MindMap Gallery Organic Chemistry-Nitrogen-Containing Compounds
Organic Chemistry Nitrogen-Containing Organic Compounds Chapter Mind Map
Edited at 2020-07-14 09:16:12One 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.
Nitrogen-containing organic compounds
amine
Classification
Classification based on the number of hydrocarbon groups directly connected to the nitrogen atom
Primary amines
Secondary amine
Tertiary amine
quaternary ammonium
Primary, secondary and tertiary amines are classified according to the number of hydrocarbon groups attached to the N atom; Distinguishing primary and secondary tertiary alcohols based on the type of C attached to the hydroxyl group
Different types of hydrocarbon groups attached to nitrogen atoms
Fatty amines
Aromatic amines
name
Distinguish between "amine", "ammonia" and "ammonium"
Amine: represents the parent (the parent of amine compounds)
Ammonia: Indicates ammonia gas and various amino groups (-NR2)
Ammonium: represents quaternary ammonium (quaternary ammonium salt, quaternary ammonium base)
Naming of simple amines: "amine" is used as the parent, and the name and number of the hydrocarbon group are added in front of the word "amine"
When there are multiple substituents attached to the N atom, treat the simple group as a substituent and indicate the position of the substituent.
Complex amines use hydrocarbons as the parent and amino groups as substituents.
The naming of quaternary ammonium salts (bases) is similar to the naming of inorganic compound ammonium salts
structure
The N atoms of ammonia and amine are SP3 unequal hybridized, and one SP3 hybrid orbital is occupied by an unshared electron pair.
The amine molecule is in the shape of a prism, with N at the top of the cone
When there are 3 different substituents attached to N, the molecule should theoretically have chirality, but there is no chirality because the two configurations are easily converted into each other.
The quaternary ammonium salt (base) in the above situation is chiral
nature
physical properties
The boiling point of amine compounds is higher than that of corresponding hydrocarbons and ethers, but lower than that of alcohols and acids.
Amines with the same number of nitrogen atoms, boiling points: primary amine > secondary amine > tertiary amine
Lower fatty amines are soluble in water
chemical properties
Basicity of amines
Alkaline influencing factors
The electrical properties of the substituents attached to the N atom
Steric hindrance of proton attacking the lone electron pair of N atom
The N-connected aromatic ring weakens the basicity of the amine (constituting the p-π conjugation effect)
Ranking of amine basicity
Aliphatic secondary amines > Aliphatic primary amines > Aliphatic tertiary amines > Ammonia > Aromatic primary amines > Aromatic secondary amines > Aromatic tertiary amines
Quaternary ammonium bases are similar in alkalinity to NaOH and are prepared from quaternary ammonium salts and silver hydroxide.
Alkylation of amines
The substitution of NH3 with halogenated hydrocarbons usually results in mixtures of primary, secondary, tertiary amines and quaternary ammonium salts
Acylation of amines
Reacts with acid chlorides, acid anhydrides, and carboxylic acids
The resulting amide is hydrolyzed into acids and amines
Amides can be used to protect amino groups (amines)
Sulfonylation of amines (Hinsbreg reaction)
Used to separate and identify different types of amines
reacts with nitrous acid
primary amine reaction
Aliphatic primary amines
Aromatic primary amines
secondary amine reaction
Aliphatic secondary amines
Aromatic secondary amines
Tertiary amine reaction
Aliphatic tertiary amine
Aromatic tertiary amines
Different reaction phenomena can be used to distinguish three amines
Electrophilic substitution reaction on benzene ring
Halogenated
Reacts with bromine water to form a white precipitate immediately
Nitrification
If it is first converted to bisulfate and then nitrified, then nitrification will occur in the meta position
sulfonation
chemical properties of amides
Hydrolysis of amides into acids and amines (for protection of amino groups)
Acidity of imide
Hoffmann degradation reaction
Chemical properties of urea
The alkalinity of urea: it forms insoluble salts with nitric acid and oxalic acid
Hydrolysis reaction
reacts with nitrous acid to release nitrogen gas
biuret reaction
Compounds containing two amide bonds in the molecule can react purple with copper ions.
Diazo and azo compounds
Introduction
Diazo: Only one end is connected to C, it is a salt; nitrogen-nitrogen triple bond
Azo: both ends are connected to C, not a salt, nitrogen-nitrogen double bond
chemical properties
diazonium salt reaction
with H2O
with KX
with CuX
With H3PO4 or EtOH or NaBH4
coupling reaction
A coupling reaction occurs between diazonium salts and phenols or aromatic amines to obtain azo compounds
If there are other substituents at the para position of the hydroxyl or amino group, the coupling reaction occurs in the ortho position.
Reaction conditions
With phenol: in weakly alkaline solution
With aromatic tertiary amines: in neutral or weakly acidic solutions
Nitro compounds
name
Nitro appears as a substituent with lower priority than hydrocarbyl and halogen
structure
The two nitrogen-oxygen bonds in the nitro group are exactly the same
The two oxygens in the nitro group each provide one electron, and the nitrogen provides two electrons, forming a four-electron three-atom p-π conjugated system.
nature
physical properties
Density is generally greater than 1, insoluble in water, soluble in organic solvents and concentrated sulfuric acid
Toxic and can be absorbed through the skin
Usually nitro compounds have a special smell - bitter or fragrant
chemical properties
The acidity of nitro compounds
More acidic than phenol
reason
硝基是强吸电子基团
存在类似酮式-烯醇式互变异构
无α-H时不产生互变异构,无酸性
硝基式和酸式互变异构可逆,加入强碱,碱与酸式反应生成相应的盐
Nitro reduction
Catalytic hydrogenation
Metal (Fe, Sn, Zn) and hydrochloric acid system reduction
Effect of nitro compounds on the electronic properties of benzene ring
Picric acid is more acidic than carbonic acid