o Cold concentrated H2SO4, followed by heating in the

presence of water
Addition of Hydrogen
o H2(g) with Nickel catalyst, at ~150oC, ~5atm
o H2(g) with Pt or Pd catalyst, at room temperature
Oxidation
o Partial bond cleavage
Cold alkali/ cold, dilute acidified KMnO4
o Total bond cleavage
Hot, acidified KMnO4
Combustion
b. Formation
Dehydration of Alcohols
o Excess, concentrated H2SO4, 180oC
o Al2O3, 400oC
Dehydrohalogenation of halogenoalkane
o Alcoholic KOH, relfux
2. Benzene
a. Reactions
Nitration
o Concentrated HNO3, concentrated H2SO4, reflux at less
than 60oC
Halogenation
o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature
Friedel-Crafts Alkylation
o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature
Friedel-Crafts Acylation
o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature
3. Alkylbenzene
a. Reactions (side-chain)
Halogenation
o Cl2(g)/Br2(l), UV light
Oxidation
o Alkaline/ acidified KMnO4, reflux
o Entire side chain is oxidized into CO 2H
b. Formation
Friedel-Crafts Alkylation
o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature
4. Alcohols
a. Reactions
Esterification
o Concentrated H2SO4, reflux
Acylation
Halogenation (hydrogen halide)
o NaCl(s), concentrated H2SO4, reflux
o HX, reflux
Halogenation (phosphorus halide)
o Cold PCl5
o Red P and Br2, reflux
o Red P and I2, reflux
Halogenation (Sulfur dichloride oxide)

Done by Nickolas Teo Jia Ming, CG 12/11

 o SOCl2, dissolved in pyridine
Dehydration
o Excess, concentrated H2SO4, 180oC

Al2O3, 400oC Organic Chem Reactions

1. Alkanes
a. Reactions
Combustion
Free-radical substitution
o Steps
Initiation
Propagation
Termination
o Conditions
Cl2(g)/Br2(l), UV light
b. Formation
Hydrogenation of Alkenes
o H2(g) with Nickel catalyst, at ~150oC, ~5atm
o H2(g) with Pt or Pd catalyst, at room temperature
Decarboxylation of sodium salt of carboxylic acid
o Heating with sodalime
2. Alkenes
a. Reactions
Addition of bromine
o Br2(l) / Br2 dissolved in CCl4, room temperature
Addition of bromine water
o Bromine water at room temperature
Addition of HBr
o HBr(g)/ HBr dissolved in CCl4, room temperature
Direct hydration
o Steam, H3PO4 catalyst, 300oC, 65 atm
Indirect hydration
o
Formation of alkyl hydrogensulfate
o Concentrated H2SO4, reflux at 80oC
Combustion
Oxidation
o For aldehyde
Acidified K2Cr2O7, heat to distill
o For carboxylic acid/ ketone
Acidified K2Cr2O7/ KMnO4, reflux
b. Formation
Alkaline hydrolysis of halogenoalkane
o Aqueous KOH, reflux
Direct hydration of alkenes
o Steam, H3PO4 catalyst, 300oC, 65 atm
Indirect hydration of alkenes
o Cold concentrated H2SO4, followed by heating in the
presence of water
Reduction of carbonyl compounds

Done by Nickolas Teo Jia Ming, CG 12/11

 o H2(g) with Ni catalyst at 140oC
o LiAlH4, dissolved in dry ether at room temperature
c. Test
Tri-iodomethane/ Iodoform test
o Alkaline I2(aq), heat
o Solid I2, NaOH(aq), heat
o NaOI(l), heat
3. Phenol
a. Reactions
Esterification
o Acid chloride and NaOH(aq)
Halogenation
o Br2 dissolved in CCl4
o Chlorine/ Bromine water at room temperature
Nitration
o Dilute HNO3, room temperature
b. Test
Neutral Iron(III) chloride solution at room temperature
o Violet coloration
Bromine water at room temperature
o Decolourisation and white precipitate
4. Aliphatic carbonyl compounds
a. Reactions
Oxidation of aldehydes
o Acidified K2Cr2O7/ KMnO4, heat
o Alkaline KMnO4, heat
o Tollens Reagent, heat
Ammoniacal silver(I) nitrate
o Fehlings Solution, heat
Alkaline copper(II) tartrate
Reduction
o H2(g) with Ni catalyst at 140oC
o LiAlH4, dissolved in dry ether at room temperature
Addition of HCN
o Slightly alkaline HCN (aq) at 10-20oC
o HCN (aq), small amount of KCN, 10-20oC
Condensation reaction with Bradys Reagent
o Bradys Reagent, room temperature.
b. Test
Tri-iodomethane test
o Alkaline I2(aq), heat
o Solid I2, NaOH(aq), heat
o NaOI(l), heat
c. Formation
Oxidation of alcohols
o Acidified K2Cr2O7/ KMnO4, heat (to distill for aldehyde)
5. Aromatic carbonyl compounds
a. Reactions
Oxidation of aldehydes
o Acidified KMnO4, heat
o Alkaline KMnO4, heat

Done by Nickolas Teo Jia Ming, CG 12/11

 o Tollens Reagent, heat
Ammoniacal silver(I) nitrate
o NOT Fehlings solution
Reduction
o LiAlH4, dissolved in dry ether at room temperature
Condensation reaction with Bradys Reagent
o Bradys Reagent, room temperature.
Electrophilic substitution of benzene ring
o Fuming HNO, concentrated H2SO4, reflux at 40oC
o Cl2, anhydrous FeCl3, at room temperature
b. Test
Tri-iodomethane test
o Alkaline I2(aq), heat
o Solid I2, NaOH(aq), heat
o NaOI(l), heat
c. Formation
For benzaldehyde
o Excess Cl2 gas and UV light, followed by reflux with
NaOH (aq)
For phenylethanone
o CH3COCl with anhydrous AlCl3 catalyst, 40oC
6. Carboxylic acid
a. Reactions
Metal, metal carbonate, alkali
o Room temperature
Formation of acyl chloride by a halogen atom
o PCl5(s), cold
o PCl3(l), cold
o SOCl2, dissolved in pyridine
Esterification
o Concentrated H2SO4, reflux
Reductions
o LiAlH4, dry ether, room temperature
b. Formation
Oxidation of primary alcohol
o Acidified K2Cr2O7/ KMnO4, reflux
Oxidation of aldehydes
o Acidified K2Cr2O7/ KMnO4, reflux
Oxidation of methyl benzene
o Acidified KMnO4, heat
o Alkaline KMnO4, heat
Acid hydrolysis of nitriles
o Dilute HCl, reflux
Alkali hydrolysis of nitriles
o Dilute NaOH, reflux, followed by acidify
7. Carboxylic acid derivatives
a. Reactions
Hydrolysis
o Ester
Dilute H2SO4, reflux
o Acyl chloride

Done by Nickolas Teo Jia Ming, CG 12/11

 Water, room temperature
o Amide
Dilute HCl, reflux
React with alcohol/ phenol
o Acyl chloride
Room temperature
Reaction with NH3
o Ester
Concentrated alcoholic NH3
o Acyl chloride
Room temperature
Reduction
o Ester
LiAlH4, dissolved in dry ether at room
temperature
o Acyl chloride
LiAlH4, dissolved in dry ether at room
temperature
o Amide
LiAlH4, dissolved in dry ether at room
temperature

b. Formation
Acyl chloride
o Formation of acyl chloride by a halogen atom
Ester
o Esterification
Amide
o Acyl chloride, NH3/ RNH2/ R2NH, cold
8. Amine
a. Reactions
Alkylation of amine
o RX dissolved in ethanol in a sealed tube; Heat
Acylation of amine
o Acyl chloride; Cold
b. Formation
Reduction of nitriles
o LiAlH4, dry ether, room temperature
o H2(g) with Ni catalyst at 140oC
o Na and ethanol
Reduction of amides
o LiAlH4, dry ether, room temperature
o H2(g) with Ni catalyst at 140oC
o Na and ethanol
9. Phenylamine
a. Reactions
Alkylation of amine
o RX dissolved in ethanol in a sealed tube; Heat
Acylation of amine
o Acyl chloride; Cold
Halogenation

Done by Nickolas Teo Jia Ming, CG 12/11

 o Br2 dissolved in CCl4
o Chlorine/ Bromine water at room temperature
b. Formation
Reduction of nitrobenzene
o Sn, concentrated HCl, reflux followed by addition of
NaOH (aq)
10. Halogenoalkane
a. Reactions
Nucleophilic substitution
o Alkaline hydrolysis
NaOH (aq); Reflux
KOH (aq); Reflux
o Formation of Nitrile
Alcoholic KCN; Reflux
o Formation of ether
Na in excess alcohol; Reflux
o Formation of ester
Silver(I) salt of carboxylic acid in alcohol; Reflux
o Formation of amine
Excess concentrated NH3 in alcohol; Reflux
Elimination
o Dehalogenation of halogenoalkane
Alcoholic KOH; Reflux
Alcoholic CH3O-Na+; Reflux
b. Formation
Free radical substitution of alkane
Halogenation of alcohols
Addition of halogen to alkene

Done by Nickolas Teo Jia Ming, CG 12/11