Spectroscopic Techniques in Organic Chemistry

To Understand Spectroscopy We Must Understand Electromagnetic Radiation (EMR)

EMR Is a Form of Energy That Has Both Wave and Particle Nature. Examples Include Light, Microwaves, and Radio Waves.

We Use Symbols to Designate the Various Properties of Waves is the wavelength of the waves or f is the frequency of the waves c is the speed of light (the speed of all EMR)

There Is a Direct Relationship Between These Variables

Speed = Wavelength x Frequency For EMR

c = = c/ = c/

For Electromagnetic Waves the Speed (c) Is a Constant

c = 2.99 x 108 m/sec c = 2.99 x 1010 cm/sec c = 186,000 miles/sec You Should Already Know These Numbers!

This Constant Speed for EMR Means a Direct, Inverse Relationship Between Wavelength and Frequency

1/
The Higher the Frequency the Shorter the Wavelength . The Longer the Wavelength the Lower the Frequency.

The Relationship Between Frequency and Wavelength

When the Wavelength Is Measured in Centimeters, the Reciprocal of the Wavelength (1/cm) Is Directly Proportional to the Frequency
1/cm Is Called the Wavenumber and Is a Commonly Used Term in Spectroscopy.

The Electromagnetic Spectrum

(A Display of Types of EMR According to Wavelength)

Spectroscopy Is the Study of the Interaction of Matter and Electromagnetic Radiation

In Organic Chemistry the Common Techniques Include Infrared Spectroscopy Nuclear Magnetic Resonance Spectroscopy UV/Visible Spectroscopy

Another Technique Commonly Used Is Mass Spectrometry

Spectrometry Is Somewhat Different Than Spectroscopy. It is defined as any of various analytical techniques in which an emission (as of particles or radiation) is dispersed according to some property (as mass or energy) of the emission and the amount of dispersion is measured

What Do We Get From These Techniques?

Specific Information Regarding the Structural Features of the Molecules Being Studied. This Includes Molecular Mass and Insight Into the Presence or Absence of Specific Patterns of Chemical Bonding in the Molecule

Infrared Spectroscopy
A Technique in Which We Examine the Absorption Patterns of Infrared Radiation by a Molecule

IR Is One Type of EMR

A Dispersive IR Spectrophotometer

FTIR

A Typical Spectrum

Characteristic Absorption Regions

Characteristic Absorptions

We Obtain an IR Spectrum to Find Out if Specific Functional Groups Are Present or Absent
By Using Computer Assisted Searches of Databases We Can Sometimes Actually Identify an Unknown Compound

Nuclear Magnetic Resonance (NMR) Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Another Technique That Allows Us to Gain Understanding About the Specific Chemical Structure of a Compound

There Are Two Main Types of NMR

Proton NMR or 1HNMR And Carbon-13 NMR or 13CNMR

We Can Do This Because

Hydrogen nuclei generate their own magnetic fields If an external magnetic field is applied, the nuclei can exist in two energy states Radio waves of the proper frequency will cause some nuclei to change energy states The frequency of the radio waves that will do this is determined, in part, by the local atomic environment in which the nuclei are found

In Proton NMR We Examine Hydrogen Environments

By Carefully Examining These Frequencies We Can Make Conclusions Regarding the Structure of the Molecule
This Is a Very Powerful Tool That Can Be Used to Deduce the Structure of a Compound

In Carbon-13 NMR We Examine Carbon Environments

CH2CH2CH2CH3

The Reason We Can Do Carbon-13 NMR Is Because, Like Protons, the 13C Atoms Also Generate a Magnetic Field
Although it takes different magnetic field strengths and different frequencies of radio waves, the principles we stated regarding proton NMR are almost the same for 13CNMR

The 13CNMR Spectrum of 2-Chloro-2-Methylbutane

CH3 CH3 CH2 C CH3 Cl

This Powerful Chemical Technique Has Been Modified to Produce a Very Powerful Medical Diagnostic Tool

Another Powerful Tool Is Mass Spectrometry

With the Proper Setup, This Is the Most Powerful Tool of All

In Mass Spectrometry We
Break molecules into different size pieces by allowing them to pass through a stream of electrons Separate the charged pieces according to their masses Identify the masses of the pieces and their abundance Reach conclusions about molecular mass and other structural features of the molecules

Here Is the Mass Spectrum of a 16-Carbon Compound

Using a Knowledge of Fragmentation Patterns and with the Help of Computers We Can
Determine the molecular mass and molecular formula of the compound Identify the presence of specific structural features in the compound Actually identify the exact compound if its mass spectrum is stored in the computers database

This Is How They Perform a Lot of Drug Testing

They Use a Combination of Gas Chromatography and Mass Spectrometry (GC-Mass Spec) to Identify Specific Chemical Compounds in Biological Samples

We Will Learn About All of These Techniques in This Class

By Combining the Techniques it Is Possible to Identify Almost Any Organic Chemical Compound

END