"><p><strong>SAFETY:</strong></p><p>As only small quantities are being used there are no particular hazards associated with this practical. However it is worth noting that some chlorinated organic compounds e.g. dioxin, 2,4,<span data-scayt-word="5-trichlorophenoxyethanoic" data-wsc-lang="en_US">5-trichlorophenoxyethanoic</span> acid (Agent Orange) and polychlorinated <span data-scayt-word="biphenyls" data-wsc-lang="en_US">biphenyls</span> (PCB&#39;s) can be extremely poisonous.</p><hr class="hidden"><p><strong>PROCEDURE:</strong></p><p><strong>(a) </strong>Add a few drops of silver nitrate solution with a concentration of 0.05 mol dm<sup>-3</sup> to separate aqueous solutions of <span data-scayt-word="NaCl" data-wsc-lang="en_US">NaCl</span>, <span data-scayt-word="NaBr" data-wsc-lang="en_US">NaBr</span> and NaI.</p><p><strong>(b)</strong> Repeat the above experiment by adding silver nitrate to a few drops of <span data-scayt-word="1-bromobutane" data-wsc-lang="en_US">1-bromobutane</span>. Do not confuse a water/oil emulsion with a solid precipitate.</p><p><strong>(c)</strong> This is a more quantitative experiment to compare the rates of hydrolysis. In each of three test-tubes place 1 cm<sup>3</sup> of ethanol. Using separate teat pipettes place 2 drops of <span data-scayt-word="1-chlorobutane" data-wsc-lang="en_US">1-chlorobutane</span> in the first test-tube, 2 drops of <span data-scayt-word="1-bromobutane" data-wsc-lang="en_US">1-bromobutane</span> in the second and 2 drops of <span data-scayt-word="1-iodobutane" data-wsc-lang="en_US">1-iodobutane</span> in the third. Stand all three test-tubes in a beaker of water at about 60-65 <sup>o</sup>C and place another test-tube containing about 5 cm<sup>3</sup> of 0.05 mol dm<sup>-3</sup> silver nitrate solution in the warm water. Wait until the contents of all the test-tubes have reached approximately 60 <sup>o</sup>C and then place 1 cm<sup>3</sup> of the silver nitrate solution into each of the other test-tubes, and quickly shake each tube to mix the contents. Note and time carefully what you observe throughout the next five minutes.</p><p><strong>(d) </strong>Repeat the above experiment using <span data-scayt-word="bromobenzene" data-wsc-lang="en_US">bromobenzene</span>, <span data-scayt-word="2-bromobutane" data-wsc-lang="en_US">2-bromobutane</span> and 2-bromo-2-methylpropane.</p><hr class="hidden"><p><strong>QUESTIONS</strong></p><strong>1. </strong>What types of reagents (<span data-scayt-word="electrophiles" data-wsc-lang="en_US">electrophiles</span> or <span data-scayt-word="nucleophiles" data-wsc-lang="en_US">nucleophiles</span>) react with halogenoalkanes? Explain your answer in terms of the polarity of the carbon-halogen bond.<p>&nbsp;<br><strong>2.</strong> Explain the significance of experiments (a) and (b).<br><br><strong>3.</strong> Does the higher temperature have an effect on the reaction with <span data-scayt-word="1-bromobutane" data-wsc-lang="en_US">1-bromobutane</span> ? Explain.<br><br><strong>4. </strong>Does changing the halogen atom affect the rate of hydrolysis? If so, explain why.<br><br><strong>5.</strong> Place the different <span data-scayt-word="bromo" data-wsc-lang="en_US">bromo</span>- compounds in increasing order of their rates of hydrolysis and try to explain the order.</p><hr class="hidden"></div><hr class="hidden"><p class="MsoNormal" style="text-align:justify"><span style="font-size:10.0pt"></span></p><p class="MsoNormal">This worksheet can also be downloaded from:</p><p class="MsoNormal"><a href="/media/ib/chemistry/files/practicals/HYDROLYSIS-OF-HALOGENOALKANES.pdf"><img alt="Standard Level" class="ico" src="../../../img/icons/standard-1.png" title="Standard Level"> <img alt="Higher Level" class="ico" src="../../../img/icons/higher-1.png" title="Higher Level"> Hydrolysis of halogenoalkanes <img class="ico" src="../../../img/icons/exercise-1.png"> </a></p><p class="MsoNormal"></p></section></article><section id="media-extras"><div class="page-actions no-print navbar inline hidden-desktop"><div class="navbar-inner"><ul class="nav"><li><a class="presentation" href="#" onclick="return false;"><i class="fa fa-desktop"></i></a></li><li><a class="print-section-blog" href="#" onclick="return false;"><i class="fa fa-print"></i></a></li><li><a class="page-bookmarker" data-ticket="IB Docs (2) Team" data-pid="18752" 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=%22Hydrolysis+of+halogenoalkanes%22+-+via+%40InThinker+%23chemistry%0A&url=https%3A%2F%2Fwww.thinkib.net%2Fchemistry%2Fpage%2F18752%2Fhydrolysis-of-halogenoalkanes"><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%2F18752%2Fhydrolysis-of-halogenoalkanes&t=Hydrolysis+of+halogenoalkanes"><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%2F18752%2Fhydrolysis-of-halogenoalkanes"><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%2F18752%2Fhydrolysis-of-halogenoalkanes"><i class="fa fa-google-plus-square"></i><span>Google +</span></a></li><li><a class="" href="mailto:?subject=Hydrolysis of halogenoalkanes&body=The study of the nucleophilic substitution reactions of halogenoalkanes cuts right across the Core and the Additional Higher Level material on the syllabus. 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