Which position is the α position of a carbonyl-containing molecule?

Phenylacetone can form two different enols.

(c) Propose mechanisms for the formation of the second enol in base.

Cytosine, uracil, and guanine have tautomeric forms with aromatic hydroxy groups. Draw these tautomeric forms.

Draw the enol tautomer for cyclopentanone

Which of the following pairs are keto–enol tautomers?

d.

e.

A β-ɣ-unsaturated carbonyl compound rearranges to a more stable conjugated ⍺,β-unsaturated compound in the presence of either acid or base. b. Propose a mechanism for the acid-catalyzed rearrangement.

Using cyclopentanone as the reactant, show the product of a. acid-catalyzed keto–enol interconversion.

Draw the enol tautomers for each of the following compounds. For compounds that have more than one enol tautomer, indicate the one that is more stable.

f.