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Question

Identify the compound that exhibits tautomerism:


A

2-Butene

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B

Lactic acid

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C

2-Pentanone

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D

Phenol

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Solution

The correct option is C

2-Pentanone


Lets just first draw the structure of each molecule.

Lactic acid -- CH3-CH(OH)-COOH

Now lets recall the defination of tautomerism.

It is a phenomenon in which a single compound exists in two readily interconvertible structures that differ in the relative position of atleast one atomic nucleus,generally hydrogen.Tautomeric structures are obtained by the simultaneous shift of H atom and double bond at1 and 3 position.That is why it is also called 1,3-shift.It is further called desmotropism or dynamic isomerism or kryptomerism .

This is only possible keto to enol form conversion and one of the necessary conditions for tautumerism is the presence of α-hydrogen

α-hydrogen is present on α- carbon

Therefore these conditions are possible only in option(C)

CH3O||CCH2CH2CH3Keto formCH3OH|C=CHCH2CH3Enol form


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