MindMap Gallery Organic Chemistry Carboxylic Acids, Carboxylic Acid Derivatives, Substituted Acids
Carboxy is a basic functional group in organic chemistry. It consists of one carbon atom, two oxygen atoms and one hydrogen atom, with the chemical formula -COOH. Compounds with carboxyl groups in the molecule are called carboxylic acids. This mind map is a compilation of knowledge about carboxylic acids, carboxylic acid derivatives, and substituted acids chapters in Organic Chemistry (Wang Xiaolan 5th Edition). I hope it will be helpful to you!
Edited at 2020-05-24 10:56:12One Hundred Years of Solitude is the masterpiece of Gabriel Garcia Marquez. Reading this book begins with making sense of the characters' relationships, which are centered on the Buendía family and tells the story of the family's prosperity and decline, internal relationships and political struggles, self-mixing and rebirth over the course of a hundred years.
One Hundred Years of Solitude is the masterpiece of Gabriel Garcia Marquez. Reading this book begins with making sense of the characters' relationships, which are centered on the Buendía family and tells the story of the family's prosperity and decline, internal relationships and political struggles, self-mixing and rebirth over the course of a hundred years.
Project management is the process of applying specialized knowledge, skills, tools, and methods to project activities so that the project can achieve or exceed the set needs and expectations within the constraints of limited resources. This diagram provides a comprehensive overview of the 8 components of the project management process and can be used as a generic template for direct application.
One Hundred Years of Solitude is the masterpiece of Gabriel Garcia Marquez. Reading this book begins with making sense of the characters' relationships, which are centered on the Buendía family and tells the story of the family's prosperity and decline, internal relationships and political struggles, self-mixing and rebirth over the course of a hundred years.
One Hundred Years of Solitude is the masterpiece of Gabriel Garcia Marquez. Reading this book begins with making sense of the characters' relationships, which are centered on the Buendía family and tells the story of the family's prosperity and decline, internal relationships and political struggles, self-mixing and rebirth over the course of a hundred years.
Project management is the process of applying specialized knowledge, skills, tools, and methods to project activities so that the project can achieve or exceed the set needs and expectations within the constraints of limited resources. This diagram provides a comprehensive overview of the 8 components of the project management process and can be used as a generic template for direct application.
Carboxylic acids, carboxylic acid derivatives, substituted acids
carboxylic acid
Classification
Classified by hydrocarbyl
(saturated/unsaturated) fatty acids
(saturated/unsaturated)alicyclic acid
Aromatic acid
According to the number of carboxyl groups
monocarboxylic acid
polycarboxylic acid
name
open chain fatty acids
The longest carbon chain containing carboxyl groups is used as the parent, and the carboxyl carbon is at the end of the chain, and the position is omitted.
Alicyclic carboxylic acids, aromatic group-containing carboxylic acids
Alicyclic group and aromatic group as substituents
structure
The carboxyl group C is SP2 hybridized, the O of the hydroxyl group is p-π conjugated with the carbonyl group, and the polarity of O—H increases.
The electropositivity of the carbonyl group is reduced, and the ability of the carboxyl group to be attacked by nucleophiles is reduced.
nature
physical properties
Due to the presence of carbon-oxygen double bonds and hydroxyl groups, carboxylic acid molecules can form dimers through hydrogen bonds. At the same time, because carboxylic acids are more polar than alcohols, aldehydes and ketones, the solubility and boiling points of carboxylic acids are higher than aldehydes and ketones with similar molecular weights.
Both the carbonyl and hydroxyl groups in carboxylic acids can form hydrogen bonds with water molecules. Carboxylic acids with low molecular weight are soluble in water. As the molecular weight increases, the hydrophobicity increases and the solubility in water decreases.
chemical properties
The acidity of carboxylic acid
Characteristics of carboxylate anions
Comparison of acidity of different carboxylic acids
The carboxyl group is connected to an electron-pushing group. The stronger the electron-pushing ability, the less acidic it is.
When forming a conjugated system with a benzene ring, etc., the benzene ring is relatively an electron-withdrawing group, and the acidity is enhanced.
An electron-withdrawing group is connected to the carboxyl group, and as the electron-withdrawal ability (electronegativity) increases, the acidity increases
Generation of carboxylic acid derivatives
Generation of acid halide
Generation of acid anhydride
Generation of ester (reaction mechanism)
Methods to improve ester yield
Formation of amide (reaction mechanism)
Amide is heated and dehydrated to nitrile (the reverse reaction can also be performed)
carboxylic acid thermal decomposition reaction
Thermal decomposition of monocarboxylic acid (irregular breakage of carbon chain, meaningless)
Thermal decomposition of dicarboxylic acids
Decarboxylation of oxalic acid and malonic acid yields monobasic acid (decarboxylation)
Succinic acid and glutaric acid are heated and dehydrated to form five (six)-membered cyclic acid anhydride (dehydration)
Adipic acid and pimelic acid are decarboxylated to form a five (six)-membered cyclic ketone with one carbon less (both decarboxylated and dehydrated)
Halogenation of α-H
Reduction of carboxylic acids (LiAlH4)
substituted carboxylic acid
Hydroxy acid
physical properties
Both hydroxyl and carboxyl groups can form hydrogen bonds with water and are generally very soluble in water.
chemical properties
Acidic
Alkyds are more acidic than corresponding carboxylic acids
The acidity of different alkyds is related to the induction effect
dehydration reaction
α-Hydroxy acid is prone to intermolecular dehydration to obtain cyclic lactide
β-Hydroxy acid easily generates α,-β unsaturated acid when heated
γ-hydroxy acid and δ-hydroxy acid undergo intramolecular dehydration when heated to obtain five-membered and six-membered ring lactones.
Oxidation of alpha-hydroxy acids
Decomposition reaction of α-hydroxy acid
Carbonyl acid
Decarboxylation reaction of α-keto acids and β-keto acids
reduction and oxidation reactions
Keto acids are not easily oxidized, but pyruvic acid is easily oxidized (conditions: Fe2, H2O2)
carboxylic acid derivatives
name
Acyl halide naming: "acyl halide"
Amide naming: "acyl amine" (the group number on the N atom is N-)
Nomenclature of acid anhydrides: Acid anhydrides are named according to their source
Ester naming: a certain acid and a certain ester (indicate which part is the acid and which part is the alcohol)
nature
physical properties
The boiling points of acid halides and esters are lower than those of the corresponding carboxylic acids (it is difficult to form hydrogen bonds)
The boiling point of N-unsubstituted amide is higher than that of the corresponding carboxylic acid (there are 2 H on N, which has strong ability to form hydrogen bonds)
chemical properties
Reactivity of different carboxylic acid derivatives
(High activity) Acid halide>Anhydride>Ester>amide (high stability)
Hydrolysis reaction
Hydrolysis of acid chloride (violent reaction to form carboxylic acid)
Hydrolysis of acid anhydride (violent hydrolysis under acid catalysis)
Hydrolysis of esters
Acid-catalyzed hydrolysis (mechanism)
Base-catalyzed hydrolysis (mechanism)
Hydrolysis of amides (reaction under acidic and alkaline conditions)
alcoholysis reaction
Alcoholysis of acid halide
Anhydride alcoholysis
Alcoholysis of esters (ester exchange)
Ammonolysis reaction
More likely to occur than alcoholysis
Aminolysis of acid halide
Triethylamine without H atoms cannot occur
Acid anhydride aminolysis
Esteraminolysis
reduction reaction
Carboxylic acid derivatives are easier to reduce than carboxylic acids and can be reduced to alcohols by catalytic hydrogenation and lithium aluminum hydride
Reduction of ester (Na ethanol)
Selective reduction of acid chlorides to aldehydes (H2, Pd, BaSO4)
Reaction with Grignard reagents—acyl chlorides, acid anhydrides, esters
Acidity and alkalinity of amides
Hofmann reaction of amides
Ester condensation reaction
Reacts under the action of sodium alkoxide to form β-keto acid ester
Keto-enol tautomerism
Synthesis of ethyl acetoacetate
Malonate synthesis method