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Spectroscopy

A systematic approach and the degree of unsaturation

  • 3 things to know
  • Components 02 and 03

Overview

Recall questions on the order in which the techniques are applied, calculating the degree of unsaturation, and why a carbon-13 spectrum may show fewer peaks than carbons.

What you need to know

Answer each one before you reveal it.

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Key term

What do carbon-13 chemical shifts indicate, which technique identifies functional groups in a systematic structure elucidation, and what is the final step?

Key term

What does observing fewer ¹³C NMR peaks than carbon atoms indicate about the molecule?

Numbers

Define degree of unsaturation (index of hydrogen deficiency).

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    In a systematic approach to structure elucidation, how is the molecular formula determined?

    Model answer

    By using elemental analysis data combined with the molecular ion peak from mass spectrometry.

  2. 2

    Which analytical technique is used to identify functional groups in a systematic structure elucidation?

    Model answer

    IR spectroscopy, by identifying characteristic absorptions.

  3. 3

    How is NMR spectroscopy used to determine the carbon skeleton and hydrogen arrangement?

    Model answer

    By determining the number of carbon and hydrogen environments from the number of peaks in ¹³C and ¹H NMR spectra.

  4. 4

    What NMR features are used to deduce the detailed structure of a molecule?

    Model answer

    Splitting patterns (to determine adjacent hydrogens) and integration (to determine the ratio of hydrogens in each environment).

  5. 5

    What is the final step in a systematic approach to structure elucidation?

    Model answer

    Verify that the proposed structure is consistent with all the spectroscopic data.

  6. 6

    What is calculated from the molecular formula to indicate rings and double bonds?

    Model answer

    The degree of unsaturation (index of hydrogen deficiency).

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AThe first step is Cl• + O₃ → ClO• + O₂.
BThe second step is ClO• + O → Cl• + O₂.
CThe overall equation is O₃ + O → 2O₂.

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In ClO⁻, chlorine has oxidation number +1.
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