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Properties of Isocyanides:

 

1.   Alkyl isocyanides are poisonous, unpleasant smelling, with lower boiling points than isomeric cyanides.

 

2.   RNC are not very soluble in water, nitrogen atom not having a lone pair of electrons available for hydrogen bonding.

 

Reactions:

 

1.   Hydrolysis:

 

                            acid
      RNC + 2H2O ———> RNH2 + HCO2H
                          dilute 
 

 

                                 H+
      CH3NC + 2H2O ———> CH3NH2 + HCO2H

      

 

      RNC are not hydrolysed by alkalis.

 

2.   Reduction:

 
              H2 / Pt
      RNC ———> R NHCH3

 

                          2o amine

 

 

                         H2 / Pt 
        CH3NC     ———>   CH3NHCH3 
  Methyl isocyanide        Dimethyl amine

 

 

3.   When alkyl isocyanides are heated for a long time, they arrange to form cyanide

 

      RNC ———> R CN

 

      CH3CH2NC ———> CH3CH2CN

 

4.   With non metals:

 

      (i)   RNC + X2 ———> RNCX2

 

            CH3NC + Cl2 ——> CH3NCCl2

 

      (ii)   RNC + S ———> RNCS

            Alkyl isothiocyanates

 

        CH3NC + S ———> CH3NCS

 

5.   Oxidation with HgO:

 

      RNC + HgO ———> RNCO + Hg

                                  Akyl isocyanates

 

     CH3NC + HgO ———> CH3NCO + Hg

 

Illustration .

 

1438_Illustration.JPG

 

  703_equation.JPG

Solution:

 

 1772_equation.JPG

 

Hence (C) is correct

 

Illustration .  Identify the end product (C)

 

 813_end product.JPG

 

Solution:

 

2297_Solution.JPG

 

Hence (A) is correct.

 
 

Exercise.

 

      (i)

 

2464_methyl isocyanate.JPG
 

            Identify A, B and C.

 

            (ii)       Write a reaction in which methyl isocyanate (MIC) is formed. What products are formed when it is hydrolysed with water?

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