Problems

 

1. What happens when bromine is added to benzene? How does it differ from the reaction of DCl with benzene when a Lewis acid like AlCl₃ is present?
   
   
2. 2,3-Diphenylcyclopropenone forms an addition product with HBr that exhibits the properties of an ionic salt. Suggest a structure for this product and a reason for its existence as a stable entity.
   
   
3. Azulene is a deep-blue hydrocarbon with resonance energy of 205 kJ/mol (49 kcal/mol). Azulene has ten π electrons, so it might be considered as one large aromatic ring. Its electrostatic potential map shows one ring to be highly electron-rich (red) and the other to be electron-poor (blue). The dipole moment is unusually large (1.0 D) for a hydrocarbon. Show how this charge separation might arise.
   

 

 

Text Books

 

•  C. M. Loudon , Organic Chemistry , Oxford University Press, New Delhi, 2002.

•  R. R. Morrison, R. N. Boyd and S. K. Bhattacharjee, Organic Chemistry , Dorling Kindersley (India) Pvt. Ltd, New Delhi, 2011.