Organic Synthesis (reagants and conditions)

Alkane -> Haloalkane

Halogen, UV light

Alkene -> Alkane

H2, Ni catalyst, 150c

Alkene -> Haloalkane

Hydrogen halide

Haloalkane -> Nitrile

CN-/ethanol

Haloalkane -> Amine

NH3/ethanol

Nitrile -> Amine

H2/Ni

Haloalkane -> Alcohol

NaOH(aq)

Alcohol -> Haloalkane

Sodium halide/H2SO4

Alkene -> Alcohol

H2O (steam)/H3PO4

Alcohol -> Alkene

H3PO4 or H2SO4, Heat

Alcohol -> Ketone

K2Cr2O7, H2SO4, reflux

Ketone -> Alcohol

NaBH4

Ketone -> Hydroxynitrile

NaCN(aq)/H+(aq)

Hydroxynitrile -> Amine

H2/Ni

Alcohol -> Aldehyde

K2Cr2O7, H2SO4, distillation

Aldehyde -> Alcohol

NaBH4

Aldehyde -> Hydroxynitrile

NaCN(aq)/H+(aq)

Nitrile/Hydroxynitrile -> Carboxylic Acid

H2O/HCl, heat

Aldehyde -> Carboxylic Acid

K2Cr2O7, H2SO4, reflux

Alcohol -> Carboxylic Acid

K2Cr2O7, H2SO4, reflux

Alcohol -> Ester

carboxylic acid/conc. H2SO4 or acid anhydride

Carboxylic Acid -> Ester

Alcohol/conc H2SO4

Ester -> Carboxylic Acid

dilute acid, heat

Ester -> Carboxylate

OH-, heat

Acyl Chloride -> Ester

alcohol

Carboxylic Acid -> Acyl Chloride

SOCl2

Acyl Chloride -> Carboxylic Acid

H2O

Acyl Chloride -> primary Amide

NH3

Acyl Chloride -> secondary Amide

primary amine