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Question

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

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Solution


(i) Ethanol to but -1-yne

CH3CH2OH+SOCl2pyridine−−−−−CH3CH2Cl+SO2+HCl

ethanol ethyl chloride

HCCH+NaNH2liq.NH3−−−−−HCCNa+

acetylene sodium acetylide

CH3CH2Cl+HCCNa+CH3CH2CCH+NaCl

but-1-yne

(ii) Ethane to bromoethane

CH3CH3+Br2UVlight−−−−−CH3CH2Bralc.KOH−−−−−−−

ethane CH2=CH2Br2BrCH2CH2Br

BrCH2CH2Bralc.KOH−−−−−−−CH2=CHBr

bromo ethene

(iii) Propene to 1 - nitropropane

CH3CH=CH2+HBrperoxide−−−−−CH3CH2CH2BrAgNO2−−−−CH3CH2CH2NO2+AgBr

1-nitro propane

(iv) Toluene to benzyl alcohol

C6H5CH3+Cl2UVlight−−−−−C6H5CH2ClNaOH−−−−C6H5CH2OH+NaCl toluene benzyl alcohol




(v) Propene to propyne

CH3CH=CH2+Br2CCl4−−CH3CH(Br)CH2(Br)NaNH2−−−−−CH3CCH

propene propyne

(vi) Ethanol to ethyl fluoride

CH3CH2OH+HClZnCl2−−−CH3CH2Cl+H2O

ethyl alcohol ethyl chloride

CH3CH2Cl+AgFCH3CH2F(Swartsreaction)

ethyl fluoride

(vii) Bromomethane to propanone

(viii) But-1-ene to but-2-ene

CH3CH2CH=CH2HBr−−CH3CH2CH(Br)CH3alc.KOH−−−−−−−

CH3CH=CHCH3 But-1-ene but-2-ene


(ix) 1 - chloro-butane to n- octane

Wurtz synthesis

2CH3CH2CH2Cl+2Nadryether−−−−−−CH3(CH2)6CH3+2NaCl

1 chloro-butane n-octane

(x) Benzene to biphenyl

Wurtz-Fittig reaction



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