The structures of the two Diels-Alder adducts formed when isoprene (2-methyl-1, 3-butadiene) reacts with ethyl propenoate are to be given and why a mixture of products is formed is to be explained. Concept introduction: In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1, 4 addition of the dienophile into the diene through a cyclic transition state. These reactions occur rapidly with dienophiles having electron withdrawing substituent groups in conjugation with the double bond and if the diene adapts a s-cis conformation during the reaction. To give: The structures of the two Diels-Alder adducts formed when isoprene (2-methyl-1, 3-butadiene) reacts with ethyl propenoate and to explain why a mixture of products is formed.

Question

When anthracene is added to the reaction of chlorobenzene with concentrated NaOH at 350 °C, an interesting Diels–Alderadduct of formula C20H14 results. The proton NMR spectrum of the product shows a singlet of area 2 around d 3 and abroad singlet of area 12 around d 7. Propose a structure for the product, and explain why one of the aromatic rings ofanthracene reacted as a diene

Answer 1

Question

Chapter 14.SE, Problem 36AP

Interpretation Introduction

Interpretation:

The structures of the two Diels-Alder adducts formed when isoprene (2-methyl-1, 3-butadiene) reacts with ethyl propenoate are to be given and why a mixture of products is formed is to be explained.

Concept introduction:

In Diels-Alder reaction, a dienophile reacts with a diene to yield a cyclic adduct. The reaction takes place through 1, 4 addition of the dienophile into the diene through a cyclic transition state. These reactions occur rapidly with dienophiles having electron withdrawing substituent groups in conjugation with the double bond and if the diene adapts a s-cis conformation during the reaction.

To give:

The structures of the two Diels-Alder adducts formed when isoprene (2-methyl-1, 3-butadiene) reacts with ethyl propenoate and to explain why a mixture of products is formed.

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