MindMap Gallery Organic Chemistry Mind Map
Organic chemistry, also known as the chemistry of carbon compounds, is the science that studies the composition, structure, properties, preparation methods and applications of organic compounds. It is an extremely important branch of chemistry.
Edited at 2021-08-26 19:21:23One 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.
organic chemistry
introduction
Organic Compounds and Organic Chemistry
nature
Complex composition and structure, flammable, low melting point, difficult to dissolve in water, easily soluble in organic solvents, slow chemical reaction rate
covalent bond
theory
type
σ bond
Head to head
π bond
Side by side
Attributes
Bond length
bond angle
bond energy
Bond polarity
polar covalent bond
nonpolar covalent bond
Two identical atoms are formed, and the bonding electron cloud is evenly distributed between the two atoms.
Molecule polarity and intermolecular forces
polarity
force
Basic types of organic chemical reactions
homolysis
free radicals
heterolysis
carbocation
carbanion
The concept of acids and bases in organic chemistry
acid-base proton theory
Any compound that can donate a proton (hydrogen ion) is an acid. The remaining part after the acid donates the proton is the conjugate base of the acid. The stronger the acid (the larger the Ka, the smaller the pKa), the weaker its conjugate base.
Acid-base electron theory
All compounds that can accept electron pairs are acids, that is, acids are electron pair acceptors.
Classification of organic compounds
According to the basic skeleton
Aliphatic compounds (open chain compounds)
Alicyclic (carbocyclic) compounds
aromatic compounds
Heterocyclic compounds
According to functional group
Carbon-carbon double bond, carbon-carbon triple bond, halogen, hydroxyl, ether bond, carbonyl group, carboxyl group
Ester bond, cyano group (-C three N), amino group, hydrogen sulfide group (-SH), sulfonic acid group (-SO3H)
Alkanes
Structure and heterogeneity
structure
The carbon-carbon bonds and carbon-hydrogen bonds in the molecule are both σ bonds, and the carbon atoms in the molecule are sp3 hybridized.
Methane: bond angle 109, bond energy 435kj/mol, bond length 109.1pm
Heterogeneous
Carbon chain isomerism
Alkane carbon atoms are connected to four other atoms, also known as saturated carbon atoms
Connected to a carbon atom is a primary carbon atom or a primary carbon atom
secondary carbon atoms
Tertiary carbon atoms
quaternary carbon atom
Conformational isomerism
Conformational stability of n-butane: para-crossed form > ortho-crossed form> partial overlapping form > full overlapping form
The conformation of ethane: Cross conformation > Overlapping conformation
name
straight chain alkanes
Branched alkanes: Select the main chain: the longest carbon chain, ethyl, methyl, iso, neo and the English italicized normal, secondary, tertiary, etc. do not participate in the sorting
nature
Pyrolysis reaction
The c-H bond and the c-c bond are broken
Halogenation reaction
Chlorination reaction of methane
The product is a mixture, and the reactivity order of different types of hydrogen is 3>2>1 The activity order of different halogens is F2>Cr2>Br2>I2 The stability of C radical is tertiary carbon>secondary carbon>primary carbon
Chain genesis: generation of free radicals Chain growth: transfer free radicals and generate products Termination of the chain: elimination of free radicals
Alkenes and alkynes
Alkenes
Structure and heterogeneity
structural isomerism
cis-trans isomerism
Condition: There are factors in the molecule that limit the free rotation between two atoms, such as double bonds and alicyclic rings. Two atoms that cannot rotate must be connected to two different atoms or groups.
name
Choose a chain with more carbon atoms as the main chain The end closest to the double bond is numbered sequentially. The order of carbon-carbon double bonds in the main chain must be indicated.
physical properties
chemical properties
Catalytic hydrogenation
electrophilic addition reaction
Addition with halogen acid
When an asymmetric alkene is added to an asymmetric reagent HX, the positively charged part of the reagent is always added to the double-bonded carbon atom containing more hydrogen, and the negatively charged part is added to the carbon atom containing less hydrogen.
Addition with halogen
Addition with sulfuric acid
Add to water
Addition with hypohalous acid
oxidation reaction
with potassium permanganate
Diolefins
Classification and naming
Accumulated dienes
Isolated diene: separated by two or more carbon-carbon single bonds
Conjugated diene: two carbon-carbon double bonds separated by a single bond
Structure and conjugation effects of conjugated dienes
π-π conjugation
p-π conjugation
σ-p hyperconjugation
σ-π hyperconjugation
Electrophilic addition reaction of conjugated dienes
Alkynes
Structure and heterogeneity
name
Certain ene certain alkyne
physical properties
chemical properties
Acidic
Alkynes with hydrogen atoms connected to the triple bond carbon are called terminal alkynes. Test: ammonia solution of silver nitrate (white precipitate) or ammonia solution of cuprous oxide (red-brown precipitate)
addition reaction
Catalytic hydrogenation
Addition with halogen
Addition with hydrohalic acid
Add to water
oxidation reaction
Naphthenic
Classification and naming
Classification
Small rings (3 to 4), normal rings (5 to 6), medium rings (7 to 11), large rings (12 and above)
name
If there are both rings and chains in an alkane molecule, compare the number of carbon atoms, whichever is more
stability
The bond angle is 109. Deviation from this angle results in the angular tension that restores the normal bond angle.
Conformation
cyclobutane
cyclopentane
cyclohexane
Chair conformation and boat conformation, the former is the dominant conformation with the lowest internal energy. With the same substituent, the conformation with more e substitutions is stable; with different substituents, the larger group is in the e substitution conformation and is more stable; the larger group is in the e substitution conformation group
nature
physical properties
chemical properties
Three- or four-membered small cycloalkanes can exhibit ring-opening addition reaction properties similar to those of alkenes.
Hydrogenation reaction: The more stable the ring, the more difficult the reaction. Break chemical bonds between carbon atoms containing more and less hydrogen
The reaction of adding halogen and hydrogen halide: the addition reaction of substituted cyclopropane and hydrohalic acid follows Markov's rule. The stability of the formed carbocation intermediate determines the orientation of the reaction. Although small cycloalkanes undergo an addition reaction, they cannot undergo an oxidation reaction with potassium permanganate at room temperature.
Aromatic hydrocarbons
Classification and naming
According to whether there is a benzene ring, it can be divided into benzene aromatic hydrocarbons and non-benzene aromatic hydrocarbons. Products in which the hydrogen atoms on the benzene ring are replaced by aliphatic hydrocarbon groups. The systematic nomenclature generally uses benzene as the parent
A benzene molecule that loses one hydrogen atom is called a phenyl group, and a toluene molecule that loses a hydrogen atom is called a benzyl group.
Monocyclic aromatic hydrocarbons
The structure of benzene
All six carbon atoms of the benzene molecule are sp2 hybridized
Physical properties of benzene and its homologues
Chemical properties of benzene and its homologues
Halogenation reaction: The hydrogen atoms on the benzene ring are replaced by halogen under a catalyst such as iron powder.
Nitration reaction: benzene is heated with concentrated sulfuric acid and concentrated nitric acid. The hydrogen atoms on the benzene ring are replaced by nitro groups to form nitrobenzene.
Reaction of benzene ring side chain: The benzene ring is not easily oxidized by oxidants such as potassium permanganate, but the hydrocarbyl benzene with a hydrogen atom in the hydrocarbyl side chain can be oxidized, and methylbenzene will be generated regardless of the length of the side chain. If there is no a hydrogen in the side chain Atoms cannot be oxidized
Positioning Effect of Electrophilic Substitution Reaction of Substituted Benzene
Divided into two categories according to different positioning effects: Ortho-para positioning group: activates the benzene ring. In addition to halogen, hydroxyl, amino, and R groups Meta positioning group: passivates benzene ring, nitro group, aldehyde group, carboxylic acid
Positioning effect of disubstituted benzene: positioning effect of activation group > passivation group. When there are two activation groups, the stronger one determines the position of the next substituent.
Condensed aromatic hydrocarbons
Naphthalene
Press Hefei
carcinogenic aromatic hydrocarbons
non-benzene aromatic hydrocarbons
annulene
Ring alkenes positive and negative ions
薁
Halogenated hydrocarbons
Classification and naming
Classification
name
A certain base halide
structure and properties
physical properties
Structure and chemical properties
nucleophilic substitution
After the tertiary carbon and silver nitrate are heated, a precipitate will be formed immediately. After the secondary carbon and silver nitrate are heated, a precipitate will be formed in a few minutes. After the primary carbon and silver nitrate are heated for a long time, a small amount of precipitate will be formed.
elimination response
Halogenated hydrocarbons eliminate the halogen on the a carbon and the hydrogen on the b carbon, giving priority to the b carbon with less hydrogen. The more hydroxyl groups there are on the double-bonded carbon, the easier the reaction will proceed.
Structure and properties of unsaturated halogenated hydrocarbons
Ethylene halohydrocarbons and halobenzenes
Halogen atoms are directly connected to carbon atoms with a pi electron cloud
Allyl halohydrocarbons and benyl halides
The halogen atom is separated from the carbon atom with a π electron cloud by a saturated carbon atom
Isolated halogenated hydrocarbons
Halogen atoms and carbon atoms with π electron clouds are separated by two or more saturated carbon atoms.
Reactivity: Allyl type = benzyl halide > isolated type > vinyl type = halobenzene
alcohol phenol ether
Alcohol
Classification and naming
primary, secondary and tertiary alcohols
structure
physical properties
chemical properties
with lively metals
Acidity: water>methanol>primary alcohol>secondary alcohol>tertiary alcohol
with hydrohalic acid
nucleophilic substitution
Activity: benzyl alcohol = allyl alcohol > tertiary alcohol > secondary alcohol > primary alcohol
Hydrochloric acid only reacts with tertiary alcohols, primary alcohols and secondary alcohols at room temperature, and Lucas reagent reacts with those having six carbon groups or less.
dehydration
Acid catalyzed generation of alkenes
Phenol
Definition
Compounds in which the hydroxyl group is directly connected to the benzene ring
physical properties
chemical properties
It is more acidic than water and can react with NaOH to form sodium benzoate. When there are substituents on its side chain, electron-withdrawing substituents such as halogen, nitro, etc. will increase its acidity, and vice versa.
Electrophilic substitution reaction on benzene ring
An aqueous solution of phenol forms a white precipitate with bromine water at room temperature.
Color development with FeCl3
Enols also have color reactions, with phenol and benzene-1,3-diphenol showing purple color.
Oxidation
Potassium permanganate, oxygen, potassium dichromate, etc., the product is quinone
ether
Classification and naming
structure
A compound in which two hydroxyl groups are connected through an oxygen atom
physical properties
chemical properties
crown ether
Chemical properties of thiols, thiophenols and thioethers
aldehydes and ketones
Classification and naming of aldehydes and ketones
Classification
Aliphatic aldehydes and ketones, aromatic aldehydes and ketones
Saturated and unsaturated
Naming
Take the longest carbon chain containing the carbonyl group as the main chain. The main chain number starts from the carbon atom of the aldehyde group. When the carbonyl group is outside the ring, the aryl group and the ring are used as substituents. Mark the position of the aldehyde group.
The structure of aldehydes and ketones
The oxygen atom and carbon atom of the carbonyl group are both Sp2 hybridized
Properties of Aldehydes and Ketones
physical properties
chemical properties
nucleophilic addition
It is easy to occur when electron-withdrawing atoms or groups are connected to the carbonyl carbon. When the connected group is large, the space is crowded and difficult to occur, and the reaction activity is reduced.
Addition with hydrocyanic acid
Aldehydes, aliphatic methyl ketones, and cyclic ketones with fewer than 8 carbon atoms can react to form a-cyanohydrins
Addition with saturated sodium bisulfite
Aldehydes, aliphatic methyl ketones and cyclic ketones with less than 8 carbon atoms can react to form white crystals of sodium a-hydroxysulfonate.
Addition to ammonia derivatives
2,4 dinitrophenylhydrazine reacts with aldehydes and ketones to produce 2,4 dinitrophenylhydrazone, which is a yellow crystal and cannot be marked with a precipitation symbol. Identify the carbonyl group.
a-H reaction
Iodoform reaction
Iodine elemental sodium hydroxide solution and acetaldehyde or methyl ketone. Iodoform is a yellow crystal with a special smell and very little water solubility.
Aldol condensation
Nothing to do with alcohol
Aldehydes are reduced to primary alcohols and ketones are reduced to secondary alcohols
Oxidation
Tollen's reagent (ammonia solution of silver nitrate) reacts with aldehyde groups to form silver mirrors
Fehling's reagent reacts with aliphatic aldehydes but not with aromatic aldehydes.
Benedict's reagent is a modified Fehling's reagent
with Schiff's reagent
Pour SO2 into the magenta solution until the red color of the solution disappears and it becomes Schiff's reagent. Aldehyde reacts with it to produce purple-red color. When concentrated sulfuric acid is added, formaldehyde will not fade, but other aldehydes will fade. Ketones do not react with Schiff's reagent.
Quinone
Classification and naming of quinone compounds
Chemical properties of quinones