Chapter 16, Problem 44PP

Interpretation Introduction

Interpretation:

For the given reaction of a triene with excess of maleic anhydride, the product formed with molecular formula ${\text{C}}_{\text{14}}{\text{H}}_{\text{12}}{\text{O}}_{\text{6}}$ should be determined.

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 $\left[\text{4+2}\right]\text{ cycloaddition}$ 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.
• The mechanism of the ring formation in the Diels-Alder reaction is drawn by using three arrows representing the shifting of π-bonds in the two π-systems in a clockwise or counter clockwise fashion, so that the ring formation will take place.
• If the first Diels-Alder product is a diene, then successive Diels-Alder reaction can occur. It is depending upon the quantity dienophile presented in the reaction. 

To draw: the product formed with molecular formula ${\text{C}}_{\text{14}}{\text{H}}_{\text{12}}{\text{O}}_{\text{6}}$ for the given reaction.