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Course Question & AnswerSpectroscopy
Purpose of Course showclose
Spectroscopy is the study of the interaction between matter and electromagnetic radiation. Molecules respond to different types of radiation in different ways, depending on the frequency (?) or wavelength (?) of the radiation. In General Chemistry, we studied spectroscopy as a tool for explaining the quantum mechanical model of the atom. In that course, we learned that light is an electromagnetic radiation of a wavelength that is visible to the human eye. We also learned that light, which exists in tiny “packets” called photons, exhibits properties of both waves and particles, a characteristic referred to as the wave-particle duality. The quantized relationship is defined as E = hv, where E is energy, h is Plank’s constant, and v is frequency.
Spectroscopy and spectrometry are often used in chemistry for the identification of substances through the spectrum from which they are emitted or by which they are absorbed. The type of spectroscopic technique is defined by the type of radiative energy used, the nature of the response, or the nature of the material being studied. In Organic Chemistry, we used spectroscopy for structure elucidation of organic molecules.
Spectrometry is the spectroscopic technique used to assess the concentration or amount of a given chemical species. In Analytical Chemistry, we studied spectroscopy primarily for measuring analyte concentrations. The instrument used for these types of measurements is called a spectrometer, spectrophotometer, or spectrograph.
This one-semester course is designed to provide you with a more thorough description of the theory behind each spectroscopic technique as well as its applications. The course is meant to build upon itself, and each unit requires a working knowledge of the material from preceding units. The first unit covers mass spectrometry (MS). It is followed by a unit on ultraviolet and visible spectroscopy (UV-Vis) and its application to structural information in addition to analytical techniques. The third unit deals with infrared spectroscopy (IR), where you will practice using the combination of the first three spectroscopic methods to obtain structural information of organic molecules. The final unit comprises nuclear magnetic resonance (NMR) spectroscopy. In this unit you will be required to combine concepts from all spectroscopic techniques discussed.
Learning Outcomes showclose
- Discuss similarities and differences between spectrometry and spectroscopy.
- Identify the basic components of spectroscopic instrumentation.
- Demonstrate a working knowledge of mass spectroscopy (MS), ultraviolet-visible (UV-Vis) spectroscopy, infrared (IR) spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy.
- Describe how a mass spectrometer produces its spectral patterns.
- Explain the information obtained from a UV-Vis spectrophotometer and how it can be used for analysis.
- Illustrate the mechanisms that give rise to the infrared absorption bands and identify to which functional groups each correspond.
- Demonstrate an understanding of the processes responsible for NMR chemical shifts and splitting patterns.
- Elucidate the structures of organic molecules from spectral data.
Course Requirements showclose
√ Have access to a computer.
√ Have continuous broadband Internet access.
√ Have the ability/permission to install plug-ins or software (e.g., Adobe Reader or Flash).
√ Have the ability to download and save files and documents to a computer.
√ Have the ability to open Microsoft files and documents (.doc, .ppt, .xls, etc.).
√ Be competent in the English language.
√ Have read the Saylor Student Handbook.
√ Have completed all “Prerequisites” of the Chemistry discipline (CHEM001: Introduction to Mechanics, CHEM002: Introduction to Electromagnetism, CHEM003: Single-Variable Calculus I, and CHEM004: Single-Variable Calculus I).
√ Have completed General Chemistry I & II (CHEM101 & CHEM102), Organic Chemistry I (CHEM103), and Analytical Chemistry (CHEM108) as listed in “The Core Program” of the Chemistry discipline.
Unit Outline show close
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Unit 1: Mass Spectrometry
Mass spectrometry (MS) is an analytical technique that is used to determine the masses of particles for the elucidation of the chemical structures of molecules. The technique has both qualitative and quantitative uses, including identifying unknown compounds, determining the isotopic composition of elements in a molecule, and revealing the structure of a compound by observing its fragmentation.
Unit 1 Time Advisory show close
This unit begins with a general discussion of the theory and instrumentation of mass spectrometers. A section on ionization and detection methods is included. The unit continues with a discussion of isotopic distributions and fragmentation patterns of organic molecules. This unit concludes with application of these principles for structure determination.
Unit 1 Learning Outcomes show close
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1.1 The Mass Spectrometer
- Reading: William Reusch’s “Virtual Text of Organic Chemistry: Mass Spectrometry”
Link: William Reusch’s “Virtual Text of Organic Chemistry: Mass Spectrometry” (HTML)
Instructions: Please read the entire webpage. Spend time using the learning tools provided in the body of the text. This material covers all of Unit 1.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Interactive Lab: OCHeM.com: Thomas Poon’s “Mass Spectrometer Simulator”
Link: Web Media: OCHeM.com: Thomas Poon’s “Mass Spectrometer Simulator” (Shockwave)
Instructions: Scroll down the list of “Shockwave Animations” to find a link entitled “Mass Spectrometer Simulator.” Click on the link; it will launch an Adobe Shockwave application in a new window. By clicking on various parts of the mass spectrometer, you will learn about each component.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: William Reusch’s “Virtual Text of Organic Chemistry: Mass Spectrometry: Practice Problems”
Link: William Reusch’s “Virtual Text of Organic Chemistry: Mass Spectrometry: Practice Problems” (HTML)
Instructions: Please scroll to the bottom of the page and work through the practice problems (Questions 1–8) found there. This site is designed to require you to attempt the problems prior to obtaining the solutions from its answer key. This material covers concepts from all of Unit 1.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: William Reusch’s “Virtual Text of Organic Chemistry: Mass Spectrometry”
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1.2 The Nature of Mass Spectra
- Reading: University of Leeds: Dr. Alison E. Ashcroft’s “An Introduction to Mass Spectrometry”
Link: University of Leeds: Dr. Alison E. Ashcroft’s “An Introduction to Mass Spectrometry” (HTML)
Instructions: Please read the entire webpage. This material covers the basics of mass spectrometry including its uses and analysis.
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- Reading: University of Leeds: Dr. Alison E. Ashcroft’s “An Introduction to Mass Spectrometry”
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1.3 Ionization and Detection Methods
- Reading: Connexions: Justin Law and Andrew R. Barron’s “Principles of Mass Spectrometry and Modern Applications”
Link: Connexions: Justin Law and Andrew R. Barron’s “Principles of Mass Spectrometry and Modern Applications” (HTML or PDF)
Instructions: Please read the entire webpage. This material focuses on ionization techniques and detection methods (mass analyzers). You can also download this material in PDF version by clicking “Download” on the top right corner of the page.
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- Reading: Connexions: Justin Law and Andrew R. Barron’s “Principles of Mass Spectrometry and Modern Applications”
- 1.4 Interpretation of Mass Spectra
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1.4.1 Isotopes
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Mass Spectrometry: Isotope Ratio Data”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “Mass Spectrometry: Isotope Ratio Data” (HTML)
Instructions: Click on the “Mass Spec” button on the left-hand side of the webpage, then click the link called “Common Elements in Organic Compounds” (Section III, E.1). Please read the entire webpage. This material presents isotopic information on elements commonly found in organic compounds, specifically C, H, N, O, Si, and S.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Mass Spectrometry: Bromine and Chlorine”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “Mass Spectrometry: Bromine and Chlorine” (HTML)
Instructions: Click on the “Mass Spec” button on the left-hand side of the webpage, then click the link called “Bromine and Chlorine” (Section III, E.2). Please read the entire webpage. This material discusses the significance of the M+2 peak in mass spectra when bromine and/or chlorine are present in a compound.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Mass Spectrometry: Isotope Ratio Data”
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1.4.2 Fragment Patterns
- Reading: University of Illinois: Paul R. Young’s “Basic Mass Spectroscopy”
Link: University of Illinois Paul R. Young’s “Basic Mass Spectroscopy” (HTML)
Instructions: Please read the material presented by following the links under “Section I: Introduction.” This material covers some basic theory of mass spectrometry and focuses on the fragmentation patterns of functional groups.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Activity: University of Illinois: Paul R. Young’s “Basic Mass Spectroscopy”
Link: University of Illinois: Paul R. Young’s “Basic Mass Spectroscopy” (HTML)
Instructions: Please work through the analysis of compounds 1–5 by following the links under “Section II: Sample Mass Spectra.”
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Mass Spectrometry: Fragmentation Patterns for Organic Functional Groups”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “Mass Spectrometry: Fragmentation Patterns for Organic Functional Groups” (HTML)
Instructions: Click on the “Mass Spec” button on the left-hand side of the webpage. Scroll down to “Section IV: Fragmentation Patterns for Organic Functional Groups.” Follow the links below each subsection (A–E) and peruse the material presented within them. This material identifies the key spectral peaks and provides representative spectra for each organic functional group. Subsection F presents a tabular summary of the key information covered.
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- Lecture: OCHeM.com: Thomas Poon’s “Mass Spectrometry”
Link: OCHem.com: Thomas Poon’s “Mass Spectrometry” (QuickTime)
Instructions: Scroll down the list of “PreLectures” to find a link entitled “Mass Spectrometry.” Click on the link; it will launch a QuickTime application in a new window. Watch the video (runtime = 32:52 minutes), which details fragmentation patterns and general trends in mass spectra.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Interactive Lab: Jean-Claude Bradley and Andrew Lang’s “Spectral Game”
Link: Jean-Claude Bradley and Andrew Lang’s “Spectral Game” (HTML)
Instructions: Please enter a username in the required field. Note: You do not need to register and this does not need to be your actual name (i.e., student1). Choose the format you prefer for your viewer and select EI for the mass spectroscopy game from the “Type” drop-down box. A general video tutorial from the creators of the game can be found here (YouTube). Please spend an ample amount of time using this game as a learning tool to increase your spectral analysis proficiency.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: OCHeM.com: Thomas Poon’s “Mass Spectrometry Problems”
Link: OCHeM.com: Thomas Poon’s “Mass Spectrometry Problems” (HTML or PDF)
Instructions: Please work through these problems dealing with interpretation of mass spectra. Then, click here for the answer key.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: The University of Arizona: Department of Chemistry’s “Introduction to Mass Spectrometry—Examples”
Link: The University of Arizona: Department of Chemistry’s “Introduction to Mass Spectrometry—Examples” (HTML)
Instructions: First use this page as a tutorial, reviewing the mass spectra for each type of functional group fragmentation. Then take the quizzes for each of the functional groups. There are 10 separate quizzes on this webpage.
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- Reading: University of Illinois: Paul R. Young’s “Basic Mass Spectroscopy”
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Unit 2: Ultraviolet-Visible Spectroscopy
Ultraviolet-visible spectroscopy (UV-Vis) refers to absorption spectroscopy in the ultraviolet-visibleregion of the electromagnetic spectrum. In this region of the electromagnetic spectrum, molecules undergo electronic transitions, where electrons move from a lower energy orbital (ground state) to one of higher energy (excited state). The nature of the electronic transition determines the nature of the spectra produced.
Unit 2 Time Advisory show close
This unit begins with a discussion of electromagnetic radiation and spectroscopy, followed by the theory of UV-Vis spectroscopy. The course continues with a discussion of types of electronic transitions and a brief review of how UV-Vis is used for analytical methods. The unit concludes with methods of empirically determining absorption wavelengths based on structural implications.
Unit 2 Learning Outcomes show close
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2.1 General Introduction to Spectroscopy
- Reading: William Reusch’s “Virtual Text of Organic Chemistry: Visible and Ultraviolet Spectroscopy”
Link: William Reusch’s “Virtual Text of Organic Chemistry: Visible and Ultraviolet Spectroscopy” (HTML)
Instructions: Please read the entire webpage. Be sure to follow the links for supplemental information required for successful completion of this course. This material covers Subunits 2.1, 2.4, 2.5, and 2.6.
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- Reading: William Reusch’s “Virtual Text of Organic Chemistry: Visible and Ultraviolet Spectroscopy”
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2.1.1 The Electromagnetic Spectrum
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “IR Spectroscopy: Background”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “IR Spectroscopy: Background” (HTML)
Instructions: Click on the “IR” button on the left-hand side of the webpage, then click the link called “Electromagnetic Radiation” (Section 1, A). Please read the entire webpage. Please note that, although the material is located under the IR spectroscopy section of this webpage, it is applicable to all spectroscopic methods because it is the interaction of the molecules with various wavelengths of light from the electromagnetic spectrum that give rise to the spectra.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “IR Spectroscopy: Background”
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2.1.2 Ultraviolet and Visible (UV-Vis) Theory
- Lecture: OCHeM.com: Thomas Poon’s “Spectroscopy, Part 1 of 4”
Link: OCHem.com: Thomas Poon’s “Spectroscopy, Part 1 of 4” (QuickTime)
Instructions: Scroll down the list of “PreLectures” to find a link entitled “Spectroscopy, Part 1 of 4”. Click on the link; it will launch a QuickTime application in a new window. Watch the video (runtime = 11:09 minutes), which gives an overview of spectroscopic methods. The energy transfer between the ground and excited states during UV-Visible spectroscopy is explained. Infrared and nuclear magnetic resonance spectroscopy are also briefly covered.
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- Lecture: OCHeM.com: Thomas Poon’s “Spectroscopy, Part 1 of 4”
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2.2 UV-Vis Spectroscopy and the Excited State
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Types of Electronic Transitions”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Types of Electronic Transitions” (HTML)
Instructions: Click on the “UV/Vis” button on the left-hand side of the webpage, then follow the links (A–D) below “Section II: Types of Electronic Transitions.” Please read all of the information presented in each section. This material explains the allowed electronic transitions observed in UV-Vis spectroscopy.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Types of Electronic Transitions”
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2.3 UV-Vis Spectroscopy as an Analytical Tool
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Background Information”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Background Information” (HTML)
Instructions: Click on the “UV/Vis” button on the left-hand side of the webpage, then follow links (A–G) below “Section I: Background Information.” Please read all of the information presented in each section. This material gives theory and experimental design and analysis for the use of UV-Vis spectroscopy as an analytical method.
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- Reading: Connexions: Brittany L. Oliva and Andrew R. Barron’s “Basics of UV-Visible Spectroscopy”
Link: Connexions: Brittany L. Oliva and Andrew R. Barron’s “Basics of UV-Visible Spectroscopy” (HTML or PDF)
Instructions: Please read through the entire webpage. This material is a review of concepts from Analytical Chemistry (CHEM108). You can also see this material in PDF format from the “Download” tab on the top right.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Background Information”
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2.4 Empirical Determination of UV/Vis Absorption Wavelengths
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Typical Absorptions for Simple Isolated Chromophores”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Typical Absorptions for Simple Isolated Chromophores” (HTML)
Instructions: Click on the “UV/Vis” button on the left-hand side of the webpage, then click on “Section III: Table of Typical Absorptions of Simple Isolated Chromophores.” This table lists the types of transitions, approximate absorption wavelengths, and relative absorptivities of various types of compounds. Please note the influence of increased conjugation on the absorption wavelengths. Conjugation is the overlap of one p-orbital with another across an intervening sigma bond. A conjugated system has a region of alternating single and double bonds. The pi electrons do not belong to a single bond or atom, but rather to a group of atoms. The system allows a delocalization of electrons across all the adjacent aligned p-orbitals, which in general may lower the overall energy (increasing the absorption wavelength) of the molecule and increase stability.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Typical Absorptions for Simple Isolated Chromophores”
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2.4.1 The Woodward?Fieser Rules for Dienes
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Empirical Rules for Calculating Uv/Vis Absorptions”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Empirical Rules for Calculating Uv/Vis Absorptions” (HTML)
Instructions: Click on the “UV/Vis” button on the left-hand side of the webpage, then click on the link “Woodward-Fieser Rules for Dienes” (Section IV, A). This material gives base absorption wavelength for cis- and trans- dienes and subsequent wavelength (energy) shifts based on additional substituents. Please work through the examples given.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Empirical Rules for Calculating Uv/Vis Absorptions”
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2.4.2 Woodward's Rules for Conjugated Carbonyl Compounds
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Empirical Rules for Calculating Uv/Vis Absorptions”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Empirical Rules for Calculating Uv/Vis Absorptions” (HTML)
Instructions: Click on the “UV/Vis” button on the left-hand side of the webpage, then click on the link “Woodward's Rules for Conjugated Carbonyl Compounds” (Section IV, B). This material gives a base absorption wavelength for conjugated carbonyl compounds and subsequent wavelength (energy) shifts based on additional substituents. Please work through the examples given.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Empirical Rules for Calculating Uv/Vis Absorptions”
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2.4.3 Substituted Benzene and Benzoyl Derivatives
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Empirical Rules for Calculating Uv/Vis Absorptions”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Empirical Rules for Calculating Uv/Vis Absorptions” (HTML)
Instructions: Click on the “UV/Vis” button on the left-hand side of the webpage, then click on links C–E in Section IV. This material gives base absorption wavelengths for mono- and di-substituted benzene and benzoyl derivatives and subsequent wavelength (energy) shifts based on additional substituents. Please work through the examples given.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Interactive Lab: Jean-Claude Bradley and Andrew Lang’s “Spectral Game”
Link: Jean-Claude Bradley and Andrew Lang’s “Spectral Game” (HTML)
Instructions: Please enter a username in the required field. Note: You do not need to register and this does not need to be your actual name (i.e., student1). Choose the format you prefer for your viewer and select UV-Vis from the “Type” drop-down box. A general video tutorial from the creators of the game can be found here (YouTube). Please spend an ample amount of time using this game as a learning tool to increase your spectral analysis proficiency.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Ultraviolet/Visible Spectroscopy: Empirical Rules for Calculating Uv/Vis Absorptions”
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Unit 3: Infrared Spectroscopy
Infrared (IR) spectroscopy is a spectroscopic technique that deals with the infrared region of the electromagnetic spectrum. The spectra arise from vibrational and rotational states of excited molecules. IR spectroscopy can be used to identify compounds and investigate sample compositions.
Unit 3 Time Advisory show close
This unit begins with discussion of the general principles and the instrumentation of IR spectroscopy. It continues with information on vibrational and rotational modes of molecules, followed by an explanation of how Hooke’s Law, which is generally applied to springs in physics courses, can be used to describe the motions of molecular bonds. The unit continues with details of spectral interpretation of organic molecules and concludes with a discussion of other applications.
Unit 3 Learning Outcomes show close
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3.1 Instrumentation
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Infrared Spectroscopy: Instrumentation”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “Infrared Spectroscopy: Instrumentation” (HTML)
Instructions: Click on the “IR” button on the left-hand side of the webpage, then click on the link “Instrumentation” (Section II). This material shows a schematic diagram of a typical IR spectrophotometer.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Reading: William Reusch’s “Virtual Text of Organic Chemistry: Infrared Spectroscopy”
Link: William Reusch’s “Virtual Text of Organic Chemistry: Infrared Spectroscopy” (HTML and Java)
Instructions: Please read the entire webpage. Please use the corresponding buttons in the second section, “Vibrational Spectroscopy,” to view the bending and stretching modes. Also, be sure to follow the links in the third section, “Group Frequencies,” to view the subtle differences in spectra within different functional groups. This supporting information is advantageous in the successful completion of this course. This material covers all subunits in Unit 3.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: William Reusch’s “Virtual Text of Organic Chemistry: Spectroscopy Problems”
Link: William Reusch’s “Virtual Text of Organic Chemistry: Spectroscopy Problems” (HTML)
Instructions: Please work through each of the four problems, following the instructions given on the page to navigate the assessment. This site is designed to require you to attempt the problems prior to obtaining the solutions from its answer key. This material covers concepts from all of Unit 3.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Infrared Spectroscopy: Instrumentation”
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3.2 Vibrational/Rotational Modes
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Infrared Spectroscopy: Molecular Vibrations”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “Infrared Spectroscopy: Molecular Vibrations” (HTML)
Instructions: Click on the “IR” button on the left-hand side of the webpage, then click on the link “Molecular Vibrations” (Section I, B). This material provides an explanation of vibrations and animations of stretching and bending modes that occur during IR spectroscopy measurements.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Infrared Spectroscopy: Molecular Vibrations”
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3.3 Hooke’s Law
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Infrared Spectroscopy: Infrared Spectroscopy Basics”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “Infrared Spectroscopy: Infrared Spectroscopy Basics” (HTML)
Instructions: Click on the “IR” button on the left-hand side of the webpage, then click on the link “Infrared Spectroscopy Basics” (Section I, C). This material discusses the application of Hooke’s law, which usually applies to force constants in springs, to the molecular vibrations in IR spectroscopy.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Infrared Spectroscopy: Infrared Spectroscopy Basics”
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3.4 Interpretation of Infrared Spectra
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Infrared Spectroscopy: General Approach to IR Spectrum Analysis”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “Infrared Spectroscopy: General Approach to IR Spectrum Analysis” (HTML)
Instructions: Click on the “IR” button on the left-hand side of the webpage, then click on the link “General Approach to IR Spectrum Analysis” (Section III). This material gives a step-by-step approach to obtaining structural data from an IR spectrum.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Infrared Spectroscopy: Example Spectra for Various Functional Groups”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “Infrared Spectroscopy: Example Spectra for Various Functional Groups” (HTML)
Instructions: Click on the “IR” button on the left-hand side of the webpage, then follow the links (A–Y) below “Section V: Example Spectra for Various Functional Groups.” This material provides representative spectra for each organic functional group. Section IV presents a table of the key wavenumber assignments in the spectra.
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- Lecture: OCHeM.com: Thomas Poon’s “Infrared Spectroscopy”
Link: OCHem.com: Thomas Poon’s “Infrared Spectroscopy” (QuickTime)
Instructions: Scroll down the list of “PreLectures” to find a link entitled “Infrared Spectroscopy.” Click on the link; it will launch a QuickTime application in a new window. Watch the video (runtime = 25:28 minutes), which explains the presentation of IR peaks and details structure elucidation from a given IR spectrum.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Lecture: OCHeM.com: Thomas Poon’s “Spectroscopy, Part 2 of 4”
Link: OCHem.com: Thomas Poon’s “Spectroscopy, Part 2 of 4” (QuickTime)
Instructions: Scroll down the list of “PreLectures” to find a link entitled “Spectroscopy, Part 2 of 4.” Click on the link; it will launch a QuickTime application in a new window. Watch the video (runtime = 13:24 minutes), which demonstrates the use of both IR and MS for organic structure determination.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: OCHeM.com: Thomas Poon’s “IR Spectroscopy Problems”
Link: OCHeM.com: Thomas Poon’s “IR Spectroscopy Problems” (HTML or PDF)
Instructions: Please work through these problems dealing with infrared spectroscopy. Then, click here for the answer key.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: OCHeM.com: Thomas Poon’s “IR and Mass Spec Problems”
Link: OCHeM.com: Thomas Poon’s “IR and Mass Spec Problems” (HTML or PDF)
Instructions: Please work through these problems dealing with structure identification from infrared spectra combined with mass spectra. Then, click here for the answer key.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “Infrared Spectroscopy: General Approach to IR Spectrum Analysis”
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3.5 Organic Functional Group Frequencies
- Reading: Connexions: Andrew R. Barron’s “Characteristic IR Vibrational Modes for Hydrocarbon Compounds”
Link: Connexions: Andrew R. Barron’s “Characteristic IR Vibrational Modes for Hydrocarbon Compounds” (HTML or PDF)
Instructions: This material can also be viewed in PDF form by clicking “Download” in the top right corner of the page. This material presents the general vibrational mode frequencies for functional groups in tabular form. Please remember the shape of the bands also reveals much of the structural information.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Interactive Lab: Jean-Claude Bradley and Andrew Lang’s “Spectral Game”
Link: Jean-Claude Bradley and Andrew Lang’s “Spectral Game” (HTML)
Instructions: Please enter a username in the required field. Note: You do not need to register and this does not need to be your actual name (i.e., student1). Choose the format you prefer for your viewer and select IR from the “Type” drop-down box. A general video tutorial from the creators of the game can be found here. Please spend an ample amount of time using this game as a learning tool to increase your spectral analysis proficiency.
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- Reading: Connexions: Andrew R. Barron’s “Characteristic IR Vibrational Modes for Hydrocarbon Compounds”
- 3.6 Other Applications of Infrared Spectroscopy
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3.6.1 Metal-Ligand Complexes
- Reading: Connexions: Jiebo Li and Andrew R. Barron’s “Fourier Transform Infrared Spectroscopy of Metal Ligand Complexes”
Link: Connexions: Jiebo Li and Andrew R. Barron’s “Fourier Transform Infrared Spectroscopy of Metal Ligand Complexes” (HTML or PDF)
Instructions: Please read the entire webpage. You can also see this material in PDF form by clicking “Download” on the top right corner of the page. This material reviews the basics of infrared spectroscopy and describes some key shift and intensity differences observed in the spectra of metal ligand complexes.
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- Reading: Connexions: Jiebo Li and Andrew R. Barron’s “Fourier Transform Infrared Spectroscopy of Metal Ligand Complexes”
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3.6.2 Functional Group Vibrational Lifetimes
- Reading: Connexions: Xiewen Wen and Andrew R. Barron’s “Pump-Probe Detection of Molecular Functional Group Vibrational Lifetime”
Link: Connexions: Xiewen Wen and Andrew R. Barron’s “Pump-Probe Detection of Molecular Functional Group Vibrational Lifetime” (HTML or PDF)
Instructions: Please read the entire webpage. You can also see this material in PDF form by clicking “Download” on the top right corner of the page. This material describes a technique used to measure the lifetimes of vibrational excited states.
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- Reading: Connexions: Xiewen Wen and Andrew R. Barron’s “Pump-Probe Detection of Molecular Functional Group Vibrational Lifetime”
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Unit 4: Nuclear Magnetic Resonance Spectroscopy
Nuclear magnetic resonance spectroscopy (NMR spectroscopy) is a technique that exploits the magnetic properties of certain nuclei. Elements containing an odd number of protons and/or neutrons within their nucleus have an intrinsic magnetic moment; in other words, their spin is not zero. Nuclei with even numbers of protons and/or neutrons have a spin of zero. In principle, NMR is applicable to any nucleus possessing spin. Quite a bit of information can be obtained from an NMR spectrum, including the number and types of functional groups in a molecule. The most important applications for the organic chemist are proton (1H) NMR and carbon-13 (13C) NMR spectroscopy.
Unit 4 Time Advisory show close
NMR spectroscopy has had a huge impact on the natural sciences. The most popular application of NMR is known by the name of Magnetic Resonance Imaging (MRI). An MRI is principally used for medical diagnostics, but it can also be used to elucidate the structure of analytes, illustrate how temperature affects chemical reactions, and determine reaction mechanisms. It is an invaluable tool for those seeking to understand protein and nucleic acid structure and function.
This unit begins with a discussion of the theory and instrumentation of NMR spectrometers and how they manipulate magnetic fields to obtain structural information of compounds. Chemical shifts, spin-spin interactions (coupling), and isomer effects will be discussed. The unit continues with a section specifically devoted to proton (1H) NMR, followed by a section on carbon-13 (13C) NMR. Advanced NMR techniques are also covered. The unit concludes with several opportunities to enhance your spectroscopic proficiency, combining all spectra from all spectroscopic methods covered in this course.
Unit 4 Learning Outcomes show close
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4.1 Introduction to Nuclear Magnetic Resonance (NMR) Spectroscopy
- Reading: William Reusch’s “Virtual Text of Organic Chemistry: Nuclear Magnetic Resonance Spectroscopy”
Link: William Reusch’s “Virtual Text of Organic Chemistry: Nuclear Magnetic Resonance Spectroscopy” (HTML)
Instructions: Please read the entire webpage. Spend some time working the example problems and be sure to follow the links for supplemental information required for successful completion of this course. This material covers all of Unit 4.
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- Reading: Connexions: Ty Hanna and Andrew R. Barron’s “Introduction to Nuclear Magnetic Resonance Spectroscopy”
Link: Connexions: Ty Hanna and Andrew R. Barron’s “Introduction to Nuclear Magnetic Resonance Spectroscopy” (HTML or PDF)
Instructions: Please read the entire webpage. You can also see this material in PDF form by clicking “Download” on the top right corner of the page. This material presents the general theory of NMR spectroscopy, including its instrumentation, interpretation, and limitations.
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- Lecture: Scribd: Dilip D. Dhavale’s “Nuclear Magnetic Resonance Spectroscopy: Basic Principles”
Link: Scribd: Dilip D. Dhavale’s “Nuclear Magnetic Resonance Spectroscopy: Basic Principles” (PowerPoint)
Instructions: Please spend a sufficient amount of time comprehending the material contained in the PowerPoint lecture. This slideshow (79 slides) contains a thorough description of the theory and application of NMR spectroscopy. This material also includes information pertaining to MRI, a medical application of NMR spectroscopy.
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- Web Media: OCHeM.com: Thomas Poon’s “Theory of NMR”
Link: Web Media: OCHeM.com: Thomas Poon’s “Theory of NMR” (Adobe Shockwave)
Instructions: Scroll down the list of Shockwave Animations to find a link entitled “Theory of NMR.” Click on the link; it will launch an Adobe Shockwave application in a new window. This material provides a basic visual demonstration of how NMR spectroscopy utilizes the magnetic field to obtain spectra.
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- Reading: William Reusch’s “Virtual Text of Organic Chemistry: Nuclear Magnetic Resonance Spectroscopy”
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4.1.1 Chemical Shift
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: Chemical Shift”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: Chemical Shift” (HTML)
Instructions: Click on the “NMR” button on the left-hand side of the webpage, then click on the link “Chemical Shift” (Section I, B). This material explains the origin of chemical shifts in NMR spectroscopy.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: Chemical Shift”
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4.1.2 Spin-Spin Interactions (Coupling)
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: Origin of Spin-Spin Splitting”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: Origin of Spin-Spin Splitting” (HTML)
Instructions: Click on the “NMR” button on the left-hand side of the webpage, then click on the link “Why Does Splitting Occur?” (Section I, E.5.a). This material explains the origin of spin-spin interaction coupling in NMR spectroscopy.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: Origin of Spin-Spin Splitting”
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4.1.3 Structural Elucidation of Isomers
- Reading: Connexions: Sequoyah King and Andrew R. Barron’s “NMR Spectroscopy of Stereoisomers”
Link: Connexions: Sequoyah King and Andrew R. Barron’s “NMR Spectroscopy of Stereoisomers” (HTML or PDF)
Instructions: Please read the entire webpage. This material explains how isomerism affects NMR spectra as well as how isomer information can be obtained from experimental results. You can access the PDF version under the download tab in the top right corner.
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- Reading: Connexions: Sequoyah King and Andrew R. Barron’s “NMR Spectroscopy of Stereoisomers”
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4.2 Proton (1H) NMR Spectroscopy
- Lecture: OCHeM.com: Thomas Poon’s “Spectroscopy, Part 4 of 4”
Link: OCHem.com: Thomas Poon’s “Spectroscopy, Part 4 of 4” (QuickTime)
Instructions: Scroll down the list of “PreLectures” to find a link entitled “Spectroscopy, Part 4 of 4.” Click on the link; it will launch a QuickTime application in a new window. Watch the video (runtime = 22:40 minutes). This material gives a detailed review of 1H-NMR and demonstrates its use as a tool for structure elucidation. Please remember 1H-NMR is the most important spectroscopic tool for structure elucidation. It can be a very selective technique, differentiating between many hydrogen atoms within a molecule or within a collection of similar molecules that differ only in terms of their local chemical environment.
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- Web Media: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: 1H Correlation Chart”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: 1H Correlation Chart” (HTML)
Instructions: Click on the “NMR” button on the left-hand side of the webpage, then click on the link “1H Correlation Chart” (Section I, E.4). This is a quick reference chart for proton NMR chemical shifts. All organic molecules referenced in peer-reviewed scientific journals must contain all of the molecule’s 1H-NMR shifts.
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- Interactive Lab: Jean-Claude Bradley and Andrew Lang’s “Spectral Game”
Link: Jean-Claude Bradley and Andrew Lang’s “Spectral Game” (HTML)
Instructions: Please enter a username in the required field. Note: You do not need to register and this does not need to be your actual name (i.e., student1). Choose the format you prefer for your viewer and select H NMR from the “Type” drop-down box. A general video tutorial from the creators of the game can be found here. Please spend an ample amount of time using this game as a learning tool to increase your spectral analysis proficiency.
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- Lecture: OCHeM.com: Thomas Poon’s “Spectroscopy, Part 4 of 4”
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4.3 Carbon-13 NMR Spectroscopy
- Lecture: OCHeM.com: Thomas Poon’s “Spectroscopy, Part 3 of 4”
Link: OCHem.com: Thomas Poon’s “Spectroscopy, Part 3 of 4” (QuickTime)
Instructions: Scroll down the list of “PreLectures” to find a link entitled “Spectroscopy, Part 3 of 4.” Click on the link; it will launch a QuickTime application in a new window. Watch the video (runtime = 18:47 minutes). This material gives a detailed review of 13C-NMR and demonstrates its use as a tool for structure elucidation. Please remember 13C-NMR is used to determine the types of carbons present in a molecule.
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- Web Media: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: 13C Correlation Chart”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: 13C Correlation Chart” (HTML)
Instructions: Click on the “NMR”button on the left-hand side of the webpage, then click on the link “13C Correlation Chart” (Section II, B). This is a quick reference chart for carbon-13 NMR chemical shifts.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Interactive Lab: Jean-Claude Bradley and Andrew Lang’s “Spectral Game”
Link: Jean-Claude Bradley and Andrew Lang’s “Spectral Game” (HTML)
Instructions: Please enter a username in the required field. Note: You do not need to register and this does not need to be your actual name (i.e., student1). Choose the format you prefer for your viewer and select C NMR from the “Type” drop-down box. A general video tutorial from the creators of the game can be found here. Please spend an ample amount of time using this game as a learning tool to increase your spectral analysis proficiency.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: William Reusch’s “Virtual Text of Organic Chemistry: Nuclear Magnetic Resonance Spectroscopy: Practice Problems”
Link: William Reusch’s “Virtual Text of Organic Chemistry: Nuclear Magnetic Resonance Spectroscopy: Practice Problems” (HTML)
Instructions: Please scroll to the bottom of the page and work through the practice problems (Questions 1–10) found there. This site is designed to require you to attempt the problems prior to obtaining the solutions from its answer key.
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- Assessment: OCHeM.com: Thomas Poon’s “NMR Spectroscopy Problems”
Link: OCHeM.com: Thomas Poon’s “NMR Spectroscopy Problems” (HTML or PDF)
Instructions: Please work through these problems dealing primarily with NMR. Then, click here for the answer key.
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- Lecture: OCHeM.com: Thomas Poon’s “Spectroscopy, Part 3 of 4”
- 4.4 Advanced NMR Techniques
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4.4.1 Double Resonance
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: Double Resonance”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: Double Resonance” (HTML)
Instructions: Click on the “NMR”button on the left-hand side of the webpage, then click on the link “Double Resonance” (Section V, A). This material explains how spin decoupling can be used to simplify complex NMR spectra.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: Double Resonance”
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4.4.2 DEPT
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: DEPT (Distortionless Enhancement by Polarization Transfer) Experiment”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: DEPT (Distortionless Enhancement by Polarization Transfer) Experiment” (HTML)
Instructions: Click on the “NMR” button on the left-hand side of the webpage, then click on the link “DEPT (Distortionless Enhancement by Polarization Transfer) Experiment” (Section V, B). This material explains how the hybridization (sp, sp2, sp3) at the carbon can be used to simplify complex NMR spectra.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: DEPT (Distortionless Enhancement by Polarization Transfer) Experiment”
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4.4.3 Nuclear Overhauser Enhancement (NOE)
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: Nuclear Overhauser Enhancement”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: Nuclear Overhauser Enhancement” (HTML)
Instructions: Click on the “NMR”button on the left-hand side of the webpage, then click on the link “Nuclear Overhauser Enhancement” (Section II, F.1). This material explains how simultaneous irradiation of two different nuclei can be used to simplify complex NMR spectra.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: Nuclear Overhauser Enhancement”
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4.4.4 Two-Dimensional NMR
- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: COSY (Correlation Spectroscopy) Experiment”
Link: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: COSY (Correlation Spectroscopy) Experiment” (HTML)
Instructions: Click on the “NMR”button on the left-hand side of the webpage, then click on the link “COSY (Correlation Spectroscopy) Experiment” (Section V, C.1). This material provides an overview of 2-D techniques and demonstrates how correlation spectroscopy is applied to simplify analysis of complex NMR spectra.
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- Web Media: Antony Williams and Andrew Lang’s “2D Spectral Game”
Link: Antony Williams and Andrew Lang’s “2D Spectral Game” (HTML)
Instructions: Please enter a username in the required field. Note: You do not need to register and this does not need to be your actual name (i.e., student1). A general video tutorial from the creators of the game can be found here. Please spend an ample amount of time using this game as a learning tool to increase your spectral analysis proficiency.
Terms of Use: Please respect the copyright and terms of use displayed on the webpage above.See a broken link? Please let us know!
- Assessment: University of Calgary: Dr. Ian Hunt’s “Interactive Spectroscopy Problems”
Link: University of Calgary: Dr. Ian Hunt’s “Interactive Spectroscopy Problems” (HTML and Java)
Instructions: Please read through the instructions on the webpage, then work through the 27 problems provided. These problems include the spectroscopic methods from the entire course.
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- Assessment: MIT OpenCourseWare: Prof. Tim Jamison’s “Organic Structure Determination: Study Materials”
Link: MIT OpenCourseWare: Prof. Tim Jamison’s “Organic Structure Determination: Study Materials” (PDF)
Instructions: Please click on the link to the PDF for “Problem Session Examples” to access the file. Printing the problem set is highly recommended. Work through the problems, then click on the PDF link entitled “Problem Session Solutions” for the answer key.
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- Assessment: MIT OpenCourseWare: Prof. Tim Jamison’s “Organic Structure Determination: Exams”
Link: MIT OpenCourseWare: Prof. Tim Jamison’s “Organic Structure Determination: Exams” (PDF)
Instructions: Please use the links on the webpage to complete both Exam 1 and Exam 2, following the instructions provided on the exams, disregarding the time limit. The exams primarily cover the different NMR spectroscopy techniques; however, some problems also include MS and IR. Use the answer keys to check your work and as a study aide for what you may have missed.
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- Reading: Central Connecticut State University: Dr. Neil Glagovich’s “NMR Spectroscopy: COSY (Correlation Spectroscopy) Experiment”
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Final Exam
- Final Exam: The Saylor Foundation's CHEM205 Final Exam
Link: The Saylor Foundation's CHEM205 Final Exam
Instructions: You must be logged into your Saylor Foundation School account in order to access this exam. If you do not yet have an account, you will be able to create one, free of charge, after clicking the link.See a broken link? Please let us know!
- Final Exam: The Saylor Foundation's CHEM205 Final Exam
