Organic Chemistry: Concepts and Applications - Headley Allan D. 2020

Heteroatomic Functional Groups and Organic Nomenclature
3.14 Structure and Properties of Nitriles

The nitriles functionality (─CN) contains an sp hybridized carbon, which is bonded to an sp hybridized nitrogen and to another group, typically an alkyl group. Nitrile rubber is a synthetic copolymer made from acrylonitrile and butadiene. Nitrile rubber is used to make protective gloves, hoses, and seals since it is highly resistant to chemicals and moisture. Methyl cyanoaclylate, another type of nitrile, is an integral ingredient of many types of glues that are used for everyday household needs. Nitriles have the functional feature shown below.

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3.14.1 Nomenclature of Nitriles

In naming nitriles, the longest continuous chain is named as an alkanenitrile. For the nitrile shown below, the longest continuous chain is named as an alkanenitrile, note that the carbon of the nitrile gets #1.

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Substituents (groups) that are bonded to the longest chain of the nitrile are assigned numbers based on the numbering system of that root name.

Problem 3.25

Give the IUPAC names for each of the following compounds.

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