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Chapter 27: Problem 56

Predict the products of the monobromination of (a) \(m\) -dinitrobenzene; (b) aniline; (c) \(p\) -bromoanisole.

Short Answer

Expert verified
The products of the monobromination will be 1-bromo-3,5-dinitrobenzene, ortho-bromoaniline and 2,4-dibromoanisole, respectively.

Step by step solution

01

Monobromination of m-Dinitrobenzene

m-Dinitrobenzene has two nitro groups which are meta to each other. Nitro group is a meta-directing group (meaning that it directs incoming groups to the position meta to it) and is electron withdrawing by inductive and resonance effect. As such, the position it leaves the most electron density at is the position meta to it, which is where bromine will add. This would give 1-bromo-3,5-dinitrobenzene as the product.
02

Monobromination of Aniline

Aniline, which is a benzene ring with an amino (-NH2) group, will react differently. The amino group donates electrons through resonance to the benzene ring (due to the unshared pair on the nitrogen), activating the ortho and para positions. So bromine will preferably add to either available ortho position (since para position is occupied), giving ortho-bromoaniline as the final product.
03

Monobromination of p-Bromoanisole

p-Bromoanisole is a benzene ring with a methoxy (-OCH3) and bromine (-Br) group on the para positions. The methoxy group is an activating group and will enhance reactivity of the aromatic ring by donating electron density. It will direct incoming bromine to the ortho or para positions (relative to it). The para positions are occupied, the available ortho positions will accept bromine to give 2,4-dibromoanisole.

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Most popular questions from this chapter

A sample of \((S)-\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{Cl}\) is hydrolyzed by water, and the resulting solution is optically inactive. (a) Write the formula of the product. (b) By which nucleophilic substitution reaction mechanism does this reaction occur?

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