Chapter 1.9, Problem DQ

The following structure is called imidazolium. Which of the following statements about imidazolium are true?

1. a. Both nitrogens are sp² hybridized, and the lone pair of electrons is in a 2p orbital.
2. b. The nitrogen on the right is sp³ hybridized, while the nitrogen on the left is sp² hybridized. The lone pair of electrons is in an sp³ hybrid orbital.
3. c. The molecule has an equivalent contributing structure not shown.
4. d. The molecule has no reasonable contributing structures.
   1. 1. Statements a and c are true.
   2. 2. Statements a and d are true.
   3. 3. Statements b and c are true.
   4. 4. Statements b and d are true.