Explain why cyclopentadiene (pKa = 15) is more acidic than pyrrole (pKa = 17) even though nitrogen is more electronegative than carbon?

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter26: Aldol And Claisen Reactions
Section: Chapter Questions
Problem 24E
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  1. Explain why cyclopentadiene (pKa = 15) is more acidic than pyrrole (pKa = 17) even though nitrogen is more electronegative than carbon?

 

  1. Why carboxylic acid with a carbonyl group at 3rd position can be decarboxylated?

 

  1. Differentiate between Aldol and Claisen condensation reaction.

 

  1. Explain why electrophilic aromatic substitution in Pyrrole takes place at C-2 positions whereas, in Pyridine it takes place at C-3 position?

 

 

  1. LDA is the base of choice for carbonyl compound to completely convert into enolate. Why?

 

  1. List the following esters in order of decreasing reactivities towards hydrolysis with reason:

Methyl benzoate, p-cyano methyl benzoate and p-hydroxy methyl benzoate

 

  1. How will you describe whether any compound has been oxidized or reduced? Support your answer with suitable examples.

 

  1. A) Define chemo selective reactions with examples.
  2. B) Give any two conditions where enol tautomer is more stable than keto tautomer.
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