Halogenoalkane

Reagents:
Cl₂ gas (or Br₂ gas)

Reaction:
Free radical substitution

Observations:
Greenish yellow Cl₂ decolorised
(or reddish brown Br₂ decolorised)
White fumes of HCl formed

Alkane

Reagents:
H₂/Ni, heat

Reaction:
Reduction

Observations:
–

Halogenoalkane

Reagents:
Cl₂ in CCl₄ (or Br₂ in CCl₄)

Reaction:
Electrophilic addition

Observations:
Greenish yellow Cl₂ decolorised
(or reddish brown Br₂ decolorised)

Halogenoalkane

Reagents:
HCl gas, rtp

Reaction:
Electrophilic addition

Observations:
–

Alcohol

Reagents:
H₂O, 300^oC, 60atm, conc. H₃PO₄

Reaction:
Electrophilic addition

Observations:
–

Diol

Reagents:
Cold dilute KMnO₄

Reaction:
Mild Oxidation

Observations:
Purple KMnO₄ decolorized.
Brown MnO₂ ppt formed in alkaline conditions

Carboxylic Acid

Reagents:
Hot acidified KMnO₄

Reaction:
Oxidative cleavage

Observations:
Purple KMnO₄ decolorized.
Brown MnO₂ ppt formed in alkaline conditions

Carbon dioxide

Reagents:
Hot acidified KMnO₄

Reaction:
Oxidative cleavage for terminal alkenes only

Observations:
Purple KMnO₄ decolorized.

Alkene

Reagents:
NaOH (alc), heat under reflux

Reaction:
Elimination

Observations:
–

Alcohol

Reagents:
NaOH(aq), heat under reflux

Reaction:
Nucleophilic substitution

Observations:
–

Amine

Reagents:
Excess NH₃ (alc), heated in a sealed tube

Reaction:
Nucleophilic substitution

Observations:
–

Nitrile

Reagents:
NaCN (alc), heat under reflux

Reaction:
Nucleophilic substitution

Observations:
–

Carboxylic acid

Reagents:
Dilute H₂SO₄, heat

Reaction:
Acid hydrolysis

Observations:
–

Carboxylate ion

Reagents:
Dilute NaOH, heat

Reaction:
Basic hydrolysis

Observations:
–

Amine

Reagents:
LiAlH₄, dry ether
(or H₂, Pd)

Reaction:
Reduction

Observations:
–

Halogenoalkane

Reagents:
PCl₃ (or PCl₅ or SOCl₂)
Conc HCl, anhydrous ZnCl₂, heat (for 1^o and 2^o alcohols only)
PBr₃ from Br₂ and red P
HBr gas from NaBr and H₂SO₄, heat
PI₃ from I₂ and red P

Reaction:
Substitution

Observations:
HCl fumes for PCl₃/PCl₅/SOCl₂ only

Alkoxide ion

Reagents:
Na metal

Reaction:
Reduction

Observations:
Effervescence of H₂ gas formed which gives pop sound with lighted splint

Carboxylic acid

Reagents:
1^o alcohol only.
KMnO₄, heat (or K₂CrO₄, heat)

Reaction:
Oxidation

Observations:
Purple KMnO₄ decolorised
(or orange K₂CrO₄ turned green)

Aldehyde

Reagents:
1^o alcohol only.
K₂CrO₄, heat with distillation

Reaction:
Oxidation

Observations:
Orange K₂CrO₄ turned green

Ketone

Reagents:
2^o alcohol only.
KMnO₄, heat (or K₂CrO₄, heat)

Reaction:
Oxidation

Observations:
Purple KMnO₄ decolorised
(or orange K₂CrO₄ turned green)

Alkene

Reagents:
Excess conc. H₂SO₄, 170⁰C
(or Al₂O3)

Reaction:
Elimination

Observations:
–

Carboxylate ion

Reagents:
I₂, NaOH, heat

Reaction:
Mild oxidation

Observations:
Yellow CHI₃ ppt formed

Ester

Reagents:
Acid, conc H₂SO₄, heat
(or acyl chloride, rtp)

Reaction:
Condensation

Observations:
Sweet smell of ester

Acid

Reagents:
KMnO₄, heat (or K₂CrO₄, heat)

Reaction:
Oxidation

Observations:
Purple KMnO₄ decolorised
(or orange K₂CrO₄ turned green)

Alcohol

Reagents:
NaBH₄ (aq), (or LiAlH₄ in dry ether, H₂ gas, Pt heat)

Reaction:
Reduction
(Aldehyde to 1^o alcohol
Ketone to 2^o alcohol)

Observations:
–

2,4-DNPH

Reagents:
2,4-DNPH, warm

Reaction:
Condensation

Observations:
Orange ppt of hydrazone formed

Carboxylate ion

Reagents:
I₂, NaOH, heat

Reaction:
Oxidation

Observations:
Yellow CHI₃ ppt formed

Carboxylate ion

Reagents:
Fehling’s solution (Cu²⁺ and NaOH), warm
Aldehyde (except benzaldehyde) only

Reaction:
Oxidation

Observations:
Brick red of Cu₂O ppt formed

Carboxylate ion

Reagents:
Tollen’s reageant (Ag₂O in NH₃)
Aldehyde only

Reaction:
Oxidation

Observations:
Silver mirror of Ag formed

Carboxylate ion

Reagents:
Na metal

Reaction:
Reduction

Observations:
Effervescence of H₂ gas formed which gives pop sound with lighted splint

Carboxylate ion

Reagents:
NaOH(aq)

Reaction:
Neutralisation

Observations:
–

Carboxylate ion

Reagents:
Na₂CO₃ (or NaHCO₃)

Reaction:
Neutralisation

Observations:
Effervescence of CO₂ gas formed which gives white ppt with limewater

Acyl chloride

Reagents:
PCl₃ (or PCl₅ or SOCl₂)

Reaction:
Neutralisation

Observations:
White fumes of HCl

Ester

Reagents:
Alcohol, conc H₂SO₄, heat

Reaction:
Condensation

Observations:
Sweet smell of ester

Alcohol

Reagents:
LiAlH₄ in dry ether

Reaction:
Reduction to 1^o alcohol

Observations:
–

Carbon dioxide

Reagents:
KMnO₄, heat
HCOOH or (COOH)₂

Reaction:
Purple KMnO₄ decolorized.
Effervescence of CO₂ gas formed which gives white ppt with limewater

Observations:
–

Ester

Reagents:
Alcohol, conc H₂SO₄, heat

Reaction:
Condensation

Observations:
Sweet smell of ester

Amide

Reagents:
Excess conc NH₃

Excess RNH₂
1^o amine to 2^o amide
2^o amine to 3^o amide
no reaction for 3^o amide

Reaction:
Condensation

Observations:
White fumes of HCl

Alcohol

Reagents:
H₂O

Reaction:
Hydrolysis

Observations:
White fumes of HCl

Carboxylic acid

Reagents:
Dilute H₂SO₄, heat under reflux

Reaction:
Acid hydrolysis

Observations:
–

Carboxylate ion

Reagents:
Dilute NaOH, heat under reflux

Reaction:
Basic hydrolysis

Observations:
–

Alkyl ammonium and carboxylic acid

Reagents:
HCl(aq)
(or CH₃COOH)

Reaction:
Neutralisation

Observations:
White crystalline solid

N-alkylamine

Reagents:
CH₃Cl, heat

Reaction:
Nucleophilic substitution

Observations:
–

Amide

Reagents:
Acyl chloride

Reaction:
Condensation

Observations:
White fumes of HCl

Alkyl ammonium

Reagents:
Dilute H₂SO₄, heat under reflux

Reaction:
Acid hydrolysis
1^o amide produce NH₄⁺

Observations:
–

Carboxylate ion and amine

Reagents:
Dilute NaOH, heat under reflux

Reaction:
Base hydrolysis
1^o amide produce NH₃

Observations:
NH₃ gas turned damp red litmus paper blue

Alkene

Reagents:
H₂/Ni, heat

Reaction:
Reduction

Observations:
–

Alcohol

Reagents:
Excess conc. H₂SO₄, 170⁰C
(or Al₂O3)

Reaction:
Elimination

Observations:
–

Alkene

Reagents:
Cl₂ in CCl₄ (or Br₂ in CCl₄)

Reaction:
Electrophilic addition

Observations:
Greenish yellow Cl₂ decolorised
(or reddish brown Br₂ decolorised)

Alkene

Reagents:
HCl gas, rtp

Reaction:
Electrophilic addition

Observations:
–

Alkene

Reagents:
PCl₃ (or PCl₅ or SOCl₂)
Conc HCl, anhydrous ZnCl₂, heat (for 1^o and 2^o alcohols only)
PBr₃ from Br₂ and red P
HBr gas from NaBr and H₂SO₄, heat
PI₃ from I₂ and red P

Reaction:
Substitution

Observations:
HCl fumes for PCl₃/PCl₅/SOCl₂ only

Halogenoalkane

Reagents:
NaOH (aq), heat under reflux

Reaction:
Nucleophilic substitution

Observations:
–

Alkene

Reagents:
H₂O, 300^oC, 60atm, conc. H₃PO₄

Reaction:
Electrophilic addition

Observations:
–

Carbonyl Compound

Reagents:
NaBH₄ (aq), (or LiAlH₄ in dry ether, H₂ gas, Pt heat)

Reaction:
Reduction
(Aldehyde to 1^o alcohol
Ketone to 2^o alcohol)

Observations:
–

Carboxylic Acid

Reagents:
LiAlH₄ in dry ether

Reaction:
Reduction to 1^o alcohol

Observations:
–

Alkene

Reagents:
Hot acidified KMnO₄

Reaction:
Oxidative cleavage

Observations:
Purple KMnO₄ decolorized.
Brown MnO₂ ppt formed in alkaline conditions

Ester

Reagents:
Dilute H₂SO₄, heat

Reaction:
Acid hydrolysis

Observations:
–

Alcohol

Reagents:
1^o alcohol only.
KMnO₄, heat (or K₂CrO₄, heat)

Reaction:
Oxidation

Observations:
Purple KMnO₄ decolorised
(or orange K₂CrO₄ turned green)

Alcohol

Reagents:
I₂, NaOH, heat

Reaction:
Mild oxidation

Observations:
Yellow CHI₃ ppt formed

Amide

Reagents:
HCl(aq)
(or CH₃COOH)

Reaction:
Neutralisation

Observations:
White crystalline solid

Carboxylic acid

Reagents:
PCl₃ (or PCl₅ or SOCl₂)

Reaction:
Neutralisation

Observations:
White fumes of HCl

Alcohol

Reagents:
Acid, conc H₂SO₄, heat
(or acyl chloride, rtp)

Reaction:
Condensation

Observations:
Sweet smell of ester

Carboxylic acid

Reagents:
Alcohol, conc H₂SO₄, heat

Reaction:
Condensation

Observations:
Sweet smell of ester

Acyl Chloride

Reagents:
ALcohol, conc H₂SO₄, heat

Reaction:
Condensation

Observations:
Sweet smell of ester

Halogenoalkane

Reagents:
Excess NH₃ (alc), heated in a sealed tube

Reaction:
Nucleophilic substitution

Observations:
–

Nitrile

Reagents:
LiAlH₄, dry ether
(or H₂, Pd)

Reaction:
Reduction

Observations:
–

Amide

Reagents:
Dilute NaOH, heat under reflux

Reaction:
Base hydrolysis
1^o amide produce NH₃

Observations:
NH₃ gas turned damp red litmus paper blue

Acyl chloride

Reagents:
Excess conc NH₃

Excess RNH₂
1^o amine to 2^o amide
2^o amine to 3^o amide
no reaction for 3^o amide

Reaction:
Condensation

Observations:
White fumes of HCl

Nitrobenzene

Reagents:
Conc HNO₃, conc H₂SO₄, heat under reflux at 55^oC

Reaction:
Electrophilic substitution

Observations:
Yellow layer of nitrobenzene formed

Bromobenzene

Reagents:
Br₂, anhydrous FeBr₃, rtp
(or Cl₂, anhydrous FeCl₃, rtp)

Reaction:
Electrophilic substitution

Observations:
Reddish brown Br₂ decolorised
(or greenish yellow Cl₂ decolorised)

1-methyl,2-nitrobenzene

Reagents:
Conc HNO₃, conc H₂SO₄, heat under reflux at 30^oC

Reaction:
Electrophilic substitution

Observations:
–

1-bromo-2-nitrobenzene

Reagents:
Br₂, anhydrous FeBr₃, rtp
(or Cl₂, anhydrous FeCl₃, rtp)

Reaction:
Electrophilic substitution

Observations:
Reddish brown Br₂ decolorised
(or greenish yellow Cl₂ decolorised)

chloromethylbenzene

Reagents:
Cl₂, UV light, boil

Reaction:
Free radical substitution

Observations:
Greenish yellow Cl₂ decolorised
White fumes of HCl formed

Benzoic acid

Reagents:
Hot acidified KMnO₄, heat under reflux

Reaction:
Side chain oxidation

Observations:
Purple KMnO₄ decolorised
White benzoic acid ppt formed

Phenoxide ion

Reagents:
Na metal

Reaction:
Reduction

Observations:
Effervescence of H₂ gas formed which gives pop sound with lighted splint

Phenyl benzoate

Reagents:
CH₃Cl, pyridine, rtp

Reaction:
Condensation

Observations:
Sweet smell of ester
White fumes of HCl formed

Phenyl benzoate

Reagents:
Phenylacetyl chloride, NaOH(aq), rtp

Reaction:
Condensation

Observations:
Sweet smell of ester
White fumes of HCl formed

1,3,5-tribromobenzene

Reagents:
Br₂(aq), rtp

Reaction:
Condensation

Observations:
Reddish brown Br₂ decolorized
White 1,3,5-tribromobenzene ppt formed
White fumes of HBr formed

Nitrophenol

Reagents:
Dilute HNO₃(aq), rtp

Reaction:
Electrophilic substitution

Observations:
Yellow layer of nitrophenol formed

1,3,5-trinitrophenol

Reagents:
Conc HNO₃(aq), rtp

Reaction:
Electrophilic substitution

Observations:
Yellow ppt of 1,3,5-trinitrophenol formed

1,3,5-trinitrophenol

Reagents:
Neutral FeCl₃(aq)

Reaction:
Electrophilic substitution

Observations:
Violet complex compound formed

Phenyl benzoate

Reagents:
Phenol, NaOH(aq), rtp

Reaction:
Condensation

Observations:
Sweet smell of ester
White fumes of HCl formed

Phenylamine

Reagents:
Sn, conc HCl, heat followed by NaOH (or H₂, Ni, heat)

Reaction:
Reduction

Observations:
Sweet smell of ester
White fumes of HCl formed

2,4,6-tribromophenylamine

Reagents:
Br₂(aq)

Reaction:
Electrophilic substitution

Observations:
Reddish brown Br₂ decolorized
White 2,4,6-tribromophenylamine ppt formed
White fumes of HBr formed