Warning: foreach() argument must be of type array|object, bool given in /var/www/html/web/app/themes/studypress-core-theme/template-parts/header/mobile-offcanvas.php on line 20

Write a general rule that can be used to predict the major product of a Diels–Alder reaction between an alkene with an electron-withdrawing substituent and a diene with a substituent that can donate electrons by resonance depending on the location of the substituent on the diene.

Short Answer

Expert verified
  1. EDG in C-1 of diene produces ortho product.
  2. EWG in C-2 of diene produces para product.
  3. EDG in alkene increases in reaction rate.

Step by step solution

01

Definition of Diels Alder reaction

Diels Alder reaction is a pericyclic reaction where a diene and dienophile reacts to form a cyclic entity. This reaction is a reversible reaction. At high temperature, the cyclic compound breaks to get back the reactants.

02

General rule

In a general manner, either HOMO of alkene and LUMO of dienophile or HOMO of dienophile and LUMO of alkene combination carry out the reaction.

For a faster reaction, energy of HOMO should be higher and LUMO should be lower. So, an electron donating group on HOMO and electron withdrawing group on LUMO can increase the reaction rate.

If energetically diene is HOMO and dienophile or alkene is LUMO, electron withdrawing group (EWG) on alkene and electron donating group (EDG) on diene can increase the reaction and the position of the group on diene and dienophile can predict the product.

When the EDG is in C-1 position of diene:

In this condition, ortho product will be formed

When the EDG is in C-2 position of diene:

In this condition, para product will be formed.

In case of alkene, EWG increases the reaction rate by decreasing the energy of LUMO and the attack will be on that carbon where EWG is attached. The above two reactions has EWG in alkene in EDG in diene.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

See all solutions

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free