Chapter 21, Problem 9PP

PRACTICE PROBLEM

1-Fluoro-2,4-dinitrobenzene is highly reactive toward nucleophilic substitution through an S_NAr mechanism. (In Section 24.5B we shall see how this reagent is used in the Sanger method for determining the structures of proteins.) What product would be formed when 1-fluoro-2,4-dinitrobenzene reacts with each of the following reagents?

(a) $\text{EtONa}$

(b) ${\text{NH}}_{\text{3}}$

(c) ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{NH}}_{\text{2}}$

(d) $\text{EtSNa}$