ORGANIC CHEM PRINT STUDY GDE & SSM
ORGANIC CHEM PRINT STUDY GDE & SSM
4th Edition
ISBN: 9781119810650
Author: Klein
Publisher: WILEY
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Chapter 17, Problem 55IP
Interpretation Introduction

Interpretation: For the given cycloheptatrienone and cyclopentadienone, the more partial negative character on the oxygen atom of cycloheptatrienone should be explained.

Concept introduction:

  • A five membered ring will be aromatic if it contains six π electrons. In order to have six π electrons, one of the carbon atoms must possess two electrons. It should be a carbanion.
  • A seven membered ring will be aromatic if it contains six π electrons. In order to have six π electrons in a seven membered ring one of the carbon atom must possess an empty p orbital. This carbocation exhibits a continuous system of overlapping and p orbitals and has six π electrons.
  • Aromatic compounds are more stable than non-aromatic compound
  • Cycloheptatrienone reveals resonance structures with aromatic character
  • Cyclopentadienone reveals resonance structures with  anti-aromatic character

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