Chapter 20, Problem 25P

Interpretation Introduction

Interpretation:

Aniline is to be converted into the given desired product mentioned in each part.

Concept introduction:

Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.

Nucleophiles are electron rich species that have negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.

Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.

Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.

Aniline is a primary aromatic amine with the chemical formula C₆H₅NH₂. It consists of a phenyl group attached to an amino group. The structure of an aniline is shown as:

Aniline and substituted aniline reacts with nitrous acid at low temperature to form benzene diazonium salts.

The reduction of nitro group results in the formation of primary amine.

When aniline reacts with acetic anhydride, the product formed after the reaction is acetanilide.

When aniline reacts with Phthalimide $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\left(\text{CO}\right)}_{\text{2}}\text{NH}\right)$, on heating it gives rise to N-Phenylphthalimide.

On nitration of acetanilide in the presence ${\text{HNO}}_{\text{3}}$ and ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$, formation of para-nitroacetanilide takes place, which on alkaline hydrolysis gives para - nitroaniline.

When acetanilide reacts with chloro sulfuric acid, it forms p-acetamido benzene sulfonyl chloride.

Further, when p-acetamido benzene sulfonyl chloride reacts with ammonia, it gives rise to p-acetamido benzene sulfonamide, which on alkaline hydrolysis gives sulfanilamide.

When an aniline reacts with two moles of methyl iodide in the presence of a base, it forms N, N-dimethylaniline.

When an aniline reacts with nitrous acid at $0^{\circ }\text{C}-5^{\circ }\text{C}$, it forms benzenediazonium halide, which on reaction with tetrafluoroboric acid forms benzenediazoniumtetaborate. On further heating of benzenediazoniumtetaborate, fluorobenzene is formed.

When benzenediazonium halide reacts with copper(I) chloride, it forms chlorobenzene.

When benzenediazonium halide reacts with copper (I) bromide, it forms bromobenzene.

When benzenediazonium halide reacts with potassium iodide, it forms iodobenzene.

When benzenediazonium halide reacts with copper (I) cyanide, it forms benzonitrile.

Alkaline hydrolysis of benzonitrile results in the formation of benzoic acid.

When benzenediazonium halide reacts with copper oxide, it forms phenol.

When benzenediazonium halide reacts with Hypo phosphorous acid in the presence of moisture, it forms benzene.