Question

Show how to carry out the following transformation in the highest yield possible. Select the appropriate reagents and draw the correct organic product at each step. The options for the reagent in each step are:
1. H+/H20/heat 2. OH-, OR
1. Fe/HCl 2. NaOH, OR
HNO3/H2SO4
(Also, the entry in the first box is not necessarily correct...I'm just lost from where to go from there.)

PLEASE help! Thanks!

Answer 1

Concepts and reason

In this question the concept used is the conversion of benzene to 4- nitro aniline or para nitro aniline. This is an example of electrophilic aromatic substitution reaction. Electrophilic aromatic substitution reactions are the reactions in which an atom attached to the aromatic system is replaced by an electrophile.

Fundamentals

Benzene is a $\pi$ electron system and is resonance stabilized. It undergoes electrophilic substitution reactions to give monosubstituted benzene. The electrophilic substitution reactions are carried out in presence of catalysts that help in generation of electrophiles (electron deficient species).

Nitration of benzene to nitro-benzene takes place as already shown in the problem.

Reduction of Nitrobenzene to Aniline. as follows:

Treatment of aniline with acetoacetate to produce N-acetyl aniline as follows:

Nitration of N- acetyl aniline to produce para-nitroacetyl aniline as follows:

Hydrolysis of para-nitro acetyl aniline to give the desired product para nitro aniline in 95% yield as follows:

Ans: