--%>

How haloalkanes are prepared from hydrocarbons?

Alkyl halides can be prepared from alkanes through substitution and from alkenes through addition of halogen acids or through allylic substitution.
    
From alkanes

When alkanes are treated with halogens, chlorine or bromine, in the presence of light or heat, they undergo free radical substitution and a mixture of mono- and poly- substituted products are obtained.

2242_alkyl halide.png 

Although, the substitution beyond monohalogenation may be suppressed by using alkane in excess yet the method is not of much practical use because of the difficulties of separation of such a mixture.

In case of higher alkanes, different isomeric products are formed even when mono-substitution is carried out.

1702_alkyl halide1.png 

In general, the ease of substitution of different types of hydrogen atoms is:

Benzylic, allylic > tertiary > secondary > primary > vinylic, aryl

The iodination of alkanes is reversible and is done by heating with iodine in the presence of oxidising agents like conc. HNO3HIO4 orHIO3. The function of using such agents is to oxidize HI formed during the reaction to iodine, and hence shift the equilibrium in the forward direction.

264_alkyl halide2.png 

Due to formation of polysubstituted products and isomeric products, this method is not suitable for the laboratory preparation of pure haloalkanes. However, this method can be used for laboratory preparation of certain specific alkyl halides as given below:
    
When all the hydrogen atoms in the alkane are equivalent are equivalent, then it can form only one product on monosubstitution. In such cases this method may be applied.

924_alkyl halide3.png 
    
Allylic and benzylic halides can be prepared from alkenes and arenes respectively by this method because allylic and benzylic hydrogen atoms are substituted much more readily than vinylic and aryl hydrogen atoms.

260_alkyl halide4.png 

In such cases vinylic aryl hydrogens being less reactive do not participate in free radical substitution.

Allylic and benzylic hydrogen atoms are substituted very easily because their substitution proceeds via allylic and benzylic free radicals as intermediates. These intermediates are stabilized by resonance and hence being stable are formed at faster rate.
    
By halide exchange

Iodoalkanes can be obtained by treating bromo or chloroalkanes with a solution of sodium iodine in acetone or methanol. For example,

1778_alkyl halide5.png 

The reaction is known as Finkelstein reaction. This reaction is based on the fact that NaI is soluble in acetone but NaBr and NaCl are not. As a result, equilibrium in the above reaction is very much in favour of forward reaction. The reaction gives best result with primary halides.

Fluoroalkanes are difficult to prepare directly by the action of alkanes with fluorine. It is because fluoride has gor a high reactivity towards the hydrogen. It extracts all the hydrogen atoms from hydrocarbon molecule.

CH4 + 2F2  71_potassium permangnate3.png  4HF + C

However, Fluoroalkanes can be obtained by treating alkyl halides with salts like AgF, Hg2F2, CoF3 or SbF3. This reaction is known as Swarts reaction.

CH3Br + AgF 71_potassium permangnate3.png CH3F + AgBr

2CH3CH2Cl + Hg2F2  71_potassium permangnate3.png  2CH3CH2F + Hg2Cl
2

For replacement of two or three halogen atoms at the same carbon CoF3 or SbF3 is used.

67_alkyl halide6.png

   Related Questions in Chemistry

  • Q : Explain structure basicity of amines.

    Basic character of amines is related to their structural arrangement. Basic strength of amines depends on the relative ease of formation of the corresponding cation by accepting a proton from the acid. Greater the stability of cation is, more is basic strength of amine.Alkyl a

  • Q : Extensive property Choose the right

    Choose the right answer from following. Which one of the following is an extensive property: (a) Molar volume (b) Molarity (c) Number of moles (d) Mole fraction

  • Q : Examples of reversible reaction

    Describe some examples of a reversible reaction?

  • Q : Kinds of insulators Describe all the

    Describe all the kinds of insulators which are present?

  • Q : Problem associated to vapour pressure

    Provide solution of this question. 60 gm of Urea (Mol. wt 60) was dissolved in 9.9 moles, of water. If the vapour pressure of pure water is P0 , the vapour pressure of solution is:(a) 0.10P0 (b) 1.10P0 (c) 0.90P0 (d) 0.99P0

  • Q : What are biodegradable polymers?

      These are polymers that can be broken into small segments by enzyme-catalysed reactions. The required enzymes are produced by microorganism. It is a known fact that the carbon-carbon bonds of chain growth polymers are inert to enzyme-catalysed reactions, and hence they are non biod

  • Q : Procedure for separating the components

    Briefly describe the procedure for separating the components of the gun-powder?

  • Q : What is Distillation Separation by

    Separation by distillation can be described with a boiling point diagram. The important process of distillation can now be investigated. From the boiling point diagram one can see that if a small amount of vapour were removed from a liquid of composit

  • Q : Acid Solutions Choose the right answer

    Choose the right answer from following. Volume of water needed to mix with 10 ml 10N NHO3 to get 0.1 N HNO3: (a) 1000 ml (b) 990 ml (c) 1010 ml (d) 10 ml

  • Q : Problem on bubble point The following

    The following mixture of hydrocarbons is obtained as one stream in a petroleum refinery.

    Discover Q & A

    Leading Solution Library
    Avail More Than 1433815 Solved problems, classrooms assignments, textbook's solutions, for quick Downloads
    No hassle, Instant Access
    Start Discovering

    18,76,764

    1959055
    Asked

    3,689

    Active Tutors

    1433815

    Questions
    Answered

    Start Excelling in your courses, Ask an Expert and get answers for your homework and assignments!!

    Submit Assignment

    ©TutorsGlobe All rights reserved 2022-2023.