Chapter 16, Problem 57P

Rank the aryl halides in each group in order of increasing reactivity in nucleophilic aromatic substitution by an addition–elimination mechanism.

a. chlorobenzene, p-fluoronitrobenzene, m-fluoronitrobenzene

b. $1$-fluoro- $2,4$-dinitrobenzene, $1$-fluoro- $3,5$-dinitrobenzene, $1$-fluoro- $3,4$-dinitrobenzene

c. $1$-fluoro- $2,4$-dinitrobenzene, $4$-chloro- $3$-nitrotoluene, $4$-fluoro- $3$-nitrotoluene