{"id":1654,"date":"2017-10-10T16:35:35","date_gmt":"2017-10-10T16:35:35","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/?post_type=chapter&#038;p=1654"},"modified":"2018-10-05T19:19:57","modified_gmt":"2018-10-05T19:19:57","slug":"infrared-spectra-of-some-common-functional-groups","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/chapter\/infrared-spectra-of-some-common-functional-groups\/","title":{"raw":"Infrared Spectra of Some Common Functional Groups","rendered":"Infrared Spectra of Some Common Functional Groups"},"content":{"raw":"<div class=\"elm-header\">\r\n<div class=\"elm-header-custom\">\r\n<div class=\"textbox learning-objectives\">\r\n<h3>Objectives<\/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 an infrared spectrum to determine the presence of functional groups, such as alcohols, amines and carbonyl groups, in an unknown compound, given a list of infrared absorption frequencies.\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"elm-main-content\" class=\"elm-content-container\">\r\n<div>\r\n<div id=\"note\">\r\n<div class=\"textbox\">\r\n<div id=\"note\">\r\n<h3 class=\"boxtitle\">Study Notes<\/h3>\r\nIn <a title=\"12.7 Interpreting Infrared Spectra\" href=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_12%3A_Structure_Determination%3A_Mass_Spectrometry_and_Infrared_Spectroscopy\/12.07_Interpreting_Infrared_Spectra\" rel=\"internal\">Chapter 12.7<\/a>, you should have learned, in broad terms, where a few key absorptions occur. Otherwise, to find the characteristic infrared absorptions of the various functional groups, refer to <a href=\"https:\/\/chem.libretexts.org\/Reference\/Reference_Tables\/Spectroscopic_Parameters\/Infrared_Spectroscopy_Absorption_Table\" target=\"_blank\" rel=\"internal noopener\">this IR table<\/a>.\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_1\">\r\n<h2 class=\"editable\">Spectral Interpretation by Application of Group Frequencies<\/h2>\r\nOne of the most common application of infrared spectroscopy is to the identification of organic compounds. The major classes of organic molecules are shown\u00a0in this category\u00a0and\u00a0also linked on the bottom page for the\u00a0number of collections of spectral information regarding organic molecules.\r\n<h3>Hydrocarbons<\/h3>\r\n<div id=\"section_2\">\r\n\r\nHydrocarbons compounds contain only C-H and C-C bonds, but there is plenty of information to be obtained from the infrared spectra arising from C-H stretching and C-H bending.\r\n\r\nIn alkanes, which have very few bands, each band in the spectrum can be assigned:\r\n<ul>\r\n \t<li>C\u2013H stretch from 3000\u20132850 cm<sup>-1<\/sup><\/li>\r\n \t<li>C\u2013H bend or scissoring from 1470-1450 cm<sup>-1<\/sup><\/li>\r\n \t<li>C\u2013H rock, methyl from 1370-1350 cm<sup>-1<\/sup><\/li>\r\n \t<li>C\u2013H rock, methyl, seen only in long chain alkanes, from 725-720 cm<sup>-1<\/sup><\/li>\r\n<\/ul>\r\nFigure 3. shows the IR spectrum of octane. Since most organic compounds have these features, these C-H vibrations are usually not noted when interpreting a routine IR spectrum. Note that the change in dipole moment with respect to distance for the C-H stretching is greater than that for others shown, which is why the C-H stretch band is the more intense.\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"550\"]<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05153652\/octane_1.png\" alt=\"octane (1).png\" width=\"550\" height=\"276\" \/> Figure 3. Infrared Spectrum of Octane[\/caption]\r\n\r\nIn alkenes compounds, each band in the spectrum can be assigned:\r\n<ul>\r\n \t<li>C=C stretch from 1680-1640 cm<sup>-1<\/sup><\/li>\r\n \t<li>=C\u2013H stretch from 3100-3000 cm<sup>-1<\/sup><\/li>\r\n \t<li>=C\u2013H bend from 1000-650 cm<sup>-1<\/sup><\/li>\r\n<\/ul>\r\nFigure 4. shows the IR spectrum of 1-octene. As alkanes compounds, these bands are not specific and are generally not noted because they are present in almost all organic molecules.\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"550\"]<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05153654\/1-octene.png\" alt=\"1-octene.png\" width=\"550\" height=\"272\" \/> Figure 4. Infrared Spectrum of 1-Octene[\/caption]\r\n\r\nIn alkynes, each band in the spectrum can be assigned:\r\n<ul>\r\n \t<li>\u2013C?C\u2013 stretch from 2260-2100 cm<sup>-1<\/sup><\/li>\r\n \t<li>\u2013C?C\u2013H: C\u2013H stretch from 3330-3270 cm<sup>-1<\/sup><\/li>\r\n \t<li>\u2013C?C\u2013H: C\u2013H bend from 700-610 cm<sup>-1<\/sup><\/li>\r\n<\/ul>\r\nThe spectrum of 1-hexyne, a terminal alkyne, is shown below.\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"550\"]<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05153656\/1-hexyne.png\" alt=\"1-hexyne.png\" width=\"550\" height=\"276\" \/> Figure 5. Infrared Spectrum of 1-Hexyne[\/caption]\r\n\r\nIn aromatic compounds,\u00a0each band in the spectrum can be assigned:\r\n<ul>\r\n \t<li>C\u2013H stretch from 3100-3000 cm<sup>-1<\/sup><\/li>\r\n \t<li>overtones, weak, from 2000-1665 cm<sup>-1<\/sup><\/li>\r\n \t<li>C\u2013C stretch (in-ring) from 1600-1585 cm<sup>-1<\/sup><\/li>\r\n \t<li>C\u2013C stretch (in-ring) from 1500-1400 cm<sup>-1<\/sup><\/li>\r\n \t<li>C\u2013H \"oop\" from 900-675 cm<sup>-1<\/sup><\/li>\r\n<\/ul>\r\nNote that this is at slightly higher frequency than is the \u2013C\u2013H stretch in alkanes. This is a very useful tool for interpreting IR spectra. Only alkenes and aromatics show a C\u2013H stretch slightly higher than 3000 cm<sup>-1<\/sup>.\r\n\r\nFigure 6. shows the spectrum of toluene.\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"550\"]<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05153659\/toluene.png\" alt=\"toluene.png\" width=\"550\" height=\"276\" \/> Figure 6. Infrared Spectrum of Toluene[\/caption]\r\n\r\n<div id=\"section_3\">\r\n<h4 class=\"editable\">Functional Groups Containing the C-O Bond<\/h4>\r\nAlcohols have IR absorptions associated with both the O-H and the C-O stretching vibrations.\r\n<ul>\r\n \t<li>O\u2013H stretch, hydrogen bonded 3500-3200 cm<sup>-1<\/sup><\/li>\r\n \t<li>C\u2013O stretch 1260-1050 cm<sup>-1<\/sup> (s)<\/li>\r\n<\/ul>\r\nFigure 7. shows the spectrum of ethanol. Note the very broad, strong band of the O\u2013H stretch.\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"550\"]<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05153701\/ethanol.png\" alt=\"ethanol.png\" width=\"550\" height=\"279\" \/> Figure 7. Infrared Spectrum of Ethanol[\/caption]\r\n\r\nThe carbonyl stretching vibration band C=O of saturated aliphatic ketones appears:\r\n<ul>\r\n \t<li>\u00a0C=O stretch\u00a0\u00a0\u00a0- aliphatic ketones 1715 cm<sup>-1<\/sup><\/li>\r\n<\/ul>\r\n- ?, ?-unsaturated ketones 1685-1666 cm<sup>-1<\/sup>\r\n\r\nFigure 8. shows the spectrum of 2-butanone. This is a saturated ketone, and the C=O band appears at 1715.\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"550\"]<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05153703\/2-butanone.png\" alt=\"2-butanone.png\" width=\"550\" height=\"283\" \/> Figure 8. Infrared Spectrum of 2-Butanone[\/caption]\r\n\r\nIf a compound is suspected to be an aldehyde, a peak always appears around 2720 cm<sup>-1<\/sup> which\u00a0often appears as a shoulder-type peak just to the right of the alkyl C\u2013H stretches.\r\n<ul>\r\n \t<li>H\u2013C=O stretch 2830-2695 cm<sup>-1<\/sup><\/li>\r\n \t<li>C=O stretch:\r\n<ul>\r\n \t<li>aliphatic aldehydes 1740-1720 cm<sup>-1<\/sup><\/li>\r\n \t<li>alpha, beta-unsaturated aldehydes 1710-1685 cm<sup>-1<\/sup><\/li>\r\n<\/ul>\r\n<\/li>\r\n<\/ul>\r\nFigure 9. shows the spectrum of butyraldehyde.\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"550\"]<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05153705\/butyraldehyde.png\" alt=\"butyraldehyde.png\" width=\"550\" height=\"287\" \/> Figure 9. Infrared Spectrum of Butyraldehyde[\/caption]\r\n\r\nThe carbonyl stretch C=O of esters appears:\r\n<ul>\r\n \t<li>C=O stretch\r\n<ul>\r\n \t<li>aliphatic from 1750-1735 cm<sup>-1<\/sup><\/li>\r\n \t<li>?, ?-unsaturated from 1730-1715 cm<sup>-1<\/sup><\/li>\r\n<\/ul>\r\n<\/li>\r\n \t<li>C\u2013O stretch from 1300-1000 cm<sup>-1<\/sup><\/li>\r\n<\/ul>\r\nFigure 10. shows the spectrum of ethyl benzoate.\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"904\"]<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05153708\/ethyl_benzoate.png\" alt=\"ethyl benzoate.png\" width=\"904\" height=\"459\" \/> Figure 10. Infrared Spectrum of Ethyl benzoate[\/caption]\r\n\r\nThe carbonyl stretch C=O of a carboxylic acid appears as an intense band from 1760-1690 cm<sup>-1<\/sup>. The exact position of this broad band depends on whether the carboxylic acid is saturated or unsaturated, dimerized, or has internal hydrogen bonding.\r\n<ul>\r\n \t<li>O\u2013H stretch from 3300-2500 cm<sup>-1<\/sup><\/li>\r\n \t<li>C=O stretch from 1760-1690 cm<sup>-1<\/sup><\/li>\r\n \t<li>C\u2013O stretch from 1320-1210 cm<sup>-1<\/sup><\/li>\r\n \t<li>O\u2013H bend from 1440-1395 and 950-910 cm<sup>-1<\/sup><\/li>\r\n<\/ul>\r\nFigure 11. shows the spectrum of hexanoic acid.\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"928\"]<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05153711\/hexanoic_acid.png\" alt=\"hexanoic acid.png\" width=\"928\" height=\"471\" \/> Figure 11. Infrared Spectrum of Hexanoic acid[\/caption]\r\n\r\n<\/div>\r\n<div id=\"section_4\">\r\n<h4 class=\"editable\">Organic Nitrogen Compounds<\/h4>\r\n<ul>\r\n \t<li>N\u2013O asymmetric stretch from 1550-1475 cm<sup>-1<\/sup><\/li>\r\n \t<li>N\u2013O symmetric stretch from 1360-1290 cm<sup>-1<\/sup><\/li>\r\n<\/ul>\r\n[caption id=\"\" align=\"aligncenter\" width=\"927\"]<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05153714\/nitromethane.png\" alt=\"nitromethane.png\" width=\"927\" height=\"471\" \/> Figure 12. Infrared Spectrum of Nitomethane[\/caption]\r\n\r\n<\/div>\r\n<div id=\"section_5\">\r\n<h4 class=\"editable\">Organic Compounds Containing Halogens<\/h4>\r\nAlkyl halides are compounds that have a C\u2013X bond, where X is a halogen: bromine, chlorine, fluorene, or iodine.\r\n<ul>\r\n \t<li>C\u2013H wag (-CH<sub>2<\/sub>X) from 1300-1150 cm<sup>-1<\/sup><\/li>\r\n \t<li>C\u2013X stretches (general) from 850-515 cm<sup>-1<\/sup>\r\n<ul>\r\n \t<li>C\u2013Cl stretch 850-550 cm<sup>-1<\/sup><\/li>\r\n \t<li>C\u2013Br stretch 690-515 cm<sup>-1<\/sup><\/li>\r\n<\/ul>\r\n<\/li>\r\n<\/ul>\r\nThe spectrum of 1-chloro-2-methylpropane are shown below.\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"904\"]<img class=\"internal default\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/1518\/2017\/10\/05153717\/1-chloro-2-methylpropane.png\" alt=\"1-chloro-2-methylpropane.png\" width=\"904\" height=\"471\" \/> Figure 13. Infrared Spectrum of 1-chloro-2-methylpropane[\/caption]\r\n\r\nFor more Infrared spectra <a class=\"external\" title=\"http:\/\/riodb01.ibase.aist.go.jp\/sdbs\/\" href=\"http:\/\/riodb01.ibase.aist.go.jp\/sdbs\/\" target=\"_blank\" rel=\"external nofollow noopener\">Spectral database of organic molecules <\/a>is\u00a0introduced to use free database. Also, the <a class=\"external\" title=\"http:\/\/en.wikipedia.org\/wiki\/Infrared_spectroscopy_correlation_table\" href=\"http:\/\/en.wikipedia.org\/wiki\/Infrared_spectroscopy_correlation_table\" target=\"_blank\" rel=\"external nofollow noopener\">infrared spectroscopy correlation <\/a>table is linked on bottom of page to find other assigned IR peaks.\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_6\">\r\n<div class=\"textbox exercises\">\r\n<h3>Exercises<\/h3>\r\n<div id=\"section_6\">\r\n<div id=\"s61717\">\r\n<div id=\"section_24\">\r\n<h4 id=\"Questions-61717\">Questions<\/h4>\r\n<strong>1.\u00a0<\/strong>The following spectra is for the accompanying compound. What are the peaks that you can I identify in the spectrum?\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\/05153720\/12.8.png\" alt=\"\" width=\"195\" height=\"112\" \/>\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\/05153723\/12.10.gif\" alt=\"\" width=\"663\" height=\"365\" \/>\r\n\r\nSource: SDBSWeb :\u00a0<a class=\"external\" title=\"http:\/\/sdbs.db.aist.go.jp\" href=\"http:\/\/sdbs.db.aist.go.jp\/\" target=\"_blank\" rel=\"external nofollow noopener\">http:\/\/sdbs.db.aist.go.jp<\/a>\u00a0(National Institute of Advanced Industrial Science and Technology, 2 December 2016)\r\n\r\n<strong>2.\u00a0<\/strong>What absorptions would the following compounds have in an IR spectra?\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\/05153725\/12.82.png\" alt=\"\" width=\"439\" height=\"362\" \/>\r\n<h3>Solutions<\/h3>\r\n[reveal-answer q=\"637753\"]Show Answer[\/reveal-answer]\r\n[hidden-answer a=\"637753\"]\r\n\r\n1. Frequency (cm-1)\u00a0\u00a0\u00a0\u00a0\u00a0 Functional Group\r\n\r\n3200\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 C\u2261C-H\r\n\r\n2900-3000\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0C-C-H, C=C-H 2100\r\n\r\nC\u2261C 1610\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 C=C\r\n\r\n(There is also an aromatic undertone region between 2000-1600 which describes the substitution on the phenyl ring.)\r\n\r\n2.A)\r\n\r\nFrequency (cm-1)\u00a0\u00a0\u00a0\u00a0\u00a0 Functional Group\r\n\r\n2900-3000\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0C-C-H, C=C-H\r\n\r\n1710\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 C=O\r\n\r\n1610\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 C=C\r\n\r\n1100\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 C-O\r\n\r\nB)\r\n\r\nFrequency (cm-1)\u00a0\u00a0\u00a0\u00a0\u00a0 Functional Group\r\n\r\n3200\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C\u2261C-H\r\n\r\n2900-3000\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C-C-H, C=C-H\r\n\r\n2100\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C\u2261C\r\n\r\n1710\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C=O\r\n\r\nC)\r\n\r\nFrequency (cm-1)\u00a0\u00a0\u00a0\u00a0\u00a0 Functional Group\r\n\r\n3300 (broad)\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 O-H\r\n\r\n2900-3000\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C-C-H, C=C-H\r\n\r\n2000-1800\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 Aromatic Overtones\r\n\r\n1710\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C=O\r\n\r\n1610\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C=C\r\n\r\n[\/hidden-answer]\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<\/div>\r\n<div id=\"section_7\">\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>William Reusch, Professor Emeritus (<a class=\"external\" title=\"http:\/\/www.msu.edu\/\" href=\"http:\/\/www.msu.edu\/\" target=\"_blank\" rel=\"external nofollow noopener\">Michigan State U.<\/a>), <a class=\"external\" title=\"http:\/\/www.cem.msu.edu\/~reusch\/VirtualText\/intro1.htm\" href=\"http:\/\/www.cem.msu.edu\/%7Ereusch\/VirtualText\/intro1.htm\" target=\"_blank\" rel=\"external nofollow noopener\">Virtual Textbook of\u00a0Organic\u00a0Chemistry<\/a><\/li>\r\n<\/ul>\r\n<\/div>\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>Objectives<\/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 an infrared spectrum to determine the presence of functional groups, such as alcohols, amines and carbonyl groups, in an unknown compound, given a list of infrared absorption frequencies.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"elm-main-content\" class=\"elm-content-container\">\n<div>\n<div id=\"note\">\n<div class=\"textbox\">\n<div id=\"note\">\n<h3 class=\"boxtitle\">Study Notes<\/h3>\n<p>In <a title=\"12.7 Interpreting Infrared Spectra\" href=\"https:\/\/chem.libretexts.org\/LibreTexts\/Athabasca_University\/Chemistry_350%3A_Organic_Chemistry_I\/Chapter_12%3A_Structure_Determination%3A_Mass_Spectrometry_and_Infrared_Spectroscopy\/12.07_Interpreting_Infrared_Spectra\" rel=\"internal\">Chapter 12.7<\/a>, you should have learned, in broad terms, where a few key absorptions occur. Otherwise, to find the characteristic infrared absorptions of the various functional groups, refer to <a href=\"https:\/\/chem.libretexts.org\/Reference\/Reference_Tables\/Spectroscopic_Parameters\/Infrared_Spectroscopy_Absorption_Table\" target=\"_blank\" rel=\"internal noopener\">this IR table<\/a>.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_1\">\n<h2 class=\"editable\">Spectral Interpretation by Application of Group Frequencies<\/h2>\n<p>One of the most common application of infrared spectroscopy is to the identification of organic compounds. The major classes of organic molecules are shown\u00a0in this category\u00a0and\u00a0also linked on the bottom page for the\u00a0number of collections of spectral information regarding organic molecules.<\/p>\n<h3>Hydrocarbons<\/h3>\n<div id=\"section_2\">\n<p>Hydrocarbons compounds contain only C-H and C-C bonds, but there is plenty of information to be obtained from the infrared spectra arising from C-H stretching and C-H bending.<\/p>\n<p>In alkanes, which have very few bands, each band in the spectrum can be assigned:<\/p>\n<ul>\n<li>C\u2013H stretch from 3000\u20132850 cm<sup>-1<\/sup><\/li>\n<li>C\u2013H bend or scissoring from 1470-1450 cm<sup>-1<\/sup><\/li>\n<li>C\u2013H rock, methyl from 1370-1350 cm<sup>-1<\/sup><\/li>\n<li>C\u2013H rock, methyl, seen only in long chain alkanes, from 725-720 cm<sup>-1<\/sup><\/li>\n<\/ul>\n<p>Figure 3. shows the IR spectrum of octane. Since most organic compounds have these features, these C-H vibrations are usually not noted when interpreting a routine IR spectrum. Note that the change in dipole moment with respect to distance for the C-H stretching is greater than that for others shown, which is why the C-H stretch band is the more intense.<\/p>\n<div style=\"width: 560px\" class=\"wp-caption aligncenter\"><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\/05153652\/octane_1.png\" alt=\"octane (1).png\" width=\"550\" height=\"276\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 3. Infrared Spectrum of Octane<\/p>\n<\/div>\n<p>In alkenes compounds, each band in the spectrum can be assigned:<\/p>\n<ul>\n<li>C=C stretch from 1680-1640 cm<sup>-1<\/sup><\/li>\n<li>=C\u2013H stretch from 3100-3000 cm<sup>-1<\/sup><\/li>\n<li>=C\u2013H bend from 1000-650 cm<sup>-1<\/sup><\/li>\n<\/ul>\n<p>Figure 4. shows the IR spectrum of 1-octene. As alkanes compounds, these bands are not specific and are generally not noted because they are present in almost all organic molecules.<\/p>\n<div style=\"width: 560px\" class=\"wp-caption aligncenter\"><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\/05153654\/1-octene.png\" alt=\"1-octene.png\" width=\"550\" height=\"272\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 4. Infrared Spectrum of 1-Octene<\/p>\n<\/div>\n<p>In alkynes, each band in the spectrum can be assigned:<\/p>\n<ul>\n<li>\u2013C?C\u2013 stretch from 2260-2100 cm<sup>-1<\/sup><\/li>\n<li>\u2013C?C\u2013H: C\u2013H stretch from 3330-3270 cm<sup>-1<\/sup><\/li>\n<li>\u2013C?C\u2013H: C\u2013H bend from 700-610 cm<sup>-1<\/sup><\/li>\n<\/ul>\n<p>The spectrum of 1-hexyne, a terminal alkyne, is shown below.<\/p>\n<div style=\"width: 560px\" class=\"wp-caption aligncenter\"><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\/05153656\/1-hexyne.png\" alt=\"1-hexyne.png\" width=\"550\" height=\"276\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 5. Infrared Spectrum of 1-Hexyne<\/p>\n<\/div>\n<p>In aromatic compounds,\u00a0each band in the spectrum can be assigned:<\/p>\n<ul>\n<li>C\u2013H stretch from 3100-3000 cm<sup>-1<\/sup><\/li>\n<li>overtones, weak, from 2000-1665 cm<sup>-1<\/sup><\/li>\n<li>C\u2013C stretch (in-ring) from 1600-1585 cm<sup>-1<\/sup><\/li>\n<li>C\u2013C stretch (in-ring) from 1500-1400 cm<sup>-1<\/sup><\/li>\n<li>C\u2013H &#8220;oop&#8221; from 900-675 cm<sup>-1<\/sup><\/li>\n<\/ul>\n<p>Note that this is at slightly higher frequency than is the \u2013C\u2013H stretch in alkanes. This is a very useful tool for interpreting IR spectra. Only alkenes and aromatics show a C\u2013H stretch slightly higher than 3000 cm<sup>-1<\/sup>.<\/p>\n<p>Figure 6. shows the spectrum of toluene.<\/p>\n<div style=\"width: 560px\" class=\"wp-caption aligncenter\"><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\/05153659\/toluene.png\" alt=\"toluene.png\" width=\"550\" height=\"276\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 6. Infrared Spectrum of Toluene<\/p>\n<\/div>\n<div id=\"section_3\">\n<h4 class=\"editable\">Functional Groups Containing the C-O Bond<\/h4>\n<p>Alcohols have IR absorptions associated with both the O-H and the C-O stretching vibrations.<\/p>\n<ul>\n<li>O\u2013H stretch, hydrogen bonded 3500-3200 cm<sup>-1<\/sup><\/li>\n<li>C\u2013O stretch 1260-1050 cm<sup>-1<\/sup> (s)<\/li>\n<\/ul>\n<p>Figure 7. shows the spectrum of ethanol. Note the very broad, strong band of the O\u2013H stretch.<\/p>\n<div style=\"width: 560px\" class=\"wp-caption aligncenter\"><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\/05153701\/ethanol.png\" alt=\"ethanol.png\" width=\"550\" height=\"279\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 7. Infrared Spectrum of Ethanol<\/p>\n<\/div>\n<p>The carbonyl stretching vibration band C=O of saturated aliphatic ketones appears:<\/p>\n<ul>\n<li>\u00a0C=O stretch\u00a0\u00a0\u00a0&#8211; aliphatic ketones 1715 cm<sup>-1<\/sup><\/li>\n<\/ul>\n<p>&#8211; ?, ?-unsaturated ketones 1685-1666 cm<sup>-1<\/sup><\/p>\n<p>Figure 8. shows the spectrum of 2-butanone. This is a saturated ketone, and the C=O band appears at 1715.<\/p>\n<div style=\"width: 560px\" class=\"wp-caption aligncenter\"><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\/05153703\/2-butanone.png\" alt=\"2-butanone.png\" width=\"550\" height=\"283\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 8. Infrared Spectrum of 2-Butanone<\/p>\n<\/div>\n<p>If a compound is suspected to be an aldehyde, a peak always appears around 2720 cm<sup>-1<\/sup> which\u00a0often appears as a shoulder-type peak just to the right of the alkyl C\u2013H stretches.<\/p>\n<ul>\n<li>H\u2013C=O stretch 2830-2695 cm<sup>-1<\/sup><\/li>\n<li>C=O stretch:\n<ul>\n<li>aliphatic aldehydes 1740-1720 cm<sup>-1<\/sup><\/li>\n<li>alpha, beta-unsaturated aldehydes 1710-1685 cm<sup>-1<\/sup><\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>Figure 9. shows the spectrum of butyraldehyde.<\/p>\n<div style=\"width: 560px\" class=\"wp-caption aligncenter\"><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\/05153705\/butyraldehyde.png\" alt=\"butyraldehyde.png\" width=\"550\" height=\"287\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 9. Infrared Spectrum of Butyraldehyde<\/p>\n<\/div>\n<p>The carbonyl stretch C=O of esters appears:<\/p>\n<ul>\n<li>C=O stretch\n<ul>\n<li>aliphatic from 1750-1735 cm<sup>-1<\/sup><\/li>\n<li>?, ?-unsaturated from 1730-1715 cm<sup>-1<\/sup><\/li>\n<\/ul>\n<\/li>\n<li>C\u2013O stretch from 1300-1000 cm<sup>-1<\/sup><\/li>\n<\/ul>\n<p>Figure 10. shows the spectrum of ethyl benzoate.<\/p>\n<div style=\"width: 914px\" class=\"wp-caption aligncenter\"><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\/05153708\/ethyl_benzoate.png\" alt=\"ethyl benzoate.png\" width=\"904\" height=\"459\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 10. Infrared Spectrum of Ethyl benzoate<\/p>\n<\/div>\n<p>The carbonyl stretch C=O of a carboxylic acid appears as an intense band from 1760-1690 cm<sup>-1<\/sup>. The exact position of this broad band depends on whether the carboxylic acid is saturated or unsaturated, dimerized, or has internal hydrogen bonding.<\/p>\n<ul>\n<li>O\u2013H stretch from 3300-2500 cm<sup>-1<\/sup><\/li>\n<li>C=O stretch from 1760-1690 cm<sup>-1<\/sup><\/li>\n<li>C\u2013O stretch from 1320-1210 cm<sup>-1<\/sup><\/li>\n<li>O\u2013H bend from 1440-1395 and 950-910 cm<sup>-1<\/sup><\/li>\n<\/ul>\n<p>Figure 11. shows the spectrum of hexanoic acid.<\/p>\n<div style=\"width: 938px\" class=\"wp-caption aligncenter\"><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\/05153711\/hexanoic_acid.png\" alt=\"hexanoic acid.png\" width=\"928\" height=\"471\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 11. Infrared Spectrum of Hexanoic acid<\/p>\n<\/div>\n<\/div>\n<div id=\"section_4\">\n<h4 class=\"editable\">Organic Nitrogen Compounds<\/h4>\n<ul>\n<li>N\u2013O asymmetric stretch from 1550-1475 cm<sup>-1<\/sup><\/li>\n<li>N\u2013O symmetric stretch from 1360-1290 cm<sup>-1<\/sup><\/li>\n<\/ul>\n<div style=\"width: 937px\" class=\"wp-caption aligncenter\"><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\/05153714\/nitromethane.png\" alt=\"nitromethane.png\" width=\"927\" height=\"471\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 12. Infrared Spectrum of Nitomethane<\/p>\n<\/div>\n<\/div>\n<div id=\"section_5\">\n<h4 class=\"editable\">Organic Compounds Containing Halogens<\/h4>\n<p>Alkyl halides are compounds that have a C\u2013X bond, where X is a halogen: bromine, chlorine, fluorene, or iodine.<\/p>\n<ul>\n<li>C\u2013H wag (-CH<sub>2<\/sub>X) from 1300-1150 cm<sup>-1<\/sup><\/li>\n<li>C\u2013X stretches (general) from 850-515 cm<sup>-1<\/sup>\n<ul>\n<li>C\u2013Cl stretch 850-550 cm<sup>-1<\/sup><\/li>\n<li>C\u2013Br stretch 690-515 cm<sup>-1<\/sup><\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>The spectrum of 1-chloro-2-methylpropane are shown below.<\/p>\n<div style=\"width: 914px\" class=\"wp-caption aligncenter\"><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\/05153717\/1-chloro-2-methylpropane.png\" alt=\"1-chloro-2-methylpropane.png\" width=\"904\" height=\"471\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 13. Infrared Spectrum of 1-chloro-2-methylpropane<\/p>\n<\/div>\n<p>For more Infrared spectra <a class=\"external\" title=\"http:\/\/riodb01.ibase.aist.go.jp\/sdbs\/\" href=\"http:\/\/riodb01.ibase.aist.go.jp\/sdbs\/\" target=\"_blank\" rel=\"external nofollow noopener\">Spectral database of organic molecules <\/a>is\u00a0introduced to use free database. Also, the <a class=\"external\" title=\"http:\/\/en.wikipedia.org\/wiki\/Infrared_spectroscopy_correlation_table\" href=\"http:\/\/en.wikipedia.org\/wiki\/Infrared_spectroscopy_correlation_table\" target=\"_blank\" rel=\"external nofollow noopener\">infrared spectroscopy correlation <\/a>table is linked on bottom of page to find other assigned IR peaks.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_6\">\n<div class=\"textbox exercises\">\n<h3>Exercises<\/h3>\n<div id=\"section_6\">\n<div id=\"s61717\">\n<div id=\"section_24\">\n<h4 id=\"Questions-61717\">Questions<\/h4>\n<p><strong>1.\u00a0<\/strong>The following spectra is for the accompanying compound. What are the peaks that you can I identify in the spectrum?<\/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\/05153720\/12.8.png\" alt=\"\" width=\"195\" height=\"112\" \/><\/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\/05153723\/12.10.gif\" alt=\"\" width=\"663\" height=\"365\" \/><\/p>\n<p>Source: SDBSWeb :\u00a0<a class=\"external\" title=\"http:\/\/sdbs.db.aist.go.jp\" href=\"http:\/\/sdbs.db.aist.go.jp\/\" target=\"_blank\" rel=\"external nofollow noopener\">http:\/\/sdbs.db.aist.go.jp<\/a>\u00a0(National Institute of Advanced Industrial Science and Technology, 2 December 2016)<\/p>\n<p><strong>2.\u00a0<\/strong>What absorptions would the following compounds have in an IR spectra?<\/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\/05153725\/12.82.png\" alt=\"\" width=\"439\" height=\"362\" \/><\/p>\n<h3>Solutions<\/h3>\n<div class=\"qa-wrapper\" style=\"display: block\"><span class=\"show-answer collapsed\" style=\"cursor: pointer\" data-target=\"q637753\">Show Answer<\/span><\/p>\n<div id=\"q637753\" class=\"hidden-answer\" style=\"display: none\">\n<p>1. Frequency (cm-1)\u00a0\u00a0\u00a0\u00a0\u00a0 Functional Group<\/p>\n<p>3200\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 C\u2261C-H<\/p>\n<p>2900-3000\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0C-C-H, C=C-H 2100<\/p>\n<p>C\u2261C 1610\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 C=C<\/p>\n<p>(There is also an aromatic undertone region between 2000-1600 which describes the substitution on the phenyl ring.)<\/p>\n<p>2.A)<\/p>\n<p>Frequency (cm-1)\u00a0\u00a0\u00a0\u00a0\u00a0 Functional Group<\/p>\n<p>2900-3000\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0C-C-H, C=C-H<\/p>\n<p>1710\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 C=O<\/p>\n<p>1610\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 C=C<\/p>\n<p>1100\u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 C-O<\/p>\n<p>B)<\/p>\n<p>Frequency (cm-1)\u00a0\u00a0\u00a0\u00a0\u00a0 Functional Group<\/p>\n<p>3200\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C\u2261C-H<\/p>\n<p>2900-3000\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C-C-H, C=C-H<\/p>\n<p>2100\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C\u2261C<\/p>\n<p>1710\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C=O<\/p>\n<p>C)<\/p>\n<p>Frequency (cm-1)\u00a0\u00a0\u00a0\u00a0\u00a0 Functional Group<\/p>\n<p>3300 (broad)\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 O-H<\/p>\n<p>2900-3000\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C-C-H, C=C-H<\/p>\n<p>2000-1800\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 Aromatic Overtones<\/p>\n<p>1710\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C=O<\/p>\n<p>1610\u00a0\u00a0\u00a0 \u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 C=C<\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<div id=\"section_7\">\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>William Reusch, Professor Emeritus (<a class=\"external\" title=\"http:\/\/www.msu.edu\/\" href=\"http:\/\/www.msu.edu\/\" target=\"_blank\" rel=\"external nofollow noopener\">Michigan State U.<\/a>), <a class=\"external\" title=\"http:\/\/www.cem.msu.edu\/~reusch\/VirtualText\/intro1.htm\" href=\"http:\/\/www.cem.msu.edu\/%7Ereusch\/VirtualText\/intro1.htm\" target=\"_blank\" rel=\"external nofollow noopener\">Virtual Textbook of\u00a0Organic\u00a0Chemistry<\/a><\/li>\n<\/ul>\n<\/div>\n<\/div>\n<\/div>\n","protected":false},"author":44985,"menu_order":4,"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-1654","chapter","type-chapter","status-publish","hentry"],"part":29,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1654","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":10,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1654\/revisions"}],"predecessor-version":[{"id":2344,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapters\/1654\/revisions\/2344"}],"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\/1654\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/media?parent=1654"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/pressbooks\/v2\/chapter-type?post=1654"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/contributor?post=1654"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-mcc-organicchemistry\/wp-json\/wp\/v2\/license?post=1654"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}