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Objectives. Preparation of Haloalkanes by Halogenation. Preparation Aryl Chlorides by Electrophilic Substitution. Halogen Exchange. Halogenation.

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Objectives

Preparation of Haloalkanesby Halogenation

Preparation Aryl Chlorides by Electrophilic Substitution

Halogen Exchange


Halogenation

Free radical chlorination or bromination of alkanes gives a complex 287 Haloalkanes and Haloarenes mixture of isomeric mono- and polyhaloalkanes, which is difficult to separate as pure compounds.

CH4 + Cl2 CH3Cl + HCl


Mechanism
Mechanism

Propagation

Termination


Features of halogenation
Features of Halogenation

F2 > Cl2 > Br2 > I2.

Attack of or on an alkane is selective

Order of reactivity is 3° > 2° > 1°




By electrophilic substitution

Aryl chlorides and bromides can be easily prepared by electrophilic substitution of arenes with chlorine and bromine respectively in the presence of Lewis acid catalysts like iron or iron(III) chloride.


Halogen Exchange

Alkyl iodides are often prepared by the reaction of alkyl chlorides/ bromides with NaI in dry acetone. This reaction is known as Finkelstein reaction.


Swarts reaction

The synthesis of alkyl fluorides is best accomplished by heating an

alkyl chloride/bromide in the presence of a metallic fluoride such as

AgF, Hg2F2, CoF2 or SbF3. The reaction is termed as Swarts reaction.


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