Tautomerization: Videos & Practice Problems

Draw the tautomeric forms of adenine and thymine with aromatic hydroxy and amino groups. 

Draw the structure of the enol tautomer of the compound given below.

Draw the structures of the enol tautomers of the following compound and identify the more stable one.

Show the product of acid-catalyzed tautomerization of 2,4-dimethylpentan-3-one.

The following reaction shows an acid-catalyzed rearrangement of a β,γ-unsaturated carbonyl compound to a more stable α,β-unsaturated compound. Draw a mechanism for this rearrangement.

Identify the pair that represents keto-enol tautomers.

Propose the acid-catalyzed mechanism of conversion of (R)- into (S)-3,5-dimethylhexan-2-one.

Due to their instability, vinyl alcohols undergo rapid isomerization to produce carbonyl compounds. Draw a mechanism for the reaction shown below.

Propose a suitable mechanism for the reaction given below.

Propose a suitable mechanism for the reaction given below.

Determine the major products of the reaction between the given structure and PCl₃.

Draw the enol tautomer of cyclohexanone.

The following ketone can form two different enols.

Suggest a suitable mechanism to show how the first enol shown above is formed under acidic conditions.

The following ketone can form two different enols.

Suggest a suitable mechanism to show how the first enol shown above is formed under basic conditions.

The following ketone can form two different enols.

Suggest a suitable mechanism to show how the second enol shown above is formed under basic conditions.

The following ketone can form two different enols.

Suggest a suitable mechanism to show how the second enol shown above is formed under acidic conditions.