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Chapter 17 - Carboxylic Acids

  • The term oxalic acid comes from one of its biological sources, plants of the genus Oxalis, one of which being rhubarb.

    • Adipic acid is one of two monomers needed to create the polymer nylon 66. (as shown in the image attached).

    • The common names for the dicarboxylic acids oxalic through adipic are remembered using a mnemonic phrase. “Oh my goodness, such delicious apples.”

  • A carboxylic acid with a carboxyl group attached to a cycloalkane ring is called by first giving the ring's name and then adding the suffix -carboxylic acid.

    • The ring's atoms are numbered starting with the carbon-containing the -COOH group.

    • Benzoic acid is the most basic aromatic carboxylic acid.

    • Numbers are used to denote the placement of substituents relative to the carboxyl group when naming derivatives.

  • Certain aromatic carboxylic acids are often known by their common names.

    • 2-hydroxybenzoic acid, for example, is more often known as salicylic acid, a term derived from the fact that this aromatic carboxylic acid was initially isolated from the bark of the willow, a tree in the genus Salix.

  • Aromatic dicarboxylic acids are called by prefixing dicarboxylic acid with benzene (e.g., 1,2-benzenedicarboxylic acid and 1,4-benzenedicarboxylic acid).

  • Each is commonly recognized by its common name: phthalic acid and terephthalic acid.

  • Terephthalic acid is one of two organic components necessary for the manufacture of Dacron polyester, often known as Dacron

  • When using common names, the Greek letters a, b, g, d, and so on are frequently employed as a prefix to find substituents.

    • In a carboxylic acid, the a-position is adjacent to the carboxyl group; an a-substituent in a common name is equal to a 2-substituent in an IUPAC name.

  • GABA is an inhibitory neurotransmitter found in the human central nervous system.

    • Alanine is one of the 20 amino acids generated from proteins.

    • Carboxylic acid IUPAC names are generated from the parent alkane by removing the suffix -e and adding -oic acid.

    • There is no need to assign a number to the carbon with the carboxyl group because it is known to be carbon 1.

    • Most functional groups are preceded by the carboxyl group.

  • Dicarboxylic acids are referred to as -dioic acids, and the parent chain contains both carboxyl groups.

    • A carbonyl group is linked to an!OH group in a carboxylic acid (-COOH).

    • A carboxyl group is polar, and carboxylic acids are connected by hydrogen bonding into dimers in the liquid and solid phases.

    • Carboxylic acids have higher boiling temperatures and are more soluble in water than equivalent molecular weight alcohols, aldehydes, ketones, and ethers.

    • A carboxylic acid is made up of two separate polar regions: a polar hydrophilic carboxyl group that promotes water solubility and a nonpolar hydrophobic hydrocarbon chain that inhibits water solubility.

    • Because the hydrophilic carboxyl group more than balances the hydrophobic hydrocarbon chain, low-molecular-weight carboxylic acids are indefinitely soluble in water.

  • However, as the carbon chain lengthens, the hydrophobic group takes over and water solubility declines.

    • pKa values for aliphatic carboxylic acids range from 4.0 to 5.0.

    • The higher acidity of carboxylic acids compared to alcohols is explained by charge delocalization via resonance in a carboxylate anion relative to an alkoxide ion, as well as the electron-drawing inductive action of the carbonyl group.

  • Electron-withdrawing substituents next to the carboxyl group increase its acidity through the inductive action.

    • The oxidation of primary alcohols and aldehydes can be used to produce carboxylic acids.

    • When a Grignard reagent is treated with carbon dioxide (CO2), it produces the magnesium salt of a carboxylic acid, which, when protonated with aqueous acid, yields a carboxylic acid.

  • Although heating is necessary, lithium aluminum hydride (LiAlH4) converts a carboxylic acid to a primary alcohol.

    • Other reducing agents, such as catalytic hydrogenation and NaBH4, cannot reduce a carboxylic acid, therefore they can be used to decrease other functional groups in the same molecule without damaging the carboxylic acid.

    • Fischer esterification is the process of producing an ester by combining a carboxylic acid with an alcohol in the presence of an acid catalyst such as sulfuric acid.

    • Fischer esterification can be reversed.

    • When a carboxylic acid is treated with diazomethane (CH2N2), a methyl ester is produced in high yield.


Chapter 17 - Carboxylic Acids

  • The term oxalic acid comes from one of its biological sources, plants of the genus Oxalis, one of which being rhubarb.

    • Adipic acid is one of two monomers needed to create the polymer nylon 66. (as shown in the image attached).

    • The common names for the dicarboxylic acids oxalic through adipic are remembered using a mnemonic phrase. “Oh my goodness, such delicious apples.”

  • A carboxylic acid with a carboxyl group attached to a cycloalkane ring is called by first giving the ring's name and then adding the suffix -carboxylic acid.

    • The ring's atoms are numbered starting with the carbon-containing the -COOH group.

    • Benzoic acid is the most basic aromatic carboxylic acid.

    • Numbers are used to denote the placement of substituents relative to the carboxyl group when naming derivatives.

  • Certain aromatic carboxylic acids are often known by their common names.

    • 2-hydroxybenzoic acid, for example, is more often known as salicylic acid, a term derived from the fact that this aromatic carboxylic acid was initially isolated from the bark of the willow, a tree in the genus Salix.

  • Aromatic dicarboxylic acids are called by prefixing dicarboxylic acid with benzene (e.g., 1,2-benzenedicarboxylic acid and 1,4-benzenedicarboxylic acid).

  • Each is commonly recognized by its common name: phthalic acid and terephthalic acid.

  • Terephthalic acid is one of two organic components necessary for the manufacture of Dacron polyester, often known as Dacron

  • When using common names, the Greek letters a, b, g, d, and so on are frequently employed as a prefix to find substituents.

    • In a carboxylic acid, the a-position is adjacent to the carboxyl group; an a-substituent in a common name is equal to a 2-substituent in an IUPAC name.

  • GABA is an inhibitory neurotransmitter found in the human central nervous system.

    • Alanine is one of the 20 amino acids generated from proteins.

    • Carboxylic acid IUPAC names are generated from the parent alkane by removing the suffix -e and adding -oic acid.

    • There is no need to assign a number to the carbon with the carboxyl group because it is known to be carbon 1.

    • Most functional groups are preceded by the carboxyl group.

  • Dicarboxylic acids are referred to as -dioic acids, and the parent chain contains both carboxyl groups.

    • A carbonyl group is linked to an!OH group in a carboxylic acid (-COOH).

    • A carboxyl group is polar, and carboxylic acids are connected by hydrogen bonding into dimers in the liquid and solid phases.

    • Carboxylic acids have higher boiling temperatures and are more soluble in water than equivalent molecular weight alcohols, aldehydes, ketones, and ethers.

    • A carboxylic acid is made up of two separate polar regions: a polar hydrophilic carboxyl group that promotes water solubility and a nonpolar hydrophobic hydrocarbon chain that inhibits water solubility.

    • Because the hydrophilic carboxyl group more than balances the hydrophobic hydrocarbon chain, low-molecular-weight carboxylic acids are indefinitely soluble in water.

  • However, as the carbon chain lengthens, the hydrophobic group takes over and water solubility declines.

    • pKa values for aliphatic carboxylic acids range from 4.0 to 5.0.

    • The higher acidity of carboxylic acids compared to alcohols is explained by charge delocalization via resonance in a carboxylate anion relative to an alkoxide ion, as well as the electron-drawing inductive action of the carbonyl group.

  • Electron-withdrawing substituents next to the carboxyl group increase its acidity through the inductive action.

    • The oxidation of primary alcohols and aldehydes can be used to produce carboxylic acids.

    • When a Grignard reagent is treated with carbon dioxide (CO2), it produces the magnesium salt of a carboxylic acid, which, when protonated with aqueous acid, yields a carboxylic acid.

  • Although heating is necessary, lithium aluminum hydride (LiAlH4) converts a carboxylic acid to a primary alcohol.

    • Other reducing agents, such as catalytic hydrogenation and NaBH4, cannot reduce a carboxylic acid, therefore they can be used to decrease other functional groups in the same molecule without damaging the carboxylic acid.

    • Fischer esterification is the process of producing an ester by combining a carboxylic acid with an alcohol in the presence of an acid catalyst such as sulfuric acid.

    • Fischer esterification can be reversed.

    • When a carboxylic acid is treated with diazomethane (CH2N2), a methyl ester is produced in high yield.


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