1. (4 pts) As you know, a major feature of amines is their basicity. Arrange the three amines shown in the box on the basis of their relative basicity by placing the letter of each structure on the appropriate line.

Most basic = __B__ > __C__ > __A__ = Least basic

Using the molecule you chose as least basic, explain why you made this choice, using at least two resonance structures (not including the starting structure shown in the box) and only one sentence. If you write more than one sentence, only first one will be read and graded.

In aniline (A), the nitrogen's lone electron pair is delocalized into the ring and thus is less available than in B; in C, the methoxy group adds electron density, so increases basicity over A.

---

2. (6 pts) Complete the following reactions. Some transformation(s) may require more than one step.