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Organic Chemistry Exam Study Guide: IR Spectroscopy, Reactions, and Nomenclature

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Q6. Which of the compounds below would give the following IR spectrum?

Background

Topic: IR Spectroscopy and Functional Group Identification

This question tests your ability to interpret IR spectra and match them to the correct organic compound based on characteristic absorption bands.

Key Terms and Formulas

  • IR Spectroscopy: A technique used to identify functional groups in organic molecules by measuring absorption of infrared light at specific wavenumbers.

  • Characteristic Absorptions:

    • C≡N (nitrile) stretch: cm-1

    • O-H (alcohol/phenol) stretch: cm-1

    • N-H (amine) stretch: cm-1

Step-by-Step Guidance

  1. Examine the IR spectrum for key peaks. Notice the strong absorption near $2249$ cm-1, which is characteristic of a nitrile (C≡N) group.

  2. Check for other significant peaks. Absence of broad O-H or N-H stretches suggests the compound does not contain alcohol or amine functional groups.

  3. Compare the spectrum to the possible answer choices. Focus on which compound contains a nitrile group and lacks O-H or N-H functionalities.

  4. Review the molecular structures of the answer choices and identify which one matches the functional group indicated by the IR spectrum.

Try solving on your own before revealing the answer!

IR spectrum of butyronitrile with C≡N stretch at 2249 cm-1

Final Answer: Compound with a nitrile group (butyronitrile)

The IR spectrum shows a strong absorption at $2249$ cm-1, which is characteristic of a C≡N stretch. Among the choices, butyronitrile (CH3CH2CH2C≡N) is the compound that contains a nitrile group and matches the spectrum.

This confirms that the correct answer is the compound with the nitrile functional group.

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