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Chapter 3: Problem 83

A compound having the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{Br}_{2}\) when heated with nitrating mixture gave two isomers of the mononitro derivative. The compound is (a) 1,2 -Dibromobenzene (b) 1,3 -Dibromobenzene (c) 1,4 -Dibromobenzene (d) either 1,3 or 1,4 -dibromobenzene

Short Answer

Expert verified
Answer: 1,3-Dibromobenzene

Step by step solution

01

Identify potential nitrating positions for each option

To determine which compound forms two mononitro-derivative isomers, we will evaluate each option in terms of where nitration can occur on the dibromobenzene compound.
02

Analyze option (a) 1,2-Dibromobenzene for nitration positions

In 1,2-Dibromobenzene, the bromine atoms are at carbon positions 1 and 2. The nitration can occur at position 3 or 5. Due to symmetry, the nitration at positions 3 and 5 would produce the same mononitro-derivative structure. So, only one mononitro-derivative isomer would form for 1,2-Dibromobenzene. Hence, option (a) is incorrect.
03

Analyze option (b) 1,3-Dibromobenzene for nitration positions

In 1,3-Dibromobenzene, the bromine atoms are placed at carbon positions 1 and 3. The nitration can occur at position 2 and also at position 5, producing two distinct mononitro-derivative structures. Therefore, two mononitro-derivative isomers can be formed for 1,3-Dibromobenzene.
04

Analyze option (c) 1,4-Dibromobenzene for nitration positions

In 1,4-Dibromobenzene, the bromine atoms are at carbon positions 1 and 4. The nitration can occur only at position 3, and not at any other positions. So, only one mononitro-derivative isomer would form for 1,4-Dibromobenzene. Hence, option (c) is incorrect.
05

Analyze option (d) either 1,3 or 1,4-Dibromobenzene for nitration positions

We have already analyzed options (b) and (c) in step 3 and step 4. Since option (d) is just a combination of these options, it is not a singular compound and, therefore, is not a valid answer.
06

Select the correct option

Based on our analysis in Steps 3 and 5, only option (b) 1,3-Dibromobenzene forms two mononitro-derivative isomers when heated with a nitrating mixture. Thus, the correct option is (b) 1,3-Dibromobenzene.

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Most popular questions from this chapter

Identify the wrong statement. (a) Phenols are stronger acids than alcohols, but weaker than carboxylic acids (b) Phenols, being stronger acids, are soluble in aqueous \(\mathrm{NaOH}\) solution and in saturated \(\mathrm{NaHCO}_{3}\) solution. (c) Phenols are acidic because of resonance stabilization of the phenoxide ion formed by ionization. (d) The \(\mathrm{pK}_{\mathrm{a}}\) of phenol is about \(10 .\)

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In which of the following reactions, Ethylbenzene is not formed as the final product? (a) \(\mathrm{C}_{6} \mathrm{H}_{6}+\mathrm{CH}_{2}=\mathrm{CH}_{2} \stackrel{\mathrm{H}_{3} \mathrm{PO}_{4}}{\longrightarrow}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Br}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{Br} \underset{\text { ether }}{\stackrel{\mathrm{Na}}{\longrightarrow}}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{3}+\mathrm{CH}_{3} \mathrm{Cl} \stackrel{\mathrm{AlCl}_{3}}{\longrightarrow}\)

\(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCl} \rightarrow \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OCOC}_{6} \mathrm{H}_{5}+\mathrm{HCl}\). This reaction is called (a) Schotten-Baumann reaction (b) Perkin reaction (c) Schmidt reaction (d) Claisen reaction

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