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href="#" class="mark-page-favorite pull-right" data-pid="915" title="Mark as favorite" onclick="return false;"><i class="fa fa-star-o"></i></a> </h1> <ol class="breadcrumb"> <li><a href="../../../chemistry.html"><i class="fa fa-home"></i></a><i class="fa fa-fw fa-chevron-right divider"></i></li><li><a href="../363/measurement.html">Measurement</a><i class="fa fa-fw fa-chevron-right divider"></i></li><li><span class="gray">Spectroscopic identification I</span></li> <span class="pull-right" style="color: #555" title="Suggested study time: 30 minutes"><i class="fa fa-clock-o"></i> 30'</span> </ol> <article id="main-article"> <p><img alt="" src="../../images/measurement-and-data/ethanol_ir_spectrum-1.png" style="width: 160px; height: 106px; float: left;">This section of the course, including mass spectrometry, infra-red spectroscopy and nuclear magnetic resonance spectrometry is easier to cope with if we have a really strong grasp of organic chemistry. In particular, a thorough knowledge of functional groups and nomenclature. It is important to learn what to expect from the spectra, and the best way to do this is through practice; the Q bank has lost of spectra in it!</p> <hr class="hidden-separator"> <div class="panel panel-has-colored-body panel-turquoise"> <div class="panel-heading"><a class="expander" href="#"><span class="fa fa-plus"></span></a> <div> <p>Key concepts</p> </div> </div> <div class="panel-body"> <div> <div class="panel-body"> <div> <p>Ensure you are confident using the terms below and learn the asterisked* definitions</p> <p>Index of hydrogen deficiency, Infrared spectrum, Fingerprint region, Mass spectrum, Molecular ion (M<sup>+</sup>), Fragment ions, Hydrogen environment, TMS, Integration trace, Chemical shift</p> <section data-levels="1" data-mode="Normal" data-n-flashcards="10" data-subject-id="7" data-topics="563"> <h5>Flashcards</h5> <p><strong>Topics:</strong> 11.3: Spectroscopic identification<br> <strong>Levels:</strong> All<br> <strong>Number of questions:</strong> 10<br> <strong>Mode:</strong> Normal</p> </section> <div class="panel panel-has-colored-body panel-has-border panel-turquoise"> <div class="panel-heading"><a class="expander" href="#"><span class="fa fa-plus"></span></a> <div> <p>Finding empirical and molecular formulae</p> </div> </div> <div class="panel-body"> <div>Using percentage composition data to find the empirical formula of a compound and how this relates to molecular formulae.</div> <div class="video-embed vimeo"><iframe allow="accelerometer; autoplay; encrypted-media; gyroscope; picture-in-picture" allowfullscreen="" mozallowfullscreen="" webkitallowfullscreen="" height="420" width="100%" src="https://player.vimeo.com/video/378281924"></iframe></div> </div> <div class="panel-footer"> <div> </div> </div> </div> </div> </div> </div> </div> <div class="panel-footer"> <div> </div> </div> </div> <div class="panel panel-yellow panel-has-colored-body"> <div class="panel-heading"><a class="expander" href="#"><span class="fa fa-plus"></span></a> <div> <p>Essentials</p> </div> </div> <div class="panel-body"> <div> <p> The revision cards contain all of the essential content:</p> <div id="carousel-215" class="dynamic-gallery carousel slide" data-id="215"><div class="carousel-inner" role="listbox"><div class="item active"><a class="fancy" href="../../../std-galleries/7-215/screenshot-2020-08-20-at-195548.png" data-fancybox="gallery-215" title="" data-caption=""><img alt="" src="../../../std-galleries/7-215/screenshot-2020-08-20-at-195548.png"></a></div><div class="item "><a class="fancy" href="../../../std-galleries/7-215/screenshot-2020-08-20-at-195607.png" data-fancybox="gallery-215" title="" data-caption=""><img alt="" src="../../../std-galleries/7-215/screenshot-2020-08-20-at-195607.png"></a></div><div class="item "><a class="fancy" href="../../../std-galleries/7-215/screenshot-2020-08-20-at-195617.png" data-fancybox="gallery-215" title="" data-caption=""><img alt="" 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</div> <div class="panel-body"> <div> <div class="panel-body"> <div> <div class="tib-quiz" data-stats="7-544-915"><div class="label label-default q-number">1</div><div class="exercise shadow-bottom"><div class="q-question"><p>An organic compound consists of 40.0% carbon, 6.7% hydrogen and 53.3% oxygen by mass, and has a molar mass of approximately 60 g mol<sup>−1</sup>.</p><p>What is the molecular formula of the compound?</p></div><div class="q-answer"><p><label class="radio"> <input class="c" type="radio"> <span>C<sub>2</sub>H<sub>4</sub>O<sub>2</sub></span></label> </p><p><label class="radio"> <input type="radio"> <span>C<sub>2</sub>HO<sub>2</sub></span></label> </p><p><label class="radio"> <input type="radio"> <span>CH<sub>2</sub>O</span></label> </p><p><label class="radio"> <input type="radio"> <span>C<sub>4</sub>H<sub>8</sub>O<sub>4</sub></span></label> </p></div><div class="q-explanation"><p>Find the simplest ratio of the number of (moles of) atoms.</p><p>Start by assuming 100g: Thus 40.0g of C atoms, 6.7g of H atoms, 53.3g of O atoms.</p><table border="0" cellpadding="0" cellspacing="0" style="width: 100%;"><tbody><tr><td style="text-align: center;"> </td><td style="text-align: center;">Carbon</td><td style="text-align: center;">Hydrogen</td><td style="text-align: center;">Oxygen</td></tr><tr><td style="text-align: center;"><p>moles = mass/molar mass</p></td><td style="text-align: center;">40.0/12.01 = 3.330557868</td><td style="text-align: center;">6.7/1.01 = 6.633663366</td><td style="text-align: center;">53.3/16.00 = 3.33125</td></tr><tr><td style="text-align: center;"><p>divide through by smallest</p></td><td style="text-align: center;">3.33../3.33.. = 1</td><td style="text-align: center;">6.63../3.33.. ≈ 2</td><td style="text-align: center;">3.33../3.33.. ≈ 1</td></tr><tr><td style="text-align: center;">whole numbers</td><td style="text-align: center;">1</td><td style="text-align: center;">2</td><td style="text-align: center;">1</td></tr></tbody></table><p>Thus the empirical formula is CH<sub>2</sub>O.</p><p>The empirical 'formula unit' has a mass of approx. 30 (12+2+16), and the molecular mass of the molecule is approx. 60.</p><p>60 / 30 = 2</p><p>So there are two 'formula units' of the empirical formula in the molecule: The molecular formula is<sub> </sub>C<sub>2</sub>H<sub>4</sub>O<sub>2</sub>.</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>What is the index of hydrogen deficiency for cyclohexene (C<sub>6</sub>H<sub>10</sub>)?</p></div><div class="q-answer"><p><label class="radio"> <input type="radio"> <span>4</span></label> </p><p><label class="radio"> <input class="c" type="radio"> <span>2</span></label> </p><p><label class="radio"> <input type="radio"> <span>3</span></label> </p><p><label class="radio"> <input type="radio"> <span>1</span></label> </p></div><div class="q-explanation"><p>The index of hydrogen deficiency is a measure of the 'double bond equivalents' in a molecule. When given a simple molecule like cyclohexene, it is possible to work out the IHD without the equation; the double bond counts as <strong>one</strong> and the ring counts as another <strong>one</strong>, so the correct answer is <strong>2</strong>.</p><p>The equation can be used:</p><p><span class="math-tex">\(IHD = (C+1)-( {H-N+X \over 2})\)</span></p><p>IHD = (6+1) – (10/2) = 7 – 5 = 2</p><p>And also gives an answer of <strong>2</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">3</div><div class="exercise shadow-bottom"><div class="q-question"><p>What is the index of hydrogen deficiency for paracetamol (acetaminophen) (C<sub>8</sub>H<sub>9</sub>NO<sub>2</sub>)?</p></div><div class="q-answer"><p><label class="radio"> <input type="radio"> <span>4</span></label> </p><p><label class="radio"> <input class="c" type="radio"> <span>5</span></label> </p><p><label class="radio"> <input type="radio"> <span>3</span></label> </p><p><label class="radio"> <input type="radio"> <span>2</span></label> </p></div><div class="q-explanation"><p>The index of hydrogen deficiency is a measure of the 'double bond equivalents' in a molecule.</p><p>The equation can be used, where the letters represent the appropriate elements and X represents any halogen (oxygen can be ignored):</p><p><span class="math-tex">\(IHD = (C+1)-{(H-N+X) \over 2}\)</span></p><p>IHD = (8+1) – (9–1+0)/2 = 9 – 4 = <strong>5</strong></p><p>Therefore the correct answer is <strong>5</strong>.</p><p>That is <strong>four </strong>double bonds and <strong>one</strong> ring:</p><p><img alt="" src="../../images/measurement-and-data/paracetamol.png" style="width: 240px; height: 146px;"></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 of these ions could be responsible for peaks found in the following mass spectrum?</p><p><strong>1:</strong> [CH<sub>3</sub>]<sup>+</sup></p><p><strong>2:</strong> [C<sub>2</sub>H<sub>3</sub>O]<sup>+</sup></p><p><strong>3:</strong> [C<sub>3</sub>H<sub>6</sub>O]<sup>+</sup></p><p><img alt="" src="../../images/measurement-and-data/c-mass-spec.png" style="width: 480px; height: 355px;"></p></div><div class="q-answer"><p><label class="radio"> <input type="radio"> <span>2 and 3 only</span></label> </p><p><label class="radio"> <input class="c" type="radio"> <span>1, 2 and 3</span></label> </p><p><label class="radio"> <input type="radio"> <span>1 and 3 only</span></label> </p><p><label class="radio"> <input type="radio"> <span>1 and 2 only</span></label> </p></div><div class="q-explanation"><p>The integer masses of the ions need to be matched to m/z values for peaks in the spectrum:</p><p>[CH<sub>3</sub>]<sup>+</sup> (12+3=15) matches the peak at m/z 15.</p><p>[C<sub>2</sub>H<sub>3</sub>O]<sup>+</sup> (24+3+16=43) matches the (large) peak at m/z 43.</p><p>[C<sub>3</sub>H<sub>6</sub>O]<sup>+</sup> (36+6+16=58) matches the molecular ion peak at m/z 58.</p><p>Therefore <strong>1, 2 and 3</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">5</div><div class="exercise shadow-bottom"><div class="q-question"><p>A mass spectrum of an organic compound of molecular formula C<sub>5</sub>H<sub>10</sub>O shows a peak at m/z 29.</p><p>Which of these ions could be responsible for the peak at m/z 29?</p><p><strong>1:</strong> [CHO]<sup>+</sup></p><p><strong>2:</strong> [C<sub>2</sub>H<sub>5</sub>]<sup>+</sup></p><p><strong>3:</strong> [NCH<sub>3</sub>]<sup>+</sup></p></div><div class="q-answer"><p><label class="radio"> <input class="c" type="radio"> <span>1 and 2 only</span></label> </p><p><label class="radio"> <input type="radio"> <span>1 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 type="radio"> <span>2 and 3 only</span></label> </p></div><div class="q-explanation"><p>All three fragment ions have integer masses of 29 that correspond to a peak at 29 m/z. However [NCH<sub>3</sub>]<sup>+</sup> contains nitrogen which is not given in the molecular formula, so [NCH<sub>3</sub>]<sup>+</sup> cannot be resonsible for the peak.</p><p>The compound C<sub>5</sub>H<sub>10</sub>O (we are not given any information on structure) could however fragment to give both [CHO]<sup>+</sup> and [C<sub>2</sub>H<sub>5</sub>]<sup>+</sup>.</p><p>Therefore <strong>1 and 2 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">6</div><div class="exercise shadow-bottom"><div class="q-question"><p>An infrared spectrum of compound X is shown below.</p><p>Which of these bond/s is/are likely to be present in compound X?</p><p><strong>1:</strong> O−H</p><p><strong>2:</strong> C=C</p><p><strong>3:</strong> C−H</p><p><img alt="" src="../../images/measurement-and-data/d-ir.png" style="width: 480px; height: 293px;"></p></div><div class="q-answer"><p><label class="radio"> <input class="c" 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 type="radio"> <span>1 and 2 only</span></label> </p></div><div class="q-explanation"><p>The data book contains a table of IR data, but it's important to learn to recognise characteristic bond absorption bands (see revision cards).</p><p>The broad and strong band at 3350cm<sup>−1</sup> indicates an <strong>O−H </strong>bond.</p><p>The (always present) collection of bands at approx. 3000 cm<sup>−1</sup> indicate <strong>C−H</strong> bonds.</p><p>However, there is <strong>not </strong>a<strong> </strong>sharp, medium band that one might expect to see approx.1620-1680 cm<sup>−1</sup> to indicate a <strong>C=C</strong> bond.</p><p>Therefore <strong>1 and 3</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">7</div><div class="exercise shadow-bottom"><div class="q-question"><p>An infrared spectrum of compound Y is shown below.</p><p>Which of these bond/s is/are likely to be present in compound Y?</p><p><strong>1:</strong> O−H</p><p><strong>2:</strong> C=O</p><p><strong>3:</strong> C−H</p><p><img alt="" src="../../images/measurement-and-data/b-ir.png" style="width: 480px; height: 301px;"></p></div><div class="q-answer"><p><label class="radio"> <input type="radio"> <span>2 and 3 only</span></label> </p><p><label class="radio"> <input type="radio"> <span>1 and 2 only</span></label> </p><p><label class="radio"> <input type="radio"> <span>1 and 3 only</span></label> </p><p><label class="radio"> <input class="c" type="radio"> <span>1, 2 and 3</span></label> </p></div><div class="q-explanation"><p>The data book contains a table of IR data, but it's important to learn to recognise characteristic bond absorption bands (see revision cards).</p><p>There are <strong>two bands overlapping</strong> here at 3000 cm<sup>−1</sup>.</p><p>The broad and strong band at approx. 3000cm<sup>−1</sup> indicates an <strong>O−H </strong>bond in a carboxylic acid, and this overlaps with the (always present) collection of bands at approx. 3000 cm<sup>−1</sup> that indicate <strong>C−H</strong> bonds.</p><p>There is also a strong band at approx.1750 cm<sup>−1</sup> to indicate a <strong>C=O</strong> bond (as you might expect in a carboxylic acid).</p><p>Therefore <strong>1</strong><strong>, 2 and 3 </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>What do the integration trace values of a set of H-NMR peaks represent?</p></div><div class="q-answer"><p><label class="radio"> <input class="c" type="radio"> <span>The ratio of the number of hydrogen atoms in each environment</span></label> </p><p><label class="radio"> <input type="radio"> <span>The chemical shift of the hydrogen environments</span></label> </p><p><label class="radio"> <input type="radio"> <span>The degree of electron shielding on the hydrogen atoms</span></label> </p><p><label class="radio"> <input type="radio"> <span>The number of hydrogen atoms in each environment</span></label> </p></div><div class="q-explanation"><p>The integration trace value, given as a number by each peak in an NMR spectrum tells us the ratio of the area under the peak, which is the <strong>ratio</strong> of the <strong>number of hydrogens </strong>in the environment. This will often be the same as the number of hydrogens, but it is given in the simplest ratio (which can be misleading).</p><p>Therefore <strong>The ratio of the number of hydrogen atoms in each environment</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">9</div><div class="exercise shadow-bottom"><div class="q-question"><p>In an H-NMR spectrum of the compound below, how many different hydrogen environments and therefore peaks will be present?</p><p>(CH<sub>3</sub>)<sub>2</sub>CHCH<sub>2</sub>CH<sub>3</sub></p></div><div class="q-answer"><p><label class="radio"> <input type="radio"> <span>3</span></label> </p><p><label class="radio"> <input type="radio"> <span>9</span></label> </p><p><label class="radio"> <input type="radio"> <span>5</span></label> </p><p><label class="radio"> <input class="c" type="radio"> <span>4</span></label> </p></div><div class="q-explanation"><p>The compound is 2-methylbutane (3D image below). The hydrogens in the two CH<sub>3</sub> groups to the left are equivalent, so form one environment. The hydrogens in the CH, CH<sub>2</sub> and the CH<sub>3</sub> group on the right all contain hydrogens which are in different environments, that is another three environments.</p><p>Therefore there are<strong> 4</strong> different hydrogen environments in total.</p><p><img alt="" src="../../images/measurement-and-data/2-methylbutane.png" style="width: 360px; height: 361px;"></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">10</div><div class="exercise shadow-bottom"><div class="q-question"><p>An H-NMR spectrum of compound Z is shown below.</p><p>Which of the following organic compounds could be compound Z?</p><p><strong>1:</strong> Propanone, CH<sub>3</sub>COCH<sub>3</sub></p><p><strong>2:</strong> Propane, CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub></p><p><strong>3:</strong> Propanol, CH<sub>3</sub>CH<sub>2</sub>OH</p><p><img alt="" src="../../images/measurement-and-data/c-nmr.png" style="width: 480px; height: 351px;"></p></div><div class="q-answer"><p><label class="radio"> <input type="radio"> <span>1 and 2 only</span></label> </p><p><label class="radio"> <input class="c" 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 type="radio"> <span>2 and 3 only</span></label> </p></div><div class="q-explanation"><p>The H-NMR spectrum shows only one peak and therefore compound Z must have only one hydrogen environment.</p><p>Propanone is symmetrical; the hydrogens in the two CH<sub>3 </sub>groups are identical. Therefore, propanone has only one hydrogen environment and will produce one peak in its H-NMR spectrum.</p><p>Propane is symmetrical too, but although the hydrogens in the two CH<sub>3 </sub>groups are identical, the CH<sub>2 </sub>group in the middle contains hydrogens in a second environment. Propane will produce two peaks in its H-NMR spectrum.</p><p>Propanol is not symmetrical. The hydrogens in the CH<sub>3</sub>, CH<sub>2</sub> and OH groups are all in different environments, so propanol will produce three peaks in its H-NMR spectrum.</p><p>Therefore <strong>1</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> </div> </div> <div class="panel-footer"> <div> </div> </div> </div> <div class="panel panel-has-colored-body panel-default"> <div class="panel-heading"><a class="expander" href="#"><span class="fa fa-plus"></span></a> <div> <p>Exam-style questions</p> </div> </div> <div class="panel-body"> <div> <h4>Paper 1</h4> <h5>Core (SL&HL): <a 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