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Question about Organic Functions: Nomenclature of Nitrile and Isonitrile

Subject Chemistry

Chemistry

Source Originais Teachy

Originais Teachy

Topic Organic Functions: Nomenclature of Nitrile and Isonitrile

Organic Functions: Nomenclature of Nitrile and Isonitrile

Difficulty Medium

Medium

(Originais Teachy 2024) - Question Medium of Chemistry

During an experiment in organic chemistry, a group of 3rd-year high school students synthesized an organic compound containing a nitrile functional group. The substance was identified through a series of solubility tests, chemical reactions, and elemental analysis of the molecular formula. In addition, the students performed a spectroscopic analysis that revealed only absorption peaks around 2200-2300 cm⁻¹ in the infrared region, with no absorption around 3300 cm⁻¹ indicating the presence of the isonitrile functional group. Considering the results obtained and interdisciplinary knowledge of organic compound nomenclature and spectroscopy in the infrared region, how could the students correctly name the synthesized compound, knowing that it contains a nitrile functional group, and what is the importance of the absence of peaks around 3300 cm⁻¹ for the identification of the functional group present?

Based on the presence of the nitrile functional group, numbering the main carbon chain and identifying substituents are unnecessary for the correct naming of the compound.

The absence of peaks around 3300 cm⁻¹ in the infrared spectrum is not relevant for the identification of the synthesized compound, as nitriles always show this absorption pattern.

The students should name the synthesized compound as a ketone because the analysis of the infrared spectrum indicated the presence of a band around 1700 cm⁻¹, characteristic of ketones.

The name of the synthesized compound should include the suffix '-isonitrile', since the identification of the functional group is based on the presence of C-N bonds and not on specific absorption bands in the infrared.

The students should name the synthesized compound using IUPAC rules for nitriles and consider the importance of the absence of peaks around 3300 cm⁻¹ to confirm the presence of the nitrile group and exclude the presence of isonitriles.

Answer sheet:

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