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Organic Chemistry I: 6.1 Electromagnetic Radiation and Molecular Spectroscopy

Organic Chemistry I
6.1 Electromagnetic Radiation and Molecular Spectroscopy
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table of contents
  1. Cover
  2. Title Page
  3. Copyright
  4. Table Of Contents
  5. Introduction
  6. Acknowledgements
  7. Chapter 1 Basic Concepts in Chemical Bonding and Organic Molecules
    1. 1.1 Chemical Bonding
    2. 1.2 Lewis Structure
    3. 1.3 Resonance Structures
    4. 1.4 Resonance structures in Organic Chemistry
    5. 1.5 Valence-Shell Electron-Pair Repulsion Theory (VSEPR)
    6. 1.6 Valence Bond Theory and Hybridization
    7. Answers to Practice Questions Chapter 1
  8. Chapter 2 Fundamental of Organic Structures
    1. 2.1 Structures of Alkenes
    2. 2.2 Nomenclature of Alkanes
    3. 2.3 Functional Groups
    4. 2.4 IUPAC Naming of Organic Compounds with Functional Groups
    5. 2.5 Degree of Unsaturation/Index of Hydrogen Deficiency
    6. 2.6 Intermolecular Force and Physical Properties of Organic Compounds
    7. Answers to Practice Questions Chapter 2
  9. Chapter 3 Acids and Bases: Organic Reaction Mechanism Introduction
    1. 3.1 Review of Acids and Bases and Ka
    2. 3.2 Organic Acids and Bases and Organic Reaction Mechanism
    3. 3.3 pKa of Organic Acids and Application of pKa to Predict Acid-Base Reaction Outcome
    4. 3.4 Structural Effects on Acidity and Basicity
    5. 3.5 Lewis Acids and Lewis Bases
    6. Answers to Practice Questions Chapter 3
  10. Chapter 4 Conformations of Alkanes and Cycloalkanes
    1. 4.1 Conformation Analysis of Alkanes
    2. 4.2 Cycloalkanes and Their Relative Stabilities
    3. 4.3 Conformation Analysis of Cyclohexane
    4. 4.4 Substituted Cyclohexanes
    5. Answers to Practice Questions Chapter 4
  11. Chapter 5 Stereochemistry
    1. 5.1 Summary of Isomers
    2. 5.2 Geometric Isomers and E/Z Naming System
    3. 5.3 Chirality and R/S Naming System
    4. 5.4 Optical Activity
    5. 5.5 Fisher Projection
    6. 5.6 Compounds with More Than One Chirality Centers
    7. Answers to Practice Questions Chapter 5
  12. Chapter 6 Structural Identification of Organic Compounds: IR and NMR Spectroscopy
    1. 6.1 Electromagnetic Radiation and Molecular Spectroscopy
    2. 6.2 Infrared (IR) Spectroscopy Theory
    3. 6.3 IR Spectrum and Characteristic Absorption Bands
    4. 6.4 IR Spectrum Interpretation Practice
    5. 6.5 NMR Theory and Experiment
    6. 6.6 ¹H NMR Spectra and Interpretation (Part I)
    7. 6.7 ¹H NMR Spectra and Interpretation (Part II)
    8. 6.8 ¹³C NMR Spectroscopy
    9. 6.9 Structure Determination Practice
    10. Answers to Practice Questions Chapter 6
  13. Chapter 7 Nucleophilic Substitution Reactions
    1. 7.1 Nucleophilic Substitution Reaction Overview
    2. 7.2 SN2 Reaction Mechanism, Energy Diagram and Stereochemistry
    3. 7.3 Other Factors that Affect SN2 Reactions
    4. 7.4 SN1 Reaction Mechanism, Energy Diagram and Stereochemistry
    5. 7.5 SN1 vs SN2
    6. 7.6 Extra Topics on Nucleophilic Substitution Reaction
    7. Answers to Practice Questions Chapter 7
  14. Chapter 8 Elimination Reactions
    1. 8.1 E2 Reaction
    2. 8.2 E1 Reaction
    3. 8.3 E1/E2 Summary
    4. 8.4 Comparison and Competition Between SN1, SN2, E1 and E2
    5. Answers to Practice Questions Chapter 8
  15. Chapter 9 Free Radical Substitution Reaction of Alkanes
    1. 9.1 Homolytic and Heterolytic Cleavage
    2. 9.2 Halogenation Reaction of Alkanes
    3. 9.3 Stability of Alkyl Radicals
    4. 9.4 Chlorination vs Bromination
    5. 9.5 Stereochemistry for Halogenation of Alkanes
    6. 9.6 Synthesis of Target Molecules: Introduction of Retrosynthetic Analysis
    7. Answers to Practice Questions Chapter 9
  16. Chapter 10 Alkenes and Alkynes
    1. 10.1 Synthesis of Alkenes
    2. 10.2 Reactions of Alkenes: Addition of Hydrogen Halide to Alkenes
    3. 10.3 Reactions of Alkenes: Addition of Water (or Alcohol) to Alkenes
    4. 10.4 Reactions of Alkenes: Addition of Bromine and Chlorine to Alkenes
    5. 10.5 Reaction of Alkenes: Hydrogenation
    6. 10.6 Two Other Hydration Reactions of Alkenes
    7. 10.7 Oxidation Reactions of Alkenes
    8. 10.8 Alkynes
    9. Answers to Practice Questions Chapter 10
  17. About the Author

6.1 Electromagnetic Radiation and Molecular Spectroscopy

Electromagnetic radiation is the radiation composed of oscillating electrical and magnetic fields. The whole electromagnetic spectrum covers the radiation in very broad range from gamma rays (emitted by the nuclei of certain radioactive elements), X-rays (used for medical examination of bones), to ultraviolet (UV) light (is responsible for sunburn, can also be used for dis-infection purpose), microwaves, and radio-frequency waves (used for radio and television communication, and of the cell phone signal). Visible light, the radiation that is visible to our bare eyes and what we commonly refer to as “light”, just accounts for a very narrow band out of the full electromagnetic spectrum.

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Figure 6.1a The Electromagnetic Spectrum

Electromagnetic radiation exhibits wave-like properties. As a general property of waves, the wavelength (λ, Greek ‘lambda‘) and frequency (ν, Greek ‘nu’, in unit of Hz or s-1, 1Hz = 1s-1) of electromagnetic radiation fits in the formula of:

c =λν                                                            Formula 6.1

where c is the speed, usually referred to as the “speed of light”, with the constant value of 2.998×108m/s in vacuum (the speed of light in air is a little bit slower than this constant but is usually regarded as the same). Because electromagnetic radiation travels at a constant speed,  wavelength (λ) and frequency (ν) are inversely proportional to each other, the longer waves have lower frequencies, and shorter waves have higher frequencies. 

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Figure 6.1b Wavelength

The energy of electromagnetic radiation can be calculated based on formula:

E = hν= hc/λ                                                 Formula 6.2

where E is energy of each photon in unit of Joule (J) and h is the Planck’s constant with value of 6.626×10-34J·s.

So radiations with higher frequencies correspond to higher energy. High energy radiation, such as gamma radiation and X-rays, is composed of very short waves – as short as 10-16m. Longer wavelengths are much less energetic, and thus are less harmful to living things. Visible light waves are in the range of 400 – 700 nm (nanometer, 1nm = 10-9m), while radio waves can be several hundred meters in length.

In a molecular spectroscopy experiment, electromagnetic radiation of a specified range of wavelengths is allowed to pass through a sample containing a compound of interest. The sample molecules absorb energy from some of the wavelengths, and as a result jump from a lower energy ‘ground state’ to some higher energy ‘excited state’.  Other wavelengths are not absorbed by the sample molecule, so they pass on through. A detector records which wavelengths were absorbed, and how much were absorbed.

As we will see in this chapter, we can learn a lot about the structure of an organic molecule by quantifying how it absorbs (or does not absorb) different wavelengths in the electromagnetic spectrum. The IR spectroscopy involves absorption of radiation in the infrared region and radio waves are applied in the NMR technique.

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Next Chapter
6.2 Infrared (IR) Spectroscopy Theory
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