How do you convert the following:

(i)Prop-1-ene to 1-fluropropane

(ii) Chlorobenzene to 2-chlorotoulene

(iii)Ethanol to propanenitrile.

OR

Write the main product when

(i) N-butyl chloride is treated with alcoholic KOH.

(ii) 2,4,6-trinitrochlorobenzene is subjected to hydrolysis.

(iii) Methylchloride is treated with AgCN

(i) CH₃-CH=CH2 CH₃-CH₂-CH₂Br CH_3-CH₂-CH₂F

We cannot do the direct addition of HF ,as acc to markonikov rule it will result in the formation of 2-fluropropane.

(ii) In this we need to add methyl group to toluene. It can be done by simple friedel crafts alkylation process.

(iii) In this we first convert ethanol into bromoethane in the presence of Br₂ and Red phosphorus. The bromoethane then finally converted into propanenitrile presence of aqueous ethanol on reaction with KCN.

CH₃-CH_2-OH CH₃CH₂Br CH₃CH₂CN

OR

(i) On reaction with alcoholic KOH, n butyl chloride will undergo elimination reaction and is converted into butene.

(ii) On hydrolysis, the Chloro( Cl) group of 2,4,6-tinitrochlorobenzene is replaced by Hydroxy OH group and results in formation of 2,4,6-trinitrophenol. It is also known as picric acid.

(iii) On reaction with AgCN, the methyl chloride is converted into methylcyanide.