TAUTOMERISM
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Last updated 3:59 AM on 10/27/22
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23 Terms
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Tautomerism
➢ Phenomenon where a single chemical compound tends to exist in two or more interconvertible structures that are different in terms of the relative position of one atomic nucleus which is generally the hydrogen
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Structural Requirement of Tautomerism
➢ Compounds contain polar molecules and weakly acidic group functional groups
➢ Involves the change in position of an atom
➢ Has no effects on bond length or such features
➢ Occurs in planar or non-planar molecules
➢ Involves the change in position of an atom
➢ Has no effects on bond length or such features
➢ Occurs in planar or non-planar molecules
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Tautomers
➢ Type of functional isomers which exist in rapid equilibrium in solution
➢ Interconvertable in solution
➢ Usually differs in position of H atom at A carbon
➢ Interconversion of tautomers can be catalyzed
➢ Can’t be separated in solution at normal temperature
➢ The more stable form dominates in equilibrium
➢ Interconvertable in solution
➢ Usually differs in position of H atom at A carbon
➢ Interconversion of tautomers can be catalyzed
➢ Can’t be separated in solution at normal temperature
➢ The more stable form dominates in equilibrium
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Tautomerism Example
➢ If we consider the simple definition of tautomerism then it is described as a type of isomerism wherein the
isomers interchange into or between one another very
easily in order to exist together in equilibrium. During the
reaction, there is proton transfer occurs in an intramolecular fashion
isomers interchange into or between one another very
easily in order to exist together in equilibrium. During the
reaction, there is proton transfer occurs in an intramolecular fashion
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Type-1 Keto-Enol tautomerism
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Cyclohexanone and cyclohexanol
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Type-1 Keto-Enol tautomerism
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Molecular Representation of Keto-Enol Tautomerism
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Molecular Representation of Keto-Enol Tautomerism
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Molecular Representation of Keto-Enol Tautomerism
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Amino-Imino Tautomerism
Example cyclohex-1-en-1-amine and cyclohexanimine
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cyclohex-1-en-1-amine and cyclohexanimine
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Lactam
type of amide formally derived from an amino alkanoic acid
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Lactim
cyclic carboximidic acid consisting of an endocyclic carbon-nitrogen double bond
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Type 3-Lactam-Lactim Tautomerism
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Type 3-Lactam-Lactim Tautomerism
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Type 3-Lactam-Lactim Tautomerism
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Cyano-Isocyano Tautomerism
➢ Type-4 Cyano-isocyano
➢ Example: Cyanic acid and isocyanic acid
➢ Example: Cyanic acid and isocyanic acid
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Cyanic acid and isocyanic acid
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Tautomerism in Non-Carbonyl Compounds
➢ Most of the non-carbonyl systems are available as a
mixture of tautomers
mixture of tautomers
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Tautomerism in Non-Carbonyl Compounds
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Tautomeric Form of Unsymmetrical Ketones
➢ In symmetric form, there is only one form of tautomer.
➢ But for an unsymmetrical form, there can be two.
➢ But for an unsymmetrical form, there can be two.
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Tautomeric Form of Unsymmetrical Ketones
