Problem 572

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.

This is an S_N1 reaction, but the carbocation is special because it's allylic.

If the Br^- nucleophile attacks the 3º resonance form, the 1,2 product is formed. (This is the product that would have formed if resonance was not involved.)

If the Br^- nucleophile attacks the 2º resonance form, the 1,4 product is formed.

Problem Details

MendelSet practice problem # 572 submitted by Matt on July 8, 2011.

Subject: Organic Chemistry

Subject Topic(s): Conjugated Dienes and the Allylic Position (Kinetic vs Thermodynamic Control)

Question Type: Mechanism (show a mechanism using curved arrows..)

Keyword(s): SN1 mechanism, conjugate addition, allylic position

Problem 572

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