ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<
ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<
2nd Edition
ISBN: 9781118872925
Author: Klein
Publisher: JOHN WILEY+SONS INC.CUSTOM
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Chapter 17.9, Problem 23ATS
Interpretation Introduction

Interpretation:

For the given compound, the structure, the product formed upon conrotatory ring opening and the products formed upon disrotatory ring opening are needed to be determined and the condition of conrotatory ring opening, the practically formed product upon disrotatory ring opening are to be explained.

Concept introduction:

  • Electrocyclic reaction is a concerted cyclization reaction of conjugated polyenes (π-system), in which one π-bond is converted into an σ-bond and remaining π-bonds shift their positions. Thereby the newly formed σ-bond connects the two ends of π-system to form a ring.
  • The mechanism for reverse of Electrocyclic reaction is drawn by using arrows representing the conversion of σ-bond to π-bond and the shifting of π-bonds in the π-system of a cyclic alkene.
  • The mechanism for reverse of Electrocyclic reaction is drawn by using arrows representing the conversion of σ-bond to π-bond and the shifting of π-bonds in the π-system of a cyclic alkene.
  • The reaction conditions (thermal or photochemical) controls the product in such a way that the rotation for end lobes (ring closure) of the HOMO of conjugated (π-system) polyene.
  • According to Woodward-Hoffmann rule for thermal and photochemical Electrocyclic reactions,
π-systems Thermal Photochemical
4- π-electrons Conrotatory Disrotatory
6- π-electrons Disrotatory Conrotatory

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Chapter 17 Solutions

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