Halogenation reaction (sunlight, high temperature, free radicals)

Oxidation reaction (combustion)

Cleavage reaction, △

addition reaction

oxidation reaction

Reacts with hydrogen, opens the ring (small ring-like alkene), only applicable to 3, 4, 5-membered rings, 5 does not react

Reacts with halogen, 3, 4, and 5-membered rings open, and 5+ substitution reaction occurs

Reacts with hydrohalic acid, 3-membered ring, addition and ring opening, 3 does not react

The only difference between small rings and alkenes is that they cannot be oxidized by common oxidants like alkenes.

When cycloalkanes react with strong oxidants under heating conditions, the rings break and generate dibasic acids.

Electrophilic substitution reaction (benzene homologues react more easily than benzene)

oxidation reaction

addition reaction

Free radical substitution of side chains

Substituted by hydroxyl group to form alcohol

Substituted by alkoxy to form ether

Substituted by cyano group to form nitrile

Replaced by nitrate to form nitrate ester and AgX precipitation

Substituted by amino group to form amine

Following Zaitsev's rule: hydrogen atoms are mainly removed from β-carbon atoms that contain less hydrogen.

Strong base, alcohol as solvent, heating

Generate format reagents

Rate: first, second, third, iodine, bromine, chlorine (decreasing);

The electron-donating induction effect weakens the acidity, and the alkalinity of sodium alcohol is the opposite. This property can be used to test

Reaction with hydrohalic acid (halogenation reaction)

Reacts with phosphorus halide or sulfoxide chloride

Intramolecular dehydration (to form alkene)

Intermolecular dehydration (to ether)

Oxidation by strong oxidants

Selective oxidizing agent (only oxidizes alcohol, not double bonds)

Catalytic dehydrogenation to aldehydes or ketones

Reacts with Cu(OH)2 to reveal dark blue color

Reacts with HIO4 to break bonds and detect quantitatively

Electron-withdrawing groups, acidity enhancement

Electron-donating group, weakening acidity

Generate phenol ether

Generate phenolic ester

oxidation reaction

Electrophilic substitution reaction on benzene ring

Concentrated hydrochloric acid, concentrated nitric acid

When the salt meets water, it decomposes into the original ether to achieve separation and purification.

Hydrohalic acid, heated

Produce alcohols and halogenated hydrocarbons

Reagents containing active hydrogen, acidic conditions

alkaline conditions

Bonus with HCN

Addition with NaHSO3 produces a white precipitate of sodium α-hydroxysulfonate

Addition to alcohol

Addition to water

Reacts with amines ammonia and its derivatives

react with format reagent

Enolization

α-halogenated

aldol condensation reaction

Disproportionation reaction (Cannizzaro reaction)

reduction reaction

oxidation reaction

Electron-withdrawing groups enhance acidity

Electron-donating groups weaken acidity

Acid halide (similar to the halogenation of alcoholic hydroxyl group)

Anhydride

ester

Amide

Carboxylic aldehydes with electron-withdrawing groups on α(β)-C are unstable

Oxalic acid, malonic acid, removes one carboxyl group and retains one

Succinic acid, glutaric acid and phthalic acid are heated and dehydrated to form cyclic anhydride

When adipic acid and pimelic acid are heated, they lose water and decarboxylate to form a ketone with one less carbon.

Hensdike reaction

Cozy reaction

LiAlH4, reduces acid to alcohol, double bonds are not affected

P as catalyst

alkyd acidic

phenolic acid acidic

Toulon's reagent, dilute nitric acid, hydrogen peroxide

Alpha-hydroxy acid, bimolecular dehydration, forming lactide

β-Hydroxy acid, intramolecular dehydration, generating unsaturated acid

γ-, δ-hydroxy acid, intramolecular dehydration to form cyclic lactone

w – Hydroxy acid, polyester

Ag(NH3)2 →decarboxylation

H2SO4,△→decarboxylation

Concentrated H2SO4, △→Decarbonylation (CO)

Decarboxylation to ketone by heating

Tautomerism ~ keto and enol

Acid halide＜anhydride＜ester＜amide

p-π conjugation reduces C

electronic effect

spatial effect

order of reactivity

Under alkaline conditions (NaOH, pyridine, triethylamine)

The condition is that sodium alkoxide

Secondary > Primary > Tertiary > Ammonia > Pyridine > Aniline

The electron-withdrawing group becomes less alkaline and the electron-donating group becomes more alkaline.

There is no H on N of the tertiary amine, and no acylation reaction occurs.

Acylation reaction can be used to protect amino groups

Generates a mixture of amines

Primary amines generate diazonium salts and release hydrogen gas quantitatively.

Secondary amine, produces yellow oil or solid

Tertiary amine, no obvious phenomenon

Primary amine, white solid, soluble in NaOH

Secondary amine, white solid, insoluble NaOH

Tertiary amine, unreactive

With bromine water, 2,4,6-tribromoaniline, white solid

Primary and secondary amines should be protected with acylating reagents

Tertiary amines can undergo Friedel-Crafts reaction directly

Diazo is a chromogenic group used in the synthesis of pigments

application

Water, △→Ph-OH

CuCl,HCl→Ph-Cl

CuCN,KCN→Ph-CN

KI→Ph-I

C2H5OH/H3PO2→Ph-H

5 member ring

Electrophilic substitution (α-position)

Pyrrole is weakly acidic

alkaline

Electrophilic substitution mainly attacks the β-position

Boil alkaline water and oxidize and disinfect with bleaching powder

Hydrolysis ClCH=CHAs

Acts with alkaline substances

oxidation

Formation of inner dipolar salt (minimum solubility)

Isoelectric point pI, the concentration of anions and cations is equal

Ba(OH)2,△

α-Amino acid reacts with ninhydrin to produce a purple color

The reaction product of proline and ninhydrin is yellow

For the determination of polypeptide or protein structure (dinitrobenzene method, DNP method)

Complete hydrolysis method

N-terminal

C-terminal

α-waving style, less stable

β-surrender, more stable

Conversion between Keto and Enol

epimerization

Name: Ligand Residue of Sugar Glycoside

Dry HCl catalysis

Toulon's reagent, Fehling's reagent

Bromine water oxidation (acidic), no isomerization

Nitric acid oxidation

enzymatic oxidation

All monosaccharides are reducing

Monosaccharide and excess phenylhydrazine, heating

Glucose, yellow crystals

Sugar phenylhydrazine→hydrazone→hydrazine

Different sugars have different crystal forms and melting points. Use sugars to identify different sugars.

The product reacts with phenols to produce colored substances, which are used for sugar identification.

Hydrolyzed into glucose and fructose

There is no optical rotation phenomenon, it cannot form reagents, and it cannot reduce Toulon's reagent and Fehling's reagent.

Hydrolyzed into two molecules of glucose

Reducibility: reduction of Toulon's reagent and Fehling's reagent

Can form maltose with phenylhydrazine

variable rotation phenomenon

Hydrolyzed into galactose and glucose