How will you convert (a) benzene to \(\mathrm{m}\) -bromo iodobenzene? (b) aniline to \(3,5-\) di iodo nitrobenzene?

Short Answer

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Question: Describe the step-by-step synthesis process for converting (a) benzene to m-bromo iodobenzene and (b) aniline to 3,5-di iodo nitrobenzene. Answer: (a) The synthesis process for converting benzene to m-bromo iodobenzene involves two steps: (1) Formation of iodobenzene through an electrophilic substitution reaction with iodine and an oxidizing agent, such as \(\mathrm{HNO}_3\), and (2) Formation of m-bromo iodobenzene by using Friedel-Crafts reaction, where bromine gas (\(\mathrm{Br}_2\)) reacts with iodobenzene in the presence of a Lewis acid catalyst, such as \(\mathrm{AlBr}_3\). (b) The synthesis process for converting aniline to 3,5-di iodo nitrobenzene involves three steps: (1) Formation of nitroaniline via a nitration reaction with a nitrating mixture of concentrated \(\mathrm{HNO}_3\) and concentrated \(\mathrm{H}_2\mathrm{SO}_4\), (2) Formation of 3,5-di iodo nitroaniline by reacting nitroaniline with iodine (\(\mathrm{I_2}\)) and potassium iodide (\(\mathrm{KI}\)) in an aqueous solution, and (3) Conversion of 3,5-di iodo nitroaniline into 3,5-di iodo nitrobenzene by a diazotization reaction followed by a Sandmeyer reaction using sodium nitrite (\(\mathrm{NaNO}_2\)), hydrochloric acid (\(\mathrm{HCl}\)), and copper(I) chloride (\(\mathrm{CuCl}\)).

Step by step solution

01

Formation of iodobenzene

First, we need to form iodobenzene from benzene. This can be done by electrophilic substitution reaction with iodine in the presence of an oxidizing agent, such as \(\mathrm{HNO}_3\). The reaction can be given as: Benzene + \(\mathrm{I_2}\) + \(\mathrm{HNO}_3\) → Iodobenzene + \(\mathrm{H_2O}\) + \(\mathrm{HI}\)
02

Formation of m-bromo iodobenzene

Next, we need to introduce a bromine atom at the meta position of iodobenzene. We can achieve this by using a Friedel-Crafts reaction in which bromine gas (\(\mathrm{Br}_2\)) reacts with iodobenzene under the presence of a Lewis acid catalyst, such as \(\mathrm{AlBr}_3\). The reaction can be given as: Iodobenzene + \(\mathrm{Br}_2\) + \(\mathrm{AlBr}_3\) → m-bromo iodobenzene + \(\mathrm{HBr}\) + \(\mathrm{AlBr}_4^-\) (b) Aniline to 3,5-di iodo nitrobenzene
03

Formation of nitroaniline

First, we need to convert aniline to nitroaniline by a nitration reaction. This can be done by reacting aniline with a nitrating mixture of concentrated \(\mathrm{HNO}_3\) and concentrated \(\mathrm{H}_2\mathrm{SO}_4\). The reaction is as follows: Aniline + \(\mathrm{HNO}_3\) + \(\mathrm{H}_2\mathrm{SO}_4\) → Nitroaniline + \(\mathrm{H}_2\mathrm{O}\) + \(\mathrm{HSO}_4^-\)
04

Formation of 3,5-di iodo nitroaniline

Next, we need to introduce iodine atoms at positions 3 and 5 of the nitroaniline. We can achieve this by reacting nitroaniline with iodine (\(\mathrm{I_2}\)) and potassium iodide (\(\mathrm{KI}\)) in an aqueous solution. The reaction can be given as: Nitroaniline + 2 \(\mathrm{I_2}\) + 2 \(\mathrm{KI}\) → 3,5-di iodo nitroaniline + 2 \(\mathrm{K}_2\mathrm{SO}_4\)
05

Formation of 3,5-di iodo nitrobenzene

Finally, we need to convert 3,5-di iodo nitroaniline into 3,5-di iodo nitrobenzene. This can be done by a diazotization reaction followed by a Sandmeyer reaction. First, we diazotize the 3,5-di iodo nitroaniline by adding sodium nitrite (\(\mathrm{NaNO}_2\)) and hydrochloric acid (\(\mathrm{HCl}\)) to form the diazonium salt. The reaction can be given as: 3,5-di iodo nitroaniline + \(\mathrm{NaNO}_2\) + \(\mathrm{HCl}\) → 3,5-di iodo nitrobenzene diazonium chloride + \(\mathrm{NaCl}\) + \(\mathrm{H}_2\mathrm{O}\) Then, to convert the diazonium salt to 3,5-di iodo nitrobenzene, we use copper(I) chloride (\(\mathrm{CuCl}\)) under acidic conditions: 3,5-di iodo nitrobenzene diazonium chloride + \(\mathrm{CuCl}\) + \(\mathrm{HCl}\) → 3,5-di iodo nitrobenzene + \(\mathrm{N}_2\) + \(\mathrm{H}_2\mathrm{O}\) + \(\mathrm{CuCl}_2\)

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