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MindMap Gallery Organic Chemistry Halogenated Hydrocarbons

Organic Chemistry Halogenated Hydrocarbons

Compounds in which hydrogen atoms in hydrocarbon molecules are replaced by halogen atoms are called haloalkanes, or haloalkanes for short. The general formula of halogenated hydrocarbons is: (Ar)R-X, X is a halogen atom, which can be regarded as the functional group of halogenated hydrocarbons, including fluorine, chlorine, bromine, and iodine. Quickly collect, complete knowledge points of alkyl halides in university organic chemistry

Edited at 2021-04-01 22:23:44

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Organic Chemistry Halogenated Hydrocarbons

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Nucleophilic substitution and elimination
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Halogenated hydrocarbons

Classification and naming

Classification

According to the attached hydrocarbon group

Halogenated alkanes

Halogenated olefins

Halogenated aromatics

Benzene

benzyl

Isolated

According to the type of carbon atoms connected

primary haloalkane

Tertiary alkyl halide

Secondary haloalkane

name

Common naming: Generally called "halogenated hydrocarbon" or "halogen" according to the attached group.

Nomenclature of haloalkanes

Number from the closest segment

Prioritize alkyl groups

Nomenclature of halogenated alkenes

Based on olefins

Number from the end closest to the double bond

Nomenclature of halogenated aromatics

When the halogen atom is directly connected to the benzene ring, the benzene ring is the parent

When not directly connected, the side chain is the parent

physical properties

solubility

Easily soluble in organic solvents

density

Except for fluoroalkyl and monohalogenated alkyl, most of the others are heavier than water

Stablize

Alkanes monochloride are relatively stable, but chloroform, alkyl bromide and alkyl iodide are easily decomposed by light.

Important halogenated hydrocarbons

Trichloroalkane

Chloroform

Colorless, sweet, non-flammable

difluorodichloromethane

refrigerant

Halothane

Anesthetic

Tetrafluoroethylene

The king of plastics, Teflon

Triclofen

Highly effective and low-toxic insecticide

chemical properties

The electronegativity of the halogen atom is large, so that the halogen atom has a partial negative charge, the α carbon atom has a positive charge, making it vulnerable to attack by nucleophiles, and the βγ carbon atom has a partial positive charge, and the βγ carbon atom has a partial positive charge. H atoms are loose and can easily be removed with halogen atoms, forming an elimination reaction.

nucleophilic substitution reaction

Replaced by hydroxyl group (alkaline hydrolysis)

Substituted by alkoxy to form ether

Preparation of ether (Williamson method for making ether)

This reaction only works for simple primary alkyl halides (elimination of secondary tertiary halides occurs)

Substituted by cyano group to form nitrile

Preparation of amines, amides, carboxylic acids, and esters with one added carbon atom

This reaction only works for simple primary alkyl halides

Replaced by nitrate to form nitrate ester

Reactivity

RI>RBr>RCl

C3RX>C2RX>CRX

Nucleophilic substitution reactivity of various structural halogenated hydrocarbons

Allyl or benzyl (immediate) > tertiary (oscillation) > primary or secondary (heating) > vinyl or benzene (no reaction)

Substituted by amino group to form amine

Nucleophilic substitution reaction process

Bimolecular process SN2

Features

Completed in one step, intermediate (breaking of old bonds and formation of new bonds at the same time)

Product configuration flips

Influencing factors

steric hindrance

reaction speed

CH3X>1>2>3

Single molecule process SN1

Features

Completed step by step, there is a carbocation intermediate (break first and then form)

The product is a racemate

Influencing factors:

Carbocation stability

reaction speed

Allyl or benzyl>tertiary>secondary>primary>CH3X

elimination response

β-Elimination of Halogenated Hydrocarbons

Conditions: strong base, alcohol solvent

Zaitsev Rule

The elimination products of halogenated hydrocarbons are mainly alkenes with more alkyl groups connected to the double bonds.

exception

When the elimination reaction of halogenated alkenes and halogenated aromatics occurs, the main product generated is conjugated olefins

elimination reaction process

Bimolecular process E2

Features

Completed in one step, intermediate (breaking of old bonds and formation of new bonds at the same time)

reaction speed

3>2>1>CH3X

Favorable factors

More β-H

Strongly alkaline reagent

high temperature

Single molecule process E1

Features

Completed step by step, there is a carbocation intermediate (break first and then form)

reaction speed

React with metals

Preparation of format reagents

Degree of difficulty

RI>RBr>RCl>RF (usually prepared with alkyl bromide)

Bo>Second>Uncle

Properties and preservation

High activity, unstable

Stored under anhydrous and oxygen-free conditions

Reaction with Grignard reagent·

rearrangement reaction

Occurs in SN1, E1

summary

Four reactions exist simultaneously

Primary halogenated hydrocarbons are mainly SN2 (the proportion of E2 increases under strong base)

Secondary halogenated hydrocarbons, strong nucleophiles, prone to SN2, strong bases are beneficial to E2

When tertiary halogenated hydrocarbons have no base, SN1 and E1 coexist

The reagent is highly alkaline and has a high concentration, so heating up is beneficial to E2

The reagent is highly nucleophilic and its small size is beneficial to SN2

In single molecule reactions, increasing temperature is beneficial to E1