Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 25, Problem 41P
Interpretation Introduction

Interpretation: The preparation of X from a constitutional isomer by a series of [2+2] cycloaddition reaction is to be predicted.

Concept introduction: Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds.

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How can X be prepared from a constitutional isomer by a series of [2 + 2] cycloaddition reactions? Interest in molecules that contain several cyclobutane rings fused together has been fueled by the discovery of pentacycloanammoxic acid methyl ester, a lipid isolated from the membrane of organelles in the bacterium Candidatus Brocadia anammoxidans. The role of this unusual natural product is as yet unknown.
How can X be prepared from a constitutional isomer by a series of [2 + 2]cycloaddition reactions? Interest in molecules that contain severalcyclobutane rings fused together has been fueled by the discovery ofpentacycloanammoxic acid methyl ester, a lipid isolated from themembrane of organelles in the bacterium Candidatus Brocadiaanammoxidans. The role of this unusual natural product is as yetunknown.
One compound that contributes to the “seashore smell” at beaches in Hawai‘i is dictyopterene D', a component of a brown edible seaweed called limu lipoa. Hydrogenation of dictyopterene D' with excess H2 in the presence of a Pd catalyst forms butylcycloheptane. Ozonolysis with O3 followed by (CH3)2S forms CH2(CHO)2, HCOCH2CH(CHO)2, and CH3CH2CHO. What are possible structures of dictyopterene D'?
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