{"id":1770,"date":"2017-10-10T15:34:07","date_gmt":"2017-10-10T15:34:07","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=1770"},"modified":"2018-10-05T19:45:26","modified_gmt":"2018-10-05T19:45:26","slug":"application-of-proton-nmr","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/application-of-proton-nmr\/","title":{"raw":"Application of Proton NMR","rendered":"Application of Proton NMR"},"content":{"raw":"<div class=\"elm-header\">\r\n<div class=\"elm-header-custom\">\r\n<div class=\"textbox learning-objectives\">\r\n<h3>Objective<\/h3>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\r\n<div>\r\n<div id=\"skills\">\r\n\r\nAfter completing this section, you should be able to use data from <sup>1<\/sup>H NMR spectra to distinguish between two (or more) possible structures for an unknown organic compound.\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\nThere will be cases in which you already know what the structure might be. In these cases:\r\n\r\n<\/div>\r\n<\/div>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\r\n<div>\r\n<ul>\r\n \t<li>You should draw attention to pieces of data that most strongly support your expected structure. This approach will demonstrate evaluative understanding of the data; that means you can look at data and decide what parts are more crucial than others.<\/li>\r\n \t<li>You should also draw attention to negative results: that is, peaks that might be there if this spectrum matched another, possible structure, but that are in fact missing.<\/li>\r\n<\/ul>\r\n<p dir=\"LTR\">One of the most complicated problems to deal with is the analysis of a mixture. This situation is not uncommon when students run reactions in lab and analyse the data.<\/p>\r\n\r\n<ul>\r\n \t<li>Sometimes the spectra show a little starting material mixed in with the product.<\/li>\r\n \t<li>Sometimes solvents show up in the spectrum.<\/li>\r\n \t<li>As you might expect, the minor component usually shows up as smaller peaks in the spectrum. If there are fewer molecules present, then there are usually fewer protons to absorb in the spectrum.<\/li>\r\n \t<li>In this case, you should probably make two completely separate sets of data tables for your analysis, one for each compound, or else one for the main compound and one for impurities.<\/li>\r\n<\/ul>\r\n<p dir=\"LTR\">Remember that integration ratios are really only meaningful within a single compound. If your NMR sample contains some benzene (C<sub>6<\/sub>H<sub>6<\/sub>) and some acetone (CH<sub>3<\/sub>COCH<sub>3<\/sub>), and there is a peak at 7.15 that integrates to 1 proton and a peak at 2.10 ppm integrating to 6 protons, it might mean there are 6 protons in acetone and 1 in benzene, but you can tell that isn't true by looking at the structure. There must be six times as many acetone molecules as benzene molecules in the sample.<\/p>\r\n<p dir=\"LTR\">There are six protons in the benzene, and they should all show up near 7 ppm.\u00a0 There are six protons in acetone, and they should all show up near 2 ppm.\u00a0 Assuming that small integral of 1H for the benzene is really supposed to be 6H, then the large integral of 6H for the acetone must also represent six times as many hydrogens, too.\u00a0 It would be 36 H.\u00a0 There are only six hydrogens in acetone, so it must represent six times as many acetone molecules as there are benzenes.<\/p>\r\n<p dir=\"LTR\">Similarly, if you have decided that you can identify two sets of peaks in the <sup>1<\/sup>H spectrum, analysing them in different tables makes it easy to keep the integration analysis completely separate too ; 1 H in one table will not be the same size integral as 1 H in the other table unless the concentrations of the two compounds in the sample are the same.<\/p>\r\n<p dir=\"LTR\">However, comparing the ratio of two integrals for two different compounds can give you the ratio of the two compounds in solution, just as we could determine the ratio of benzene to acetone in the mixture described above.<\/p>\r\nWe will look at two examples of sample mixtures that could arise in lab.\u00a0 Results like these are pretty common events in the labIn the first example, a student tried to carry out the following reaction, a borohydride reduction of an aldehyde.\u00a0 The borohydride should give a hydride anion to the C=O carbon; washing with water should then supply a proton to the oxygen, giving an alcohol.<a title=\"NaBH4red.gif\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/14288\/NaBH4red.gif?revision=1\" rel=\"internal\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154629\/NaBH4red.gif\" alt=\"image\" border=\"0\" \/><\/a>\r\n\r\nHer reaction produced the following spectrum.<a title=\"NMR in1.gif\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/14289\/NMR_in1.gif?revision=1\" rel=\"internal\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154632\/NMR-in1.gif\" alt=\"image\" border=\"0\" \/><\/a>\r\n\r\n(simulated data)\r\n\r\nFrom this data, she produced the table below.<a title=\"nmrmixtable.gif\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/14290\/nmrmixtable.gif?revision=1\" rel=\"internal\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154634\/nmrmixtable.gif\" alt=\"image\" border=\"0\" \/><\/a>\r\n<p dir=\"LTR\">Notice how she calculated that ratio.\u00a0 She found a peak in molecule 1, the aldehyde, that she was pretty sure corresponded to the aldehydic hydrogen, the H attached to the C=O; in other words, the CH=O.\u00a0 She found another peak from molecule 2, the alcohol, that she was pretty sure represented the two hydrogens on the carbon attached to oxygen, the CH<sub>2<\/sub>-O.<\/p>\r\n<p dir=\"LTR\">The integrals for those two peaks are equal.\u00a0 They are both 2H in her table.\u00a0 However, she notes that within each molecule, the first integral really represents 1H and the second represents 2H.\u00a0 That means there must be twice as many of molecule 1 as there are molecule 2.\u00a0 That way, there would be 2 x CH=O, and its integral would be the same as the 1 x CH<sub>2<\/sub>-O in the other molecule.<\/p>\r\n<p dir=\"LTR\">One way to approach this kind of problem is to:<\/p>\r\n\r\n<ul>\r\n \t<li>\u00a0choose one peak from each of the two compounds you want to compare.<\/li>\r\n \t<li>decide how many hydrogens each peak is supposed to represent in a molecule.\u00a0 Is it supposed to be a CH<sub>2<\/sub>, a CH, a CH<sub>3<\/sub>?<\/li>\r\n \t<li>divide the integral value for that peak by that number of hydrogens it is supposed to represent in a molecule.<\/li>\r\n \t<li>compare the two answers\u00a0 (integral A \/ ideal # H) vs (integral B \/ ideal # H).<\/li>\r\n \t<li>the ratio of those two answers is the ratio of the two molecules in the sample.<\/li>\r\n<\/ul>\r\n<p dir=\"LTR\">So there is twice as much aldehyde as alcohol in the mixture.\u00a0 In terms of these two compounds alone, she has 33% alcohol and 66% aldehyde.\u00a0 That's ( 1\/(1+2) ) x100% for the alcohol, and ( 2\/(1+2) ) x100% for the aldehyde.\u00a0 That calculation just represents the amount of individual component divided by the total of the components she wants to compare.<\/p>\r\n<p dir=\"LTR\">There are a number of things to take note of here.<\/p>\r\n\r\n<ul>\r\n \t<li>Her reaction really didn't work very well.\u00a0 She still has majority starting material, not product.<\/li>\r\n \t<li>She will get a good grade on this lab. Although the experiment didn't work well, she has good data, and she has analyzed it very clearly.<\/li>\r\n \t<li>She has separated her data table into different sections for different compounds. Sometimes that makes it easier to analyze things.<\/li>\r\n \t<li>She has noted the actual integral data (she may have measured the integral with a ruler) and also converted it into a more convenient ratio, based on the integral for a peak that she felt certain about.<\/li>\r\n \t<li>She went one step further, and indicated the internal integration ratio within each individual compound.<\/li>\r\n \t<li>She calculated the % completion of the reaction using the integral data for the reactant and product, and she made clear what part of the data she used for that calculation.\u00a0 A similar procedure could be done if a student were just trying to separate two components in a mixture rather than carry out a reaction.<\/li>\r\n \t<li>She also calculated the overall purity of the mixture, including a solvent impurity that she failed to remove.<\/li>\r\n \t<li>However, CHCl<sub>3<\/sub> is not included in her analysis of purity.\u00a0 CHCl<sub>3<\/sub> really isn't part of her sample; it was just present in the NMR solvent, so it doesn't represent anything in the material she ended up with at the end of lab.<\/li>\r\n<\/ul>\r\n<p dir=\"LTR\">Another student carried out a similar reaction, shown below.\u00a0 He also finished the reaction by washing with water, but because methanol is soluble in water, he had to extract his product out of the water.\u00a0 He chose to use dichloromethane for that purpose.<a title=\"NaBH4red3.gif\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/14291\/NaBH4red3.gif?revision=1\" rel=\"internal\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154642\/NaBH4red3.gif\" alt=\"image\" border=\"0\" \/><\/a><\/p>\r\n<p dir=\"LTR\">He obtained the following data.<a title=\"NMR in2.gif\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/14292\/NMR_in2.gif?revision=1\" rel=\"internal\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154644\/NMR-in2.gif\" alt=\"image\" border=\"0\" \/><\/a><\/p>\r\n<p dir=\"LTR\">From this data, he constructed the following table.<a title=\"nmrtablecrap2.gif\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/14293\/nmrtablecrap2.gif?revision=1\" rel=\"internal\"><img class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154646\/nmrtablecrap2.gif\" alt=\"image\" border=\"0\" \/><\/a><\/p>\r\n<p dir=\"LTR\">There are some things to learn about this table, too.<\/p>\r\n\r\n<ul>\r\n \t<li>Does the integration ratio really match the integral data?\u00a0 Or is this just wishful thinking?<\/li>\r\n \t<li>This table might reflect what he wants to see in the data.\u00a0 But what else could be in the data?<\/li>\r\n \t<li>CHCl<sub>3<\/sub> is often seen in NMR spectra if CDCl<sub>3<\/sub> is used for the NMR sample. It's there, at 7.2 ppm.<\/li>\r\n \t<li>\"Leftover\" or residual solvent is very common in real lab data.\u00a0 There it is, CH<sub>2<\/sub>Cl<sub>2<\/sub> from the extraction, at 5.4 ppm.<\/li>\r\n \t<li>What about water?\u00a0 Sometimes people don't dry their solutions properly before evaporating the solvent.\u00a0 There is probably water around 1.5 to 1.6 ppm here.<\/li>\r\n<\/ul>\r\n<p dir=\"LTR\">This student might not get a very good grade; the sample does not even show up in the spectrum, so he lost it somewhere.\u00a0 But his analysis is also poor, so he will really get a terrible grade.<\/p>\r\n\r\n<div>\r\n<div id=\"example\">\r\n<div class=\"textbox examples\">\r\n<h3>Example<\/h3>\r\n<div>\r\n<div id=\"example\">\r\n<p dir=\"LTR\">Three students performed a synthesis of a fragrant ester, ethyl propanoate, CH<sub>3<\/sub>CH<sub>2<\/sub>CO<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub>.\u00a0 During their reactions, they each used a different solvent.\u00a0 The students were able to see peaks in the NMR spectrum for ethyl propanoate, as well as peaks for chloroform (CHCl<sub>3<\/sub>, in the CDCl<sub>3<\/sub> they used to make their NMR samples).<\/p>\r\n\r\n<ul>\r\n \t<li>See the first student's spectrum.<\/li>\r\n \t<li>See the second student's spectrum.<\/li>\r\n \t<li>See the third student's spectrum.<\/li>\r\n<\/ul>\r\n<p dir=\"LTR\">They were also able to determine that they had some leftover solvent in their samples by consulting a useful table of solvent impurities in NMR (which they found in Goldberg et. al., Organometallics 2010, 29, 2176-2179).<\/p>\r\n\r\n<ol>\r\n \t<li>What is the ratio of leftover solvent to ethyl propanoate in each sample?<\/li>\r\n \t<li>What is the percent of each sample that is leftover solvent<\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_1\">\r\n<h3 class=\"editable\">Additional NMR Examples<\/h3>\r\nFor each molecule, predict the number of signals in the <sup>1<\/sup>H-NMR and the <sup>13<\/sup>C-NMR spectra (do not count split peaks - eg. a quartet counts as only one signal). Assume that diastereotopic groups are non-equivalent.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154649\/image142.png\" alt=\"image142.png\" width=\"660\" height=\"467\" \/>\r\n\r\n<strong>P5.2: <\/strong>For each of the 20 common amino acids, predict the number of signals in the proton-decoupled <sup>13<\/sup>C-NMR spectrum.\r\n\r\n<strong>P5.3:<\/strong>\u00a0 Calculate the chemical shift value (expressed in Hz, to one decimal place) of each sub-peak on the <sup>1<\/sup>H-NMR doublet signal below.\u00a0 Do this for:\r\n\r\na) a spectrum obtained on a 300 MHz instrument\r\n\r\nb) a spectrum obtained on a 100 MHz instrument\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154652\/image144.png\" alt=\"image144.png\" width=\"161\" height=\"287\" \/>\r\n\r\n<strong>P5.4:<\/strong>\u00a0 Consider a quartet signal in an <sup>1<\/sup>H-NMR spectrum obtained on a 300 MHz instrument. The chemical shift is recorded as 1.7562 ppm, and the coupling constant is J = 7.6 Hz.\u00a0 What is the chemical shift, expressed to the nearest 0.1 Hz, of the furthest downfield sub-peak in the quartet?\u00a0 What is the resonance frequency (again expressed in Hz) of this sub-peak?)\r\n\r\n<strong>P5.5: <\/strong>One easily recognizable splitting pattern for the aromatic proton signals from disubstituted benzene structures is a pair of doublets.\u00a0 Does this pattern indicate <em>ortho<\/em>, <em>meta<\/em>, or <em>para<\/em> substitution?\r\n\r\n<strong>P5.6 :<\/strong>Match spectra below to their corresponding structures A-F.\r\n\r\n<u>Structures:<\/u>\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154654\/image145.png\" alt=\"image145.png\" width=\"659px\" height=\"268px\" \/>\r\n\r\n<strong>Spectrum <\/strong><strong>1<\/strong>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u00a0\u03b4<\/strong><\/td>\r\n<td><strong>\u00a0splitting<\/strong><\/td>\r\n<td><strong>\u00a0integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>4.13<\/td>\r\n<td>q<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.45<\/td>\r\n<td>t<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.94<\/td>\r\n<td>quintet<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.27<\/td>\r\n<td>t<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>Spectrum 2<\/strong>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u00a0\u03b4<\/strong><\/td>\r\n<td><strong>\u00a0splitting<\/strong><\/td>\r\n<td><strong>\u00a0integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.68<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.99<\/td>\r\n<td>t<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.95<\/td>\r\n<td>quintet<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>Spectrum 3<\/strong>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u00a0\u03b4<\/strong><\/td>\r\n<td><strong>\u00a0splitting<\/strong><\/td>\r\n<td><strong>\u00a0integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>4.14<\/td>\r\n<td>q<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.62<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.26<\/td>\r\n<td>t<\/td>\r\n<td>1.5<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>Spectrum 4<\/strong>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u00a0\u03b4<\/strong><\/td>\r\n<td><strong>\u00a0splitting<\/strong><\/td>\r\n<td><strong>\u00a0integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>4.14<\/td>\r\n<td>q<\/td>\r\n<td>4<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.22<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.27<\/td>\r\n<td>t<\/td>\r\n<td>6<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.13<\/td>\r\n<td>s<\/td>\r\n<td>9<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>Spectrum 5<\/strong>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u00a0\u03b4<\/strong><\/td>\r\n<td><strong>\u00a0splitting<\/strong><\/td>\r\n<td><strong>\u00a0integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>4.18<\/td>\r\n<td>q<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.92<\/td>\r\n<td>q<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.23<\/td>\r\n<td>t<\/td>\r\n<td>1.5<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>0.81<\/td>\r\n<td>t<\/td>\r\n<td>1.5<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>Spectrum 6<\/strong>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u00a0\u03b4<\/strong><\/td>\r\n<td><strong>\u00a0splitting<\/strong><\/td>\r\n<td><strong>\u00a0integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.69<\/td>\r\n<td>s<\/td>\r\n<td>1.5<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.63<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>P5.7:<\/strong>\u00a0 Match spectra 7-12 below to their corresponding structures G-L .\r\n\r\n<u>Structures:<\/u>\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154657\/image148.png\" alt=\"image148.png\" width=\"559\" height=\"319\" \/>\r\n\r\n<u>Spectrum 7:<\/u>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u03b4<\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.96<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>5.88<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.17<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.98<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 8<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.36<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.55<\/td>\r\n<td>q<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.26<\/td>\r\n<td>q<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.99<\/td>\r\n<td>d<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>0.96<\/td>\r\n<td>t<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 9<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.57<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.30<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.00<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.84<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<\/div>\r\n<u>Spectrum 10<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.83<\/td>\r\n<td>t<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.27<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.07<\/td>\r\n<td>s<\/td>\r\n<td>9<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 11<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.75<\/td>\r\n<td>t<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.30<\/td>\r\n<td>dd<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.21<\/td>\r\n<td>m<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>0.98<\/td>\r\n<td>d<\/td>\r\n<td>6<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 12<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>8.08<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>4.13<\/td>\r\n<td>t<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.70<\/td>\r\n<td>m<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>0.96<\/td>\r\n<td>t<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>P5.8:<\/strong>\u00a0 Match the <sup>1<\/sup>H-NMR spectra 13-18 below to their corresponding structures M-R .\r\n\r\n<u>Structures<\/u>:\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154700\/image150.png\" alt=\"image150.png\" width=\"496\" height=\"357\" \/>\r\n\r\n<u>Spectrum 13<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u03b4<\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>8.15<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.33<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 14<\/u>: 1-723C (structure O)\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u03b4<\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.05<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.24<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 15<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u03b4<\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>8.57<\/td>\r\n<td>s (b)<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.89<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.30<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.28<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 16<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u03b4<\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.05<\/td>\r\n<td>s (b)<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>8.03<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.34<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>5.68<\/td>\r\n<td>s (b)<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>4.31<\/td>\r\n<td>s<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 17<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u03b4<\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.76<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.57<\/td>\r\n<td>s (b)<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.44<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.78<\/td>\r\n<td>q<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.25<\/td>\r\n<td>t<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 18<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u03b4<\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>4.03<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.51<\/td>\r\n<td>t<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.02<\/td>\r\n<td>t<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>P5.9:<\/strong>\u00a0 Match the <sup>1<\/sup>H-NMR spectra 19-24 below to their corresponding structures S-X.\r\n\r\n<u>Structures<\/u>:\r\n\r\n<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154703\/image152.png\" alt=\"image152.png\" width=\"600\" height=\"325\" \/>\r\n\r\n<u>Spectrum 19<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u03b4<\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.94<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.77<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.31<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.43<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 20<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u03b4<\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>10.14<\/td>\r\n<td>s<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>8.38<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>8.17<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.75<\/td>\r\n<td>t<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 21:<\/u>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u03b4<\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.98<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.81<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.50<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 22<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u03b4<\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.15-7.29<\/td>\r\n<td>m<\/td>\r\n<td>2.5<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.86<\/td>\r\n<td>t<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.73<\/td>\r\n<td>t<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.12<\/td>\r\n<td>s<\/td>\r\n<td>1.5<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 23<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u03b4<\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.10<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.86<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.78<\/td>\r\n<td>s<\/td>\r\n<td>1.5<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.61<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.12<\/td>\r\n<td>s<\/td>\r\n<td>1.5<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 24<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong>\u03b4<\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.23-7.30<\/td>\r\n<td>m<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.53<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>P5.10:<\/strong>\u00a0 Match the <sup>1<\/sup>H-NMR spectra 25-30 below to their corresponding structures AA-FF.\r\n\r\n<u>Structures<\/u>:\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154706\/image154.png\" alt=\"image154.png\" width=\"688\" height=\"366\" \/>\r\n\r\n<u>Spectrum 25<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.96<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.79<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.33<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.72<\/td>\r\n<td>q<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.24<\/td>\r\n<td>t<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 26<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.73<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.71<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.68<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.06<\/td>\r\n<td>s<\/td>\r\n<td>6<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 27<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>\u00a0splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.20-7.35<\/td>\r\n<td>m<\/td>\r\n<td>10<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>5.12<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.22<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 28<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>8.08<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.29<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.87<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>5.11<\/td>\r\n<td>s<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.78<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 29<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.18<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.65<\/td>\r\n<td>m<\/td>\r\n<td>1.5<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.2<\/td>\r\n<td>q<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.13<\/td>\r\n<td>t<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 30<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>8.32<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>4.19<\/td>\r\n<td>t<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.83<\/td>\r\n<td>t<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.40<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>P5.11:<\/strong>\u00a0 Match the <sup>1<\/sup>H-NMR spectra 31-36 below to their corresponding structures GG-LL\r\n\r\n<u>Structures<\/u>:\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154709\/image155a.png\" alt=\"image155a.png\" width=\"681px\" height=\"363px\" \/>\r\n\r\n<u>Spectrum 31<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.98<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.64<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.54<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>4.95<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.23<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.17<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 32<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.08<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.72<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.53<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>4.81<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.15<\/td>\r\n<td>7-tet<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.24<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.22<\/td>\r\n<td>d<\/td>\r\n<td>6<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 33<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.08<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.71<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.54<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.69<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.54<\/td>\r\n<td>s<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 34<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.63<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.45<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.77<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.95<\/td>\r\n<td>q<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.05<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.33<\/td>\r\n<td>t<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 35<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.49<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.20<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.49<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>4.82<\/td>\r\n<td>s<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.963<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u>Spectrum 36<\/u>:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.58<\/td>\r\n<td>s(b)<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.31<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.36<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.67<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.55<\/td>\r\n<td>d<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.21<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.11<\/td>\r\n<td>s<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>P5.12:<\/strong> Use the NMR data given to deduce structures.\r\n\r\na ) Molecular formula: C<sub>5<\/sub>H<sub>8<\/sub>O\r\n\r\n<u><sup>1<\/sup><\/u><u>H-NMR:<\/u>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.56<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>6.25<\/td>\r\n<td>d (J~1 Hz)<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>5.99<\/td>\r\n<td>d (J~1 Hz)<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.27<\/td>\r\n<td>q<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.18<\/td>\r\n<td>t<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u><sup>13<\/sup><\/u><u>C-NMR<\/u>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>DEPT<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>194.60<\/td>\r\n<td>CH<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>151.77<\/td>\r\n<td>C<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>132.99<\/td>\r\n<td>CH<sub>2<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>20.91<\/td>\r\n<td>CH<sub>2<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>11.92<\/td>\r\n<td>CH<sub>3<\/sub><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\nb) Molecular formula: C<sub>7<\/sub>H<sub>14<\/sub>O<sub>2<\/sub>\r\n\r\n<u><sup>1<\/sup><\/u><u>H-NMR:<\/u>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.85<\/td>\r\n<td>d<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.32<\/td>\r\n<td>q<\/td>\r\n<td>2<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.93<\/td>\r\n<td>m<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.14<\/td>\r\n<td>t<\/td>\r\n<td>3<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>0.94<\/td>\r\n<td>d<\/td>\r\n<td>6<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u><sup>13<\/sup><\/u><u>C-NMR<\/u>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>DEPT<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>174.47<\/td>\r\n<td>C<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>70.41<\/td>\r\n<td>CH<sub>2<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>27.77<\/td>\r\n<td>CH<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>27.64<\/td>\r\n<td>CH<sub>2<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>19.09<\/td>\r\n<td>CH<sub>3<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>9.21<\/td>\r\n<td>CH<sub>3<\/sub><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\nc) Molecular formula: C<sub>5<\/sub>H<sub>12<\/sub>O\r\n\r\n<u><sup>1<\/sup><\/u><u>H-NMR:<\/u>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.38<\/td>\r\n<td>s<\/td>\r\n<td>2H<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.17<\/td>\r\n<td>s<\/td>\r\n<td>1H<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>0.91<\/td>\r\n<td>s<\/td>\r\n<td>9H<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u><sup>13<\/sup><\/u><u>C-NMR<\/u>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>DEPT<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>73.35<\/td>\r\n<td>CH<sub>2<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>32.61<\/td>\r\n<td>C<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>26.04<\/td>\r\n<td>CH<sub>3<\/sub><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\nd) Molecular formula: C<sub>10<\/sub>H<sub>12<\/sub>O\r\n\r\n<u><sup>1<\/sup><\/u><u>H-NMR:<\/u>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.18-7.35<\/td>\r\n<td>m<\/td>\r\n<td>2.5<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.66<\/td>\r\n<td>s<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>2.44<\/td>\r\n<td>q<\/td>\r\n<td>1<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.01<\/td>\r\n<td>t<\/td>\r\n<td>1.5<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<u><sup>13<\/sup><\/u><u>C-NMR<\/u>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>DEPT<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>208.79<\/td>\r\n<td>C<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>134.43<\/td>\r\n<td>C<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>129.31<\/td>\r\n<td>CH<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>128.61<\/td>\r\n<td>CH<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>126.86<\/td>\r\n<td>CH<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>49.77<\/td>\r\n<td>CH<sub>2<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>35.16<\/td>\r\n<td>CH<sub>2<\/sub><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>7.75<\/td>\r\n<td>CH<sub>3<\/sub><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>P5.13:<\/strong>\r\n\r\n<sup>13<\/sup>C-NMR data is given for the molecules shown below.\u00a0 Complete the peak assignment column of each NMR data table.\r\n\r\n<strong>a)<\/strong>\r\n\r\n<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154716\/image158.png\" alt=\"image158.png\" width=\"123\" height=\"73\" \/>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>DEPT<\/strong><\/td>\r\n<td><strong>carbon #<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>161.12<\/td>\r\n<td>CH<\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>65.54<\/td>\r\n<td>CH<sub>2<\/sub><\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>21.98<\/td>\r\n<td>CH<sub>2<\/sub><\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>10.31<\/td>\r\n<td>CH<sub>3<\/sub><\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>b)<\/strong>\r\n\r\n<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154717\/image160.png\" alt=\"image160.png\" width=\"91\" height=\"120\" \/>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\r\n<td><strong>DEPT<\/strong><\/td>\r\n<td><strong>carbon #<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>194.72<\/td>\r\n<td>C<\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>149.10<\/td>\r\n<td>C<\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>146.33<\/td>\r\n<td>CH<\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>16.93<\/td>\r\n<td>CH<sub>2<\/sub><\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>14.47<\/td>\r\n<td>CH<sub>3<\/sub><\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>12.93<\/td>\r\n<td>CH<sub>3<\/sub><\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>c)<\/strong>\r\n\r\n<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154719\/image162.png\" alt=\"image162.png\" width=\"208\" height=\"113\" \/>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr style=\"height: 15px\">\r\n<td style=\"height: 15px\"><strong><strong><strong>\u03b4<\/strong><\/strong><\/strong><\/td>\r\n<td style=\"height: 15px\"><strong>DEPT<\/strong><\/td>\r\n<td style=\"height: 15px\"><strong>carbon #<\/strong><\/td>\r\n<\/tr>\r\n<tr style=\"height: 15px\">\r\n<td style=\"height: 15px\">171.76<\/td>\r\n<td style=\"height: 15px\">C<\/td>\r\n<td style=\"height: 15px\"><\/td>\r\n<\/tr>\r\n<tr style=\"height: 18px\">\r\n<td style=\"height: 18px\">60.87<\/td>\r\n<td style=\"height: 18px\">CH<sub>2<\/sub><\/td>\r\n<td style=\"height: 18px\"><\/td>\r\n<\/tr>\r\n<tr style=\"height: 15px\">\r\n<td style=\"height: 15px\">58.36<\/td>\r\n<td style=\"height: 15px\">C<\/td>\r\n<td style=\"height: 15px\"><\/td>\r\n<\/tr>\r\n<tr style=\"height: 18px\">\r\n<td style=\"height: 18px\">24.66<\/td>\r\n<td style=\"height: 18px\">CH<sub>2<\/sub><\/td>\r\n<td style=\"height: 18px\"><\/td>\r\n<\/tr>\r\n<tr style=\"height: 18.6562px\">\r\n<td style=\"height: 18.6562px\">14.14<\/td>\r\n<td style=\"height: 18.6562px\">CH<sub>3<\/sub><\/td>\r\n<td style=\"height: 18.6562px\"><\/td>\r\n<\/tr>\r\n<tr style=\"height: 18px\">\r\n<td style=\"height: 18px\">8.35<\/td>\r\n<td style=\"height: 18px\">CH<sub>3<\/sub><\/td>\r\n<td style=\"height: 18px\"><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>d)<\/strong>\r\n\r\n<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154721\/image164.png\" alt=\"image164.png\" width=\"221\" height=\"94\" \/>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong><strong>\u03b4<\/strong><\/strong><\/strong><\/td>\r\n<td><strong>DEPT<\/strong><\/td>\r\n<td><strong>carbon #<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>173.45<\/td>\r\n<td>C<\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>155.01<\/td>\r\n<td>C<\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>130.34<\/td>\r\n<td>CH<\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>125.34<\/td>\r\n<td>C<\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>115.56<\/td>\r\n<td>CH<\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>52.27<\/td>\r\n<td>CH<sub>3<\/sub><\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>40.27<\/td>\r\n<td>CH<sub>2<\/sub><\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>e<\/strong>)\r\n\r\n<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154723\/image166.png\" alt=\"image166.png\" width=\"148\" height=\"145\" \/>\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong><strong>\u03b4<\/strong><\/strong><\/strong><\/td>\r\n<td><strong>DEPT<\/strong><\/td>\r\n<td><strong>carbon #<\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>147.79<\/td>\r\n<td>C<\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>129.18<\/td>\r\n<td>CH<\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>115.36<\/td>\r\n<td>CH<\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>111.89<\/td>\r\n<td>CH<\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>44.29<\/td>\r\n<td>CH<sub>2<\/sub><\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>12.57<\/td>\r\n<td>CH<sub>3<\/sub><\/td>\r\n<td><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\n<strong>P5.14:<\/strong>\u00a0 You obtain the following data for an unknown sample.\u00a0 Deduce its structure.\r\n\r\n<strong><sup>1<\/sup>H-NMR<\/strong>:\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154726\/image168.png\" alt=\"image168.png\" width=\"720\" height=\"360\" \/>\r\n\r\n<strong><sup>13<\/sup>C-NMR<\/strong>:\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154728\/image169.jpg\" alt=\"image169.jpg\" width=\"695px\" height=\"353px\" \/>\r\n\r\n<strong>Mass Spectrometry:<\/strong>\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154730\/image171.png\" alt=\"image171.png\" width=\"765px\" height=\"384px\" \/>\r\n\r\n<strong>P5.15:<\/strong>You take a <sup>1<\/sup>H-NMR spectrum\u00a0 of a sample that comes from a bottle of 1-bromopropane.\u00a0 However, you suspect that the bottle might be contaminated with 2-bromopropane.\u00a0 The NMR spectrum shows the following peaks:\r\n<table style=\"border-spacing: 0px\" border=\"1\" cellpadding=\"0\">\r\n<tbody>\r\n<tr>\r\n<td><strong><strong><strong>\u03b4<\/strong><\/strong><\/strong><\/td>\r\n<td><strong>splitting<\/strong><\/td>\r\n<td><strong>integration <\/strong><\/td>\r\n<\/tr>\r\n<tr>\r\n<td>4.3<\/td>\r\n<td>septet<\/td>\r\n<td>0.0735<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>3.4<\/td>\r\n<td>triplet<\/td>\r\n<td>0.661<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.9<\/td>\r\n<td>sextet<\/td>\r\n<td>0.665<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.7<\/td>\r\n<td>doublet<\/td>\r\n<td>0.441<\/td>\r\n<\/tr>\r\n<tr>\r\n<td>1.0<\/td>\r\n<td>triplet<\/td>\r\n<td>1.00<\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\nHow badly is the bottle contaminated?\u00a0 Specifically, what percent of the molecules in the bottle are 2-bromopropane?\r\n\r\n<strong><u>Challenge problems<\/u><\/strong>\r\n\r\n<strong>C5.1: <\/strong>All of the <sup>13<\/sup>C-NMR spectra shown in this chapter include a signal due to CDCl<sub>3<\/sub>, the solvent used in each case.\u00a0 Explain the splitting pattern for this signal.\r\n\r\n<strong>C5.2: <\/strong>Researchers wanted to investigate a reaction which can be\u00a0 catalyzed by the enzyme alcohol dehydrogenase in yeast.\u00a0 They treated 4'-acylpyridine (1) with living yeast, and isolated the alcohol product(s) (some combination of 2A and\u00a0 2B).\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154733\/image174.png\" alt=\"image174.png\" width=\"597\" height=\"139\" \/>\r\n\r\na) Will the products 2A and 2B have identical or different <sup>1<\/sup>H-NMR spectra? Explain.\r\n\r\nb) Suggest a <sup>1<\/sup>H-NMR experiment that could be used to determine what percent of starting material (1) got turned into product (2A and 2B).\r\n\r\nc) With purified 2A\/2B, the researchers carried out the subsequent reaction shown below to make 3A and 3B, known as 'Mosher's esters'.\u00a0 Do 3A and 3B have identical or different <sup>1<\/sup>H-NMR spectra?\u00a0 Explain.\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154737\/image176.png\" alt=\"image176.png\" width=\"341\" height=\"426\" \/>\r\n\r\nd) Explain, very specifically, how the researchers could use <sup>1<\/sup>H-NMR to determine the relative amounts of 2A and 2B formed in the reaction catalyzed by yeast enzyme.\r\n\r\n<\/div>\r\n<div id=\"section_2\">\r\n<div class=\"textbox exercises\">\r\n<div id=\"section_2\">\r\n<h3 class=\"editable\">Exercise<\/h3>\r\n<div id=\"s61718\">\r\n<div id=\"section_40\">\r\n<h4 id=\"Questions-61718\">Question<\/h4>\r\nHow can H<sup>1<\/sup> NMR determine products? For example, how can you tell the difference between the products of this reaction?\r\n\r\n<img class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154740\/13-13qu.png\" alt=\"\" width=\"506\" height=\"107\" \/>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<h3>Solution<\/h3>\r\n<div id=\"section_2\">\r\n<div id=\"s61718\">\r\n<div id=\"section_41\">\r\n<p id=\"Solutions-61718\">[reveal-answer q=\"757268\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"757268\"]Yes, you are able to determine the difference in the spectra. For the 2-chloro compound will have multiple quartets while the 1-chloro compound will only have a quintet and a triplet for the signals in the ring.\u00a0[\/hidden-answer]<\/p>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_3\">\r\n<h3 class=\"editable\">Contributors<\/h3>\r\n<ul>\r\n \t<li><a class=\"external\" title=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" href=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" target=\"_blank\" rel=\"external nofollow noopener\">Dr. Dietmar Kennepohl<\/a> FCIC (Professor of Chemistry, <a class=\"external\" title=\"http:\/\/www.athabascau.ca\/\" href=\"http:\/\/www.athabascau.ca\/\" target=\"_blank\" rel=\"external nofollow noopener\">Athabasca University<\/a>)<\/li>\r\n \t<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\r\n \t<li><a title=\"Organic_Chemistry_With_a_Biological_Emphasis\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry_Textbook_Maps\/Map%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\" rel=\"internal\">Organic Chemistry With a Biological Emphasis <\/a>by\u00a0<a class=\"external\" title=\"http:\/\/facultypages.morris.umn.edu\/~soderbt\/\" href=\"http:\/\/facultypages.morris.umn.edu\/%7Esoderbt\/\" target=\"_blank\" rel=\"external nofollow noopener\">Tim Soderberg<\/a>\u00a0(University of Minnesota, Morris)<\/li>\r\n \t<li><a href=\"http:\/\/employees.csbsju.edu\/cschaller\/srobi.htm\" rel=\"cc:attributionURL\">Chris P Schaller, Ph.D.<\/a>, <a class=\"external\" title=\"http:\/\/www.csbsju.edu\/Chemistry.htm\" href=\"http:\/\/www.csbsju.edu\/Chemistry.htm\" target=\"_blank\" rel=\"external nofollow noopener\">(College of Saint Benedict \/ Saint John's University)<\/a><\/li>\r\n<\/ul>\r\n<\/div>\r\n<\/div>","rendered":"<div class=\"elm-header\">\n<div class=\"elm-header-custom\">\n<div class=\"textbox learning-objectives\">\n<h3>Objective<\/h3>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div>\n<div id=\"skills\">\n<p>After completing this section, you should be able to use data from <sup>1<\/sup>H NMR spectra to distinguish between two (or more) possible structures for an unknown organic compound.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<p>There will be cases in which you already know what the structure might be. In these cases:<\/p>\n<\/div>\n<\/div>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div>\n<ul>\n<li>You should draw attention to pieces of data that most strongly support your expected structure. This approach will demonstrate evaluative understanding of the data; that means you can look at data and decide what parts are more crucial than others.<\/li>\n<li>You should also draw attention to negative results: that is, peaks that might be there if this spectrum matched another, possible structure, but that are in fact missing.<\/li>\n<\/ul>\n<p dir=\"LTR\">One of the most complicated problems to deal with is the analysis of a mixture. This situation is not uncommon when students run reactions in lab and analyse the data.<\/p>\n<ul>\n<li>Sometimes the spectra show a little starting material mixed in with the product.<\/li>\n<li>Sometimes solvents show up in the spectrum.<\/li>\n<li>As you might expect, the minor component usually shows up as smaller peaks in the spectrum. If there are fewer molecules present, then there are usually fewer protons to absorb in the spectrum.<\/li>\n<li>In this case, you should probably make two completely separate sets of data tables for your analysis, one for each compound, or else one for the main compound and one for impurities.<\/li>\n<\/ul>\n<p dir=\"LTR\">Remember that integration ratios are really only meaningful within a single compound. If your NMR sample contains some benzene (C<sub>6<\/sub>H<sub>6<\/sub>) and some acetone (CH<sub>3<\/sub>COCH<sub>3<\/sub>), and there is a peak at 7.15 that integrates to 1 proton and a peak at 2.10 ppm integrating to 6 protons, it might mean there are 6 protons in acetone and 1 in benzene, but you can tell that isn&#8217;t true by looking at the structure. There must be six times as many acetone molecules as benzene molecules in the sample.<\/p>\n<p dir=\"LTR\">There are six protons in the benzene, and they should all show up near 7 ppm.\u00a0 There are six protons in acetone, and they should all show up near 2 ppm.\u00a0 Assuming that small integral of 1H for the benzene is really supposed to be 6H, then the large integral of 6H for the acetone must also represent six times as many hydrogens, too.\u00a0 It would be 36 H.\u00a0 There are only six hydrogens in acetone, so it must represent six times as many acetone molecules as there are benzenes.<\/p>\n<p dir=\"LTR\">Similarly, if you have decided that you can identify two sets of peaks in the <sup>1<\/sup>H spectrum, analysing them in different tables makes it easy to keep the integration analysis completely separate too ; 1 H in one table will not be the same size integral as 1 H in the other table unless the concentrations of the two compounds in the sample are the same.<\/p>\n<p dir=\"LTR\">However, comparing the ratio of two integrals for two different compounds can give you the ratio of the two compounds in solution, just as we could determine the ratio of benzene to acetone in the mixture described above.<\/p>\n<p>We will look at two examples of sample mixtures that could arise in lab.\u00a0 Results like these are pretty common events in the labIn the first example, a student tried to carry out the following reaction, a borohydride reduction of an aldehyde.\u00a0 The borohydride should give a hydride anion to the C=O carbon; washing with water should then supply a proton to the oxygen, giving an alcohol.<a title=\"NaBH4red.gif\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/14288\/NaBH4red.gif?revision=1\" rel=\"internal\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154629\/NaBH4red.gif\" alt=\"image\" border=\"0\" \/><\/a><\/p>\n<p>Her reaction produced the following spectrum.<a title=\"NMR in1.gif\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/14289\/NMR_in1.gif?revision=1\" rel=\"internal\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154632\/NMR-in1.gif\" alt=\"image\" border=\"0\" \/><\/a><\/p>\n<p>(simulated data)<\/p>\n<p>From this data, she produced the table below.<a title=\"nmrmixtable.gif\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/14290\/nmrmixtable.gif?revision=1\" rel=\"internal\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154634\/nmrmixtable.gif\" alt=\"image\" border=\"0\" \/><\/a><\/p>\n<p dir=\"LTR\">Notice how she calculated that ratio.\u00a0 She found a peak in molecule 1, the aldehyde, that she was pretty sure corresponded to the aldehydic hydrogen, the H attached to the C=O; in other words, the CH=O.\u00a0 She found another peak from molecule 2, the alcohol, that she was pretty sure represented the two hydrogens on the carbon attached to oxygen, the CH<sub>2<\/sub>-O.<\/p>\n<p dir=\"LTR\">The integrals for those two peaks are equal.\u00a0 They are both 2H in her table.\u00a0 However, she notes that within each molecule, the first integral really represents 1H and the second represents 2H.\u00a0 That means there must be twice as many of molecule 1 as there are molecule 2.\u00a0 That way, there would be 2 x CH=O, and its integral would be the same as the 1 x CH<sub>2<\/sub>-O in the other molecule.<\/p>\n<p dir=\"LTR\">One way to approach this kind of problem is to:<\/p>\n<ul>\n<li>\u00a0choose one peak from each of the two compounds you want to compare.<\/li>\n<li>decide how many hydrogens each peak is supposed to represent in a molecule.\u00a0 Is it supposed to be a CH<sub>2<\/sub>, a CH, a CH<sub>3<\/sub>?<\/li>\n<li>divide the integral value for that peak by that number of hydrogens it is supposed to represent in a molecule.<\/li>\n<li>compare the two answers\u00a0 (integral A \/ ideal # H) vs (integral B \/ ideal # H).<\/li>\n<li>the ratio of those two answers is the ratio of the two molecules in the sample.<\/li>\n<\/ul>\n<p dir=\"LTR\">So there is twice as much aldehyde as alcohol in the mixture.\u00a0 In terms of these two compounds alone, she has 33% alcohol and 66% aldehyde.\u00a0 That&#8217;s ( 1\/(1+2) ) x100% for the alcohol, and ( 2\/(1+2) ) x100% for the aldehyde.\u00a0 That calculation just represents the amount of individual component divided by the total of the components she wants to compare.<\/p>\n<p dir=\"LTR\">There are a number of things to take note of here.<\/p>\n<ul>\n<li>Her reaction really didn&#8217;t work very well.\u00a0 She still has majority starting material, not product.<\/li>\n<li>She will get a good grade on this lab. Although the experiment didn&#8217;t work well, she has good data, and she has analyzed it very clearly.<\/li>\n<li>She has separated her data table into different sections for different compounds. Sometimes that makes it easier to analyze things.<\/li>\n<li>She has noted the actual integral data (she may have measured the integral with a ruler) and also converted it into a more convenient ratio, based on the integral for a peak that she felt certain about.<\/li>\n<li>She went one step further, and indicated the internal integration ratio within each individual compound.<\/li>\n<li>She calculated the % completion of the reaction using the integral data for the reactant and product, and she made clear what part of the data she used for that calculation.\u00a0 A similar procedure could be done if a student were just trying to separate two components in a mixture rather than carry out a reaction.<\/li>\n<li>She also calculated the overall purity of the mixture, including a solvent impurity that she failed to remove.<\/li>\n<li>However, CHCl<sub>3<\/sub> is not included in her analysis of purity.\u00a0 CHCl<sub>3<\/sub> really isn&#8217;t part of her sample; it was just present in the NMR solvent, so it doesn&#8217;t represent anything in the material she ended up with at the end of lab.<\/li>\n<\/ul>\n<p dir=\"LTR\">Another student carried out a similar reaction, shown below.\u00a0 He also finished the reaction by washing with water, but because methanol is soluble in water, he had to extract his product out of the water.\u00a0 He chose to use dichloromethane for that purpose.<a title=\"NaBH4red3.gif\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/14291\/NaBH4red3.gif?revision=1\" rel=\"internal\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154642\/NaBH4red3.gif\" alt=\"image\" border=\"0\" \/><\/a><\/p>\n<p dir=\"LTR\">He obtained the following data.<a title=\"NMR in2.gif\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/14292\/NMR_in2.gif?revision=1\" rel=\"internal\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154644\/NMR-in2.gif\" alt=\"image\" border=\"0\" \/><\/a><\/p>\n<p dir=\"LTR\">From this data, he constructed the following table.<a title=\"nmrtablecrap2.gif\" href=\"https:\/\/chem.libretexts.org\/@api\/deki\/files\/14293\/nmrtablecrap2.gif?revision=1\" rel=\"internal\"><img decoding=\"async\" class=\"aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154646\/nmrtablecrap2.gif\" alt=\"image\" border=\"0\" \/><\/a><\/p>\n<p dir=\"LTR\">There are some things to learn about this table, too.<\/p>\n<ul>\n<li>Does the integration ratio really match the integral data?\u00a0 Or is this just wishful thinking?<\/li>\n<li>This table might reflect what he wants to see in the data.\u00a0 But what else could be in the data?<\/li>\n<li>CHCl<sub>3<\/sub> is often seen in NMR spectra if CDCl<sub>3<\/sub> is used for the NMR sample. It&#8217;s there, at 7.2 ppm.<\/li>\n<li>&#8220;Leftover&#8221; or residual solvent is very common in real lab data.\u00a0 There it is, CH<sub>2<\/sub>Cl<sub>2<\/sub> from the extraction, at 5.4 ppm.<\/li>\n<li>What about water?\u00a0 Sometimes people don&#8217;t dry their solutions properly before evaporating the solvent.\u00a0 There is probably water around 1.5 to 1.6 ppm here.<\/li>\n<\/ul>\n<p dir=\"LTR\">This student might not get a very good grade; the sample does not even show up in the spectrum, so he lost it somewhere.\u00a0 But his analysis is also poor, so he will really get a terrible grade.<\/p>\n<div>\n<div id=\"example\">\n<div class=\"textbox examples\">\n<h3>Example<\/h3>\n<div>\n<div id=\"example\">\n<p dir=\"LTR\">Three students performed a synthesis of a fragrant ester, ethyl propanoate, CH<sub>3<\/sub>CH<sub>2<\/sub>CO<sub>2<\/sub>CH<sub>2<\/sub>CH<sub>3<\/sub>.\u00a0 During their reactions, they each used a different solvent.\u00a0 The students were able to see peaks in the NMR spectrum for ethyl propanoate, as well as peaks for chloroform (CHCl<sub>3<\/sub>, in the CDCl<sub>3<\/sub> they used to make their NMR samples).<\/p>\n<ul>\n<li>See the first student&#8217;s spectrum.<\/li>\n<li>See the second student&#8217;s spectrum.<\/li>\n<li>See the third student&#8217;s spectrum.<\/li>\n<\/ul>\n<p dir=\"LTR\">They were also able to determine that they had some leftover solvent in their samples by consulting a useful table of solvent impurities in NMR (which they found in Goldberg et. al., Organometallics 2010, 29, 2176-2179).<\/p>\n<ol>\n<li>What is the ratio of leftover solvent to ethyl propanoate in each sample?<\/li>\n<li>What is the percent of each sample that is leftover solvent<\/li>\n<\/ol>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_1\">\n<h3 class=\"editable\">Additional NMR Examples<\/h3>\n<p>For each molecule, predict the number of signals in the <sup>1<\/sup>H-NMR and the <sup>13<\/sup>C-NMR spectra (do not count split peaks &#8211; eg. a quartet counts as only one signal). Assume that diastereotopic groups are non-equivalent.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154649\/image142.png\" alt=\"image142.png\" width=\"660\" height=\"467\" \/><\/p>\n<p><strong>P5.2: <\/strong>For each of the 20 common amino acids, predict the number of signals in the proton-decoupled <sup>13<\/sup>C-NMR spectrum.<\/p>\n<p><strong>P5.3:<\/strong>\u00a0 Calculate the chemical shift value (expressed in Hz, to one decimal place) of each sub-peak on the <sup>1<\/sup>H-NMR doublet signal below.\u00a0 Do this for:<\/p>\n<p>a) a spectrum obtained on a 300 MHz instrument<\/p>\n<p>b) a spectrum obtained on a 100 MHz instrument<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154652\/image144.png\" alt=\"image144.png\" width=\"161\" height=\"287\" \/><\/p>\n<p><strong>P5.4:<\/strong>\u00a0 Consider a quartet signal in an <sup>1<\/sup>H-NMR spectrum obtained on a 300 MHz instrument. The chemical shift is recorded as 1.7562 ppm, and the coupling constant is J = 7.6 Hz.\u00a0 What is the chemical shift, expressed to the nearest 0.1 Hz, of the furthest downfield sub-peak in the quartet?\u00a0 What is the resonance frequency (again expressed in Hz) of this sub-peak?)<\/p>\n<p><strong>P5.5: <\/strong>One easily recognizable splitting pattern for the aromatic proton signals from disubstituted benzene structures is a pair of doublets.\u00a0 Does this pattern indicate <em>ortho<\/em>, <em>meta<\/em>, or <em>para<\/em> substitution?<\/p>\n<p><strong>P5.6 :<\/strong>Match spectra below to their corresponding structures A-F.<\/p>\n<p><u>Structures:<\/u><\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154654\/image145.png\" alt=\"image145.png\" width=\"659px\" height=\"268px\" \/><\/p>\n<p><strong>Spectrum <\/strong><strong>1<\/strong><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u00a0\u03b4<\/strong><\/td>\n<td><strong>\u00a0splitting<\/strong><\/td>\n<td><strong>\u00a0integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>4.13<\/td>\n<td>q<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>2.45<\/td>\n<td>t<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>1.94<\/td>\n<td>quintet<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>1.27<\/td>\n<td>t<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>Spectrum 2<\/strong><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u00a0\u03b4<\/strong><\/td>\n<td><strong>\u00a0splitting<\/strong><\/td>\n<td><strong>\u00a0integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>3.68<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<tr>\n<td>2.99<\/td>\n<td>t<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>1.95<\/td>\n<td>quintet<\/td>\n<td>1<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>Spectrum 3<\/strong><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u00a0\u03b4<\/strong><\/td>\n<td><strong>\u00a0splitting<\/strong><\/td>\n<td><strong>\u00a0integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>4.14<\/td>\n<td>q<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.62<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>1.26<\/td>\n<td>t<\/td>\n<td>1.5<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>Spectrum 4<\/strong><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u00a0\u03b4<\/strong><\/td>\n<td><strong>\u00a0splitting<\/strong><\/td>\n<td><strong>\u00a0integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>4.14<\/td>\n<td>q<\/td>\n<td>4<\/td>\n<\/tr>\n<tr>\n<td>3.22<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>1.27<\/td>\n<td>t<\/td>\n<td>6<\/td>\n<\/tr>\n<tr>\n<td>1.13<\/td>\n<td>s<\/td>\n<td>9<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>Spectrum 5<\/strong><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u00a0\u03b4<\/strong><\/td>\n<td><strong>\u00a0splitting<\/strong><\/td>\n<td><strong>\u00a0integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>4.18<\/td>\n<td>q<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>1.92<\/td>\n<td>q<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>1.23<\/td>\n<td>t<\/td>\n<td>1.5<\/td>\n<\/tr>\n<tr>\n<td>0.81<\/td>\n<td>t<\/td>\n<td>1.5<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>Spectrum 6<\/strong><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u00a0\u03b4<\/strong><\/td>\n<td><strong>\u00a0splitting<\/strong><\/td>\n<td><strong>\u00a0integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>3.69<\/td>\n<td>s<\/td>\n<td>1.5<\/td>\n<\/tr>\n<tr>\n<td>2.63<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>P5.7:<\/strong>\u00a0 Match spectra 7-12 below to their corresponding structures G-L .<\/p>\n<p><u>Structures:<\/u><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154657\/image148.png\" alt=\"image148.png\" width=\"559\" height=\"319\" \/><\/p>\n<p><u>Spectrum 7:<\/u><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u03b4<\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>9.96<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>5.88<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.17<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<tr>\n<td>1.98<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 8<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>9.36<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.55<\/td>\n<td>q<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.26<\/td>\n<td>q<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>1.99<\/td>\n<td>d<\/td>\n<td>3<\/td>\n<\/tr>\n<tr>\n<td>0.96<\/td>\n<td>t<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 9<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>9.57<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.30<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.00<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>1.84<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<\/div>\n<p><u>Spectrum 10<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>9.83<\/td>\n<td>t<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.27<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>1.07<\/td>\n<td>s<\/td>\n<td>9<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 11<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>9.75<\/td>\n<td>t<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.30<\/td>\n<td>dd<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>2.21<\/td>\n<td>m<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>0.98<\/td>\n<td>d<\/td>\n<td>6<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 12<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>8.08<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>4.13<\/td>\n<td>t<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>1.70<\/td>\n<td>m<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>0.96<\/td>\n<td>t<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>P5.8:<\/strong>\u00a0 Match the <sup>1<\/sup>H-NMR spectra 13-18 below to their corresponding structures M-R .<\/p>\n<p><u>Structures<\/u>:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154700\/image150.png\" alt=\"image150.png\" width=\"496\" height=\"357\" \/><\/p>\n<p><u>Spectrum 13<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u03b4<\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>8.15<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.33<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 14<\/u>: 1-723C (structure O)<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u03b4<\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>6.05<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.24<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 15<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u03b4<\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>8.57<\/td>\n<td>s (b)<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>7.89<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.30<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.28<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 16<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u03b4<\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>9.05<\/td>\n<td>s (b)<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>8.03<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.34<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>5.68<\/td>\n<td>s (b)<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>4.31<\/td>\n<td>s<\/td>\n<td>2<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 17<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u03b4<\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>7.76<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>7.57<\/td>\n<td>s (b)<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.44<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.78<\/td>\n<td>q<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>1.25<\/td>\n<td>t<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 18<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u03b4<\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>4.03<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.51<\/td>\n<td>t<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.02<\/td>\n<td>t<\/td>\n<td>1<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>P5.9:<\/strong>\u00a0 Match the <sup>1<\/sup>H-NMR spectra 19-24 below to their corresponding structures S-X.<\/p>\n<p><u>Structures<\/u>:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154703\/image152.png\" alt=\"image152.png\" width=\"600\" height=\"325\" \/><\/p>\n<p><u>Spectrum 19<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u03b4<\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>9.94<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>7.77<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>7.31<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>2.43<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 20<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u03b4<\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>10.14<\/td>\n<td>s<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>8.38<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>8.17<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>7.75<\/td>\n<td>t<\/td>\n<td>1<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 21:<\/u><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u03b4<\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>9.98<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>7.81<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>7.50<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 22<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u03b4<\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>7.15-7.29<\/td>\n<td>m<\/td>\n<td>2.5<\/td>\n<\/tr>\n<tr>\n<td>2.86<\/td>\n<td>t<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.73<\/td>\n<td>t<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.12<\/td>\n<td>s<\/td>\n<td>1.5<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 23<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u03b4<\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>7.10<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.86<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>3.78<\/td>\n<td>s<\/td>\n<td>1.5<\/td>\n<\/tr>\n<tr>\n<td>3.61<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.12<\/td>\n<td>s<\/td>\n<td>1.5<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 24<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong>\u03b4<\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>7.23-7.30<\/td>\n<td>m<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>3.53<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>P5.10:<\/strong>\u00a0 Match the <sup>1<\/sup>H-NMR spectra 25-30 below to their corresponding structures AA-FF.<\/p>\n<p><u>Structures<\/u>:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154706\/image154.png\" alt=\"image154.png\" width=\"688\" height=\"366\" \/><\/p>\n<p><u>Spectrum 25<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>9.96<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>7.79<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>7.33<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>2.72<\/td>\n<td>q<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>1.24<\/td>\n<td>t<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 26<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>9.73<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>7.71<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>6.68<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>3.06<\/td>\n<td>s<\/td>\n<td>6<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 27<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>\u00a0splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>7.20-7.35<\/td>\n<td>m<\/td>\n<td>10<\/td>\n<\/tr>\n<tr>\n<td>5.12<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.22<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 28<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>8.08<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>7.29<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>6.87<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>5.11<\/td>\n<td>s<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>3.78<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 29<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>7.18<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.65<\/td>\n<td>m<\/td>\n<td>1.5<\/td>\n<\/tr>\n<tr>\n<td>3.2<\/td>\n<td>q<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>1.13<\/td>\n<td>t<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 30<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>8.32<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>4.19<\/td>\n<td>t<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>2.83<\/td>\n<td>t<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>2.40<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>P5.11:<\/strong>\u00a0 Match the <sup>1<\/sup>H-NMR spectra 31-36 below to their corresponding structures GG-LL<\/p>\n<p><u>Structures<\/u>:<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154709\/image155a.png\" alt=\"image155a.png\" width=\"681px\" height=\"363px\" \/><\/p>\n<p><u>Spectrum 31<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>6.98<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.64<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.54<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>4.95<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.23<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<tr>\n<td>2.17<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 32<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>7.08<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.72<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.53<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>4.81<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>3.15<\/td>\n<td>7-tet<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.24<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<tr>\n<td>1.22<\/td>\n<td>d<\/td>\n<td>6<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 33<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>7.08<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>6.71<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>6.54<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>3.69<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<tr>\n<td>3.54<\/td>\n<td>s<\/td>\n<td>2<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 34<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>9.63<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>7.45<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>6.77<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>3.95<\/td>\n<td>q<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>2.05<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<tr>\n<td>1.33<\/td>\n<td>t<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 35<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>9.49<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>7.20<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>6.49<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>4.82<\/td>\n<td>s<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>1.963<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u>Spectrum 36<\/u>:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>9.58<\/td>\n<td>s(b)<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>9.31<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>7.36<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.67<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.55<\/td>\n<td>d<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.21<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<tr>\n<td>2.11<\/td>\n<td>s<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>P5.12:<\/strong> Use the NMR data given to deduce structures.<\/p>\n<p>a ) Molecular formula: C<sub>5<\/sub>H<sub>8<\/sub>O<\/p>\n<p><u><sup>1<\/sup><\/u><u>H-NMR:<\/u><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>9.56<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>6.25<\/td>\n<td>d (J~1 Hz)<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>5.99<\/td>\n<td>d (J~1 Hz)<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.27<\/td>\n<td>q<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>1.18<\/td>\n<td>t<\/td>\n<td>3<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u><sup>13<\/sup><\/u><u>C-NMR<\/u><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>DEPT<\/strong><\/td>\n<\/tr>\n<tr>\n<td>194.60<\/td>\n<td>CH<\/td>\n<\/tr>\n<tr>\n<td>151.77<\/td>\n<td>C<\/td>\n<\/tr>\n<tr>\n<td>132.99<\/td>\n<td>CH<sub>2<\/sub><\/td>\n<\/tr>\n<tr>\n<td>20.91<\/td>\n<td>CH<sub>2<\/sub><\/td>\n<\/tr>\n<tr>\n<td>11.92<\/td>\n<td>CH<sub>3<\/sub><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p>b) Molecular formula: C<sub>7<\/sub>H<sub>14<\/sub>O<sub>2<\/sub><\/p>\n<p><u><sup>1<\/sup><\/u><u>H-NMR:<\/u><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>3.85<\/td>\n<td>d<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>2.32<\/td>\n<td>q<\/td>\n<td>2<\/td>\n<\/tr>\n<tr>\n<td>1.93<\/td>\n<td>m<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>1.14<\/td>\n<td>t<\/td>\n<td>3<\/td>\n<\/tr>\n<tr>\n<td>0.94<\/td>\n<td>d<\/td>\n<td>6<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u><sup>13<\/sup><\/u><u>C-NMR<\/u><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>DEPT<\/strong><\/td>\n<\/tr>\n<tr>\n<td>174.47<\/td>\n<td>C<\/td>\n<\/tr>\n<tr>\n<td>70.41<\/td>\n<td>CH<sub>2<\/sub><\/td>\n<\/tr>\n<tr>\n<td>27.77<\/td>\n<td>CH<\/td>\n<\/tr>\n<tr>\n<td>27.64<\/td>\n<td>CH<sub>2<\/sub><\/td>\n<\/tr>\n<tr>\n<td>19.09<\/td>\n<td>CH<sub>3<\/sub><\/td>\n<\/tr>\n<tr>\n<td>9.21<\/td>\n<td>CH<sub>3<\/sub><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p>c) Molecular formula: C<sub>5<\/sub>H<sub>12<\/sub>O<\/p>\n<p><u><sup>1<\/sup><\/u><u>H-NMR:<\/u><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>3.38<\/td>\n<td>s<\/td>\n<td>2H<\/td>\n<\/tr>\n<tr>\n<td>2.17<\/td>\n<td>s<\/td>\n<td>1H<\/td>\n<\/tr>\n<tr>\n<td>0.91<\/td>\n<td>s<\/td>\n<td>9H<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u><sup>13<\/sup><\/u><u>C-NMR<\/u><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>DEPT<\/strong><\/td>\n<\/tr>\n<tr>\n<td>73.35<\/td>\n<td>CH<sub>2<\/sub><\/td>\n<\/tr>\n<tr>\n<td>32.61<\/td>\n<td>C<\/td>\n<\/tr>\n<tr>\n<td>26.04<\/td>\n<td>CH<sub>3<\/sub><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p>d) Molecular formula: C<sub>10<\/sub>H<sub>12<\/sub>O<\/p>\n<p><u><sup>1<\/sup><\/u><u>H-NMR:<\/u><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration<\/strong><\/td>\n<\/tr>\n<tr>\n<td>7.18-7.35<\/td>\n<td>m<\/td>\n<td>2.5<\/td>\n<\/tr>\n<tr>\n<td>3.66<\/td>\n<td>s<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>2.44<\/td>\n<td>q<\/td>\n<td>1<\/td>\n<\/tr>\n<tr>\n<td>1.01<\/td>\n<td>t<\/td>\n<td>1.5<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><u><sup>13<\/sup><\/u><u>C-NMR<\/u><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>DEPT<\/strong><\/td>\n<\/tr>\n<tr>\n<td>208.79<\/td>\n<td>C<\/td>\n<\/tr>\n<tr>\n<td>134.43<\/td>\n<td>C<\/td>\n<\/tr>\n<tr>\n<td>129.31<\/td>\n<td>CH<\/td>\n<\/tr>\n<tr>\n<td>128.61<\/td>\n<td>CH<\/td>\n<\/tr>\n<tr>\n<td>126.86<\/td>\n<td>CH<\/td>\n<\/tr>\n<tr>\n<td>49.77<\/td>\n<td>CH<sub>2<\/sub><\/td>\n<\/tr>\n<tr>\n<td>35.16<\/td>\n<td>CH<sub>2<\/sub><\/td>\n<\/tr>\n<tr>\n<td>7.75<\/td>\n<td>CH<sub>3<\/sub><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>P5.13:<\/strong><\/p>\n<p><sup>13<\/sup>C-NMR data is given for the molecules shown below.\u00a0 Complete the peak assignment column of each NMR data table.<\/p>\n<p><strong>a)<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154716\/image158.png\" alt=\"image158.png\" width=\"123\" height=\"73\" \/><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>DEPT<\/strong><\/td>\n<td><strong>carbon #<\/strong><\/td>\n<\/tr>\n<tr>\n<td>161.12<\/td>\n<td>CH<\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>65.54<\/td>\n<td>CH<sub>2<\/sub><\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>21.98<\/td>\n<td>CH<sub>2<\/sub><\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>10.31<\/td>\n<td>CH<sub>3<\/sub><\/td>\n<td><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>b)<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154717\/image160.png\" alt=\"image160.png\" width=\"91\" height=\"120\" \/><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong>\u03b4<\/strong><\/strong><\/td>\n<td><strong>DEPT<\/strong><\/td>\n<td><strong>carbon #<\/strong><\/td>\n<\/tr>\n<tr>\n<td>194.72<\/td>\n<td>C<\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>149.10<\/td>\n<td>C<\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>146.33<\/td>\n<td>CH<\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>16.93<\/td>\n<td>CH<sub>2<\/sub><\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>14.47<\/td>\n<td>CH<sub>3<\/sub><\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>12.93<\/td>\n<td>CH<sub>3<\/sub><\/td>\n<td><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>c)<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154719\/image162.png\" alt=\"image162.png\" width=\"208\" height=\"113\" \/><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr style=\"height: 15px\">\n<td style=\"height: 15px\"><strong><strong><strong>\u03b4<\/strong><\/strong><\/strong><\/td>\n<td style=\"height: 15px\"><strong>DEPT<\/strong><\/td>\n<td style=\"height: 15px\"><strong>carbon #<\/strong><\/td>\n<\/tr>\n<tr style=\"height: 15px\">\n<td style=\"height: 15px\">171.76<\/td>\n<td style=\"height: 15px\">C<\/td>\n<td style=\"height: 15px\"><\/td>\n<\/tr>\n<tr style=\"height: 18px\">\n<td style=\"height: 18px\">60.87<\/td>\n<td style=\"height: 18px\">CH<sub>2<\/sub><\/td>\n<td style=\"height: 18px\"><\/td>\n<\/tr>\n<tr style=\"height: 15px\">\n<td style=\"height: 15px\">58.36<\/td>\n<td style=\"height: 15px\">C<\/td>\n<td style=\"height: 15px\"><\/td>\n<\/tr>\n<tr style=\"height: 18px\">\n<td style=\"height: 18px\">24.66<\/td>\n<td style=\"height: 18px\">CH<sub>2<\/sub><\/td>\n<td style=\"height: 18px\"><\/td>\n<\/tr>\n<tr style=\"height: 18.6562px\">\n<td style=\"height: 18.6562px\">14.14<\/td>\n<td style=\"height: 18.6562px\">CH<sub>3<\/sub><\/td>\n<td style=\"height: 18.6562px\"><\/td>\n<\/tr>\n<tr style=\"height: 18px\">\n<td style=\"height: 18px\">8.35<\/td>\n<td style=\"height: 18px\">CH<sub>3<\/sub><\/td>\n<td style=\"height: 18px\"><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>d)<\/strong><\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154721\/image164.png\" alt=\"image164.png\" width=\"221\" height=\"94\" \/><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong><strong>\u03b4<\/strong><\/strong><\/strong><\/td>\n<td><strong>DEPT<\/strong><\/td>\n<td><strong>carbon #<\/strong><\/td>\n<\/tr>\n<tr>\n<td>173.45<\/td>\n<td>C<\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>155.01<\/td>\n<td>C<\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>130.34<\/td>\n<td>CH<\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>125.34<\/td>\n<td>C<\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>115.56<\/td>\n<td>CH<\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>52.27<\/td>\n<td>CH<sub>3<\/sub><\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>40.27<\/td>\n<td>CH<sub>2<\/sub><\/td>\n<td><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>e<\/strong>)<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154723\/image166.png\" alt=\"image166.png\" width=\"148\" height=\"145\" \/><\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong><strong>\u03b4<\/strong><\/strong><\/strong><\/td>\n<td><strong>DEPT<\/strong><\/td>\n<td><strong>carbon #<\/strong><\/td>\n<\/tr>\n<tr>\n<td>147.79<\/td>\n<td>C<\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>129.18<\/td>\n<td>CH<\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>115.36<\/td>\n<td>CH<\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>111.89<\/td>\n<td>CH<\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>44.29<\/td>\n<td>CH<sub>2<\/sub><\/td>\n<td><\/td>\n<\/tr>\n<tr>\n<td>12.57<\/td>\n<td>CH<sub>3<\/sub><\/td>\n<td><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><strong>P5.14:<\/strong>\u00a0 You obtain the following data for an unknown sample.\u00a0 Deduce its structure.<\/p>\n<p><strong><sup>1<\/sup>H-NMR<\/strong>:<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154726\/image168.png\" alt=\"image168.png\" width=\"720\" height=\"360\" \/><\/p>\n<p><strong><sup>13<\/sup>C-NMR<\/strong>:<\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154728\/image169.jpg\" alt=\"image169.jpg\" width=\"695px\" height=\"353px\" \/><\/p>\n<p><strong>Mass Spectrometry:<\/strong><\/p>\n<p><img decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154730\/image171.png\" alt=\"image171.png\" width=\"765px\" height=\"384px\" \/><\/p>\n<p><strong>P5.15:<\/strong>You take a <sup>1<\/sup>H-NMR spectrum\u00a0 of a sample that comes from a bottle of 1-bromopropane.\u00a0 However, you suspect that the bottle might be contaminated with 2-bromopropane.\u00a0 The NMR spectrum shows the following peaks:<\/p>\n<table style=\"border-spacing: 0px\" cellpadding=\"0\">\n<tbody>\n<tr>\n<td><strong><strong><strong>\u03b4<\/strong><\/strong><\/strong><\/td>\n<td><strong>splitting<\/strong><\/td>\n<td><strong>integration <\/strong><\/td>\n<\/tr>\n<tr>\n<td>4.3<\/td>\n<td>septet<\/td>\n<td>0.0735<\/td>\n<\/tr>\n<tr>\n<td>3.4<\/td>\n<td>triplet<\/td>\n<td>0.661<\/td>\n<\/tr>\n<tr>\n<td>1.9<\/td>\n<td>sextet<\/td>\n<td>0.665<\/td>\n<\/tr>\n<tr>\n<td>1.7<\/td>\n<td>doublet<\/td>\n<td>0.441<\/td>\n<\/tr>\n<tr>\n<td>1.0<\/td>\n<td>triplet<\/td>\n<td>1.00<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p>How badly is the bottle contaminated?\u00a0 Specifically, what percent of the molecules in the bottle are 2-bromopropane?<\/p>\n<p><strong><u>Challenge problems<\/u><\/strong><\/p>\n<p><strong>C5.1: <\/strong>All of the <sup>13<\/sup>C-NMR spectra shown in this chapter include a signal due to CDCl<sub>3<\/sub>, the solvent used in each case.\u00a0 Explain the splitting pattern for this signal.<\/p>\n<p><strong>C5.2: <\/strong>Researchers wanted to investigate a reaction which can be\u00a0 catalyzed by the enzyme alcohol dehydrogenase in yeast.\u00a0 They treated 4&#8242;-acylpyridine (1) with living yeast, and isolated the alcohol product(s) (some combination of 2A and\u00a0 2B).<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154733\/image174.png\" alt=\"image174.png\" width=\"597\" height=\"139\" \/><\/p>\n<p>a) Will the products 2A and 2B have identical or different <sup>1<\/sup>H-NMR spectra? Explain.<\/p>\n<p>b) Suggest a <sup>1<\/sup>H-NMR experiment that could be used to determine what percent of starting material (1) got turned into product (2A and 2B).<\/p>\n<p>c) With purified 2A\/2B, the researchers carried out the subsequent reaction shown below to make 3A and 3B, known as &#8216;Mosher&#8217;s esters&#8217;.\u00a0 Do 3A and 3B have identical or different <sup>1<\/sup>H-NMR spectra?\u00a0 Explain.<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154737\/image176.png\" alt=\"image176.png\" width=\"341\" height=\"426\" \/><\/p>\n<p>d) Explain, very specifically, how the researchers could use <sup>1<\/sup>H-NMR to determine the relative amounts of 2A and 2B formed in the reaction catalyzed by yeast enzyme.<\/p>\n<\/div>\n<div id=\"section_2\">\n<div class=\"textbox exercises\">\n<div id=\"section_2\">\n<h3 class=\"editable\">Exercise<\/h3>\n<div id=\"s61718\">\n<div id=\"section_40\">\n<h4 id=\"Questions-61718\">Question<\/h4>\n<p>How can H<sup>1<\/sup> NMR determine products? For example, how can you tell the difference between the products of this reaction?<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"internal default aligncenter\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05154740\/13-13qu.png\" alt=\"\" width=\"506\" height=\"107\" \/><\/p>\n<\/div>\n<\/div>\n<\/div>\n<h3>Solution<\/h3>\n<div id=\"section_2\">\n<div id=\"s61718\">\n<div id=\"section_41\">\n<p id=\"Solutions-61718\">\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q757268\">Show Answer<\/span><\/p>\n<div id=\"q757268\" class=\"hidden-answer\" style=\"display: none\">Yes, you are able to determine the difference in the spectra. For the 2-chloro compound will have multiple quartets while the 1-chloro compound will only have a quintet and a triplet for the signals in the ring.\u00a0<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_3\">\n<h3 class=\"editable\">Contributors<\/h3>\n<ul>\n<li><a class=\"external\" title=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" href=\"http:\/\/science.athabascau.ca\/staff-pages\/dietmark\" target=\"_blank\" rel=\"external nofollow noopener\">Dr. Dietmar Kennepohl<\/a> FCIC (Professor of Chemistry, <a class=\"external\" title=\"http:\/\/www.athabascau.ca\/\" href=\"http:\/\/www.athabascau.ca\/\" target=\"_blank\" rel=\"external nofollow noopener\">Athabasca University<\/a>)<\/li>\n<li>Prof. Steven Farmer (<a class=\"external\" title=\"http:\/\/www.sonoma.edu\" href=\"http:\/\/www.sonoma.edu\" target=\"_blank\" rel=\"external nofollow noopener\">Sonoma State University<\/a>)<\/li>\n<li><a title=\"Organic_Chemistry_With_a_Biological_Emphasis\" href=\"https:\/\/chem.libretexts.org\/Textbook_Maps\/Organic_Chemistry_Textbook_Maps\/Map%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)\" rel=\"internal\">Organic Chemistry With a Biological Emphasis <\/a>by\u00a0<a class=\"external\" title=\"http:\/\/facultypages.morris.umn.edu\/~soderbt\/\" href=\"http:\/\/facultypages.morris.umn.edu\/%7Esoderbt\/\" target=\"_blank\" rel=\"external nofollow noopener\">Tim Soderberg<\/a>\u00a0(University of Minnesota, Morris)<\/li>\n<li><a href=\"http:\/\/employees.csbsju.edu\/cschaller\/srobi.htm\" rel=\"cc:attributionURL\">Chris P Schaller, Ph.D.<\/a>, <a class=\"external\" title=\"http:\/\/www.csbsju.edu\/Chemistry.htm\" href=\"http:\/\/www.csbsju.edu\/Chemistry.htm\" target=\"_blank\" rel=\"external nofollow noopener\">(College of Saint Benedict \/ Saint John&#8217;s University)<\/a><\/li>\n<\/ul>\n<\/div>\n<\/div>\n","protected":false},"author":44985,"menu_order":13,"template":"","meta":{"_candela_citation":"[]","CANDELA_OUTCOMES_GUID":"","pb_show_title":"on","pb_short_title":"","pb_subtitle":"","pb_authors":[],"pb_section_license":""},"chapter-type":[],"contributor":[],"license":[],"class_list":["post-1770","chapter","type-chapter","status-publish","hentry"],"part":29,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1770","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/users\/44985"}],"version-history":[{"count":11,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1770\/revisions"}],"predecessor-version":[{"id":2358,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1770\/revisions\/2358"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/parts\/29"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1770\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=1770"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=1770"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=1770"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=1770"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}