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Question bank: Organic Functions: Nomenclature of Nitrile and Isonitrile

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Question 1:

Medium

During a presentation of projects, a group of students analyzed an organic substance which, after research and analysis, was found to be a nitrile and its respective isonitrile derivative. Given the formula of the nitrile CH3(CH2)2CN, what is the correct nomenclature of this nitrile and its isonitrile derivative?
Organic Functions: Nomenclature of Nitrile and Isonitrile
Question 2:

Easy

What would be the molecular formula of propylcarbilamine?
Organic Functions: Nomenclature of Nitrile and Isonitrile
Question 3:

Hard

During an Organic Chemistry class, a group of 3rd-year high school students dedicated themselves to investigating the applicability of organic compounds in new technologies. They found that both nitriles and isonitriles are used in the synthesis of pharmaceutical products and plastic materials, but they have significant differences in their structures and nomenclatures. Furthermore, the ability to correctly identify these organic functions is essential for the development of innovative chemical processes. Considering a linear carbon chain with five carbon atoms, where the functional group —C≡N is attached to the primary carbon, and another identical chain where the same functional group is attached to nitrogen, forming an isonitrile compound, the student is asked to name both substances according to the IUPAC nomenclature rules, correctly differentiating nitrile from isonitrile.
Organic Functions: Nomenclature of Nitrile and Isonitrile
Question 4:

Medium

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?
Organic Functions: Nomenclature of Nitrile and Isonitrile
Question 5:

Hard

The chemical industry uses a wide range of organic compounds in synthesis processes and manufacturing of various products. The proper nomenclature of these compounds is crucial not only for communication among professionals but also to ensure the safety and effectiveness of operations. Consider ethyl 2-bromo-4-methylpentanedioate, an intermediate in the synthesis of a vascular medication that aims to dilate blood vessels. This compound contains a specific functional group that can be derived from both a nitrile and an isonitrile. The correct identification of this functional group is essential for understanding the medication's mechanism of action and for optimizing synthesis processes. If a characteristic absorption of 2230 cm^-1 is observed during the spectral analysis of the compound in the infrared spectrum, what is the functional group present in the compound, and how should we name it considering IUPAC rules?
Organic Functions: Nomenclature of Nitrile and Isonitrile
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