>>
Study Material >>
IIT JEE Chemistry >>
Organic Chemistry >>
Amines and Nitrogen Containing Compounds >>
Properties of Isocyanides
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 .
|

|

Solution:

Hence (C) is correct
Illustration . Identify the end product (C)

Exercise.
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?