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MindMap Gallery Alcohol, phenol, ether

Alcohol, phenol, ether

Mind map of organic chemistry alcohols, phenols, and ethers. Sharing of essential review materials. Used for review and preview to improve learning efficiency. I hope it will be helpful to everyone preparing for the exam.

Edited at 2024-04-09 11:05:20

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Alcohol, phenol, ether

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Outline

Organic compounds
- 68
MMTvG07J
Carbohydrate
- 79
- 1
MMq7I2q4
Alkenes mind map
- 113
- 2
- 1
PlotWizard
condensation reaction
- 49
JackTyler·881
phenol
- 78
Brooooke_00
alcohol
- 49
natalie__
Understand organic compounds
- 24
Gavinnblake

Alcohol, phenol, ether

alcohol

Classification and naming

common nomenclature

systematic nomenclature

unsaturated alcohol

Polyol

physical properties

Boiling point: 1. The boiling point of alcohol is higher than that of alkanes with similar relative molecular mass. 2. The boiling point of polyhydric alcohol is higher than the boiling point of monovalent alcohol with similar relative molecular mass. 3. Among the isomers of alcohols, primary monovalent alcohol has the highest boiling point (secondary alcohol). , tertiary branched chain, lower boiling point) 4 Alkyl group will hinder the formation of hydrogen bonds, so as the relative molecular mass increases, the boiling points of alcohols, halogenated hydrocarbons and alkanes are closer (the boiling points of alcohols increase as the relative molecular mass increases)

Water solubility: Methyl, ethylene, propyl alcohol and water are miscible in any proportion. Starting from butanol, the water solubility gradually weakens (the alkyl group increases and the solubility decreases. The reason is the same as 4) (the more hydroxyl groups, the greater the solubility)

Because alcohol has a hydroxyl group, it forms hydrogen bonds with water and is miscible with water × Higher alcohols are difficult to dissolve in water

chemical properties

The O in the hydroxyl group is hybridized in the form of unequal sp3 (except when the hydroxyl group is directly connected to the double bond carbon atom - enol, O is sp2 hybridized)

Acidic: Reacts with active metals

Breaking H reflects acidity - O and H are polar bonds and are easy to break

Acidic H2O>Alcohol-methyl is an electron-donating substituent, which weakens the polarity of the O and H bonds.

The more methyl groups, the slower the reaction

The stronger the corresponding salt and alkalinity (weak acid and strong alkali)

Hydrolysis reaction of sodium alkoxide: Alcohol and sodium hydroxide cannot react (weak acid does not generate strong acid)

Alcohol can be dissolved in strong acid (chemical reaction produces salt)

Nucleophilic substitution with concentrated hydrohalic acid

HI is more likely to break bonds and has a more active nucleophilic reaction with alcohol, so the I negative ion is more nucleophilic.

For the same hydrohalic acid, the reaction activity is: tertiary alcohol > secondary alcohol > primary alcohol - the more stable the carbocation intermediate produced by the reaction, the higher the activity of the reactant, and the faster the reaction

Reaction mechanism 1: SN1 nucleophilic substitution - such as tertiary alcohols and hydrohalic acids

Reaction mechanism 2: proceed according to the SN2 reaction mechanism - such as primary alcohols and hydrohalic acids

identify

Lucas reagent (anhydrous Zncl2 dissolved in concentrated hydrochloric acid) identifies primary, secondary, and tertiary alcohols with less than 6 carbon atoms.

HI HBr can react with various alcohols without catalysis, while Hcl requires catalysis

-The more stable the carbocation intermediate generated by the reaction is, the higher the activity of the reactants is and the faster the reaction is.

Principle: Alcohols with less than 6 carbon atoms can be dissolved in Lucas reagent

Identification of monohydric alcohols and polyhydric alcohols

Tertiary alcohols can be distinguished from primary or secondary alcohols by the color change of the oxidizing agent (tertiary alcohols do not undergo oxidation reactions)

Reacts with phosphorus halides and thionyl chloride

Alkaline: esterification reaction

Reacts with oxygen-containing inorganic and organic acids and acid anhydrides to dehydrate to form esters

dehydration reaction

intramolecular dehydration

Follow Zaichev's rules

E1 reaction mechanism-reaction rate: tertiary alcohol>secondary alcohol>primary alcohol

Intermolecular dehydration-nucleophilic substitution

Proceed according to the reaction mechanism of SN2 - primary alcohols and secondary alcohols mainly carry out this reaction, tertiary alcohols are difficult to

oxidative dehydrogenation

Oxidation

Tertiary alcohols can be distinguished from primary or secondary alcohols by the color change of the oxidizing agent (tertiary alcohols do not react)

Dehydrogenation

phenol

name

At this time, there is no phenol, and the hydroxyl group is expressed as a substituent.

physical properties

Phenol is a colorless solid, acidic, also known as carbolic acid

Can be oxidized by air into pink and turn into deep red for a long time

Can form intermolecular hydrogen bonds and can form hydrogen bonds with water, so it has solubility in water

chemical properties

Structural properties: O is SP2 hybridized and does not participate in the hybridized P orbital and P-π conjugation of the benzene ring. The electrons are transferred to the benzene ring. O-H is easily broken and has weak acidity.

Acidic

Therefore, the reaction between carbonic acid and sodium phenolate can produce phenol (strong acid makes weak acid)

There are electron-withdrawing substituents on the aromatic ring - the acidity is enhanced; there are electron-donating substituents - the acidity is weakened.

Color reaction: shows blue-purple color with ferric chloride

The stable enol form can also react with ferric chloride to produce a color reaction

electrophilic substitution

Reaction of phenol and bromine water

Phenol reacts with bromine in CCL4 solution to obtain monobromophenol

It reacts with dilute nitric acid at room temperature to produce o-nitrophenol and p-nitrophenol. If concentrated nitric acid and concentrated sulfuric acid react to produce 2,4,6 trinitrophenol.

oxidation reaction

Phenol can be oxidized to p-benzoquinone (yellow) by oxidants

ether

O in the ether bond is hybridized with inequality SP3

Classification

According to whether the two hydrocarbon groups connected to the ether bond are the same, they are divided into single ethers and mixed ethers.

According to whether the two hydrocarbon groups connected to the ether bond have aromatic rings, they are divided into aliphatic ethers and aromatic ethers.

name

Cyclic ethers are named after "epoxyalkane"

physical properties

Methyl ether and methyl ethyl ether are gaseous. Most ethers are liquid.

Low boiling point, small solubility in water except cyclic ether and crown ether

chemical properties

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