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Which of the following should be stabilized by resonance and why?

Which of the following should be stabilized by resonance and why?

Introductory Chemistry: An Active Learning Approach
Introductory Chemistry: An Active Learning Approach
6th Edition
ISBN:9781305079250
Author:Mark S. Cracolice, Ed Peters
Publisher:Mark S. Cracolice, Ed Peters
Chapter21: Organic Chemistry
Section: Chapter Questions
Problem 21.4TC
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Which of the following should be stabilized by resonance and why?

**Question 8** Which of the following should be stabilized by resonance and *why*? **Diagram Description:** The image contains two chemical structures labeled (a) and (b). - **Structure (a):** This structure depicts a cyclohexene ring with a pentagon containing a double bond and a nitrogen atom in its structure, indicative of a pyrrole ring. - **Structure (b):** This structure includes a cyclohexene connected to a six-membered ring (benzene) with a double bond, which is connected to another five-membered ring containing a nitrogen atom. **Analysis:** To determine which structure is stabilized by resonance, evaluate the presence of conjugated systems and delocalizable electrons, especially in relation to nitrogen’s lone pair and potential overlap with adjacent π bonds.
Transcribed Image Text:**Question 8** Which of the following should be stabilized by resonance and *why*? **Diagram Description:** The image contains two chemical structures labeled (a) and (b). - **Structure (a):** This structure depicts a cyclohexene ring with a pentagon containing a double bond and a nitrogen atom in its structure, indicative of a pyrrole ring. - **Structure (b):** This structure includes a cyclohexene connected to a six-membered ring (benzene) with a double bond, which is connected to another five-membered ring containing a nitrogen atom. **Analysis:** To determine which structure is stabilized by resonance, evaluate the presence of conjugated systems and delocalizable electrons, especially in relation to nitrogen’s lone pair and potential overlap with adjacent π bonds.
Expert Solution
Step 1

Aromatic compounds are those which has (4n+2)π electron system i.e. follows Huckel rule. 

  • planar 
  • cyclic 
  • conjugation system 

Antiaromatic compounds follows 4n rule or we can say they have 4,8,12π electrons 

 

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