20.1 Naming Carboxylic Acids and Nitriles
3 min read•may 7, 2024
Carboxylic acids and nitriles are key players in organic chemistry. These compounds have unique structures and naming conventions that set them apart. Understanding their nomenclature is crucial for identifying and working with these important molecules.
IUPAC naming rules provide a systematic approach to naming these compounds. For carboxylic acids, the ending is key, while nitriles use the suffix. are still used for simple acids, and play a role in naming acid derivatives.
Carboxylic Acids and Nitriles
IUPAC naming of carboxylic acids
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- Identify the longest carbon chain containing the (-) as the parent chain
- Replace the -e ending of the corresponding alkane with -oic acid to indicate the presence of a carboxylic acid functional group
- Number the carbon chain starting from the carboxyl carbon to give the lowest possible numbers to
- Indicate the positions and names of any substituents using numbers and prefixes (2-methylpentanoic acid)
- Common names for simple carboxylic acids still widely used (examples of )
- (HCOOH), simplest carboxylic acid
- (CH3COOH), found in vinegar
- (CH3CH2COOH), used as a preservative
- (CH3CH2CH2COOH), responsible for the smell of rancid butter
- Acyl groups (RCO-) derived from carboxylic acids by removing the -OH group
- Named by replacing the -ic acid ending with -yl (, , )
- Represent the carboxylic acid minus the hydroxyl group
- Used in naming acid derivatives (acetyl chloride, propionyl bromide)
Nomenclature of nitriles
- Nitriles contain the - functional group, a carbon atom triple-bonded to a nitrogen atom
- for nitriles
- Identify the longest carbon chain containing the -CN group as the parent chain
- Replace the -e ending of the corresponding alkane with -nitrile ()
- Number the carbon chain starting from the nitrile carbon to give the lowest possible numbers to substituents
- Indicate the positions and names of any substituents using numbers and prefixes ()
- for nitriles
- Use the prefix to indicate the presence of a -CN group
- Name the parent compound as usual (based on the longest carbon chain)
- Indicate the position of the -CN group using numbers ()
Structures from acid and nitrile names
- Drawing carboxylic acids
- Identify the parent alkane from the name (pentane from pentanoic acid)
- Replace the -oic acid ending with a (-COOH) at the end of the chain
- Attach any substituents at the indicated positions (2-methylpentanoic acid has a methyl group on the second carbon)
- Drawing nitriles (IUPAC)
- Identify the parent alkane from the name (butane from butanenitrile)
- Replace the -nitrile ending with a -CN group at the end of the chain
- Attach any substituents at the indicated positions (2-methylbutanenitrile has a methyl group on the second carbon)
- Drawing nitriles (prefix)
- Draw the structure of the parent compound (pentane for 2-cyanopentane)
- Attach a -CN group at the position indicated by the number preceding the cyano- prefix (2-cyanopentane has the -CN on the second carbon)
IUPAC Nomenclature and Common Names
- IUPAC nomenclature provides systematic naming rules for organic compounds
- Common names are still widely used for some simple compounds
- Substituents are groups attached to the parent chain and are named using prefixes
- Functional groups determine the compound's class and are prioritized in naming
Key Terms to Review (27)
-nitrile: A nitrile is a functional group consisting of a carbon-nitrogen triple bond (-C≡N). Nitriles are found in various organic compounds and play an important role in the context of naming carboxylic acids and nitriles.
-oic Acid: -oic acid is a functional group in organic chemistry that refers to a carboxylic acid with the general formula R-COOH, where R represents an alkyl or aryl group. This term is particularly relevant in the context of understanding functional groups and the naming of carboxylic acids and nitriles.
2-cyanopentane: 2-cyanopentane is an organic compound with the chemical formula CH3CH2CH2CH2CN. It is a nitrile, a functional group containing a carbon-nitrogen triple bond, and is classified as a pentane derivative with a cyano group (-CN) substituted at the second carbon position.
2-methylbutanenitrile: 2-methylbutanenitrile is a nitrile compound with a methyl group attached to the second carbon of a butane chain. Nitriles are an important class of organic compounds that contain a carbon-nitrogen triple bond and are commonly used in the synthesis of various chemicals and pharmaceuticals.
Acetic Acid: Acetic acid is a weak organic acid with the chemical formula CH3COOH. It is a colorless liquid with a distinctive sour odor and is the main component of vinegar. Acetic acid is a versatile compound that plays important roles in various organic chemistry topics, including functional groups, oxidation of alkenes, reduction of carbonyl compounds, naming of carboxylic acids, and the chemistry of esters.
Acetyl: The acetyl group, represented by the chemical formula -COCH3, is a functional group commonly encountered in organic chemistry. It is derived from the acetic acid molecule and plays a crucial role in various biochemical processes, particularly in the context of carboxylic acids and nitriles.
Acyl Groups: Acyl groups are functional groups derived from carboxylic acids by the removal of the hydroxyl (-OH) group, leaving behind a carbonyl (C=O) group bonded to a hydrocarbon chain or aromatic ring. These groups are essential in the context of naming carboxylic acids and nitriles, as they form the basis for the nomenclature of these important organic compounds.
Alkanenitrile: An alkanenitrile is an organic compound that contains a nitrile functional group (-C≡N) attached to an alkane backbone. Alkanenitriles are important intermediates in the synthesis of various nitrogen-containing compounds and are commonly used in the production of pharmaceuticals, polymers, and other industrial chemicals.
Alkanoic Acid: Alkanoic acids, also known as carboxylic acids, are a class of organic compounds characterized by the presence of a carboxyl functional group (-COOH). They are important in the context of 20.1 Naming Carboxylic Acids and Nitriles, as they represent the simplest and most common type of carboxylic acids.
Butyric Acid: Butyric acid is a short-chain fatty acid with the chemical formula CH3CH2CH2COOH. It is a colorless, oily liquid with a distinctive unpleasant odor, and is found naturally in butter, parmesan cheese, and the digestive tract of humans and animals.
Butyryl: Butyryl is a functional group derived from the carboxylic acid butyric acid. It is a four-carbon acyl group that can be found in various organic compounds, particularly in the context of carboxylic acids and nitriles.
Carbonyl group: A carbonyl group is a functional group characterized by a carbon atom double-bonded to an oxygen atom, represented as C=O. This group is pivotal in organic chemistry as it forms the backbone of various important classes of compounds, influencing their chemical properties and reactivity.
Carboxyl group: A carboxyl group is a functional group consisting of a carbon atom double-bonded to an oxygen atom and single-bonded to a hydroxyl group (-COOH). It is characteristic of carboxylic acids, giving these compounds their acidic properties.
Carboxyl Group: The carboxyl group is a functional group consisting of a carbon atom double-bonded to an oxygen atom and single-bonded to a hydroxyl group (-COOH). It is a key structural feature in various organic compounds, including carboxylic acids, amino acids, and proteins, and plays a crucial role in their chemical reactivity and properties.
CN: The CN functional group, also known as the nitrile group, is a carbon-nitrogen triple bond that is commonly found in organic compounds, particularly in the context of carboxylic acids and nitriles. It is a versatile and important functional group in organic chemistry.
Common Names: Common names, also known as trivial names or popular names, are informal designations used to identify chemical compounds that are more easily recognizable than their formal systematic names. These simplified names are widely used in everyday conversations and literature, providing a more accessible way to refer to various organic compounds, including aldehydes, ketones, carboxylic acids, nitriles, and amines.
COOH: COOH is the chemical formula for the carboxyl group, a functional group consisting of a carbonyl carbon atom (C=O) bonded to a hydroxyl group (OH). This group is commonly found in carboxylic acids and is responsible for their acidic properties.
Cyano-: The prefix 'cyano-' is derived from the Greek word 'kyanos,' meaning 'blue.' In the context of organic chemistry, it refers to a functional group or substituent containing a carbon-nitrogen triple bond (C≡N), known as the cyano or nitrile group. This prefix is commonly used in the naming and identification of compounds containing this functional group.
Formic Acid: Formic acid is the simplest carboxylic acid, with the chemical formula HCOOH. It is a colorless, pungent liquid that is found naturally in the venom of ants and is also produced synthetically. Formic acid is an important chemical compound that is relevant in the context of naming carboxylic acids and nitriles, understanding the structure and properties of carboxylic acids, and analyzing the spectroscopy of carboxylic acids and nitriles.
Functional Groups: Functional groups are specific arrangements of atoms within a molecule that determine the chemical reactivity and physical properties of that molecule. These groups play a crucial role in understanding and predicting the behavior of organic compounds.
IUPAC Nomenclature: IUPAC nomenclature is a standardized system for naming organic compounds, developed by the International Union of Pure and Applied Chemistry (IUPAC). It provides a consistent and unambiguous way to identify and communicate the structure of organic molecules.
Nitrile Group: The nitrile group, also known as the cyano group, is a functional group consisting of a carbon-nitrogen triple bond (-C≡N). It is an important functional group in organic chemistry, particularly in the context of naming carboxylic acids and nitriles.
Pentanenitrile: Pentanenitrile is a nitrile compound with the chemical formula CH3CH2CH2CH2CN. It is a colorless, flammable liquid with a pungent odor and is used as a precursor in the synthesis of various organic compounds.
Prefix Nomenclature: Prefix nomenclature is a system used to name organic compounds, particularly carboxylic acids and nitriles, where prefixes are added to the base name of the compound to provide specific information about its structure and functional groups.
Propionic Acid: Propionic acid is a short-chain carboxylic acid with the chemical formula CH3CH2COOH. It is a colorless liquid with a pungent odor and is commonly used in the food industry as a preservative and in the production of various chemicals.
Propionyl: Propionyl is a functional group in organic chemistry that consists of a carbonyl carbon atom bonded to a methyl group. It is an acyl group derived from the carboxylic acid, propionic acid, and is commonly encountered in the context of naming carboxylic acids and nitriles.
Substituents: Substituents are atoms or functional groups that replace hydrogen atoms in a molecule's structure. They are an essential concept in organic chemistry, as they play a crucial role in determining the properties, reactivity, and naming of various organic compounds.