When 2,4-dinitrochlorobenzene is treated with sodium hydroxide at 100°C followed by protonation ________.
A) 2,4-dinitrophenol is formed via an addition-elimination nucleophilic aromatic substitution mechanism
B) 2,4-dinitrophenol is formed via an elimination-addition nucleophilic aromatic substitution mechanism
C) 3,5-dinitrophenol is formed via an elimination-addition nucleophilic aromatic substitution mechanism
D) 3,5-dinitrophenol is formed via an electrophilic aromatic substitution mechanism
E) 2,4-dinitrophenol is formed via an electrophilic aromatic substitution mechanism

Question

Quizplus · Accepted Answer

Treatment with sodium hydroxide at high temperature (100°C) is indicative of a nucleophilic substitution reaction taking place. Additionally, the starting material is a halogen-substituted aromatic compound, which often undergo nucleophilic aromatic substitution reactions. An addition-elimination mechanism involves attack of the hydroxide nucleophile on the electrophilic carbon of the chloro group, followed by protonation to form the final product. This mechanism is consistent with the formation of 2,4-dinitrophenol.

When 2,4-Dinitrochlorobenzene Is Treated with Sodium Hydroxide at 100°C Followed