part 1

Organic Chemistry Ch. 14: Infrared Spectroscopy and Mass Spectroscopy

Overview of IR Spectroscopy

  • Specifics of the IR signal and its physical origin:
    • The infrared (IR) signal originates from molecular vibrations, which involve the stretching and bending of bonds.
  • Factors affecting the frequency (Wavenumber) of absorption:
    • Various factors alter the wavenumber, including bond strength and mass differences of the atoms involved.
  • Details of the IR signal:
    • Signals can be classified as weak or strong based on intensity, which relates to how well the bonds interact with IR radiation.
  • Characteristics of Functional Groups IR spectrums:
    • Different functional groups produce distinct peaks in an IR spectrum, allowing for identification of their presence in organic molecules.

14.1 Introduction to Spectroscopy / Overview

  • Learning Objectives:
    • By the end of this chapter, students should be proficient in interpreting the IR spectrum of organic molecules.
    • This includes:
    • Identifying various functional groups.
    • Recognizing bonding patterns such as double vs triple carbon-carbon bonds.
  • Impact of Molecular Structure on Spectrum:
    • Structure influences the exact spectrum observed; factors like conjugation can cause shifts in the expected wavenumber.

14.3 Signal Characteristics: Wavenumber / What This Indicates

  • Factors influencing frequency (wavenumber) of stretching vibrations:
    1. Bond strength:
    • Stronger bonds vibrate at higher frequencies.
    1. Mass difference of the atoms:
    • A larger mass difference leads to higher stretching frequencies.

14.3 Signal Characteristics: Wavenumber / Types of Bonds

  • Wavenumber Formula and Empirical Observations:
    • The observed wavenumbers correlate with specific types of bonds based on empirical data, assisting in bond identification during analysis.

14.3 Signal Characteristics: Wavenumber / Diagnostic and Fingerprint Regions

  • Diagnostic Region:
    • Defined as the region above 1500extcm11500 ext{cm}^{-1}; peaks here provide clear stark information about functional groups.
  • Fingerprint Region:
    • Located below 1500extcm11500 ext{cm}^{-1}; this region typically contains many overlapping signals, complicating individual signal analysis.

14.3 Signal Characteristics: Wavenumber / C-H Bond Spectra

  • C-H Bond Frequencies:
    • Alkyl C-H Bonds:
    • Occur just under 3000extcm13000 ext{cm}^{-1}
    • Alkenyl and Alkynyl C-H Bonds:
    • Occur just above 3000extcm13000 ext{cm}^{-1}.

14.3 Signal Characteristics: Wavenumber / Resonance

  • Effect of Resonance on Bond Strength:
    • Resonance affects the delocalization of electrons, which impacts the strength of covalent bonds, thus altering the wavenumber of stretching signals.
  • Examples:
    • Consider the C=O stretching values for compounds with varying resonance structures; the more delocalized the p electrons, the weaker the p bond and consequently lower the stretching frequency.

14.3 Signal Characteristics: Wavenumber / Conjugation

  • Conjugation Effect on Stretching Frequencies:
    • Conjugated carbonyls exhibit lower stretching frequencies due to resonance stabilization.
    • Examples:
    • A typical carbonyl might absorb near 1740extcm11740 ext{cm}^{-1}, while a conjugated ester might absorb at 1710extcm11710 ext{cm}^{-1}.

14.4 Signal Characteristics: Intensity / Overview

  • Variability in Signal Strength (Intensity):
    • IR signals can range from weak to strong, which can be graphed on a transmittance curve.
    • Example graph description:
    • Percent transmittance is plotted against wavenumber (cm⁻¹).

14.4 Signal Characteristics: Intensity / Dipole Moment

  • Oscillation of Dipole Moment:
    • During stretching vibration of a bond, its dipole moment oscillates, influencing how IR radiation interacts with the bond.
    • Dipole Moment Formula:
    • The dipole moment is determined by the distance between partial charges and the magnitude of those charges, which creates an electric field around the bond.

14.4 Signal Characteristics: Intensity / Polarity

  • Impact of Bond Polarity on IR Signals:
    • Greater polarity in a bond increases the likelihood of interactions between the electromagnetic waves of the electric field and the IR radiation.
    • Therefore, higher bond polarity leads to stronger IR signals in the spectrum.

14.4 Signal Characteristics: Intensity / Symmetrical Bond

  • Symmetry and Signal Observation:
    • If a bond is perfectly symmetrical, stretching frequencies will not be detected in the IR spectrum.
    • Additionally, vibrations of multiple equivalent bonds can result in stronger overall signals.
    • Although C-H bonds are not significantly polar, they often produce strong signals due to their abundance in organic compounds.