Enolate Practice Problems

The following two reactions show the alkylation of a ketoester under two different conditions. Draw the structures of A and B and indicate whether each of these products is formed under kinetic control or thermodynamic control.

Predict the product of the reaction given below.

Draw the deuterated product of the reaction given below.

Determine which of the following compounds would be fully deprotonated by a solution of sodium ethoxide in ethanol.

Draw the important resonance forms for the following ketone when the α-carbon atom of the ketone is deprotonated, giving an enolate ion.

(i) pentan-3-one

(ii) cyclohexanone

The aldol reaction is stereospecific and proceeds via the Zimmerman–Traxler transition state depicted below.

(a) Illustrate the arrow-pushing mechanism for step A and step B.

(b) Explain why this mechanism is favorable.

Draw the enolate(s) formed by the treatment of the following molecule with a base.

Draw the significant resonance structures of the enolate that result from the deprotonation of methyl 2-cyanobutanoate with a strong base.

Provide the significant resonance structures of the enolate that forms from the deprotonation of 1-cyclopentyl-2-nitroethanone with a strong base.

Given the following alkenone.

(i) Identify the most acidic hydrogens in the molecule.

(ii) When the most acidic hydrogen is removed, show structures of the significant resonance contributors of the resulting carbanion.

Given the following aldehyde below.

(i) Indicate the most acidic hydrogens in the molecule.

(ii) When the most acidic hydrogen is removed, draw the significant resonance contributors of the resulting carbanion.

Provide the significant resonance structures of the enolate that result from the deprotonation of dimethyl malonate.

Give the significant resonance structures of the possible enolate(s) that result from the deprotonation of the compound shown below.

Provide the significant resonance structures of the possible enolate(s) that result from the deprotonation of the compound shown below.

Draw the significant resonance structures of the possible enolate(s) that result from the deprotonation of the compound shown below.

Draw the resonance structures of the enolate ions produced by the deprotonation of the below-given compounds through a base.
a. cyclopentane-1,3-dione
b. methyl acetoacetate 

A mixture of cis and trans isomers is obtained by dissolving trans-5-bromo-2-methylcyclohexanone in aqueous NaOH. Show the mechanism of this isomerization. 

For the following compound:

(i) Indicate the most acidic hydrogen in the molecule.

(ii) Upon the removal of the most acidic hydrogen, draw the significant resonance contributors of the resultant carbanion.

Consider the molecule below:

(i) Indicate the most acidic hydrogen in the molecule.

(ii) Draw the significant resonance contributors of the resultant carbanion obtained upon the removal of the most acidic hydrogen.

The ketone shown below can form two different enols.

Draw the structures of these two enols. Which of these enols is more stable?