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NaCN in aqueous ethanol solution

R 1 OH / c.H 2 SO 4 catalyst. Cr 2 O 7 2- / H + (aq). Al 2 O 3 (s) / 300 C. reflux. reflux. or c.H 2 SO 4 / reflux followed by H 2 O. alcohol. alkene. aldehyde. carboxylic acid. ester. NaCN in aqueous ethanol solution. c.NH 3 (aq). room temp. halogenoalkane. reflux. nitrile.

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NaCN in aqueous ethanol solution

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  1. R1OH / c.H2SO4 catalyst Cr2O72- / H+(aq) Al2O3(s) / 300C reflux reflux or c.H2SO4 / reflux followed by H2O alcohol alkene aldehyde carboxylic acid ester NaCN in aqueous ethanol solution c.NH3(aq) room temp halogenoalkane reflux nitrile acyl chloride primary amide alkane amine carboxylic acid (reacts as above) secondary amine esterification oxidation oxidation elimination Cr2O72- / H+(aq) / reflux H+(aq) / H2O NaBH4 reduction hydrolysis substitution substitution acylation HBr(aq) room temp NaOH(aq) reflux NaBr(s) / c.H2SO4 reflux substitution R1OH room temp addition SCl2O reflux addition H2(g)/Ni 150C 5 atm acylation substitution substitution hydrolysis acylation Br2(l) sunlight substitution R1NH2 room temp c. NH3(aq) heat in a sealed tube H+(aq)/H2O reflux Notes: 1. The formation of a nitrile from a halogenoalkane is a carbon-carbon bond forming reaction. The carboxylic acid formed from the nitrile has an extra carbon atom in the side-chain. All the other reactions are simple functional group interconversions. 2. The halogenoalkane shown will only be a minor product of the reaction from the alkene. The main product will be the isomer with the Br atom attached to the second carbon atom. 3. You may wish to add other reactions to this toolkit. For example the formation of a secondary alcohol from an alkene RCH=CHR1 and its subsequent oxidation to the ketone.

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