MindMap Gallery Organic Chemistry Alcohols and Phenol Ethers
This is a mind map about alcohol phenolic ethers. It lists the classification, nomenclature, structure and properties of alcohols; the structure and properties of alcohols; the classification, nomenclature, structure and properties of alcohols; the nomenclature and chemical properties of cyclic ethers. Click to learn and see if it can help you understand alcohol and phenol ethers.
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Avatar 3 centers on the Sully family, showcasing the internal rift caused by the sacrifice of their eldest son, and their alliance with other tribes on Pandora against the external conflict of the Ashbringers, who adhere to the philosophy of fire and are allied with humans. It explores the grand themes of family, faith, and survival.
This article discusses the Easter eggs and homages in Zootopia 2 that you may have discovered. The main content includes: character and archetype Easter eggs, cinematic universe crossover Easter eggs, animal ecology and behavior references, symbol and metaphor Easter eggs, social satire and brand allusions, and emotional storylines and sequel foreshadowing.
[Zootopia Character Relationship Chart] The idealistic rabbit police officer Judy and the cynical fox conman Nick form a charmingly contrasting duo, rising from street hustlers to become Zootopia police officers!
Alcohol phenol ether
alcohol
Classification
According to the type of carbon atom attached to the hydroxyl group
Primary alcohol
Secondary alcohol
Tertiary alcohol
According to the number of hydroxyl groups in the molecule
Monohydric alcohol
diol
Polyol
name
Choose the longest carbon chain containing hydroxyl groups as the main chain
If there are unsaturated bonds such as double bonds and triple bonds in the main chain, the main chain should contain
The order of naming should be such that the position of the hydroxyl group is the smallest.
structure
O in the hydroxyl group is SP3 hybridized. O has two lone pairs of electrons. O—H and C—O are both strong polar bonds.
nature
physical properties
Related to the formation of hydrogen bonds
Boiling point: higher than hydrocarbons of similar molecular weight
Solubility: Lower alcohols are soluble in water (as the ratio of hydroxyl groups to C atoms increases, the water solubility increases)
Hydrophilic group: -OH, -NH2, -COOH, etc., can form hydrogen bonds Hydrophobic group: —R, —Ar, —X
chemical properties
Acidity and alkalinity
Weakly acidic (weaker than water, stronger than alkyne hydrogen)
The order of acid strength: CH3OH>CH3CH2OH>(CH3)2CHOH>(CH3)3COH
Weakly alkaline
It makes ethanol dissolve in concentrated sulfuric acid, and this property can be used to remove a small amount of alcohol in alkanes.
The O atom is SP3 hybridized and contains two lone pairs of electrons. Under certain conditions, H protons are obtained to form a pseudo salt.
Esterification of alcohol
Alcohol and organic acid react to form ester and water
Alcohol reacts with inorganic oxygen-containing acid to form inorganic acid ester
The alcoholic hydroxyl group is halogenated
SN1 reaction mechanism
Halogenated by halogenated hydrogen
Reactivity: Allyl alcohol/benzyl alcohol>tertiary alcohol>secondary alcohol>primary alcohol
For the same alcohol, the order of activity of hydrohalic acid is: HI>HBr>HCl>HF
When certain alcohols with specific structures react according to the SN1 reaction mechanism, the alkyl groups will rearrange.
Reacts with Lucas reagent (concentrated hydrochloric acid solution of anhydrous zinc chloride)
Used to identify primary, secondary and tertiary alcohols with less than 6 C atoms
Other halogenating reagents: PX3, PX5, SOCl2, etc., no rearrangement in the reaction
Dehydration of alcohol
Intramolecular dehydration (170°C): elimination reaction
Following Zaitsev's rule, if conjugation can be formed, the conjugated system will be formed first
Rearrangement of C ions (methyl migration rearrangement) may occur
Intermolecular dehydration (140°C): substitution reaction
for the preparation of symmetric ethers
Williamson reaction: synthesis of asymmetric ethers (consistent with the mechanism of substitution by alkoxy groups in halogenated hydrocarbons)
Oxidation of alcohol
Oxidation of monohydric alcohols
Primary alcohols are oxidized to acids
Secondary alcohols are oxidized to ketones
Tertiary alcohols are difficult to oxidize
Sarrett reagent oxidation method (PCC oxidation): pyridine complex of chromium trioxide
Oxidize primary and secondary alcohols to aldehydes and ketones without affecting olefinic bonds
Dehydrogenation reaction (Cu catalyzed heating to high temperature)
Industrial production method (oxidation using air)
Oxidation of vicinal diol
cyclic ether
name
When naming, indicate the position of the carbon atom to which the oxygen atom is attached.
Chemical properties of ethylene oxide
react with format reagent
Reacts with compounds containing active H to form bifunctional compounds
H2O, H—OR, H—NH2, H—X, etc.
ether
Classification
Monoether
Mixed ether
cyclic ether
name
Aliphatic monoether
Add the name of the hydrocarbon group in front of the ether and omit the word "two"
Aromatic monoether
Add the name of the aryl group in front of the ether. The word "二" cannot be omitted.
Mixed ether
The small group comes first and the large group comes last. If it contains an aryl group, the aryl group comes first.
Ethers with complex structures
Treat RO—(or ArO—) as a substituent
structure
O atom in fatty ether: unequal SP3 hybridization, with certain polarity
O atom in aromatic ether: SP2 hybridization (forming p-π conjugation)
nature
physical properties
Weak polarity, small molecular ether can form hydrogen bonds with water or alcohol, is more soluble in water than alkanes, and can be dissolved in many polar solvents
No hydrogen bonds are formed between molecules, and the boiling point is similar to that of hydrocarbons. Liquid ether is volatile, flammable and explosive.
chemical properties
alkalinity of ether
It forms a pseudo salt with strong acids such as concentrated sulfuric acid (to obtain a stable homogeneous solution), making the ether dissolve in the strong acid.
Ether is soluble in strong acid and can be used to identify or separate ether and alkanes (or halogenated hydrocarbons)
Dissolve BF3 with ether to make it liquid, convenient for organic synthesis
Breaking of ether bonds
Ether reacts with concentrated HI or HBr under heating to obtain halogenated hydrocarbons and hydroxyl compounds
law
脂肪族醚:较小基团与氧的一端断裂
芳香族醚:烷基与氧一端断裂,生成酚和卤代烃
Used for quantitative determination of methoxyl groups (halogenated hydrocarbons can react with AgNO3 to obtain AgI precipitation)
Auto-oxidation of ether (α-H)
When there is an H atom connected to α-H, a peroxidation reaction occurs
When tested with starch-KI test paper, if the test paper turns blue, it indicates the presence of peroxide.
Use FeSO4 or NaSO3 (reducing agent) to remove peroxides
phenol
name
Add the name of the aryl group before the word "phenol", and put other substituents in front
structure
P-π conjugation is formed between the hydroxyl group and the benzene ring, and the P electrons of the hydroxyl group can be transferred to the benzene ring. The C—O bond is strengthened and the C—H bond is weakened.
nature
physical properties
It is a colorless liquid or solid at room temperature and is easily oxidized. It will turn light red or red after being stored for a long time.
Melting and boiling point: phenol can form intermolecular hydrogen bonds The melting and boiling point is higher than that of aromatic hydrocarbons or aryl halides with similar molecular weights.
The hydroxyl group on the phenol can form hydrogen bonds with water molecules and has a certain solubility in water.
However, o-nitrophenol has intramolecular hydrogen bonds and has a lower boiling point than its meta and para isomers.
chemical properties
The acidity of phenol
Acidity: R—OH<H2O<C6H5—OH<H2CO3<RCOOH
Effects of the acidity of phenol
When an electron-withdrawing group is attached to the benzene ring, the acidity increases
When an electron-donating group is attached to the benzene ring, the acidity of phenol is weakened
When CO2 is introduced into the sodium salt solution of phenol, since carbonic acid is more acidic than phenol, it can displace phenol.
Color development of phenol
Phenol and compounds with enol structure (p-π conjugation) develop color when exposed to FeCl3 solution (for identification)
Ether-forming reaction of phenol (Williamson ether-forming reaction)
The difference from alcohol is that alcohol uses Na as a catalyst and phenol uses NaOH as a catalyst.
Esterification reaction of phenol
It is difficult to directly form esters from phenol and carboxylic acid (both are acidic)
Generally, esters are prepared by reacting acid chlorides or acid anhydrides with phenols.
Electrophilic substitution on the aromatic ring of phenol
Halogenation reaction
The reaction between phenol and bromine water produces 2,4,6-tribromophenol (white precipitate)
The reaction between phenol and bromine in CCl4 solution is monosubstitution
nitrification reaction
Sulfonation reaction
The ortho-substituted product is obtained at room temperature, and the para-position product is obtained at 100°C.
Friedel-Crafts reaction
oxidation reaction of phenol
Phenol will be oxidized to quinone in the air. The more phenolic hydroxyl groups, the easier it is to be oxidized.
Phenol generates p-benzoquinone under the catalysis of K2Cr2O7/H
O-phenol generates o-quinone under Ag2O catalysis (easier)
It is a three-membered ring with high tension, active properties, and easy ring-opening addition between C—O bonds.