Complete the drawing of the product that the Diels-Alder reaction, skipping stereochemistry. The Diels- Alder reaction in between butadiene and also dimethyl maleatc yields a ring structure, as presented in the product listed below Complete the framework by drawing any absent bonds and indicating the stereochemistry that the brand-new stereocenters.

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The principle used to solve this inquiry is to attract the framework of the product in the Diels-Alder reaction of the given substrates. The cycloaddition reaction of diene v a dienophile to offer a cyclic adduct is known as Diels-Alder reaction. The stereo chemistry of the product in the Diels-Alder reaction relies on the stereochemistry of the change state.

Diels-Alder reaction is the <4+2> cycloaddition reaction the conjugated diene v an alkene or an alkyne with electron withdrawing team to provide six-membered rings. The product is created by the concerted device in which movement of 3 pairs of electron takes place. For example,


The stereochemical demands of Diels-Alder shift state:

Diels-Alder reaction is a concerted process so the change state determines the stereochemistry that the product. So the change state relies on the adhering to requirements.

1) s-cis construction of the diene is compelled for Diels-Alder reaction because it allows the preferably overlap in between end p-orbitals the diene through those that dienophile.

2) Syn enhancement takes ar in Diels-Alder reaction therefore the substituents on diene and also dienophile which room on the exact same side will be cis in the product.

3) Endo rule: The electron-withdrawing in dienophile with p-orbitals method one of central carbon atom (C2 or C3) the diene, i beg your pardon is called as secondary overlap, it stabilizes the shift state. Because of this reason, the electron-withdrawing teams occupy the place which is closest come the main carbon atom (C2 or C3) the diene and the position is called as endo position. This dominance is dubbed as endo rule.



The frameworks of given diene and dienophile room as follows:


In the over structurtes, diene is in s-cis kind which is required condition for Diels-Alder reaction. The dienophile is one alkyne substrate with

as electron withdrawing group. Thus, the <4+2> cycloaddition of the over diene and dienophile offers substituted cyclohexa-1,4-diene together product. The product of the Diels-Alder reaction is displayed below.

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The structures of given diene and also dienophile room as follows:


In the above structurtes, diene is in s-cis type which is required problem for Diels-Alder reaction. The electron withdrawing team in dienophile is

group therefore it will occupy the endo position in the product follow endo rule. Therefore, Diels-Alder reaction the the offered staring materials gives substituted cyclohexene together product which is shown listed below with stereochemistry.


Ans: component A

The framework of the product that the Diels-Alder reaction is presented below.


Part B

The framework of the product that the Diels-Alder reaction in addition to the stereochemistry is displayed below.