How will you bring about the following conversions ?
(i) Ethanol to but - 1 - yne
(ii) Ethane to bromoethane
(iii) Propene to 1 - nitropropane
(iv) Toluene to benzyl alcohol
(v) Propene to propyne
(vi) Ethanol to ethyl fluoride
(vii) Bromomethane to propanone
(viii) But-1-ene to but-2-ene
(ix) l - chlorobutane to n- octane
(x) Benzene to biphenyl
(i) Ethanol to but -1-yne
CH3−CH2−OH+SOCl2pyridine−−−−−−→CH3−CH2−Cl+SO2↑+HCl↑
ethanol ethyl chloride
HC≡CH+NaNH2liq.NH3−−−−−−→HC≡C−Na+
acetylene sodium acetylide
CH3−CH2−Cl+HC≡C−Na+⟶CH3−CH2−C≡CH+NaCl
but-1-yne
(ii) Ethane to bromoethane
CH3−CH3+Br2UVlight−−−−−−→CH3CH2Bralc.KOH−−−−−−−−→
ethane CH2=CH2Br2−−→Br−CH2CH2−Br
Br−CH2−CH2−Bralc.KOH−−−−−−−−→CH2=CHBr
bromo ethene
(iii) Propene to 1 - nitropropane
CH3CH=CH2+HBrperoxide−−−−−−→CH3CH2CH2BrAgNO2−−−−−→CH3CH2CH2NO2+AgBr
1-nitro propane
(iv) Toluene to benzyl alcohol
C6H5−CH3+Cl2UVlight−−−−−−→C6H5−CH2ClNaOH−−−−−→C6H5−CH2OH+NaCl toluene benzyl alcohol
(v) Propene to propyne
CH3CH=CH2+Br2CCl4−−−→CH3CH(Br)−CH2(Br)NaNH2−−−−−−→CH3C≡CH
propene propyne
(vi) Ethanol to ethyl fluoride
CH3CH2OH+HClZnCl2−−−−→CH3−CH2−Cl+H2O
ethyl alcohol ethyl chloride
CH3CH2−Cl+AgF⟶CH3CH2−F(Swartsreaction)
ethyl fluoride
(vii) Bromomethane to propanone
(viii) But-1-ene to but-2-ene
CH3CH2CH=CH2HBr−−−→CH3CH2CH(Br)−CH3alc.KOH−−−−−−−−→
CH3CH=CH−CH3 But-1-ene but-2-ene
(ix) 1 - chloro-butane to n- octane
Wurtz synthesis
2CH3CH2CH2−Cl+2Nadryether−−−−−−−→CH3(CH2)6CH3+2NaCl
1 chloro-butane n-octane
(x) Benzene to biphenyl
Wurtz-Fittig reaction