Chapter 23.8, Problem 23.13P

(a)

Interpretation Introduction

Interpretation:

Synthesis of 3-nitrophenol has to be proposed using 3-nitroaniline as starting material.

Concept Introduction:

Conversion of aromatic amines to phenol:

Aromatic amines converted to arenediazonium salt by reacting with $NaN{O}_2$ in presence of aqueous sulfuric acid which further on heating with water forms a phenol.

(b)

Interpretation Introduction

Interpretation:

Synthesis of 3-bromo nitrobenzene has to be proposed using 3-nitroaniline as starting material.

Concept Introduction:

Reaction of a primary aromatic amine with sodium nitrite:

The reaction of a primary aromatic amine with sodium nitrite in presence of aqueous $HCl$ gives an arenediazonium salt.

Sandmeyer reaction:  It reaction type of organic reaction where the diazonium group in an arenediazonium salt gets replaced by $-Cl,-\text{Br or }-\text{CN}$ groups on reacting with $\text{HCl/CuCl, HBr/CuBr or HCN/CuCN}$.

Hydrogenation:

Hydrogenation means the addition of hydrogen molecules to the unsaturated compound which makes them saturated hydrocarbon in the presence of catalyst.

(c)

Interpretation Introduction

Interpretation:

Synthesis of 1,3-dihydroxybenzene has to be proposed using 3-nitroaniline as starting material.

Concept Introduction:

Reaction of a primary aromatic amine with sodium nitrite:

The reaction of a primary aromatic amine with sodium nitrite in presence of aqueous $HCl$ gives an arenediazonium salt.

Hydrogenation:

Hydrogenation means the addition of hydrogen molecules to the unsaturated compound which makes them saturated hydrocarbon in the presence of catalyst.

(d)

Interpretation Introduction

Interpretation:

Synthesis of 3-fluoroaniline has to be proposed using 3-nitroaniline as starting material.

Concept Introduction:

Schiemann reaction: It is a method used to introduce fluorine into an aromatic ring. The reaction of a primary aromatic amine with sodium nitrite in presence of aqueous $HCl$ followed by the reaction with $NaB{F}_4{\text{ or HBF}}_4$ that results in the introduction of a fluorine atom in the compound.

(e)

Interpretation Introduction

Interpretation:

Synthesis of 3-fluorophenol has to be proposed using 3-nitroaniline as starting material.

Concept Introduction:

Conversion of aromatic amines to phenol:

Aromatic amines converted to arenediazonium salt by reacting with $NaN{O}_2$ in presence of aqueous sulfuric acid which further on heating with water forms a phenol.

Schiemann reaction: It is a method used to introduce fluorine into an aromatic ring. The reaction of a primary aromatic amine with sodium nitrite in presence of aqueous $HCl$ followed by the reaction with $NaB{F}_4{\text{ or HBF}}_4$ that results in the introduction of a fluorine atom in the compound.

(f)

Interpretation Introduction

Interpretation:

Synthesis of 3-hydroxybenzonitrile has to be proposed using 3-nitroaniline as starting material.

Concept Introduction:

Hydrogenation:

Hydrogenation means the addition of hydrogen molecules to the unsaturated compound which makes them saturated hydrocarbon in the presence of catalyst.

Reaction of a primary aromatic amine with sodium nitrite:

The reaction of a primary aromatic amine with sodium nitrite in presence of aqueous $HCl$ gives an arenediazonium salt.

Sandmeyer reaction:  It reaction type of organic reaction where the diazonium group in an arenediazonium salt gets replaced by $-Cl,-\text{Br or }-\text{CN}$ groups on reacting with $\text{HCl/CuCl, HBr/CuBr or HCN/CuCN}$.