Question: (a) Only a small amount (less than 0.01%) of the enol form of diethyl malonate is present at equilibrium. Write a structural formula for this

(a) Only a small amount (less than 0.01%) of the enol form of diethyl malonate is present at equilibrium. Write a structural formula for this enol.
(b) Enol forms are present to the extent of about 8% in ethyl acetoacetate. There are three constitutionally isomeric enols possible. Write structural formulas for these three enols.
Which one do you think is the most stable? The least stable Why?
(c) Bromine reacts rapidly with both diethyl malonate and ethyl acetoacetate. The reaction is acid-catalyzed and liberates hydrogen bromide. What is the product formed in each reaction?

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a Both carbonyl groups of diethyl malonate are equivalent and so enolization can ... View full answer

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