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 N a N O 2 in presence of aqueous sulfuric acid which further on heating with water forms a phenol.

Question

How could you convert butanenitrile into the following compounds? Write each step showing the reagents needed. (a) 1-Butanol (b) Butylamine

Answer 1

Question

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 NaNO2 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, −Br or −CN groups on reacting with 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 NaBF4 or HBF4 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 NaNO2 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 NaBF4 or HBF4 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, −Br or −CN groups on reacting with HCl/CuCl, HBr/CuBr or HCN/CuCN.

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Answer 2

Question

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 NaNO2 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, −Br or −CN groups on reacting with 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 NaBF4 or HBF4 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 NaNO2 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 NaBF4 or HBF4 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, −Br or −CN groups on reacting with HCl/CuCl, HBr/CuBr or HCN/CuCN.

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Answer 3

Question

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 NaNO2 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, −Br or −CN groups on reacting with 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 NaBF4 or HBF4 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 NaNO2 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 NaBF4 or HBF4 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, −Br or −CN groups on reacting with HCl/CuCl, HBr/CuBr or HCN/CuCN.

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Answer 4

Question

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 NaNO2 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, −Br or −CN groups on reacting with 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 NaBF4 or HBF4 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 NaNO2 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 NaBF4 or HBF4 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, −Br or −CN groups on reacting with HCl/CuCl, HBr/CuBr or HCN/CuCN.

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Answer 5

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 NaNO2 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, −Br or −CN groups on reacting with 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 NaBF4 or HBF4 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 NaNO2 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 NaBF4 or HBF4 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, −Br or −CN groups on reacting with HCl/CuCl, HBr/CuBr or HCN/CuCN.

Answer 6

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 NaNO2 in presence of aqueous sulfuric acid which further on heating with water forms a phenol.

Answer 7

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 NaNO2 in presence of aqueous sulfuric acid which further on heating with water forms a phenol.

Answer 8

(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, −Br or −CN groups on reacting with 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.

Answer 9

(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, −Br or −CN groups on reacting with 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.

Answer 10

(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.

Answer 11

(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.

Answer 12

(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 NaBF4 or HBF4 that results in the introduction of a fluorine atom in the compound.

Answer 13

(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 NaBF4 or HBF4 that results in the introduction of a fluorine atom in the compound.

Answer 14

(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 NaNO2 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 NaBF4 or HBF4 that results in the introduction of a fluorine atom in the compound.

Answer 15

(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 NaNO2 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 NaBF4 or HBF4 that results in the introduction of a fluorine atom in the compound.

Answer 16

(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, −Br or −CN groups on reacting with HCl/CuCl, HBr/CuBr or HCN/CuCN.

Answer 17

(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, −Br or −CN groups on reacting with HCl/CuCl, HBr/CuBr or HCN/CuCN.

Answer 18

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Ch. 23.1 - Prob. 23.1P Ch. 23.2 - Prob. 23.2P Ch. 23.2 - Prob. 23.3P Ch. 23.2 - Prob. 23.4P Ch. 23.5 - Prob. 23.5P Ch. 23.5 - Prob. AQ Ch. 23.5 - What is the hybridization of the nitrogen in...Ch. 23.5 - Prob. CQ Ch. 23.5 - The pKas of the conjugate acids of aniline and...Ch. 23.5 - Prob. EQ

Chapter 23 Solutions