Nucleophilic Aromatic Substitution Practice Problems

Draw a suitable mechanism for the reaction given below.

Predict the product of the reaction given below.

Identify the reaction mechanisms involved in the following reactions.

Compare the resonance contributors for the intermediate that forms when a nucleophile reacts with i) o-chloronitrobenzene and ii) m-chloronitrobenzene. Explain why nucleophiles do not react at the meta position.

Propose a mechanism to show how a mixture of meta and para-substituted products are obtained from the reaction of p-chlorocumene (1-chloro-4-isopropylbenzene) with sodium hydroxide at 350 °C.

Draw the mechanism for the reactions given below.
a. 2,4-dinitrochlorobenzene + ammonia
b. p-nitrobromobenzene + hydrazine (excess)

Draw the mechanism for the reactions given below.
a. 2,4-dinitrobromobenzene + sodium methoxide
b. 2,4-diethylchlorobenzene + sodium hydroxide + heat

Draw a plausible mechanism for the reaction between 4-chloropyridine and ethoxide ion. In your proposed mechanism, illustrate how the intermediate is stabilized by delocalization of the charge onto the nitrogen atom.

Explain how a nitro substituent on a benzene ring can facilitate a nucleophilic attack on the ortho and para positions.

Consider the following nucleophilic aromatic substitution reaction: 

What is the structure of the product formed?

Propose a mechanism for the rearrangement shown below: