Chlorobenzene to p-nitrophenol

How the following conversions can be carried out? (i) Ethyl chloride to propanoic acid (ii) But-1-ene to n-butyliodide (iii) 2-ChIoropropane to 1-propanol (iv) Isopropyl alcohol to iodoform (v) Chlorobenzene to p-nitrophenol (vi) 2-Bromopropane to 1-bromopropane (vii) Chloroethane to butane (viii) Benzene to diphenyl (ix) tert-Butyl bromide to isobutyl bromide (x) Aniline to phenylisocyanide

Hint: The reaction of chlorobenzene to p- chloronitrobenzene is an electrophilic substitution reaction in which a nitro group is substituted on a benzene ring. The first step would be the generation of electrophile i.e. nitronium ion. Then this nitronium ion will get substituted on the benzene ring. Complete step by step answer : The benzene is an aromatic compound. It is stabilised because of resonance. It does not undergo addition reactions because if it does, then the resonance of the ring is disturbed and it gets destabilised. Thus, it undergoes electrophilic substitution reaction. The reaction of chlorobenzene to p- chloronitrobenzene is an electrophilic substitution reaction in which a nitro group is substituted on a benzene ring. The electrophile is nitronium ion. The reaction takes place in two steps. Step 1 : This step involves the generation of electrophile that is nitronium ion. The sulphuric acid and nitric acid react to form nitronium ion and some other products. The reaction is as- $2O $ Step 2 : This step involves the attack of benzene on nitronium ion to give para products. The resonance is disturbed initially but later on after removal of proton, the resonance is restored. So, one gets a para-substituted product. The reaction is written as -

Conversion of Chlorobenzene to p-nitrophenol:- Step 1: Formation of Phenol When the Chlorobenzene is reacted with Sodium hydroxide ( NaOH ) , it produces Phenol: Step 2: Formation of p-nitrophenol The Phenol formed now is reacted with concentrated Nitric acid and concentrated Sulphuric acid, it produces ortho nitrophenol and para nitrophenol: This conversion of Chlorobenzene to p-nitrophenol is a 2 step reaction.

Firstly,react chlorobenzene with NaOH at 623 K and 320 atm. pressure by this sodium phenoxide ion will form. Then by acidification of sodium phenoxide ion phenol is obtained. Then react phenol with dilute HNO3 at low temperature(298 K), phenol yeild the mixture of ortho and para nitrophenol. The ortho and para nitrophenol are seperated by steam distillation. So due to this we obtain o-nitrophenol(4-nitrophenol) as major product.

This reaction was used to synthesis phenol in some time ago. This reaction is called as Dow Process. Concentrated NaOH solution and 350 0C temperature is required to prepare phenol from chlorobenzene. C 6H 5-Cl + NaOH → C 6H 5-OH + C 6H 5-O-C 6H 5 + NaCl Due to formation of diphenyl ether and sodium chloride, phenol cannot be obtained as a pure compound. Therefore, has to do a Reaction of C 6H 5Cl and concentrated NaOH is a When electron-withdrawing groups are attached to the benzene ring of chlorobenzene When electron-withdrawing groups such as nitro groups (-NO 2) are connected to the ortho and para positions relative to the chlorine atom, increases the substitution reaction with NaOH. This means, substitution reaction of 2-Nitrochlorobenzene, 4-Nitrochlorobenzene and 2,4,6-Trinitrochlorobenzene with NaOH is much easier than chlorobenzene. Concentration and required temperature for the substitution reaction is less in 2-Nitrochlorobenzene, 4-Nitrochlorobenzene and 2,4,6-Trinitrochlorobenzene. • Chlorobenzene - C 6H 5Cl • Diphenyl ether - C 6H 5-O-C 6H 5 • Phenol - C 6H 5OH Due to difficulties of this NaOH and chlorobenzene reaction, we can follow below reactions to prepare phenol as an alternative method. But this process takes some steps and time to complete. Chlorobenzene to phenol through grignard reagent, benzene, nitrobenzene, aniline • First, • Then, • As next step, • In the final step, C 6H 5Cl + dilute NaOH, what will be the product? With dilute NaOH, chlorine at...

Question Updated on: 13/06/2023 How the following conversions can be carried out? (i). Propene to propane-1-ol (ii). Ethanol to but-1-yne (iii). 1-Bromopropane to 2-bromopropane (iv). Toluene to benzyl alcohol (v)Benzene to 4-Bromonitrobenzene (vi). Benzyl alcohol to 2-phenylethanoic acid (vii) Ethanol to propanenitrite (viii). Aniline to chlorobenzene (ix). 2-Chlorobutane to 3,4-dimethylhexane (x). 2-Methylpropene to 2-chloro-2-methylpropane (xi). Ethyl chloride to propanoic acid (xii). But-1-ene to n-butyl iodie (xiii). 2-Chloropropane to propan-1-ol (xiv). Isopropyl alcohol to iodoform (xv). Chlorobenzene to p-nitrophenol (xvi). 2-Bromopropane to 1-bromopropane (xvii) Chloroethane to butane (xviii) Benzene to diphenyl (xix). tert-Butyl bromide to isobutyl bromide (xx). Aniline to phenyl isocyanide. How the following conversions can be carried out? (i) Propene to propan-1-ol (ii) Ethanol to but-1-yne (iii) 1-Bromopropane to 2-bromopropane (iv) Toluene to benzyl alcohol (v) Benzene to 4-bromonitrobenzene (vi) Benzyl alcohol to 2-phenylethanoic acid (vii) Ethanol to propanenitrile (viii) Aniline to chlorobenzene (ix) 2-Chlorobutane to 3, 4-dimethylhexane (x) 2-Methyl-1-propene to 2-chloro-2-methylpropane (xi) Ethyl chloride to propanoic acid (xii) But-1-ene to n-butyliodide (xiii) 2-Chloropropane to 1-propanol (xiv) Isopropyl alcohol to iodoform (xv) Chlorobenzene to p-nitrophenol (xvi) 2-Bromopropane to 1-bromopropane (xvii) Chloroethane to butane (xviii) Benzene to diphe...