Naming Carboxylic Acids - IUPAC Nomenclature

The Organic Chemistry Tutor
3 May 201814:30
EducationalLearning
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TLDRThis video focuses on naming carboxylic acids, beginning with common examples like formic acid (methanoic acid) and acetic acid (ethanoic acid). It explains the IUPAC naming rules for various carboxylic acids, including those with substituents like chlorine, methoxy, and amino groups. The video covers naming molecules with functional groups such as ketones, ethers, and alkenes, and introduces cyclic compounds like benzoic acid and cyclohexane carboxylic acid. It concludes with examples of dioic acids, highlighting common names like oxalic, malonic, succinic, glutaric, adipic, maleic, and fumaric acids.

Takeaways
  • 🔍 The video focuses on the nomenclature of carboxylic acids, providing examples of common and IUPAC names.
  • 🧪 Formic acid is the common name for a one-carbon carboxylic acid, while its IUPAC name is methanoic acid.
  • 🍋 Acetic acid is commonly known for a two-carbon carboxylic acid, with the IUPAC name ethanoic acid.
  • 🥥 Butyric acid is the common name for a four-carbon carboxylic acid, and its IUPAC name is butanoic acid.
  • 📝 The naming of carboxylic acids with substituents involves identifying the position of the substituent (alpha, beta, gamma) and using appropriate prefixes.
  • 🌐 For carboxylic acids with multiple substituents, the IUPAC name requires numbering the carbon chain to give the lowest possible numbers to the substituents and listing them in alphabetical order.
  • 🔑 The presence of functional groups such as amino, methoxy, or oxo in the molecule affects the IUPAC naming, with the carboxylic acid group taking priority in numbering.
  • 💧 Cyclic carboxylic acids are named by combining the name of the ring (e.g., cyclohexane) with 'carboxylic acid', and any substituents are named with their respective positions.
  • 🔄 The video explains how to name carboxylic acids with double bonds, such as 'trans' or 'cis', by including the position of the double bond in the name.
  • 💊 Dioic acids, which contain two carboxylic acid groups, are named by numbering from the end closest to the substituents and using the prefix 'di-'.
  • 📚 Common names for some dicarboxylic acids are provided, such as oxalic (two carbons), malonic (three carbons), and adipic (six carbons) acids.
Q & A

  • What is the common name and IUPAC name for a one-carbon carboxylic acid?

    -The common name is formic acid, and the IUPAC name is methanoic acid.

  • What are the common and IUPAC names for a carboxylic acid with two carbon atoms?

    -The common name is acetic acid, and the IUPAC name is ethanoic acid.

  • How do you name a four-carbon carboxylic acid?

    -The common name is butyric acid, and the IUPAC name is butanoic acid.

  • What is the common name and IUPAC name for a carboxylic acid with a chlorine atom on the beta carbon?

    -The common name is beta-chlorobutyric acid, and the IUPAC name is 3-chlorobutanoic acid.

  • How do you name a carboxylic acid with a methoxy group on the gamma carbon?

    -The common name is gamma-methoxybutyric acid, and the IUPAC name is 4-methoxybutanoic acid.

  • What is the IUPAC name for a six-carbon carboxylic acid with an NH2 group on carbon 4?

    -The IUPAC name is 4-aminohexanoic acid.

  • How do you name a carboxylic acid with multiple functional groups including amino, methoxy, and oxo groups?

    -The IUPAC name is 4-amino-6-methoxy-5-oxoheptanoic acid.

  • What is the name for a carboxylic acid attached to a benzene ring?

    -The name is benzoic acid.

  • How do you name a carboxylic acid attached to a cyclohexane ring?

    -The name is cyclohexanecarboxylic acid.

  • What is the name for a carboxylic acid with a methyl group on the third carbon of a cyclohexane ring?

    -The name is 3-methylcyclohexanecarboxylic acid.

  • How do you name a molecule with a cyclohexane ring attached to an eight-carbon chain with a carboxylic acid?

    -The name is 5-cyclohexyloctanoic acid.

  • What is the IUPAC name for a carboxylic acid with an alkene on the third carbon?

    -The IUPAC name is trans-3-hexenoic acid.

  • How do you name a molecule with two carboxylic acids and a methyl group on carbon 2?

    -The name is 2-methylpentanedioic acid.

  • What is the name for a molecule with bromine on the second carbon and a hydroxy group on the third carbon of a six-carbon chain with two carboxylic acids?

    -The name is 2-bromo-3-hydroxyhexanedioic acid.

  • What are the common names for two-carbon and three-carbon dicarboxylic acids?

    -The common name for a two-carbon dicarboxylic acid is oxalic acid, and for a three-carbon dicarboxylic acid, it is malonic acid.

  • What is the common name for a four-carbon dicarboxylic acid?

    -The common name is succinic acid.

  • What is the common name for a five-carbon dicarboxylic acid?

    -The common name is glutaric acid.

  • What is the common name for a six-carbon dicarboxylic acid?

    -The common name is adipic acid.

  • What is the common name for a four-carbon dicarboxylic acid with a cis alkene?

    -The common name is maleic acid.

  • What is the common name for a four-carbon dicarboxylic acid with a trans alkene?

    -The common name is fumaric acid.

Outlines
00:00
🧪 Naming Carboxylic Acids: Basics and Examples

This paragraph introduces the process of naming carboxylic acids, starting with simple examples like formic and acetic acids. It explains the common and IUPAC names based on the number of carbon atoms. The paragraph also covers the naming of substituted carboxylic acids, such as beta-chlorobutyric and gamma-methoxybutyric acids, emphasizing the importance of the alpha carbon and the order of substituents.

05:00
🔍 Advanced Carboxylic Acid Nomenclature: Substituents and Rings

The second paragraph delves into more complex carboxylic acid nomenclature, including those with multiple substituents and cyclic structures. It discusses the naming of acids with amino, ketone, and ether groups, as well as the alphabetical order of substituents. Examples of benzoic and cyclohexane carboxylic acids are provided, along with the naming of molecules with multiple carboxylic acid groups, such as 'dioic acids'.

10:01
🌟 Carboxylic Acids with Functional Groups: Alkenes, Halogenation, and More

This paragraph focuses on the nomenclature of carboxylic acids that contain additional functional groups like alkenes, halogens, and hydroxyl groups. It explains how to number the carbon chain to give the lowest possible numbers to substituents and how to name the geometric isomers (cis/trans). Common names for various dicarboxylic acids, such as oxalic, malonic, and adipic acids, are also introduced, along with examples of naming more complex molecules with these functional groups.

Mindmap
Keywords
💡Carboxylic Acids
Carboxylic acids are organic compounds containing a carboxyl group (-COOH). They are the focus of the video, which aims to teach viewers how to name them according to IUPAC rules. For example, formic acid is a one-carbon carboxylic acid, and acetic acid is a two-carbon carboxylic acid.
💡Common Name
The common name is the traditional or trivial name given to a chemical compound, often derived from historical usage or properties. In the context of the video, common names like 'formic acid' and 'acetic acid' are contrasted with their IUPAC names.
💡IUPAC Name
The IUPAC name is the systematic name given to a chemical compound following the rules of the International Union of Pure and Applied Chemistry. The video script explains how to derive IUPAC names for various carboxylic acids, such as 'methanoic acid' for a one-carbon carboxylic acid.
💡Substituent
A substituent is an atom or group of atoms that replace hydrogen atoms in a hydrocarbon molecule. The video discusses how to name carboxylic acids with substituents, such as 'beta chloro butyric acid', where 'chloro' is the substituent on the beta carbon.
💡Alpha, Beta, Gamma Carbon
These terms refer to the position of carbon atoms in a molecule relative to a functional group, such as the carboxyl group in carboxylic acids. The video uses these terms to explain the naming of carboxylic acids with multiple carbons, like 'beta chloro butyric acid' where 'beta' indicates the second carbon.
💡Methoxy Group
A methoxy group is an ether functional group consisting of an oxygen atom bonded to a methyl group (-O-CH3). In the video, 'gamma methoxy butyric acid' is an example where the methoxy group is attached to the gamma carbon of the carboxylic acid.
💡Amino Group
The amino group is a functional group consisting of a nitrogen atom bonded to two hydrogen atoms (-NH2). The video mentions '4-amino hexanoic acid' as an example of a carboxylic acid with an amino group attached to the fourth carbon.
💡Ketone Function Group
A ketone is a functional group with a carbonyl group (C=O) bonded to two other carbon atoms. The script uses '5-oxo heptanoic acid' to illustrate a carboxylic acid with a ketone group on the fifth carbon.
💡Ether
An ether is an organic compound containing an ether group, which consists of an oxygen atom bonded to two alkyl or aryl groups. The video script mentions '6-methoxy' as an example of an ether group in the context of naming a carboxylic acid.
💡Benzene Ring
A benzene ring is a six-carbon atom ring with alternating single and double bonds, characteristic of aromatic compounds. 'Benzoic acid' is an example from the video where a carboxylic acid is attached to a benzene ring.
💡Cyclohexane Ring
A cyclohexane ring is a six-membered ring of carbon atoms, often found in cyclic compounds. The video script explains how to name carboxylic acids with a cyclohexane ring, such as '3-methyl cyclohexane carboxylic acid'.
💡Alkene
An alkene is an unsaturated hydrocarbon containing a carbon-carbon double bond. The video uses 'trans-3-hexenoic acid' to demonstrate the naming of a carboxylic acid with an alkene functional group.
💡Dioic Acid
A dioic acid is a carboxylic acid containing two carboxyl groups. The script explains how to name such compounds, like '2-methylpentane dioic acid', where 'dioic' indicates the presence of two carboxylic acid groups.
💡Cis and Trans Isomers
Cis and trans isomers are stereoisomers of compounds with double bonds, differing in the orientation of substituents around the double bond. The video mentions 'trans-3-hexanoic acid' to illustrate the naming of a carboxylic acid with a specific geometric isomerism.
💡Common Names of Dioic Acids
The video script lists common names for dioic acids based on the number of carbon atoms, such as 'oxalic acid' for a two-carbon dioic acid, and 'adipic acid' for a six-carbon dioic acid, providing a quick reference for naming these compounds.
💡Maleic Acid and Fumaric Acid
Maleic acid and fumaric acid are specific examples of four-carbon dicarboxylic acids with different geometric isomers of the central double bond. The video explains that 'maleic acid' has a cis configuration, while 'fumaric acid' has a trans configuration.
Highlights

The video focuses on the nomenclature of carboxylic acids, starting with common examples.

One carbon carboxylic acid is named formic acid in common terms and methanoic acid according to IUPAC.

Acetic acid, a two-carbon carboxylic acid, is known as ethanoic acid in IUPAC nomenclature.

Butyric acid, with four carbons, is called butanoic acid in IUPAC naming.

Naming carboxylic acids with substituents involves identifying the alpha, beta, and gamma carbons.

Beta chloro butyric acid is an example of a carboxylic acid with a chlorine substituent.

Gamma methoxy butyric acid demonstrates the inclusion of an ether group in the nomenclature.

A six-carbon carboxylic acid with an NH2 group is named 4-amino hexanoic acid.

Combining functional groups in nomenclature requires alphabetical order, as seen with 4-amino 6-methoxy 5-oxo heptanoic acid.

Benzoic acid is named for its benzene ring attached to a carboxylic acid.

Cyclohexane carboxylic acid and cyclopentane carboxylic acid are named based on their respective ring structures.

3-methyl cyclohexane carboxylic acid illustrates the naming of a carboxylic acid with a methyl substituent on a ring.

Cyclohexyl as a substituent on a carboxylic acid chain is named as 5-cyclohexyl octanoic acid.

Alkene functional groups in carboxylic acids are named with prefixes like 'hexene' for the alkene part.

Trans and cis isomers in carboxylic acids are differentiated by their hydrogen atom positions, such as trans-3-hexanoic acid.

Dioic acids, with two carboxylic acid groups, are named with numbering to give the lowest possible numbers to substituents.

2-methylpentane dioic acid is an example of a carboxylic acid with a methyl group and two carboxylic acid groups.

2-bromo 3-hydroxy hexane dioic acid demonstrates the combination of halide and hydroxyl groups in nomenclature.

Common names for dioic acids include oxalic, malonic, sacinic, glutaric, adipic, maleic, and fumaric acids.

Transcripts

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Carboxylic AcidsIUPAC NamingChemistry EducationOrganic ChemistryAcid ExamplesMolecular StructureNomenclature RulesEducational VideoChemical BondsSubstituent Groups