What is the formula of Chlorobenzene? Preparation, Properties and uses

What is the formula of Chlorobenzene? Preparation, Properties and uses

Preparation

Laboratory Method

Aniline: Benzenediazonium chloride is obtained by replicating aniline with a mixture of NaNO2 and HCl at 0-5°C. Chlorobenzene is obtained by heating benzenediazonium chloride in the presence of cupreous chloride and hydrochloric acid. 

C6H5NH2 + NH2 + HCl C6H5 – N = N – Cl + 2H2O

The first reaction is called diazotization reaction and the second reaction is called sandmeyer reaction.

Read more about diazotization reaction and sandmeyer reaction

C6H5 – N = N – Cl C6H5Cl + N2

Method of use

In a flask, dissolve 20 gram aniline in dilute HCl and cool it to 5°C. In this flask, NaNO2 solution is added, resulting in benzenediazonium chloride. Fill this solution in a separating funnel and drop it into a 500 ml flask.

In this flask, 10 gram cupreous chloride and 100 ml HCl solution water is kept on the heat. This flask is equipped with an ejector air capacitor. It mixes all the benzenediazonium chloride in the flask, then heats the flask at 60°C for half an hour on a water heater.

Benzene to Chlorobenzene

Chlorobenzene can be obtained from chlorination of benzene.

The chlorobenzene floats on the upper surface of the solution in the form of oily fluid. It is separated from the mixture by steam distillation method. The chlorobenzene thus obtained is dried by anhydrous CaCl2 and distilled at 132°C to obtain pure Chlorobenzene.

Phenol: Chlorobenzene is obtained by the reaction of phenol with phosphorus pentachloride.

C6H5OH + PCl5 C6H5Cl + POCl3 + HCl

Benzene: Chlorobenzene can be obtained from chlorination of benzene.

C6H6 + Cl2 C6H5Cl + HCl

Industrial Method

Chlorobenzene is obtained by mixing a mixture of benzene vapors, hydrogen chloride gas and oxygen (oxygen) at 250°C on a copper oxide catalyst. This reaction is used for the industrial manufacture of chlorobenzene. This method of industrial manufacture of chlorobenzene is called Rasching method.

2C6H6 + 2HCl + O2 2C6H5Cl + 2H2O

Physical properties

chlorobenzene is a colorless, volatile and aromatic liquid. Its boiling point is 132°C. It is insoluble in water and soluble in alcohol and ether. It is heavier than water and its relative density is 1.12.

Chlorobenzene Phenyl chloride

Chemical properties

A chlorine atom in a molecule of chlorobenzene is attached to a benzene ring ie benzene nucleus. The chemical reactions of chlorobenzene can be divided into two parts.

  • Reaction of Chlorine Atom
  • Reaction of benzene nucleus

 

The reaction of Chlorine Atom

In these reactions, the chlorine atom is displaced by other atoms and groups. Due to the resonance in chlorobenzene, the chlorine atom is strongly attached to the benzene ring and its activation works.

In alkyl halide, the bond between the halogen atom and the alkyl group is relatively weak. Therefore, in alkyl halides, the halogen atom has high reactivity and can be easily displaced by many other atoms or groups.

Chlorobenzene Chlorine bond

Additionally, the chlorine atom in chlorobenzene contains partial positive charge. Whereas the chlorine atom in ethyl chloride is partially negative. Therefore, chlorine atom is not easily released as chloride atom chloride ion (Cl) upon invasion of a nucleic lubricating reagent. Therefore, chlorobenzene has low reactivity to chlorine.

The major reactions of chlorobenzene in which the chlorine atom participates.

Is the following.

Reaction with NaOH: phenol is obtained by heating chlorobenzene with aqueous NaOH at about 300°C.

C6H5Cl + NaOH C6H5OH + NaCl

Reaction with Ammonia: Aniline is obtained by heating chlorobenzene with ammonia at high pressure and around 250°C in the presence of Cu2O.

C6H5Cl + NH3 C6H5NH2 + HCl

Aniline is also obtained when chlorobenzene is reacted with NaNH2 or KNH2 in a fluid ammonia solution.

C6H5Cl + NaNH2 C6H5NH2 + NaCl

Reaction with cuprous cyanide: Phenyl cyanide (benzonitrile) is obtained by heating chlorobenzene with cuprous cyanide (CuCN) at about 250°C in the presence of pyridone.

C6H5Cl + CuCN C6H5CN + CuCl

Reduction: On the reaction of chlorobenzene with Na – Hg and water, it is reduced and benzene is obtained. This reaction can also be carried out by Ni Al alloy and NaOH.

C6H5Cl + 2H C6H6 + HCl

wurtz fittig reaction: The ether solution reacts with a homologous mixture of chlorobenzene and an alkyl halide to obtain an alkyl substituted benzene derivative, which is commonly called Arene.

Example:

C6H5Cl + 2Na + ClCH3 C6H5CH3 + 2NaCl

This reaction is called wurtz fittig reaction.

Reaction Magnesium: ether solution reacts with magnesium to form phenylmagnesium chloride which is a grignard reagent.

C6H5Cl + Mg C6H5 – Mg – Cl

Benzene nucleus reactions

Chlorobenzene has chlorine atoms ortho and para director group. Hence ortho and para substitution products are obtained on halogenation, nitration, sulfuration, etc. of Chlorobenzene. The chlorine atom is a weakly deactivating group.

This implies that the reactivity for substitution reactions of chlorobenzene is somewhat lower than that of benzene. The increasing order of reactivity for substitution reactions of benzene, toluene, and chlorobenzene is as follows.

Chlorobenzene < Benzene < Toluene

The major reactions of chlorobenzene in which the benzene nucleus participates.

Halogenation: A mixture of ortho and para diChlorobenzene is obtained when chlorine is reacted with chlorine in the absence of sunlight and in the presence of halogen carrier.

chlorobenzene Halogenation

Nitration: A mixture of ortho and para chloro nitrobenzene is obtained by the reaction of chlorobenzene with concentrated HNO3 and concentrated H2SO4.

Chlorobenzene Nitration

Sulfuration: A mixture of ortho and para Chlorobenzene sulfonic acid is obtained by the reaction of Chlorobenzene with the corresponding H2SO4.

Chlorobenzene Sulfuration

Friedel Crafts Reaction: A mixture of ortho and para chlorotoluene is obtained when the chlorobenzene is reacted with methyl chloride in the presence of anhydrous AlCl3.

chlorotoluene

Reaction with chloral: pp-Dichloro-diphenyl-trichloroethane formed upon heating Chlorobenzene with chloral in the presence of concentrated sulfuric acid. It is also called D.D.T..

It is a strong and major disinfectant. for more detail click here

Chlorobenzene to D.D.T.

What is chlorobenzene used for?

It is used in the manufacture of aniline, phenole, chloronitrobenzene, and disinfectant DDT.

Sanjay Bhandari

Hello Friends, My name is Sanjay Bhandari. I am a chemistry Teacher.

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