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title="Suggested study time: 30 minutes"><i class="fa fa-clock-o"></i> 30'</span> </ol> <article id="main-article"> <p><strong>Topic 21.1</strong></p> <p><strong>Paper 1 style questions </strong>are multiple choice. You are <strong>not permitted to use a calculator or the data book</strong> for these questions, but you should use a periodic table.</p> <p>A <strong>periodic table pop-up</strong> is available on the left hand menu.</p> <div class="greenBg"> <div class="tib-quiz" data-stats="7-888-2776"><div class="label label-default q-number">1</div><div class="exercise shadow-bottom"><div class="q-question"><p>Which technique might be used to determine the bond lengths and bond angles in solid benzene?</p></div><div class="q-answer"><p><label class="radio"> <input type="radio"> <span>Infrared spectroscopy</span></label> </p><p><label class="radio"> <input class="c" type="radio"> <span>X-ray crystallography</span></label> </p><p><label class="radio"> <input type="radio"> <span>Nuclear magnetic resonance spectroscopy</span></label> </p><p><label class="radio"> <input type="radio"> <span>Mass spectrometry</span></label> </p></div><div class="q-explanation"><p>X-ray crystallography is a method of determining crystal structures. X-rays are fired at a crystal sample and diffract to create three dimensional patterns and pictures that crystallographers can read and decipher to give information about the arrangements of particles and electron density in substances:</p><p>Bond lengths and bond angles are determined with x-ray crystallography.</p><p>The other techniques give a lot of information about the structure of organic compounds, but do not tend to give direct information about bond lengths and angles.</p><p><strong>X-ray crystallography</strong> is the correct answer.</p></div><div class="actions"><span class="score" data-score="0"></span><button class="btn btn-default btn-sm btn-xs-block text-xs-center check"><i class="fa fa-check-square-o"></i> Check</button></div></div><div class="label label-default q-number">2</div><div class="exercise shadow-bottom"><div class="q-question"><p>Which can be identified in a molecule using infrared (IR) spectroscopy?</p></div><div class="q-answer"><p><label class="radio"><input type="radio"> The molecular mass</label></p><p><label class="radio"><input type="radio"> The bond lengths and angles</label></p><p><label class="radio"><input type="radio"> The number of hydrogen environments</label></p><p><label class="radio"><input class="c" type="radio"> The presence of a carbonyl group</label></p></div><div class="q-explanation"><p>Infrared (IR) spectroscopy is used to identify the bonds that are present in a molecule. This allows the identification of potential functional groups.</p><p><strong>The presence of a carbonyl group</strong> is therefore the correct answer.</p><p>The number of hydrogen environments could be determined by <sup>1</sup>H-NMR; The molecular mass by Mass Spectrometry; Bond lengths and angles by X-ray Crystallography.</p></div><div class="actions"><span class="score" data-score="0"></span><button class="btn btn-default btn-sm btn-xs-block text-xs-center check"><i class="fa fa-check-square-o"></i> Check</button></div></div><div class="label label-default q-number">3</div><div class="exercise shadow-bottom"><div class="q-question"><p>Which technique would be the most effective method to distinguish between 2-chloropropane and 1-chloropropane?</p></div><div class="q-answer"><p><label class="radio"><input type="radio"> IR spectroscopy</label></p><p><label class="radio"><input type="radio"> Mass spectrometry</label></p><p><label class="radio"><input type="radio"> Reaction with AgNO<sub>3</sub>(aq) and ethanol</label></p><p><label class="radio"><input class="c" type="radio"> <sup>1</sup>H-NMR spectroscopy</label></p></div><div class="q-explanation"><p><sup>1</sup><strong>H-NMR spectroscopy</strong> is the correct answer, as this would be the most effective technique: 1-chloropropane would exhibit three hydrogen environments (3:2:2) and 2-chloropropane would exhibit two hydrogen environments (6:1) as it is symmetrical (also the splitting patterns would be very different).</p><p>Infrared (IR) spectroscopy is used to identify the bonds that are present in a molecule. This allows the identification of potential functional groups, but would not easily distinguish between 2-chloropropane and 1-chloropropane.</p><p>Mass spectrometry, in the hands of skilled practitioner could be used, as the fragmentation patterns of the molecules would be different, but it would not be the most effective technique.</p><p>Reaction with silver nitrate solution, AgNO<sub>3</sub>(aq) and ethanol, would generate a white precipitate (AgCl(s)) but would not distinguish between 2-chloropropane and 1-chloropropane.</p></div><div class="actions"><span class="score" data-score="0"></span><button class="btn btn-default btn-sm btn-xs-block text-xs-center check"><i class="fa fa-check-square-o"></i> Check</button></div></div><div class="label label-default q-number">4</div><div class="exercise shadow-bottom"><div class="q-question"><p>Which compound gives this <sup>1</sup>H-NMR spectrum?</p><p><img alt="" src="../../images/measurement-and-data/e-nmr.png" style="width: 480px; height: 357px;"></p></div><div class="q-answer"><p><label class="radio"> <input type="radio"> CH<sub>3</sub>CH<sub>2</sub>OH</label></p><p><label class="radio"> <input class="c" type="radio"> <span>CH<sub>3</sub>CH<sub>2</sub>CN</span></label></p><p><label class="radio"> <input type="radio"> CH<sub>3</sub>CHCH<sub>2</sub></label></p><p><label class="radio"> <input type="radio"> CH<sub>3</sub>COCH<sub>2</sub>Cl</label></p></div><div class="q-explanation"><p>There are two peaks in the spectrum, so the compound has two hydrogen environments.</p><p>The peak at approximately 1.2ppm is a triplet because it is split by two nearest neighbours (according to the n+1 rule); presumably a CH<sub>2</sub> group on the next carbon.</p><p>The peak at approximately 2.4ppm is a quartet because it is split by three nearest neighbours (according to the n+1 rule); presumably a CH<sub>3</sub> group on the next carbon.</p><p>Propanenitrile (CH<sub>3</sub>CH<sub>2</sub>CN) has three hydrogens in the CH<sub>3</sub> group that will split the neighbouring hydrogen environment (CH<sub>2</sub> group) at 2.4ppm into a quartet, and vice versa to give the triplet at 1.2ppm.</p><p>Thus <strong>CH<sub>3</sub>CH<sub>2</sub>CN</strong> is the correct answer.</p><p>CH<sub>3</sub>CH<sub>2</sub>OH and CH<sub>3</sub>CHCH<sub>2</sub> both<sub> </sub>have three hydrogen environments. CH<sub>3</sub>COCH<sub>2</sub>Cl has two hydrogen environments, but they are separated by an C=O group, are therefore not neighbouring, so would not split one-another.</p></div><div class="actions"><span class="score" data-score="0"></span><button class="btn btn-default btn-sm btn-xs-block text-xs-center check"><i class="fa fa-check-square-o"></i> Check</button></div></div><div class="label label-default q-number">5</div><div class="exercise shadow-bottom"><div class="q-question"><p>Which compound produced this <sup>1</sup>H-NMR spectrum?</p><p><img alt="" src="../../images/measurement-and-data/l-nmr.png" style="width: 480px; height: 365px;"></p></div><div class="q-answer"><p><label class="radio"> <input type="radio"> <span>CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Cl</span></label> </p><p><label class="radio"> <input type="radio"> CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH </label></p><p><label class="radio"> <input type="radio"> CH<sub>3</sub>CO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> </label></p><p><label class="radio"> <input class="c" type="radio"> CH<sub>3</sub>CH<sub>2</sub>CONH<sub>2</sub> </label></p></div><div class="q-explanation"><p>The NMR spectrum shows three hydrogen environments, with hydrogen ratio of 2:2:3. The splitting pattern suggests that the CH<sub>2</sub> and CH<sub>3</sub> are neighbouring (split into a quartet and triplet respectively), but the two protons at ppm 6.2 are not split by neighbouring protons.</p><p>Therefore <strong>CH<sub>3</sub>CH<sub>2</sub>CONH<sub>2</sub> i</strong>s the correct answer.</p><p>CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>OH has four hydrogen environments; CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Cl would have a different splitting pattern (all environments would be split as they are all neighbouring); CH<sub>3</sub>CO<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> would show peak integrals of 3:2:3 (rather than 2:2:3).</p></div><div class="actions"><span class="score" data-score="0"></span><button class="btn btn-default btn-sm btn-xs-block text-xs-center check"><i class="fa fa-check-square-o"></i> Check</button></div></div><div class="label label-default q-number">6</div><div class="exercise shadow-bottom"><div class="q-question"><p>Which are true statements about what <sup>1</sup>H-NMR spectra can always tell us about a molecule?</p><p><strong>1:</strong> The total number of hydrogen atoms</p><p><strong>2:</strong> The number of hydrogen atoms attached to adjacent atoms</p><p><strong>3:</strong> The total number of hydrogen environments</p></div><div class="q-answer"><p><label class="radio"> <input type="radio"> <span>1 and 3 only</span></label> </p><p><label class="radio"> <input type="radio"> <span>1 only</span></label> </p><p><label class="radio"> <input type="radio"> <span>2 only</span></label> </p><p><label class="radio"> <input class="c" type="radio"> <span>2 and 3 only</span></label> </p></div><div class="q-explanation"><p><sup>1</sup>H-NMR spectroscopy<strong> </strong>summary:</p><p><strong>Peaks</strong>: The number of peaks tells us the number of different hydrogen <strong>environments</strong>.</p><p><strong>Ratio</strong>: The <strong>integration trace </strong>or whole number written adjacent to each peak tells us the <strong>ratio</strong> of the number of hydrogens in each environment.</p><p><strong>Splitting</strong>: The <strong>spin-spin splitting </strong>pattern of each peak tells us the number of hydrogens in neighbouring environments (on adjacent atoms).</p><p><strong>Shift</strong>: The chemical shift table (<strong>data book</strong>) can help us with the types of hydrogens (functional groups etc.) in the molecule.</p><p>Therefore <strong>2 and 3</strong> <strong>only</strong> is the correct answer. Since <sup>1</sup>H-NMR will <strong>not</strong> always tell us the total number of hydrogen atoms in a molecule (as sometimes we aere just given the <strong>ratio</strong>).</p></div><div class="actions"><span class="score" data-score="0"></span><button class="btn btn-default btn-sm btn-xs-block text-xs-center check"><i class="fa fa-check-square-o"></i> Check</button></div></div><div class="label label-default q-number">7</div><div class="exercise shadow-bottom"><div class="q-question"><p>Which of these properties contribute to why tetramethylsilane (TMS) is used as a reference standard for <sup>1</sup>H-NMR?</p><p><strong>1:</strong> The protons are all in the same environment</p><p><strong>2:</strong> The chemical shift is low relative to other proton environments</p><p><strong>3:</strong> It has high chemical reactivity</p></div><div class="q-answer"><p><label class="radio"> <input type="radio"> <span>1 and 3 only</span></label> </p><p><label class="radio"> <input type="radio"> <span>2 and 3 only</span></label> </p><p><label class="radio"> <input type="radio"> <span>1, 2 and 3</span></label> </p><p><label class="radio"> <input class="c" type="radio"> <span>1 and 2 only</span></label> </p></div><div class="q-explanation"><p>Tetramethylsilane, (CH<sub>3</sub>)<sub>4</sub>Si, is used as a reference for <sup>1</sup>H-NMR spectroscopy<strong> </strong>because:</p><ul><li>All 12 hydrogen atoms are in the same environment so it gives one large sharp peak.</li><li>The chemical shift is low (set as zero) relative other proton environments.</li><li>It is unreactive, so does not intefere with the sample being tested.</li><li>It is volatile (evaporates easily) so can easily be removed from a sample.</li></ul><p>Therefore <strong>1 and 2</strong> <strong>only</strong> is the correct answer.</p></div><div class="actions"><span class="score" data-score="0"></span><button class="btn btn-default btn-sm btn-xs-block text-xs-center check"><i class="fa fa-check-square-o"></i> Check</button></div></div><div class="label label-default q-number">8</div><div class="exercise shadow-bottom"><div class="q-question"><p>Which are correct statements about the <sup>1</sup>H-NMR spectrum of propan-2-ol?</p><p><strong>1:</strong> There will be four peaks in the spectrum (four hydrogen environments)</p><p><strong>2:</strong> The integration trace will show a ratio of 1:1:6</p><p><strong>3:</strong> There will be a quartet peak in the spectrum</p></div><div class="q-answer"><p><label class="radio"> <input type="radio"> <span>1 and 3 only</span></label> </p><p><label class="radio"> <input type="radio"> <span>1 only</span></label> </p><p><label class="radio"> <input type="radio"> <span>3 only</span></label> </p><p><label class="radio"> <input class="c" type="radio"> <span>2 only</span></label> </p></div><div class="q-explanation"><p>The 3D image of propan-2-ol in shown below.</p><p><img alt="" src="../../images/measurement-and-data/screenshot-2020-08-20-at-21.10.46.png" style="width: 240px; height: 236px;"></p><p>The hydrogens in the two CH<sub>3</sub> groups on the ends of the molecule are all in the same environment (the molecule is symmetrical). So there are three hydrogen environments in total (not four).</p><p>The ratio of hydrogens in the environments is 1:1:6 (CH, OH and the two CH<sub>3</sub> groups) so the integration trace will show a 1:1:6 ratio.</p><p>The H on the middle carbon will split the two CH<sub>3</sub> (six hydrogen) peak into two (doublet), according to the n+1 rule. The two CH<sub>3</sub> groups (6 hydrogens) will spilt the single C-H into a multiplet (theoretically into 7).</p><p>Remember that OH hydrogens tend not to split or be split. So the hydrogen on the OH will be a singlet peak.</p><p>Therefore <strong>2 </strong><strong>only</strong> is the correct answer.</p></div><div class="actions"><span class="score" data-score="0"></span><button class="btn btn-default btn-sm btn-xs-block text-xs-center check"><i class="fa fa-check-square-o"></i> Check</button></div></div><div class="totals"><span class="score"></span><button class="btn btn-success btn-block text-center check-total"><i class="fa fa-check-square-o"></i> Check</button></div></div><hr> </div> <div class="page-container panel-self-assessment" data-id="2776"> <div class="panel-heading">MY PROGRESS</div> <div class="panel-body understanding-rate"> <div class="msg"></div> <label class="label-lg">Self-assessment</label><p>How much of <strong>Measurement AHL (HL only) paper 1 questions</strong> have you understood?</p><div class="slider-container text-center"><div id="self-assessment-slider" class="sib-slider self-assessment " data-value="1" data-percentage=""></div></div> <label class="label-lg">My notes</label> <textarea name="page-notes" class="form-control" rows="3" placeholder="Write your notes here..."></textarea> </div> <div class="panel-footer text-xs-center"> <span id="last-edited" class="mb-xs-3"> </span> <div class="actions mt-xs-3"> <button id="save-my-progress" type="button" class="btn btn-sm btn-primary text-center btn-xs-block"> <i class="fa fa-fw fa-floppy-o"></i> Save </button> </div> </div></div> <div id="modal-feedback" class="modal fade" tabindex="-1" role="dialog"> <div class="modal-dialog" role="document"> <div class="modal-content"> <div class="modal-header"> <h4 class="modal-title">Feedback</h4> <button type="button" class="close hidden-xs hidden-sm" data-dismiss="modal" aria-label="Close"> <span aria-hidden="true">×</span> </button> </div> <div class="modal-body"> <div class="errors"></div> <p><strong>Which of the following best describes your feedback?</strong></p> <form method="post" style="overflow: hidden"> <div class="form-group"> <div class="radio"><label style="color: #121212;"><input type="radio" name="feedback-type" value="Recommendation"> Recommend</label></div><div class="radio"><label style="color: #121212;"><input type="radio" name="feedback-type" value="Problem"> Report a problem</label></div><div class="radio"><label style="color: #121212;"><input type="radio" name="feedback-type" value="Improvement"> Suggest an improvement</label></div><div class="radio"><label style="color: #121212;"><input type="radio" name="feedback-type" value="Other"> Other</label></div> </div> <hr> <div class="row"> <div class="col-md-6"> <div class="form-group"> <label for="feedback-name">Name</label> <input type="text" class="form-control" name="feedback-name" placeholder="Name" value=" "> </div> </div> <div class="col-md-6"> <div class="form-group"> <label for="feedback-email">Email address</label> <input type="email" class="form-control" name="feedback-email" placeholder="Email" value="@airmail.cc"> </div> </div> </div> <div class="form-group"> <label for="feedback-comments">Comments</label> <textarea class="form-control" name="feedback-comments" style="resize: vertical;"></textarea> </div> <input type="hidden" name="feedback-ticket" value="082b9c9c4ae3624d"> <input type="hidden" name="feedback-url" value="https://studyib.net/chemistry/page/2776/measurement-ahl-hl-only-paper-1-questions"> <input type="hidden" name="feedback-subject" value="7"> <input type="hidden" name="feedback-subject-name" value="Chemistry"> <div class="pull-left"> </div> </form> </div> <div class="modal-footer"> <button type="button" class="btn btn-primary btn-xs-block feedback-submit mb-xs-3 pull-right"> <i class="fa fa-send"></i> Send </button> <button type="button" class="btn btn-default btn-xs-block m-xs-0 pull-left" data-dismiss="modal"> Close </button> </div> </div> </div></div> <style type="text/css" media="screen">/* Important part */
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