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MindMap Gallery Chapter 7 Alcohol and Phenol Ethers

Chapter 7 Alcohol and Phenol Ethers

"Organic Chemistry" final review mind map, with clear context and comprehensive content, is a good helper for review. Welcome to use it! The other chapters are on the homepage. It’s not easy to make. Please give it a like! 🥰

Edited at 2023-10-24 10:49:53

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Chapter 7 Alcohol and Phenol Ethers

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Outline

Chapter 14 Protein
- 32
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Chapter 10 Nitrogen-Containing Compounds
- 27
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Chapter 9 Carboxylic Acids and Carboxylic Acid Derivatives
- 86
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Chapter 1 Signals and Systems
- 287
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Chapter 4 Aromatic Hydrocarbons
- 67
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Chapter 7 Alcohol and Phenol Ethers

alcohol

structure

hydrocarbyl hydroxyl

There are hydrogen bonds

nature

physical properties

Lower monohydric alcohol

Solubility miscible with water

The hydrophilic characteristics are obvious

Common hydrophilic groups: —OH, —COOH, —NH2, —SO3H Common lipophilic groups: —R, —Ar, —COOR, C—O—C

boiling point

The larger the molecular mass, the higher the

The fewer branches, the higher the

density

Fatty alcohols are larger than alkanes, less than 1, and aromatic alcohols are larger than 1

Chemical Properties (Figure)

Acidity and alkalinity

Acidic (proton transfer)

Weaker acid than water

The R group donates electrons, causing the O-H bond to become less polar and less acidic.

Alkaline (weak)

The hydroxyl oxygen has a lone pair of electrons and can accept protons from strong acids to form protonated alcohols (yang salts)

Yang salt is soluble in strong acid and can distinguish alkanes, halogenated hydrocarbons and alcohols that are insoluble in water.

Halogenated

Halogenated by hydrogen halide

active

Allyl alcohol | Benzyl alcohol > Tertiary alcohol > Secondary alcohol > Primary alcohol

HI>HBr>HCl>HF

Mechanism (picture)

Primary alcohol may be SN2 mechanism

Secondary tertiary alcohols may be SN1 mechanisms, undergoing carbocation intermediates and rearrangement

Lucas test

Lucas reagent

Anhydrous zinc chloride in concentrated hydrochloric acid solution

use

Identification of primary, secondary, tertiary and tertiary alcohols

Below 6C

Tertiary alcohol

Immediately turbid at room temperature

Benzyl, allyl type

Immediately turbid at room temperature

Secondary alcohol

Turns cloudy after a few minutes at room temperature

Primary alcohol

No reaction at room temperature, turbid when heated

Halogenated by tri(penta)phosphorus halide, thionyl chloride, etc.

Laboratory preparation of halogenated hydrocarbons (picture)

Esterification (reversible)

Acid dehydroxylation alcohol dehydrogenation

Reactivity

Methanol>Primary alcohol>Secondary alcohol>Tertiary alcohol

Glycerin trinitrate (nitroglycerin)

dehydration

Alcohols dehydrate on heating under acid catalysis

Higher temperature (170)

Intramolecular dehydration (elimination reaction) gives ene

Follow Zaitsev's rules

lower temperature (140)

Tertiary alcohols generally undergo intramolecular dehydration at 80-90℃

Intermolecular dehydration gives ether

Degree of difficulty

Carbocation stability determines

Tertiary alcohol>Secondary alcohol>Primary alcohol

May produce rearrangement product P120

Williamson reaction

The substitution reaction between sodium alkoxide and halogenated hydrocarbons produces ether compounds (an effective method for synthesizing asymmetric ethers)

Tertiary halogenated hydrocarbons, vinyl halogenated hydrocarbons, and aromatic halogenated hydrocarbons cannot be used.

Oxidation

Oxidation of monohydric alcohols

Reaction on α—H

Primary alcohol

aldehyde-carboxylic acid

Secondary alcohol

ketone

Tertiary alcohol

Not easily oxidized

PCC oxidation method

The complex formed by chromium trioxide and pyridine can quickly oxidize primary and secondary alcohols into aldehydes and ketones with high yield and does not affect C=C

Industrial catalytic dehydrogenation

Oxidation of vicinal diol

Oxidized by periodic acid and quantitatively converted into carbonyl compounds

iodometric method

phenol

Structure (picture)

P-π conjugation, electron density decreases with oxygen and increases with benzene

-OH activates benzene

nature

physical properties

state

Pure colorless liquid or solid, light pink-red-brown after oxidation

boiling point

It is higher if there is hydrogen bonding, and it is lower if it contains intramolecular hydrogen bonding, for example, nitrophenol

water soluble

Slightly soluble in water, easily soluble in benzene, ether, ethanol and other organic solvents

density

Greater than 1

Toxic and corrosive

chemical properties

Weakly acidic

The negative charge (lone pair of electrons) of phenoxide anions can be dispersed into the benzene ring, increasing stability and acidity.

Acidity: carboxylic acid>carbonic acid>phenol>water>alcohol

color reaction

Both phenol and enol structures can complex with ferric chloride to develop color

use

Identify phenolic and enolic compounds

Phenol reacts with ferric chloride to form blue-purple color

Ether-forming reaction (Williamson reaction)

Phenol (nucleophile) reacts with halogenated hydrocarbons or sulfate esters in alkaline solution to form ethers

esterification reaction

Can react with acids, acid chlorides, and acid anhydrides

Electrophilic substitution on benzene ring

Halogenated

Reacts with bromine water to form white precipitated tribromophenol (identification, quantification)

Nitrification

It is acidified by dilute nitric acid at room temperature to obtain two products in the ortho-para position, with the ortho-position being the main product.

The ortho position forms intramolecular hydrogen bonds, and the six-membered chelate is easily volatile. The para position forms intermolecular hydrogen bonds and is not easy to volatilize.

Concentrated nitric acid is heated to obtain trinitrophenol (picric acid)

sulfonation

reacts with concentrated sulfuric acid

room temperature

adjacent position

100℃

Counterpoint

Friedel-Crafts reaction Friedel-Crafts reaction

Alkylation

Acylation

Excess aluminum chloride

oxidation reaction

Forms p-benzoquinone with acidic potassium dichromate

The more hydroxyl groups there are, the easier it is to be oxidized

1,2,3-Ploroglucinol (pyrogallic acid) readily absorbs oxygen

ether

Mixed ether naming

Small groups come first, large groups come last, and those containing aryl groups come first.

StructureP131

Not a linear molecule

nature

physical properties

state

A liquid with a certain fragrance, methyl ether is a liquid

boiling point

Boiling points are roughly similar to alkanes

Solubility

Small dipole moment, weakly polar molecule, low-grade ethers are slightly soluble in water, most ethers are insoluble

chemical properties

Alkaline (weak)

reacts with concentrated acid to form yang salt

Breaking of ether bonds

The phenoxy group is not broken (conjugated)

React with concentrated HI or HBr under heating conditions to obtain halogenated hydrocarbons and hydroxyl compounds

Determination of methoxyl group (Zeizer method)

auto-oxidation

The α position is easily oxidized and generates peroxide

Testing method: KI starch test paper, if present, it turns blue Removal method: add ferrous sulfate or sodium sulfite

cyclic ether

Ethylene oxide

picture

crown ether

phase transfer catalytic reaction

representative compound

alcohol

Methanol

Commonly known as wood alcohol

Originally derived from wood distillation Industrially produced from carbon monoxide and hydrogen

Colorless liquid, miscible with water and most organic solvents

It does not form a constant boiling mixture with water and can be separated by fractional distillation.

Metal magnesium can remove trace amounts of water

Complexes formed with calcium chloride cannot be dried with calcium chloride

Highly toxic

ethanol

Fermentation of sugars, preparation of ethylene by adding water

Form a constant boiling mixture with water

Colorless flammable liquid

Complexes with calcium chloride

Ethylene glycol

Commonly known as glycol

Colorless, odorless, sweet, transparent liquid

Preparation by oxidation of ethylene or hydrolysis of ethylene oxide

engine antifreeze

Glycerol

Commonly known as glycerin

Colorless and sweet viscous liquid, easily soluble in water, insoluble in ether and chloroform

Oil hydrolysis preparation

cyclohexanol

Commonly known as myo-inositol

White crystal, easily soluble in water, insoluble in ethanol and ether

necessary for biological growth

Benzyl alcohol

Also known as benzyl alcohol

Colorless liquid, fragrant aroma

Slightly soluble in water, miscible with organic solvents

Will be oxidized to benzaldehyde

Weak anesthesia, antisepsis, 2% aqueous solution is called "painless water"

phenol

Commonly known as carbolic acid

Easily oxidized, store away from light

Disinfection

Pentachlorophenol is a colorless crystal, used for weeding, wood preservation, and termite control.

Cresol

Also known as coal phenol

Cresol soap solution is commonly known as "Lysol"

mixture of three isomers

o-cresol

m-cresol

p-cresol

Disinfection

benzene

three isomers

Resorcin does not exist and needs to be synthesized artificially Sterilizes, is less irritating than phenol, and can treat skin diseases

Catechol and hydroquinone

reducing agent, developer

Polymerization inhibitor to prevent polymer monomers from being oxidized and polymerized by oxidants

Pair-Lab Antioxidants

Ortho-adrenaline contains this structure

Vitamin E

Also known as tocopherol and pregnol

Widely present in vegetable oils, there are three types of αβγ, with the highest α activity

Yellow oily substance, insoluble in water, easily soluble in organic solvents

Stable to heat and alkali in anaerobic state, easily oxidized

Antioxidant, scavenge free radicals

Bisphenol A

BPA

White needle-like crystal, slightly soluble in water, aliphatic hydrocarbons, soluble in acetone, ethanol, acetic acid, and dilute alkali.

Enhances the properties of plastic products, but can cause endocrine disorders

ether

Ether

Colorless liquid, highly volatile and flammable, will explode in case of fire

Have anesthetic effect

herbicide

2,4-Dichloro-4’-nitrodiphenyl ether

Yellow needle-shaped crystal, difficult to dissolve in water, easily soluble in organic solvents

Tetrahydrofuran

THF

Colorless transparent liquid with ether smell, miscible with water, alcohol, ketone, benzene, ester, ether and hydrocarbons

Neutral polar aprotic solvent

Oxygen atoms coordinate with Lewis acid

There are hydrogen bonds

Increased water solubility

boiling point increase

hydrogen bond

definition

A very weak bond formed by the combination of an atom in a molecule with an atom containing an unshared electron pair, such as O, N, F, and sometimes S, Cl, etc.

Influence

intramolecular hydrogen bonding

Molecular association, boiling point increased

intermolecular hydrogen bonding

Reduce molecular association, lower boiling point