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Naming Nitriles: Understanding Systematic and Common Nomenclature

Nitrile Nomenclature: A Comprehensive Guide

Nitriles are organic compounds containing a CN group. They are essential reagents in many industrial processes and are also found in various natural products.

There are two ways to classify nitriles: systematic nomenclature and common names. This article will discuss the naming conventions for nitriles in both systems.

1) Systematic Nomenclature of Nitriles

Naming Conventions for Nitriles in Systematic Nomenclature

Systematic nomenclature is a set of rules used to name organic compounds systematically and consistently. In this system, nitriles are named by adding the suffix “-nitrile” to the parent alkane. The CN group is considered a substituent and is given the prefix “cyano.”

The position of the CN group is indicated by a number assigned to the carbon atom to which it is attached. For example, the nitrile derived from propane is named propanenitrile.

The prefix “cyano” is only used when the CN group is not the highest priority group in the compound.

Naming Nitriles on a Ring

When a nitrile is present on a ring, it is named as a carbonitrile. The ring is assigned a numbering system starting with the carbon atom bearing the CN group as carbon 1.

If the CN group has the highest priority, it is indicated with the prefix “cyano.”

If there are multiple CN groups, they are named using the prefixes “dicyano,” “tricyano,” and so on, depending on the number of CN groups present.

2) Common Names of Nitriles

Derivatives of Carboxylic Acids in Common Nomenclature

In common nomenclature, nitriles are named by adding the suffix “-onitrile” to the name of the carboxylic acid from which they are derived. For example, acetonitrile is a nitrile derived from acetic acid.

The suffix “-onitrile” indicates that the -COOH group has been replaced by -CN.

Nomenclature for Nitriles as Substituents

Nitriles can also be named as substituents in common nomenclature. In this case, the prefix “cyano” is used to indicate the presence of the CN group. The substituent name is listed alphabetically along with any other substituents present.

For example, 2-cyanobenzene is a benzene ring with a cyano group at position 2.

In conclusion, nitriles are essential organic compounds found in many industrial and natural products. They can be named in two ways: systematic nomenclature and common names. Understanding the naming conventions for nitriles is essential in organic chemistry and can make it easier to identify and understand the properties of these important compounds.

FAQs:

  1. What is a nitrile?

    A nitrile is an organic compound that contains a CN group.

  2. How are nitriles named in systematic nomenclature?

    In systematic nomenclature, nitriles are named by adding the suffix “-nitrile” to the parent alkane, with the CN group considered a substituent and given the prefix “cyano.”

  3. How are nitriles named in common nomenclature?

    In common nomenclature, nitriles are named by adding the suffix “-onitrile” to the name of the carboxylic acid from which they are derived.

  4. How are nitriles named on a ring?

    When a nitrile is present on a ring, it is named as a carbonitrile, with the ring assigned a numbering system starting with the carbon atom bearing the CN group as carbon 1.

  5. How are nitriles named as substituents?

    Nitriles can be named as substituents using the prefix “cyano,” which is listed alphabetically along with other substituents present.

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