--%>
Assignment Help - homework help

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. HNO3, HIO4 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 + Hg2Cl2

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 : Describe Transformation Matrices. Each

    Each symmetry operation can be represented by a transformation matrix.You have seen what happens when a molecule is subjected to the symmetry operation that corresponds to any of the symmetry elements of the point group to which the molecule belongs. The m

    		•
  • Q : Vitamines 7 enzyme cofactor what is the

    what is the relationship between vitamins and enzyme cofactors

    		•
  • Q : Show your calculations Superphosphate

    Superphosphate has the formulae: CaH4 (PO4)2H2).  Calculate the percentage of phosphorus in this chemical.  Show your calculations  (around ten lines);  also Work out how to make up a nutrient mixtur

    		•
  • Q : Problem on decinormal Select the right

    Select the right answer of the question. How much water is required to dilute 10 ml of 10 N hydrochloric acid to make it exactly decinormal (0.1 N): (a) 990 ml (b) 1000 ml (c) 1010 ml (d) 100 ml

    		•
  • Q : How haloalkanes are prepared from

    This is the common method for preparing haloalkanes in laboratory. Alcohols can be converted to haloalkanes by substitution of - OH group with a halogen atom. Different reagents can be used to get haloa

    		•
  • Q : Chem Silicon has three naturally

    Silicon has three naturally occurring isotopes. 28Si, mass = 27.976927; 29Si, mass = 28.976495; 30Si, mass = 29.973770 and 3.10% abundance. What is the abundance of 28Si?

    		•
  • Q : What is heat capacity and how to

    The temperature reliance of internal energy and enthalpy depends on the heat capacities at constant volume and constant pressure. The internal energy and enthalpy of chemical systems and the energy changes that accompany chemical reactions depend on the

    		•
  • Q : Molar concentration Choose the right

    Choose the right answer from following. Molar concentration (M) of any solution : a) No. of moles of solute/Volume of solution in litre (b) No. of gram equivalent of solute / volume of solution in litre (c) No. of moles os solute/ Mass of solvent in kg  (

    		•
  • Q : Explain Photoelectron Spectroscopy. The

    The energies of both the outer and inner orbitals of atoms and molecules can be determined by photoelectron spectroscopy.Energy changes of the outermost or highest energy electron of molecules were dealt with here in a different passion. The energies of ot

    		•
  • Q : Inorganic Chemistry Inorganic

    Inorganic Chemistry:In the year 1869, Russian Chemist Dmitry Mendeleyev forms the periodic table of the element. Since Newlands did before him in the year 1863, Mendeleyev categorizes the el

    		•