ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
4th Edition
ISBN: 9781119761105
Author: Klein
Publisher: WILEY
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Chapter 16, Problem 75IP
Interpretation Introduction

Interpretation:

A mechanism should be proposed for the given transformation.

Concept introduction:

  • Cycloaddition reaction is a concerted addition reaction of two reactants to form a ring; in which two π-bonds are converted to two σ-bonds.
  • Diels-Alder reaction is a [4+2] cycloaddition reaction, in which a π-system having four atoms (diene) and a π-system having two atoms (dienophile) are undergoing in cycloaddition reaction and producing a substituted cyclohexene.
  • Retro-Diels Alder reaction of a Diels-Alder product is an inverse process of Diels-Alder reaction. It will give the diene and dienophile used for the Diels-Alder reaction.  
  • The mechanism of the Retro-Diels Alder reaction for the Diels-Alder product is drawn by using three arrows representing the shifting of one-π-bond and conversion of two σ-bonds to two π-bonds in the Diels-Alder product in a clockwise or counter clockwise fashion, so that the diene and dienophile will form.

To propose: a mechanism for the given transformation.

#assumes the Retro-Diels Alder reaction is involved in the given transformation.

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