conjugate addition

MS 909 - Conjugated Dienes and the Allyl Position Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 10

Keywords: allylic position, conjugate addition

Description: Covers topics related to the allyl position and conjugated dienes:

  • Allyl cation, anion, and radical resonance forms
  • What conjugated dienes can or can't undergo Diels-Alder reactions
  • Allylic brominations using N-bromosuccinimide (NBS)
  • 1,2 and 1,4 additions (thermodynamic vs kinetic conditions)

Total Problems: 4

Problem # 581

Draw all products for the two reactions below.

The allylic alkene gives two products- the 1,2 product, and the 1,4 product. 

However, the benzylic alkene only gives the one product (analogous to the 1,2 product), instead of multiple products (like the 1,4 product, 1,6 product, and 1,8 product). Why is this the case?

Problem # 572

Let's work through a conjugate addition problem.

Write out the mechnanism for the formation of the 1,2 and 1,4 products of the reaction below.

Problem # 522

Let's work through a 1,2 and 1,4 addition. Draw the structures for each of the species in the six boxes below. Also draw curved arrows to show electron movement.