Diels-Alder Reaction Practice Problems

Even though the methyl group does not donate by resonance, the given reaction exhibits the same regiochemistry. Explain this result.

The illustration below exemplifies a Diels-Alder reaction that results in a lone product regardless of whether the attack of the diene is from the bottom or the top. Draw the product that is formed when the diene approaches from the bottom. Verify that the product is the same as when the diene approached from the top. What is unique about the product that makes this possible?

Draw the product(s) of the following Diels-Alder reaction. Explain the formation of the product(s) by suggesting a mechanism.

Show the mechanism of the given Diels-Alder reaction. Which regioisomer will form, the 1,3- or 1,4-product? 

Draw the expected product of the following Diels–Alder cycloaddition reaction.

Similar to the Diels-Alder reaction, the ene reaction substitutes one π bond in the diene with a C—H bond. Provide the mechanism for the reaction shown. Don't forget to label the hydrogens and number the carbons in the final product. Also, keep track of the new and broken bonds.

Explain why diene B does not react in a Diels-Alder reaction with the dienophile maleic anhydride, however, diene A engages in a fast and efficient Diels-Alder reaction.

From the Diels–Alder reaction shown below, draw its resulting product. 

From the Diels–Alder reaction shown below, draw its resulting product. 

From the Diels–Alder reaction shown below, draw its resulting product. 

In the Diels-Alder reaction shown below, a Lewis acid-Lewis base complex forms with the dienophile. Predict what will happen to the rate of the reaction and justify your answer.

In the following reaction, when the diene approaches the dienophile from the top, only one product is formed. Draw the product. 

The first step of the following series of reactions is Stille coupling. In a basic solution, the product (A) of the first step tautomerizes to produce compound B, and compound B is immediately converted to compound C.

(a) Draw the structure of compound A.

(b) Propose a mechanism for the formation of compound B from compound A.

When (2E,4E)-hexa-2,4-diene and (2E,4E)-3,4-dimethylhexa-2,4-diene are heated together, multiple different Diels-Alder products can be produced. Identify the products, disregarding stereochemistry.

Illustrate the steps of the given reaction:

Draw the final products of the given chemical reaction.

Provide a general principle that may be utilized in anticipating the main product of a Diels-Alder reaction involving an alkene that has a substituent that can withdraw electrons and a diene that has a substituent that, based on its placement, can donate electrons through resonance.

The two reactants in this Diels-Alder reaction are used to create the A ring of progesterone (a steroid). What results from this reaction?

The two reactants in this Diels-Alder reaction are used to create the C ring of Androgen (a steroid). What results from this reaction?

How is the rate of a Diels-Alder reaction affected when a diene contains an electron-donating substituent?

How is the rate of a Diels-Alder reaction affected when a dienophile contains an electron-donating substituent?

How is the rate of a Diels-Alder reaction affected when a diene contains an electron-withdrawing substituent?

Draw the final products of the given chemical reaction.

In the following Diels–Alder reaction, predict the final products. Include stereochemistry, if applicable, .

Show the product(s) of the following reaction. Explain how the product(s) is/are formed by showing the mechanism.

Draw the plausible products for the following reactions. The suitable stereochemistry of the product must be shown.

The intramolecular Diels-Alder reaction is a notable version of such a reaction in which the diene and the dienophile are in the same molecule. This type of Diels-Alder reaction forms two new rings. If the following molecules undergo Diels-Alder reactions, draw the compound produced, including its stereochemistry. [Note: Lewis acid catalysts are utilized. However, we will ignore this in this case.]

Predict the plausible product for the Diels–Alder reaction given below.

The given pairs of structures are reactants in Diels-Alder reactions. Draw their charge-separated resonance forms.

Draw the structures of the major products in the given chemical reactions.

Determine the structure of the major products in the given chemical reaction. Show stereochemistry if applicable.

Refer to the concerted reactions shown below. Identify the reaction with a more stable transition state and justify your answer.

Benzyne is a very reactive dienophile due to its unstable triple bond. Predict what product will form when benzyne reacts with 2,3-dimethylenesuccinic acid.

An important type of the Diels-Alder reaction is the intramolecular reaction, where the diene and dienophile are connected together. This Diels–Alder reaction results in the formation of two new rings. What is the product for the intramolecular Diels-Alder reaction of the following compound? For this problem, the use of Lewis acid catalysts can be disregarded.

An important type of the Diels-Alder reaction is the intramolecular reaction, where the diene and dienophile are connected together. This Diels–Alder reaction results in the formation of two new rings. Determine the product for the intramolecular Diels-Alder reaction of the compound shown below. For this problem, the use of Lewis acid catalysts can be disregarded.

Predict the major product when the ethoxy group is attached to the C2 of molecule A instead of C1

Explain whether the products obtained from the reaction of 1,3-butadiene with trans-1,2-dibromoethene are optically active or not; Provide reasoning for your answer.

Explain why or why not the compounds produced from the reaction of 2,3-dimethylbuta-1,3-diene with cis-1,2-dibromoethene are optically active.