Organic Chemistry Summary by Functional Group

Reagents and
Reactant (Major) Product Type of reaction Observation, if any
Conditions
A
L
K
Cl2 gas (or Br2) Free Radical Greenish yellow Cl2 decolourised
A CH3CH3 CH3CH2Cl
N UV light Substitution White fumes of HCl formed
E
S
Reduction
H2 / Ni, heat
CH3CH2CH3 (Catalytic NA
(or H2 / Pt, r.t.p)
Hydrogenation)
Br2 in CCl4
CH3CHBrCH2Br Red Brown Br2 decolourised
(Or Cl2 in CCl4)

HBr (g), r.t.p CH3CHBrCH3 (major) Electrophilic NA

Addition
CH3CH=CH2
A H2O(g), 300°C, 60 atm,
L CH3CH(OH)CH3 NA
conc H3PO4
K
E Purple KMnO4 decolourised,
N Cold dilute KMnO4 CH3CH(OH)CH2OH Mild Oxidation brown ppt of MnO2 formed
E (only in alkaline conditions).
S CH3COOH Oxidative
Hot acidified KMnO4 Purple KMnO4 decolourised
CO2, H2O Cleavage

In general, for reaction with hot acidified KMnO4, (where R is any alkyl group)
H H HO R R

! C O CO2, H2O " C O C O

# C O C O

H R R R R
Conc HNO3,
Yellow layer of nitrobenzene
Conc H2SO4, NO2
produced
Reflux at 55 °C

Br2, anhydrous FeBr3,

r.t.p
Br Red-brown Br2 decolourised
(or Cl2, anhydrous
FeCl3) Electrophilic
A Substitution
R Conc HNO3, CH3
E Conc H2SO4, NA
N Refluxat 30 °C NO2 CH3
NO2
E
S CH3
Br2, anhydrous FeBr3,
Red-brown Br2 decolourised
CH3
r.t.p Br CH3
Br

Free radical Yellow green Cl2 decolourised

Cl2, UV light or boil CH2Cl
substitution White fumes of HCl formed

Acidified KMnO4, heat Oxidation of Purple KMnO4 decolourised.

COOH
under reflux side chain White ppt of benzoic acid.

Alcoholic NaOH
CH2=CH2 Elimination NA
Heat under reflux
H
A Aqueous NaOH,
CH3CH2OH NA
L Heat under reflux
O CH3CH2Br
G Excess alcoholic NH3, Nucleophilic
CH3CH2NH2 NA
E heat in a sealed tube Substitution
N
O Alcoholic NaCN, heat
CH3CH2CN NA
A under reflux
L
K 1 Dilute H2SO4, heat CH3CH2COOH Acid Hydrolysis NA
A
N
E 2 CH3CH2CN Dilute NaOH, heat CH3CH2COO− Base Hydrolysis NA
S
LiAlH4 in dry ether
3 CH3CH2CH2NH2 Reduction NA
(or H2 / Pd cat)
 Reagents and
Reactant (Major) Product Type of reaction Observation, if any
Conditions
PCl3 / PCl5 / SOCl2 Steamy fumes of HCl produced
Conc HCl, anhydrous CH3CH2Cl
ZnCl2, heat (only for NA
1°° and 2°° ROH)
PBr3 (from Br2 and red
CH3CH2OH Substitution
phosphorus)
CH3CH2Br
HBr gas(from NaBr and
NA
conc H2SO4,heat)
PI3 (from I2 and red
CH3CH2I
phosphorus)

OH Any halogenating agent No reaction - NA

CH3CH2OH CH3CH2O−Na+ Effervescence of H2 gas evolved

Na metal - + Reduction which gave a pop sound with
OH O Na lighted splint

CH3CH2OH No reaction - No visible observation

NaOH(aq), rtp - + Phenol layer dissolves into
OH O Na Acid-base
aqueous NaOH layer

Hot acidified K2Cr2O7 or

CH3COOH
CH3CH2OH KMnO4 Orange K2Cr2O7 turned green /
1°° ROH Hot acidified K2Cr2O7 Purple KMnO4 decolourised
CH3CHO Oxidation
distillation
CH3CH(OH)CH3 Hot acidified K2Cr2O7 or Orange K2Cr2O7 turned green /
CH3COCH3
2°° ROH KMnO4 Purple KMnO4 decolourised
(CH3)3COH Hot acidified K2Cr2O7 or Orange K2Cr2O7 remains / Purple
Not oxidised -
3°° ROH KMnO4 KMnO4 remains

H Excess, conc
Y CH3CH2OH H2SO4,170 °C CH2=CH2 Elimination NA
D Al2O3, 350 °C
R
O H
X
RCO2−Na+
Y CH 3 C R I2, NaOH, heat Mild oxidation Yellow ppt of CHI3 formed
CHI3
OH
CH3CO2H,
Sweet smell of ester
conc H2SO4, heat
CH3CH2OH CH3CO2CH2CH3
CH3COCl, rtp
CH3CO2H, Condensation (or
No reaction
conc H2SO4, heat nucleophilic acyl
CH3COCl, substitution) Sweet smell of ester
OCOCH3 White fumes of HCl formed
OH pyridine, rtp

COCl
OCO
NaOH, rtp
Br
Reddish brown Br2 decolourised,
Br2(aq) Br OH White ppt formed
White fumes of HBr formed
Br

OH
Dilute HNO3 Electrophilic Yellow layer formed
O2 N OH substitution
OH NO2
NO2

Conc HNO3 O2N OH Yellow ppt formed

NO2

Neutral FeCl3(aq) - Complex formation Purple colouration

 Reagents and
Reactant (Major) Product Type of reaction Observation, if any
Conditions
CH3CH2CHO Orange K2Cr2O7 turned green /
CH3COOH Oxidation
Aldehyde Hot acidified K2Cr2O7 or Purple KMnO4 decolourised
KMnO4
CH3COCH3
Not oxidised - No colour change
Ketone
CH3CH2CHO CH3CH2CH2OH
Aldehyde NaBH4(aq) or 1°° ROH
LiAlH4 in dry ether or Reduction NA
CH3COCH3 H2 gas, Pt CH3CH(OH)CH3
Ketone 2°° ROH
R HCN(g), trace NaOH R CN
Nucleophilic
C O (or trace NaCN), C NA
Addition
C 10 – 20 °C R OH
R
A
R O 2N
R R
B 2,4-DNPH,
O C O Condensation Orange ppt formed
warm C N NH NO2
N R
Y R
L R
S C O RCO2−
I2, NaOH, heat Oxidation Yellow ppt formed
CHI3
CH3
CH3CH2CHO
CH3CH2CO2−
Aldehyde (except Oxidation Brick red ppt formed
benzaldehyde) Fehling’s solution (Cu2+ Cu2O
and NaOH), warm
CH3COCH3
Not oxidised - No ppt formed
Ketone
CH3CH2CHO CH3CH2CO2−
Oxidation Silver mirror formed
Aldehyde Tollen’s reagent (Ag2O Ag
CH3COCH3 in NH3), warm
Not oxidised - No silver mirror
Ketone
Effervescence of H2 gas evolved
Na metal CH3CO2−Na+ + H2 Reduction which gave a pop sound with
lighted splint
C NaOH(aq) CH3CO2−Na+ + H2O Acid-base NA
A
Effervescence of CO2 gas
R
Na2CO3 or NaHCO3 CH3CO2−Na+ + CO2 + H2O Acid-base evolved which gave a white ppt
B
with limewater
O
X CH3CO2H (Nucleophilic)
PCl3 / PCl5 / SOCl2 CH3COCl White fumes of HCl
Y substitution
LI Condensation (or
CH3CH2OH
C CH3CO2CH2CH3 nucleophilic acyl Sweet smell of ester
Conc H2SO4, heat
A substitution)
C CH3CH2OH
I LiAlH4 in dry ether Reduction NA
1°° ROH
D
S Hot acidified KMnO4 Not oxidised - No colour change
HCO2H Purple KMnO4 decolourised,
Hot acidified KMnO4 CO2, H2O Oxidation
(COOH)2 effervescence of CO2 gas
CH3CH2OH
CH3CO2CH2CH3
rtp
CH3COCl
A OH
OCOCH3 Sweet smell of ester
C White fumes of HCl
Pyridine, rtp
Y
L OH
COCl OCO
Condensation (or
C NaOH, rtp nucleophilic acyl
H CH3CONH2 substitution)
L CH3COCl Excess conc NH3 White fumes of HCl
1° amide
O
R Excess RNH2 CH3CONHR
CH3COCl White fumes of HCl
I 1° amine 2° amide
D Excess R2NH CH3CONR2
CH3COCl White fumes of HCl
E 2° amine 3° amide
S Excess R3N
CH3COCl No reaction NA
3° amine
CH3COCl H2O CH3CO2H Hydrolysis White fumes of HCl
 Reagents and
Reactant (Major) Product Type of reaction Observation, if any
Conditions
E Dilute H2SO4, heat
S CH3CO2H, CH3CH2OH Acid hydrolysis NA
under reflux
T CH3CO2CH2CH3
E Dilute NaOH, heat
CH3CO2−Na+, `CH3CH2OH Base hydrolysis NA
R under reflux
NO 2 NH2
Sn, conc HCl,heat,
followed by NaOH reduction NA
Or H2,Ni, heat

CH3CH2NH2 Aq HCl CH3CH2NH3+Cl− Acid-base White crystalline solid

N
I CH3CH2NH2 CH3COOH (aq) [CH3CH2NH3+][CH3COO−] Acid-base White crystalline solid
T
R
O CH3Cl, heat
Nucleophilic
G CH3CH2NH2 Or any other CH3CH2NHCH3 NA
substitution
E halogenoalkane
N CH3CH2NH2 CH3COCl CH3CONHCH2CH3 Condensation White fumes of HCl
NH2
C NH2
O Br Br
Reddish−brown bromine
M decolourises, white ppt of
Electrophilic
P Aq Br2 2,4,6−tribromophenylamine
substitution
O formed and white fumes of HBr
U seen.
N Br
D Dilute H2SO4, heat CH3COOH
Acid hydrolysis NA
S CH3CONH2 under reflux NH4+
1°° amide Dilute NaOH, heat CH3COO −
Pungent NH3 gas evolved which
Base hydrolysis
under reflux NH3 turns red litmus blue
Dilute H2SO4, heat CH3COOH
Acid hydrolysis NA
CH3CONHCH2CH3 under reflux CH2CH2NH3+
2°° amide
Dilute NaOH, heat CH3COO−
Base hydrolysis NA
under reflux CH2CH2NH2