Chapter 3, Problem 31EQ

The reaction just described is reversible. Deprotonation of the conjugate acid of an organic base by water provides another example of simultaneous making and breaking of sigma bonds. Thus, in the deprotonation of anilinium ion by water, the base is water, which has unshared electrons on the ________ atom. The acid is ________ ion. A pair of ________ electrons on the oxygen atom of water is pushed toward the ________ atom. Simultaneously, the pair of ________ electrons between the hydrogen and ________ atom of the anilinium ion is pushed toward the ________ atom. Thus, the oxygen- ________ sigma bond is made and a hydrogen- ________ sigma bond is broken. The nitrogen atom, which possessed a positive charge, is now ________, and the oxygen atom, which was neutral, now possesses a formal ________ charge.