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

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy
Section14.SE: Something Extra
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When anthracene is added to the reaction of chlorobenzene with concentrated NaOH at 350 °C, an interesting Diels–Alder
adduct of formula C20H14 results. The proton NMR spectrum of the product shows a singlet of area 2 around d 3 and a
broad singlet of area 12 around d 7. Propose a structure for the product, and explain why one of the aromatic rings of
anthracene reacted as a diene

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