MindMap Gallery Alcohol, phenol, ether
Alcohols, phenols, and ethers are all oxygenated derivatives of hydrocarbons, and they have important applications in organic chemistry. The content of this mind map is clear and rich. If you like it, you can like it and save it~
Edited at 2023-10-30 06:51:22El cáncer de pulmón es un tumor maligno que se origina en la mucosa bronquial o las glándulas de los pulmones. Es uno de los tumores malignos con mayor morbilidad y mortalidad y mayor amenaza para la salud y la vida humana.
La diabetes es una enfermedad crónica con hiperglucemia como signo principal. Es causada principalmente por una disminución en la secreción de insulina causada por una disfunción de las células de los islotes pancreáticos, o porque el cuerpo es insensible a la acción de la insulina (es decir, resistencia a la insulina), o ambas cosas. la glucosa en la sangre es ineficaz para ser utilizada y almacenada.
El sistema digestivo es uno de los nueve sistemas principales del cuerpo humano y es el principal responsable de la ingesta, digestión, absorción y excreción de los alimentos. Consta de dos partes principales: el tracto digestivo y las glándulas digestivas.
El cáncer de pulmón es un tumor maligno que se origina en la mucosa bronquial o las glándulas de los pulmones. Es uno de los tumores malignos con mayor morbilidad y mortalidad y mayor amenaza para la salud y la vida humana.
La diabetes es una enfermedad crónica con hiperglucemia como signo principal. Es causada principalmente por una disminución en la secreción de insulina causada por una disfunción de las células de los islotes pancreáticos, o porque el cuerpo es insensible a la acción de la insulina (es decir, resistencia a la insulina), o ambas cosas. la glucosa en la sangre es ineficaz para ser utilizada y almacenada.
El sistema digestivo es uno de los nueve sistemas principales del cuerpo humano y es el principal responsable de la ingesta, digestión, absorción y excreción de los alimentos. Consta de dos partes principales: el tracto digestivo y las glándulas digestivas.
Alcohol, phenol, ether
alcohol
Classification
According to the hydrocarbon structure
Saturated alcohol
unsaturated alcohol
aromatic alcohol
According to the number of hydroxyl groups
Monohydric alcohol
diol
Polyol
According to the type of carbon atom attached to the hydroxyl group
Luska's reagent can be used to distinguish primary, secondary and tertiary alcohols with less than five carbon atoms.
Tertiary alcohols become turbid immediately, secondary alcohols become turbid within 5 to 10 minutes, and primary alcohols do not separate.
Primary alcohol (primary alcohol)
Secondary alcohol (secondary alcohol)
Tertiary alcohol (tertiary alcohol)
name
First look for the longest carbon chain with hydroxyl groups as the parent chain
When numbering, try to keep the number of the hydroxyl group as small as possible
physical properties
polar molecules
Have a higher melting and boiling point
The more hydroxyl groups, the higher the boiling point
The fewer branches, the higher the boiling point
The longer the carbon chain, the higher the boiling point
water soluble
As the alkyl area increases, water solubility decreases
chemical properties
Can form hydrogen bonds in water
Has a certain acidity
Has certain nucleophilicity, is nucleophilic and alkaline, and can be protonated
reacts with acid to form ester
Substitution reaction
Identification of primary, secondary and tertiary quaternary carbons using Format reagents
In acidic conditions, H combines with -OH which is difficult to remove and becomes H2O which is easy to remove, making the reaction easier to proceed. Mechanism: For benzyl, allyl, tertiary and secondary alcohols, the reaction mechanism is SN1, and most primary alcohols are SN2.
Rearrangement of SN1
alcohol halogenated reagent = halogenated hydrocarbon
Reactivity and elimination direction
1. The more stable the intermediate carbocation is, the easier it is to perform 2. Elimination reactivity of different alcohols: Level 3>Level 2>Level 1 3. The reaction to generate the conjugated system is easier to carry out 4. Comply with Zaitsev rules 5. Carbocation rearrangement may occur
Zaitsev's rule: Tend to generate alkenes with more alkyl groups on both sides, that is, eliminate the side with less H
子主题
elimination response
Follow the trans elimination rules and mainly generate trans products
Rearrangements may occur to produce more stable alcohols
When Al2O3 is used as a catalyst, no rearrangement occurs.
oxidation reaction
Reagent selection
Under certain conditions, double bonds may not be affected
sensitive to acid
Sarit reagent:
Sensitive to alkali
Jones reagent:
Sensitive to both acid and alkali
Active manganese dioxide MnO2 oxidation
Oxidation type
Ofenol oxidation
Ketones can be used to oxidize alcohols without destroying double bonds.
Oxidation of vicinal diol
First replace the hydroxyl group with the double bond, and then install it
pinacol oxidation
Preparation method
Monohydric alcohol
Utilize olefins
Hydroboration reaction or hydration reaction
Utilize halogenated hydrocarbons
replace
Utilize aldehydes or ketones
Perform a restore
Use Grignard reagent
vicinal diol
Oxidation of Alkenes
Hydrolysis of epoxy compounds
phenol
definition
The hydroxyl group is directly attached to the benzene ring
Ar-OH
physical properties
At room temperature, most are crystalline solids
Hydrocarbons with melting and boiling points higher than their equivalent molecular mass
Have certain solubility in water
itself colorless
Easily oxidized to pink
chemical properties
Acidic
reason
Conjugation makes phenoxide anions more stable, while alkoxide anions cannot
Influencing factors
The stronger the electron-withdrawing ability of the groups on the benzene ring, the stronger the acidity of phenol.
The more electron-withdrawing groups there are, the stronger the acidity.
The effect of a group in the ortho-para position is greater than that in the meta-position
When in ortho-paraposition, there is both induction effect and conjugation effect; when in meta-position, there is only induction effect.
Color reaction with FeCl3
Anything with an enol structure can undergo a color reaction
Claisen rearrangement
Example
rule
Prioritize to the adjacent position, then to the opposite position
mechanism
Formation of phenolic ester
When heated by a Lewis acid, Fores rearrangement occurs
Can be controlled by temperature, low temperature mainly gets alignment (relative to hydroxyl), high temperature mainly obtains the ortho position
Halogenation reaction
The hydroxyl group is the first type of positioning group, which activates the phenyl group to obtain ortho-para phenol.
When CS2 is used as the solvent, the para product can be selectively obtained.
nitrification reaction
ortho product
Strong intramolecular hydrogen bonding force and high volatility
Para product
Strong intermolecular hydrogen bonding force and low volatility
Can be separated by steam distillation
Sulfonation reaction
Friedel-Crafts reaction
Sulfuric acid, phosphoric acid, and boron trifluoride are often used as catalysts
oxidation reaction
Easily oxidized to pink quinone, it is often used as an antioxidant
preparation
Sulfonate preparation method
It has been basically eliminated due to the following reasons: Poor compatibility of photon groups Violent reaction High equipment requirements Causes great pollution High energy consumption requirements
isophenol method
About 0.6t of acetone can be obtained per ton of phenol
ether
Classification
According to whether the hydrocarbon groups on both sides are the same
Simple ether (symmetric ether)
Mixed ethers
According to shape and functional group
Aromatic ethers
With phenyl
ring-shaped
cyclic ether
Contains multiple oxygen
crown ether
name
simple ether
Hydrocarbyl ether
Example: Methyl ether
Mixed ethers
Write down the hydrocarbon groups in sequence Simple base first phenyl first
complex ether
The smaller hydrocarbon group and oxygen together are called an oxygen group
physical properties
no active hydrogen
No hydrogen bonds between molecules
Lower melting and boiling point
Oxygen and water in molecules form hydrogen bonds
It also has good coordination effect on metals (Grignard reagent)
Ethers with smaller hydrocarbon groups have better solubility in water
Has good volatility and flammability
chemical properties
Oxygen salts can be formed at low temperatures or room temperature
Under the substitution of hydrogen halide, the ether bond is broken to form an alcohol and a halogenated hydrocarbon.
Generally, smaller hydrocarbon groups form halogenated hydrocarbons (The reaction of tertiary hydrocarbyl ethers produces tertiary haloalkanes)
Mechanism: After the oxygen cation is formed, the ether bond is easily broken SN2 reaction
Oxidation
It will automatically oxidize to peroxide at room temperature, and peroxide is easy to explode when heated, so ether compounds cannot be evaporated to dryness by distillation.
Stabilizers are usually added, such as (2,6-di-tert-p-phenol, or BHT, which is used to scavenge free radicals and prevent oxidation and polymerization reactions)
cyclic ether ring opening
Acid-catalyzed ring opening
Features
Nucleophiles attack carbon atoms with more substituents
Base-catalyzed ring opening
Features
Nucleophiles attack carbon atoms with less substituents
preparation
Under the condition of heating with concentrated sulfuric acid, alcohol is dehydrated to prepare symmetrical ether
Williamson's ether synthesis