--%>
Assignment Help - homework help

What are the chemical properties of haloalkanes?

Haloalkanes are extremely reactive category of aliphatic compounds. Their reactivity is due to the presence of polar carbon-halogen bond in their molecules.


The chemical reactions of haloalkanes can be divided into four ways:
    
Nucleophilic substitution reactions

In haloalkanes, the halogen atoms are attached to the carbon atom. The bond between carbon and halogen is polar in character because the halogen atom is more electronegative than carbon.

Due to the presence of partial positive charge on the carbon atom, the nucleophilies can attack on electron deficient carbon thereby resulting the displacement of weaker nucleophile is generally stronger than it.

The order of reactivity of various alkyl halides towards nucleophilic substitution in the order:

Order of reactivity: RI > RBr > RCI > RF

This order of reactivity can be explained on the basis of strength of C-X bond. The C-X bond is the weakest in R-I and the strongest in R-F as is clear from the bond energy data for methyl halides. In fact, the C-F bond is so strong that organic fluorides do not undergo nucleophilic substitution under ordinary conditions.

Bond

C-I

C-Br

C-Cl

C-F

Bond Enthalpies (kJ/mole)

234

293

351

452

Bond length (pm)

214

193

178

139

Dipole moment (Debye)

1.636

1.830

1.860

1.847


Examples of nucleophilic substitution reactions of haloalkanes
    
Replacement of hydroxyl group (Formation of alcohols).

Haloalkanes on treatment with aqueous solution of KOH or moist silver oxide (Ag2O/H2O) give alcohols.
                        
2388_haloalkanes.png 
    
Replacement Alkoxy group (Formation of ethers). (Williamson Synthesis):

Haloalkanes on treatment with alcoholic sodium or potassium alkoxide form ethers. This reaction is called as Williamson Synthesis.
        
1935_haloalkanes1.png 

Ethers can also be prepared by heating alkyl halides with dry silver oxide, Ag2O
                
1005_haloalkanes3.png  
    
Replacement by Cyano Group (Formation of cyanides or nitrites)

Haloalkanes on treatment with alcoholic KCN solution give alkanenitriles or alkyl cyanides as the major product with a small amount of alkyl isocyanide.

2173_haloalkanes2.png 

The reaction of alkyl halides with KCN gives us an important method for increasing the length of carbon chain by one carbon atom i.e. rising of series.

   Related Questions in Chemistry

  • Q : Mole fraction Give me answer of

    Give me answer of following question. The sum of the mole fraction of the components of a solution is : (a) 0 (b) 1 (c) 2 (d) 4.

    		•
  • Q : Cations Chromium(III) hydroxide is

    Chromium(III) hydroxide is highly insoluble in distilled water but dissolves readily in either acidic or basic solution. Briefly explain why the compound can dissolve in acidic or in basic but not in neutral solution. Write appropriate equations to support your answer

    		•
  • Q : Molar mass of solute The boiling point

    The boiling point of benzene is 353.23 K. If 1.80 gm of a non-volatile solute was dissolved in 90 gm of benzene, the boiling point is increased to 354.11 K. Then the molar mass of the solute is: (a) 5.8g mol-1  (b)

    		•
  • Q : Donnan Membrane Equilibria The electric

    The electric charge acquired by macromolecules affects the equilibrium set up across a semipermeable membrane.Laboratory studies of macromolecule solutions as in osmotic pressure and dialysis studies confine the macromolecules to one compartment while allo

    		•
  • Q : What is schrodinger wave equation? The

    The Schrodinger wave equation generalizes the fitting-in-of-waves procedure.The waves that "fit" into the region to which the particle is contained can be recognized "by inspection" only for a few simple systems. For other problem a mathematical procedure

    		•
  • Q : Short note on the function of

    Write down a short note on the function of mitochondria?

    		•
  • Q : What are aliphatic amines and its

    In common system, the aliphatic amines are named by using prefix for alkyl group followed by the word amine.In case of mixed amines, the name of alkyl groups are arranged in alphabetical order. This is followed by the word amine. However, for simple secondary or tertiary amines anothe

    		•
  • Q : Organic structure of cetearyl alcohol

    Show the organic structure of cetearyl alcohol and state what the organic family is? Briefly state it.

    		•
  • Q : What is Flash Photolysis Reactions.

    An example illustrates the type of mechanism that can be written to explain the development of flash photolysis reactions. Often, as the reactions in the ozone layer of the earth's atmosphere, we are interested in the kinetic behavior of species that are not a

    		•
  • Q : Organic and inorganic chemistry Write

    Write down a short note on the differences between the organic and inorganic chemistry?

    		•