Chemistry > Isomerism > 3.0 Tautomerism

  Isomerism
    1.0 Isomerism
    2.0 Structural Isomerism
    3.0 Tautomerism
    4.0 Geometrical isomerism in the compounds containing C=N
    5.0 Optical Isomerism
    6.0 Optical isomerism in compounds having more than one chiral carbons
    7.0 Optically active compounds having no asymmetric carbon

3.2 Cause of tautomerism

Migration of acidic hydrogen from $\alpha - $carbon to electronegative atom which is bonded with multiple bond is the cause of tautomerism and this phenomenon is known as tautomerism.



(i) Both (I) and (II) are isomers known as tautomers.

(ii) Tautomers are always in equilibrium state.

(iii) Number of sigma, pi and lone pair of electrons in both tautomers are always same.

(iv) Tautomerism is a chemical phenomenon which takes place only in liquid state.

(v) Tautomersim is catalysed by acid as well as base.

(vi) Tautomers are always reversible functional groups, functional isomers.

Tautomerism is of several types the two important types are dyad and triad systems.

(a) Dyad System: It involves the oscillation of $H$ atom between two polyvalent atoms, e.g., hydrogen cyanide (I) and hydrogen isocyanide (II).



In the above example the H atom vibrates between carbon and nitrogen atoms. The alkyl derivatives of (I) are called cyanides while those of (II) isocyanides.

(b) Triad System: In it one $H$ atom oscillates between three polyvalent atoms.

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