MindMap Gallery Organic Chemistry - Halogenated Hydrocarbons
Compounds in which hydrogen atoms in hydrocarbon molecules are replaced by halogen atoms are called halogenated hydrocarbons. This mind map details the relevant knowledge of halogenated hydrocarbons in university organic chemistry, concisely and clearly.
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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.
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[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!
Halogenated hydrocarbons
Classification of halogenated hydrocarbons
Different according to the structure of the hydrocarbon group in the molecule
Saturated halogenated hydrocarbons (halogenated alkanes)
Unsaturated halogenated hydrocarbon
Halogenated olefins
Halogenated alkynes
Depending on the number of halogen atoms contained in the molecule
Monohalogenated hydrocarbon
polyhalogenated hydrocarbons
By type of carbon atom directly connected to the halogen atom
primary halogenated hydrocarbons
Secondary halogenated hydrocarbons
Tertiary halogenated hydrocarbons
Nomenclature of halogenated hydrocarbons
common nomenclature
Named according to the group attached to the halogen atom
systematic nomenclature
Halogen atoms always serve as substituents, and the corresponding hydrocarbon group always serves as the parent
Physical properties of halogenated hydrocarbons
state
It is generally a colorless liquid at room temperature (except methyl chloride, ethyl chloride, and methyl bromide are gases)
boiling point
The boiling point is higher than that of the corresponding alkanes; as the number of carbon atoms increases, the boiling point increases
Solubility
Insoluble in water, easily soluble in organic solvents (some can be used directly as solvents)
density
Larger than the corresponding alkanes; decreases as the number of carbon atoms increases
Halogenated alkenes and halogenated aromatics
Classification
Ethylene type
Allyl type
Isolated
chemical properties
Chemical properties of halogenated hydrocarbons
Reactivity of halogenated hydrocarbons
R-I>R-Br>R-Cl
nucleophilic substitution reaction
substituted by hydroxyl
Reacts with water to form alcohol (reversible)
Reacts with strong alkali aqueous solution (high conversion rate)
substituted by cyano
Carry out in alcohol solution, use sodium cyanide and potassium cyanide as reagents
As a method of growing carbon chains in organic chemical synthesis
Substituted by alkoxy
The halogen atom is replaced by an alkoxy group (RO—) to form an ether (Williamson reaction)
substituted by amino
Halogenated hydrocarbons react with amino groups to form amines
Substituted by nitroxyl
Heat together with silver nitrate ethanol solution to produce silver halide precipitation (identification of halogenated hydrocarbons)
reaction mechanism
SN1
First, the C-X bond is broken to form a carbocation intermediate, and then the nucleophile attacks the central carbon atom.
Rate: PhCH2X>CH3X>RCH2X>R2CHX>R3CX
SN2
The hydrogen-oxygen bond attacks the carbon atom to form a transition state, and then the C-X bond breaks
Rate: PhCH2X,R3CX>R2CHX>RCH2X>CH3X
elimination response
When an alkyl halide is heated in an alcohol solution of a base, a molecule of hydrogen halide can be removed to form an alkene.
reaction mechanism
E1
The carbocation intermediate is first, then the β hydrogen atom is lost and a π bond is formed.
E2
The reaction is completed in one step, and the cleavage of the leaving group, the neutralization of the β hydrogen atom with the base, and the generation of the π bond are coordinated.
reaction with metals
Comment
Halogenated hydrocarbons can react with a variety of metals to generate metal-organic compounds. Grignard reagents are the most important type of metal-organic compounds and one of the most important reagents in organic synthesis.
Preparation of Green's reagent
R-X Mg (anhydrous ether)—>RMgX (Green's reagent)
interaction with sodium
Preparation of higher alkanes