Summary of reagents and their functions

Reagent Responding Functional Product formed Observation Type of reactionf

Groups
Sodium Alcohols Sodium salt of alcohol Fizzes due to the evolution oxidation
Phenols Sodium salt of phenol of hydrogen gas
Carboxylic acids Sodium salt of carboxylic acid
Sodium hydroxide Phenols Sodium salt of phenol Salt formed dissolves Neutralisation
(cold) Carboxylic acids Sodium salt of carboxylic acid Salt formed dissolves
Sodium hydroxide Besides the above reactions,
(hot) Hydrolysis of esters Acid salt + alcohol
Hydrolysis of amides Acid salt + amines Hydrolysis
Hydrolysis of Acid salt + ammonia Pungent smelling gas of
nitriles(cyanides) NH3
Aqueous Bromine Alkene Dibromoaddition product Orange disappears CaCaEleADD

Phenol 2,4,6-tribromophenol White precipitate, Orange

disappears Electrophilic
Phenylamine 2,4,6-tribromophenylamine White precipitate, Orange Substitution
disappears
Cold acidified dil.KMnO4 Alkene Diol Purple turns colourless oxidation
Hot acidified con.KMnO4 Alkene Depending on the compound Purple turns colourless
(carboxylic acid, ketone,CO2)

On distillation - Aldehydes Oxidation

Primary alcohol On reflux - Carboxylic acid Purple turns colourless

Secondary alcohol Ketone Purple turns colourless

Alkaline KMnO4, heat, Side chain alkyl group Whatever may be the length of the Purple turns colourless
followed by hydrolysis attached to the benzene ring side chain, benzoic acid is the
with acid product + CO2
Acidified K2Cr2O7, heat Primary alcohol On distillation - Aldehydes Orange turns green
On reflux - Carboxylic acid Oxidation

Secondary alcohol Ketone Orange turns green

2,4-DNPH Aldehydes and ketones Condensed product with Orange red precipitate Conden-
=N-NH2 group sation
Fehling's reagent Only aldehydes Corresponding carboxylic acid Blue turns red Oxidation
Tollen's reagent Only aldehydes Corresponding carboxylic acid Silver mirror formation Oxidation
NaHCO3 or Na2CO3 Only carboxylic acids Sodium salt of carboxylic acid Brisk effervescence of CO2 Neutralisation
Br2, FeBr3, r.t Benzene Bromobenzene HBr colourless gas evolved Electrophilic
Cl2, FeCl3, r.t Chlorobenzene HCl white steamy fumes Substitution
CH3Cl, FeCl3, r.t Benzene Methylbenzene HCl white steamy fumes Electrophilic
Substitution
CH3COCl, FeCl3, r.t Benzene Phenylmethylketone HCl white steamy fumes Electrophilic
Substitution
HNO3, H2SO4, 55 - 600C Benzene Nitrobenzene No specific observation Electrophilic
Substitution
SOCl2, r.t Alcohols, carboxylic acids RCH2OH into RCH2Cl Pungent smelling SO2 and
RCOOH into RCOCl white steamy fumes of HCl Nucleophilic
Substitution
PCl5, r.t Alcohols, carboxylic acids RCH2OH into RCH2Cl White steamy fumes of HCl
RCOOH into RCOCl along with POCl3
Acylchlorides such as
CH3COCl Alcohols Esters formed White steamy fumes of HCl
PhCOCl Phenols Phenolic esters formed White steamy fumes of HCl Nucleophilic
Amines Amides formed White steamy fumes of HCl Substitution
Hot Alkaline aqueous Methylketones CH3CO- Carboxylic acid with one carbon Yellow precipitate
iodine CH3CH(OH)- atom less and CHI3 Oxidation
OH-, I2, heat followed by CH3CHO
hydrolysis with H+ CH3CH2OH
NH3 CH3COCl - Acylchloride Amides White steamy fumes Nucleophilic
CH3NH2 CH3CH2Cl - Alkylchloride Amines White steamy fumes substitution

Sn, conc.HCl, reflux, Ph-NO2 Ph-NH2 No specific observation Reduction

followed by hydrolysis
with aq.NaOH
HNO2, HCl, 0-100C Ph-NH2 Ph-N=N+Cl-(Diazotisation) No specific observation condensation
NaBH4, EtOH, reflux Aldehydes Primary alcohol No specific observation Reduction
ketones Secondary alcohol No specific observation
H2, Ni Aldehydes Primary alcohol No specific observation
Ketones Secondary alcohol
C=C, C=O, C=N, Reduction

H2, Ni hot conditions

Even benzene ring Cyclohexane ring No specific observation
LiAlH4 Aldehydes Primary alcohol No specific observation
 Ketones Secondary alcohol No specific observation Reduction
-CONH2 -CH2NH2 No specific observation
Dil.acid or conc.acid, PhenylAmines PhenylAmmonium chloride Salt formed dissolves neutralisation
Esters Carboxylic acid + alcohol No specific observation
Dil.acid or conc.acid, Amides Carboxylic acid + ammonia or Pungent smelling gas of
reflux amines NH3 Hydrolysis
Nitriles (cyanides) Carboxylic acid + ammonia
Pungent smelling gas
Summary of reagents and their functions

Reagent Responding Functional Product formed Observation Type of reactionf

Groups
Sodium Alcohols Sodium salt of alcohol Fizzes due to the evolution oxidation
Phenols Sodium salt of phenol of hydrogen gas
Carboxylic acids Sodium salt of carboxylic acid
Sodium hydroxide Phenols Sodium salt of phenol Salt formed dissolves Neutralisation
(cold) Carboxylic acids Sodium salt of carboxylic acid Salt formed dissolves
Sodium hydroxide Besides the above reactions,
(hot) Hydrolysis of esters Acid salt + alcohol
Hydrolysis of amides Acid salt + amines Hydrolysis
Hydrolysis of Acid salt + ammonia Pungent smelling gas of
nitriles(cyanides) NH3
Aqueous Bromine Alkene Dibromoaddition product Orange disappears CaCaEleADD

Phenol 2,4,6-tribromophenol White precipitate, Orange

disappears Electrophilic
Phenylamine 2,4,6-tribromophenylamine White precipitate, Orange Substitution
disappears
Cold acidified dil.KMnO4 Alkene Diol Purple turns colourless oxidation
Hot acidified Alkene Depending on the compound Purple turns colourless
con.KMnO4 (carboxylic acid, ketone,CO2)

On distillation - Aldehydes Oxidation

Primary alcohol On reflux - Carboxylic acid Purple turns colourless

Secondary alcohol Ketone Purple turns colourless

Alkaline KMnO4, heat, Side chain alkyl group Whatever may be the length of the Purple turns colourless
followed by hydrolysis attached to the benzene ring side chain, benzoic acid is the
with acid product + CO2
Acidified K2Cr2O7, heat Primary alcohol On distillation - Aldehydes Orange turns green
On reflux - Carboxylic acid Oxidation

Secondary alcohol Ketone Orange turns green

2,4-DNPH Aldehydes and ketones Condensed product with Orange red precipitate Conden-
=N-NH2 group sation
Fehling's reagent Only aldehydes Corresponding carboxylic acid Blue turns red Oxidation
Tollen's reagent Only aldehydes Corresponding carboxylic acid Silver mirror formation Oxidation
NaHCO3 or Na2CO3 Only carboxylic acids Sodium salt of carboxylic acid Brisk effervescence of CO2 Neutralisation
Br2, FeBr3, r.t Benzene Bromobenzene HBr colourless gas evolved Electrophilic
Cl2, FeCl3, r.t Chlorobenzene HCl white steamy fumes Substitution
CH3Cl, FeCl3, r.t Benzene Methylbenzene HCl white steamy fumes Electrophilic
Substitution
CH3COCl, FeCl3, r.t Benzene Phenylmethylketone HCl white steamy fumes Electrophilic
Substitution
HNO3, H2SO4, 55 - 600C Benzene Nitrobenzene No specific observation Electrophilic
Substitution
SOCl2, r.t Alcohols, carboxylic acids RCH2OH into RCH2Cl Pungent smelling SO2 and
RCOOH into RCOCl white steamy fumes of HCl Nucleophilic
Substitution
PCl5, r.t Alcohols, carboxylic acids RCH2OH into RCH2Cl White steamy fumes of HCl
RCOOH into RCOCl along with POCl3
Acylchlorides such as
CH3COCl Alcohols Esters formed White steamy fumes of HCl
PhCOCl Phenols Phenolic esters formed White steamy fumes of HCl Nucleophilic
Amines Amides formed White steamy fumes of HCl Substitution
Hot Alkaline aqueous Methylketones CH3CO- Carboxylic acid with one carbon Yellow precipitate
iodine CH3CH(OH)- atom less and CHI3 Oxidation
OH-, I2, heat followed by CH3CHO
hydrolysis with H+ CH3CH2OH
NH3 CH3COCl - Acylchloride Amides White steamy fumes Nucleophilic
CH3NH2 CH3CH2Cl - Alkylchloride Amines White steamy fumes substitution

Sn, conc.HCl, reflux, Ph-NO2 Ph-NH2 No specific observation Reduction

followed by hydrolysis
with aq.NaOH
HNO2, HCl, 0-100C Ph-NH2 Ph-N=N+Cl-(Diazotisation) No specific observation condensation
NaBH4, EtOH, reflux Aldehydes Primary alcohol No specific observation Reduction
ketones Secondary alcohol No specific observation
H2, Ni Aldehydes Primary alcohol No specific observation
Ketones Secondary alcohol
C=C, C=O, C=N, Reduction

H2, Ni hot conditions Even benzene ring Cyclohexane ring No specific observation
LiAlH4 Aldehydes Primary alcohol No specific observation
Ketones Secondary alcohol No specific observation Reduction
-CONH2 -CH2NH2 No specific observation
Dil.acid or conc.acid, PhenylAmines PhenylAmmonium chloride Salt formed dissolves neutralisation
Esters Carboxylic acid + alcohol No specific observation
Dil.acid or conc.acid, Amides Carboxylic acid + ammonia or Pungent smelling gas of
reflux amines NH3 Hydrolysis
Nitriles (cyanides) Carboxylic acid + ammonia
Pungent smelling gas