Organic Chemistry NCEA level 3

Alkane ——> Haloalkane

Substitution, HX, UV light

Haloalkane ——> Alcohol

Substitution, NaOH(aq) or KOH(aq), heat under reflux

Haloalkane ——> Amine

Substitution, NH3(alc), heat in sealed tube

Haloalkane ——> Alkene 

Elimination, KOH(alc), heat under reflux 

Alkene ——> Dihaloalkane 

Addition, X2

Alkene ——> Haloalkane

Addition, HX

Alkene ———> Alkane

Addition (hydrogenation), H2 gas, Ni catalyst, heat

Alkene ——> Alcohol

Addition (hydration), H2O/H+ and heat

Alkene ——> Diol 

Oxidation, acidified MnO4- (purple to colourless)

Alkene ———> Polymer

Polymerisation, addition, monomers, high pressure, catalyst

Alcohol ——> Haloalkane

Substitution, PCl3, PCl5 or SOCl2

Alcohol ——> Alkene

Elimination (dehydration), Conc H2SO4 or Al2O3, Heat

Primary Alcohol ——> Aldehyde

Oxidation, MnO4-/H+ or Cr2O7/H+, distillation

Primary Alcohol ——> Carboxylic Acid

Oxidation, MnO4-/H+ or Cr2O7/H+, Reflux

Secondary Alcohol ——> Ketone

Oxidation, MnO4-/H+ or CrO72-/H+, Reflux

Aldehyde ——> Carboxylic Acid

Oxidation, MnO4-/H+ or Cr2O7/H+, Reflux

Aldehyde ——> Primary Alcohol 

Reduction, NaBH4

Carboxylic Acid ——> Acyl Chloride

Substitution, SOCl2

Carboxylic Acid ———> Salt + Water

Acid base, NaOH or metal carbonate

Carboxylic Acid ———> Ester

Esterification, condensation, Alcohol and conc H2SO4, heat under reflux

Acid Chloride ———> Ester

Esterification/ condensation, uses an Alcohol and produces HCl(g)

Acid Chloride ———> Amide

Condensation, NH3 (ammonia)

Acid Chloride ———> Secondary Amine

Condensation, Amine

Acid Chloride ———> Carboxylic Acid

Hydrolysis, H2O

Ester ———> Carboxylic Acid + Alcohol

Acidic Hydrolysis, dilute H2SO4, heat under reflux

Ester ———> Carboxylate Salt + Alcohol

Basic Hydrolysis, NaOH(aq), heat under reflux

Amine ———> Secondary Amine

Substitution, Haloalkane, heat in a sealed tube

Amine ———> Amide

Condensation, acid chloride

Amine ———> Ammonium salt

Acid base, acid eg HCl

Cr2O72-

Orange ——> Green

MnO4-

Purple to colourless

Tollens reagent 

Test for Aldehyde, oxidation, Silver mirror, heat, produce carboxylic acid

Benedicts/Fehlings solution,

test for Aldehyde (Ketone won’t react) Blue —> Brick red precipitate, oxidation, produces Carboxylic acid.

Amide ——> Carboxylic Acid + Ammonium Ion

acidic hydrolysis, H2SO4 (aq) and heat or H2O/H+ and heat

1 degree Amide ——> Carboxylate ion + ammonia

Hydrolosis, OH- and heat