Chapter 19.12, Problem 28CC

(a)

Interpretation Introduction

Interpretation:

The reagents required to convert benzene to the following compounds have to be identified.

Chlorobenzene

Concept Introduction:

• Benzene is an electron rich Aromatic compound. It undergoes aromatic electrophilic substitution reaction. 

• The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.

• Chlorination of  benzene is imparting $\text{-Cl}$ group in the ring by replacing one of its Hydrogen atoms.

(b)

Interpretation Introduction

Interpretation:

The reagents required to convert benzene to the following compounds have to be identified.

Nitrobenzene

Concept Introduction:

• Benzene is an electron rich Aromatic compound. It undergoes aromatic electrophilic substitution reaction. 

• The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.

• Nitration  of  benzene is known as inserting ${\text{-NO}}_2$ group into the benzene Carbon by replacing one of its Hydrogen atoms.

(c)

Interpretation Introduction

Interpretation:

The reagents required to convert benzene to the following compounds have to be identified.

Bromobenzene

Concept Introduction:

• Benzene is an electron rich Aromatic compound. It undergoes aromatic electrophilic substitution reaction. 

• The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.

• Bromination of  benzene is installing $\text{-Br}$ group in the ring by replacing one of its Hydrogen atoms.

(d)

Interpretation Introduction

Concept Introduction:

• Benzene and its related compounds undergo aromatic electrophilic substitution reactions since they are Aromatic compounds. The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.

• Friedel Crafts reaction is an electrophilic substitution reaction. This reaction involves $\text{C-C}$ bond formation between benzene Carbon and any other alkyl or aryl or acyl carbon. Thus this reaction is constructive to impart alkyl, aryl or acyl group onto benzene ring. So this reaction is commonly known as Friedel Crafts acylation if acyl group is imparted on benzene ring or Friedel Crafts alkylation if alkyl group is imparted on benzene ring.

• Any of Lewis acids such as ${\text{AlCl}}_{\text{3,}}{\text{FeCl}}_{\text{3}}\text{,}{\text{BF}}_{\text{3}}\text{etc}$ is required to initiate the reaction. The Lewis acid act as catalyst assists in the formation of electrophile. 

(e)

Interpretation Introduction

Interpretation:

The reagents required to convert benzene to the following compounds have to be identified.

Propylbenzene

Concept Introduction:

• Benzene and its related compounds undergo aromatic electrophilic substitution reactions since they are Aromatic compounds. The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.

• Friedel Crafts reaction is an electrophilic substitution reaction. This reaction involves $\text{C-C}$ bond formation between benzene Carbon and any other alkyl or aryl or acyl carbon. Thus this reaction is constructive to impart alkyl, aryl or acyl group onto benzene ring. So this reaction is commonly known as Friedel Crafts acylation if acyl group is imparted on benzene ring or Friedel Crafts alkylation if alkyl group is imparted on benzene ring.

• Any of Lewis acids such as ${\text{AlCl}}_{\text{3,}}{\text{FeCl}}_{\text{3}}\text{,}{\text{BF}}_{\text{3}}\text{etc}$ is required to initiate the reaction. The Lewis acid act as catalyst assists in the formation of electrophile.

• The order of the stability of carbocation is –

Tertiary carbocation > Secondary carbocation > Primary carbocation.

• Carbonyl functional group can be converted to methylene group by a reaction known as Clemmenson reduction

(f)

Interpretation Introduction

Concept Introduction:

• Benzene and its related compounds undergo aromatic electrophilic substitution reactions since they are Aromatic compounds. The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.

• Friedel Crafts reaction is an electrophilic substitution reaction. This reaction involves $\text{C-C}$ bond formation between benzene Carbon and any other alkyl or aryl or acyl carbon. Thus this reaction is constructive to impart alkyl, aryl or acyl group onto benzene ring. So this reaction is commonly known as Friedel Crafts acylation if acyl group is imparted on benzene ring or Friedel Crafts alkylation if alkyl group is imparted on benzene ring.

• Any of Lewis acids such as ${\text{AlCl}}_{\text{3,}}{\text{FeCl}}_{\text{3}}\text{,}{\text{BF}}_{\text{3}}\text{etc}$ is required to initiate the reaction. The Lewis acid act as catalyst assists in the formation of electrophile.

(g)

Interpretation Introduction

Interpretation:

The reagents required to convert benzene to the following compounds have to be identified.

Aniline (aminobenzene)

Concept Introduction:

• Benzene and its related compounds undergo aromatic electrophilic substitution reactions since they are Aromatic compounds. The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.

• Nitration of benzene is known as inserting ${\text{-NO}}_2$ group into the benzene Carbon by replacing one of its Hydrogen atoms.

• Various reagents are available such as Sodium sulfide, Sodium hydrosulfite, Tin(II) chloride, $\text{Zn/HCl}$ etc to convert nitro group to amino group by reduction.

(h)

Interpretation Introduction

Interpretation:

The reagents required to convert benzene to the following compounds have to be identified.

Benzoic acid

Concept Introduction:

• Benzene and its related compounds undergo aromatic electrophilic substitution reactions since they are Aromatic compounds. The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.

• Friedel Crafts reaction is an electrophilic substitution reaction. This reaction involves $\text{C-C}$ bond formation between benzene Carbon and any other alkyl or aryl or acyl carbon. Thus this reaction is constructive to impart alkyl, aryl or acyl group onto benzene ring. So this reaction is commonly known as Friedel Crafts acylation if acyl group is imparted on benzene ring or Friedel Crafts alkylation if alkyl group is imparted on benzene ring.

• Oxidation of alkyl side chain in alkylbenzene forms Carboxilic acid.

(i)

Interpretation Introduction

Interpretation:

The reagents required to convert benzene to the following compounds have to be identified.

Toluene

Concept Introduction:

• Benzene and its related compounds undergo aromatic electrophilic substitution reactions since they are Aromatic compounds.

• Friedel Crafts reaction is an electrophilic substitution reaction. This reaction involves $\text{C-C}$ bond formation between benzene Carbon and any other alkyl or aryl or acyl carbon. Thus this reaction is constructive to impart alkyl, aryl or acyl group onto benzene ring. So this reaction is commonly known as Friedel Crafts acylation if acyl group is imparted on benzene ring or Friedel Crafts alkylation if alkyl group is imparted on benzene ring.