ORGANIC REAGENTS

REAGENTS THEIR USES

(1) X2/CCl4/CS2/CHCl3/CH2Cl2 Anti addition of X2 on multiple bond.

X2 = Br2, Cl2

OH OH

(2) Br2 + CCl4 / CS2/CH3COOH 

Br

(3) Br2/CCl4,  HUNSDIECKER REACTION

O
R – C – O – Ag  R – Br
(one ‘C’ less product)

(4) I2 / CCl4 BIRNBAUM SIMONINI REACTION

O O
R – C – O – Ag  R – C – O – R

(5) Br2/KOH or NaOH / / NaOX HOFFMANN BROMAMIDE DEGRADATION

O
R – C – NH2  R–NH2
Amide into Amine with one ‘C’ less

(6) X2 + NaOH or NaOX HALOFORM REACTION

(7) Br2 / h; Cl2/h ; I2 / HgO or HIO3 /  Halogenation of alkane

R – H  R – X
Cl
Cl Cl
* h
+ Cl2(excess) 
Cl Cl
Cl
(8) X2 / red P ; X2 = Br2, Cl2 HVZ REACTION
CH3–COOH  CH 2  COOH
|
X
ONLY  HYDROGENS ARE REPLACED

Page No.1
 REAGENTS THEIR USES

(9) Cl2 / FeCl3 ; Br2 / FeCl3 ; I2 / HIO3 ; Halogenation of aromatic compound

X

Br2 / Fe ; HOCl ; Br2 + H2O 

M
M Br Br

* Br
2 
H 2O

Br
M = –OH , –NH2

(10) Br2 + H2O ; Interhalogen compound ; Anti addition on alkene

Br2 / aq. Brine solution;
NOCl (Tilden reagent); HOCl

(11) HOCl Addition on alkyne

Alkyne  Enol to Carbonyl compound
* HOCl oxidises aldehyde into
carboxylic acid

(12) HBr, HCl, HI Hydrohalogenation of alkene and alkynes

according to Markovnikov’s rule

(13) HBr / peroxide; CBrCl3, CIBr3, CBrF3, Addition of alkene and alkyne according
CHCl3, CHI3, RSH, COCl2 to Antimarkovnikov’s rule

(14) (i) O3 ; (ii) Zn / H2O ; Me2S ; Ph3P Reductive ozonolysis of alkene and alkyne

(15) O3 / H2O or O3 / H2O2 Oxidative ozonolysis of alkene and alkyne

(16) Cold dilute alkaline KMnO4 or Hydroxylation of alkene

dil.KMnO4 or Bayer’s reagent ; (preparation of syndiol on alkene)
OsO4 / NaHSO3

(17) Peroxy acids ; RCO3H; mcpba; H2S2O8; Epoxydation of alkene (Prielshavie reaction)
H2SO5 (Carro’s acid)

(18) Hydrolysis of epoxide in acidic and Anti-diol formation

basic medium

(19) Conc. H2SO4; H3PO4/; Al2O3/; Dehydration of alcohol into alkene

POCl3 / ; ThO2 / 

Page No.2
 REAGENTS THEIR USES
(20) N-Bromo succinimide (NBS) Allylic substitution

N-Chloro succinimide (NCS) CH 2  CH  CH 2  CH 2  CH  CH 2

| |
Br2 at low concentration H X
X2 at high concentration
t-Butyloxy chloride (Me3COCl) / h or 
SO2Cl2 / h or 

(21) H / H2O or H3O or dil. H2SO4 HYDRATION OF ALKENE

(i) (CH3COO)2 Hg / H2O MARKOVNIKOFF ADDITION OF

(ii) NaBH4 WATER WITH REAARRANGEMENT

(i) B2H6 / THF ADD WATER BY ANTIMARKOVNIKOV

(ii) H2O2 / OH¯ RULE NO REARRANGEMENT

(I) Hg (OAc) 2 / H 2O ADD WATER BY MARKOVNIKOV RULE

(II) NaBH 4 / OH  NO REARRANGEMENT
(i) (Sia)2BH / THF
(ii) (H2O2/OH¯) HYDRATION OF ALKYNE

(i) 9-BBN / THF

(ii) H2O2 / OH¯

(22) HgSO4 / dil. H2SO4 or Hg2+ Hydration of alkyne (Kucherov reaction)

(23) Mg Hg + H2O ; Zn–Hg + H2O Vicinal diol (Pinacol) formation by

Na – Hg + H2O compound having ketone group
* Pinacol conc
 .H 2SO 4
 Pinacolone
or H 3PO 4 / 

(24) Conc. H2SO4 Sulphonation of aromatic compound

(25) HNO3 + HClO4 ; conc. HNO3 ; Nitration of aromatic compound

solid N2O5 ; NO2F + BF3 ; AcONO2 ;
HNO2 / HNO3

(26) Anhydrous AlCl3 (i) Isomerisation of alkane

Alkane  Branched alkane

(ii) Friedal craft’s alkylation

Page No.3
 REAGENTS THEIR USES

+ RX  + HX

(iii) FRIEDEL CRAFT ACYLATION

OH OH
O
COR
+ R – C – Cl  +

COR
(iv) FRIES REARRANGEMENT

OCOR OH OH
COR
AlCl3 +


COR

(27) SbCl5 / , H;AlCl3 / , H SEMIPINACOL PINACOLONE REARRANGEMENT

AgNO3 / , H

(28) CHCl3 + NaOH /  ; H3O RIEMER TIEMANN REACTION

OH OH

CHO
+ CHCl3 + NaOH 
H3O

(29) CHCl3 + NaOH ,  CARBYLAMINE OF ISOCYANIDE TEST


R–NH2+CHCl3+ NaOH R–N  C +NaCl+H2O

OH OH
COOH
(30) CCl4 + NaOH, H3O + CCl4 + NaOH 

H 3O

(31) CO2 + NaOH , H3O KOLBE SCHMIDT REACTION

OH OH
COOH
H3O
+ CO2 + NaOH

(32) NaOH + CaO,  DECARBOXYLATION

Page No.4
 REAGENTS THEIR USES
O
(3 : 1) R – C – OH  R–H + CaCO3 

(33) N3H + conc. H2SO4 SCHMIDT REACTION

O
conc.H SO
R–C–OH +N3H  2
4
R–NH2+CO2+H2O+N2

O O
(34) CH2N2 (diazomethane) R–C–OH + CH2N2  R–C–OCH3 + N2

(35) Fused NaOH, high temperature, Dow process

Cl OH

high pressure 

(36) NaNO2 / HCl or HNO2 Diazotisation of Amine

(37) NaNO2 / HCl,  Aniline into diazonium chloride

(38) CuCl, CuBr, CuCN, H2O, H3PO2 Diazonium chloride into chlorobenzene,
Bromobenzene, Benzonitrile, Phenol, Benzene
respectively.

(39) Na /dry ether Wurtz reaction

2R – X  R – R
Fittig reaction

2 X
Wurtz-fittig reaction

X + RX + R + R–R

(40) Cu /  Ulmann’s reaction

2 I

(41) Ag /  CHCl3  HC  CH

(42) Zn dust Phenol to Benzene

(43) Zn dust,  ; NaI / Acetone Dehalogenation of Antivicinal dihalide

Page No.5
 REAGENTS THEIR USES

Cl
|
H 2 C  CH 2  H2C = CH2
|
Cl

(44) Alc. KOH; NaNH2 Dehydrohalogenation

(45) Aq. KOH Alkyl halide into Alcohol

(46) PCl5 / P2O5 / P4O10 / POCl3 /  Dehydration of amides into nitriles

(47) PCl5 R–OH  R–Cl

R–O–R’  R–Cl + R’–Cl + POCl3
OH

 Ph3PO4 (major)

R R Cl
O 
R R Cl

(48) SOCl2 Darzon method

Alkyl alcohol  Alkyl chloride

(49) HI Ether convert into alcohol and ALkyl halide

(50) HCN Carbonyl compound into cyanohydrin

(51) Aq. KCN R–X + aq. KCN  R–CN (cyanide)


(52) AgCN R–X + AgCN  R  N  C (isocyanide)

(53) KNO 2 R–X + KNO2  R–O–N=O (Alkyl nitrite)

(54) AgNO2 R–X + AgNO2  R–NO2 (Nitro Alkane)

(55) Moist Ag2O R–X + Moist Ag2O  R–OH

Page No.6
 REAGENTS THEIR USES

DISTINGUISHING TESTS

(1) HCl + anhydrous ZnCl2 Lucas test (To distinguish 1°,2°,3° alcohols)

(2) AgNO3 + NH4OH (Tollen’s reagent) Tollen’s test to identify aldehyde

(3) Fehling solution Fehling test

Only aliphatic aldehyde gives this test (red ppt.)

(4) Benedict solution Benedict test

Only Aliphatic aldehyde gives this test

(5) 2,4-DNP 2,4-DNP test

Test for ketone and aldehyde

(6) Hinsberg reagent Hinsberg test

C6H5SO2Cl to differentiate 1°, 2°, 3° amine

(7) CHCl3 + NaOH Carbylamine or Isocyanide test

(for primary amine)

(8) NaNO2 + HCl Libermann’s Nitroso test for phenol

(9) Beilstein test / Flame test Test of alkyl halide

Alkyl halide give blue green colour flame when
heated with Cu wire

(10) Victor Mayer test To differentiate

(i) 1°, 2°, 3° Alcohol
(ii) 1°, 2°, 3° Alkyl halide
(iii) 1°, 2°, 3° Nitro Alkane

(11) Test of Methanol

OH OH O
COOH 
C–OMe
MeOH
 /H
 (Oil of winter green)

(12) Test for carboxylic acids :

(i) Litmus test
(ii) With Na Metal
(iii) Reaction with NaOH
(iv) With NaHCO3

(13) Test of Phenol :

(i) With Na Metal (ii) With NaOH (iii) With aqueous FeCl3

Page No.7
 ORGANIC REAGENTS

REAGENTS THEIR USES

(1) X2/CCl4/CS2/CHCl3/CH2Cl2 Anti addition of X2 on multiple bond.

X2 = Br2, Cl2

OH OH

(2) Br2 + CCl4 / CS2/CH3COOH 

Br

(3) Br2/CCl4,  HUNSDIECKER REACTION

O
R – C – O – Ag  R – Br
(one ‘C’ less product)

(4) I2 / CCl4 BIRNBAUM SIMONINI REACTION

O O
R – C – O – Ag  R – C – O – R

(5) Br2/KOH or NaOH / / NaOX HOFFMANN BROMAMIDE DEGRADATION

O
R – C – NH2  R–NH2
Amide into Amine with one ‘C’ less

(6) X2 + NaOH or NaOX HALOFORM REACTION

(7) Br2 / h; Cl2/h ; I2 / HgO or HIO3 /  Halogenation of alkane

R – H  R – X
Cl
Cl Cl
* h
+ Cl2(excess) 
Cl Cl
Cl
(8) X2 / red P ; X2 = Br2, Cl2 HVZ REACTION
CH3–COOH  CH 2  COOH
|
X
ONLY  HYDROGENS ARE REPLACED

Page No.1
 REAGENTS THEIR USES

(9) Cl2 / FeCl3 ; Br2 / FeCl3 ; I2 / HIO3 ; Halogenation of aromatic compound

X

Br2 / Fe ; HOCl ; Br2 + H2O 

M
M Br Br

* Br
2 
H 2O

Br
M = –OH , –NH2

(10) Br2 + H2O ; Interhalogen compound ; Anti addition on alkene

Br2 / aq. Brine solution;
NOCl (Tilden reagent); HOCl

(11) HOCl Addition on alkyne

Alkyne  Enol to Carbonyl compound
* HOCl oxidises aldehyde into
carboxylic acid

(12) HBr, HCl, HI Hydrohalogenation of alkene and alkynes

according to Markovnikov’s rule

(13) HBr / peroxide; CBrCl3, CIBr3, CBrF3, Addition of alkene and alkyne according
CHCl3, CHI3, RSH, COCl2 to Antimarkovnikov’s rule

(14) (i) O3 ; (ii) Zn / H2O ; Me2S ; Ph3P Reductive ozonolysis of alkene and alkyne

(15) O3 / H2O or O3 / H2O2 Oxidative ozonolysis of alkene and alkyne

(16) Cold dilute alkaline KMnO4 or Hydroxylation of alkene

dil.KMnO4 or Bayer’s reagent ; (preparation of syndiol on alkene)
OsO4 / NaHSO3

(17) Peroxy acids ; RCO3H; mcpba; H2S2O8; Epoxydation of alkene (Prielshavie reaction)
H2SO5 (Carro’s acid)

(18) Hydrolysis of epoxide in acidic and Anti-diol formation

basic medium

(19) Conc. H2SO4; H3PO4/; Al2O3/; Dehydration of alcohol into alkene

POCl3 / ; ThO2 / 

Page No.2
 REAGENTS THEIR USES
(20) N-Bromo succinimide (NBS) Allylic substitution

N-Chloro succinimide (NCS) CH 2  CH  CH 2  CH 2  CH  CH 2

| |
Br2 at low concentration H X
X2 at high concentration
t-Butyloxy chloride (Me3COCl) / h or 
SO2Cl2 / h or 

(21) H / H2O or H3O or dil. H2SO4 HYDRATION OF ALKENE

(i) (CH3COO)2 Hg / H2O MARKOVNIKOFF ADDITION OF

(ii) NaBH4 WATER WITH REAARRANGEMENT

(i) B2H6 / THF ADD WATER BY ANTIMARKOVNIKOV

(ii) H2O2 / OH¯ RULE NO REARRANGEMENT

(I) Hg (OAc) 2 / H 2O ADD WATER BY MARKOVNIKOV RULE

(II) NaBH 4 / OH  NO REARRANGEMENT
(i) (Sia)2BH / THF
(ii) (H2O2/OH¯) HYDRATION OF ALKYNE

(i) 9-BBN / THF

(ii) H2O2 / OH¯

(22) HgSO4 / dil. H2SO4 or Hg2+ Hydration of alkyne (Kucherov reaction)

(23) Mg Hg + H2O ; Zn–Hg + H2O Vicinal diol (Pinacol) formation by

Na – Hg + H2O compound having ketone group
* Pinacol conc
 .H 2SO 4
 Pinacolone
or H 3PO 4 / 

(24) Conc. H2SO4 Sulphonation of aromatic compound

(25) HNO3 + HClO4 ; conc. HNO3 ; Nitration of aromatic compound

solid N2O5 ; NO2F + BF3 ; AcONO2 ;
HNO2 / HNO3

(26) Anhydrous AlCl3 (i) Isomerisation of alkane

Alkane  Branched alkane

(ii) Friedal craft’s alkylation

Page No.3
 REAGENTS THEIR USES

+ RX  + HX

(iii) FRIEDEL CRAFT ACYLATION

OH OH
O
COR
+ R – C – Cl  +

COR
(iv) FRIES REARRANGEMENT

OCOR OH OH
COR
AlCl3 +


COR

(27) SbCl5 / , H;AlCl3 / , H SEMIPINACOL PINACOLONE REARRANGEMENT

AgNO3 / , H

(28) CHCl3 + NaOH /  ; H3O RIEMER TIEMANN REACTION

OH OH

CHO
+ CHCl3 + NaOH 
H3O

(29) CHCl3 + NaOH ,  CARBYLAMINE OF ISOCYANIDE TEST


R–NH2+CHCl3+ NaOH R–N  C +NaCl+H2O

OH OH
COOH
(30) CCl4 + NaOH, H3O + CCl4 + NaOH 

H 3O

(31) CO2 + NaOH , H3O KOLBE SCHMIDT REACTION

OH OH
COOH
H3O
+ CO2 + NaOH

(32) NaOH + CaO,  DECARBOXYLATION

Page No.4
 REAGENTS THEIR USES
O
(3 : 1) R – C – OH  R–H + CaCO3 

(33) N3H + conc. H2SO4 SCHMIDT REACTION

O
conc.H SO
R–C–OH +N3H  2
4
R–NH2+CO2+H2O+N2

O O
(34) CH2N2 (diazomethane) R–C–OH + CH2N2  R–C–OCH3 + N2

(35) Fused NaOH, high temperature, Dow process

Cl OH

high pressure 

(36) NaNO2 / HCl or HNO2 Diazotisation of Amine

(37) NaNO2 / HCl,  Aniline into diazonium chloride

(38) CuCl, CuBr, CuCN, H2O, H3PO2 Diazonium chloride into chlorobenzene,
Bromobenzene, Benzonitrile, Phenol, Benzene
respectively.

(39) Na /dry ether Wurtz reaction

2R – X  R – R
Fittig reaction

2 X
Wurtz-fittig reaction

X + RX + R + R–R

(40) Cu /  Ulmann’s reaction

2 I

(41) Ag /  CHCl3  HC  CH

(42) Zn dust Phenol to Benzene

(43) Zn dust,  ; NaI / Acetone Dehalogenation of Antivicinal dihalide

Page No.5
 REAGENTS THEIR USES

Cl
|
H 2 C  CH 2  H2C = CH2
|
Cl

(44) Alc. KOH; NaNH2 Dehydrohalogenation

(45) Aq. KOH Alkyl halide into Alcohol

(46) PCl5 / P2O5 / P4O10 / POCl3 /  Dehydration of amides into nitriles

(47) PCl5 R–OH  R–Cl

R–O–R’  R–Cl + R’–Cl + POCl3
OH

 Ph3PO4 (major)

R R Cl
O 
R R Cl

(48) SOCl2 Darzon method

Alkyl alcohol  Alkyl chloride

(49) HI Ether convert into alcohol and ALkyl halide

(50) HCN Carbonyl compound into cyanohydrin

(51) Aq. KCN R–X + aq. KCN  R–CN (cyanide)


(52) AgCN R–X + AgCN  R  N  C (isocyanide)

(53) KNO 2 R–X + KNO2  R–O–N=O (Alkyl nitrite)

(54) AgNO2 R–X + AgNO2  R–NO2 (Nitro Alkane)

(55) Moist Ag2O R–X + Moist Ag2O  R–OH

Page No.6
 REAGENTS THEIR USES

DISTINGUISHING TESTS

(1) HCl + anhydrous ZnCl2 Lucas test (To distinguish 1°,2°,3° alcohols)

(2) AgNO3 + NH4OH (Tollen’s reagent) Tollen’s test to identify aldehyde

(3) Fehling solution Fehling test

Only aliphatic aldehyde gives this test (red ppt.)

(4) Benedict solution Benedict test

Only Aliphatic aldehyde gives this test

(5) 2,4-DNP 2,4-DNP test

Test for ketone and aldehyde

(6) Hinsberg reagent Hinsberg test

C6H5SO2Cl to differentiate 1°, 2°, 3° amine

(7) CHCl3 + NaOH Carbylamine or Isocyanide test

(for primary amine)

(8) NaNO2 + HCl Libermann’s Nitroso test for phenol

(9) Beilstein test / Flame test Test of alkyl halide

Alkyl halide give blue green colour flame when
heated with Cu wire

(10) Victor Mayer test To differentiate

(i) 1°, 2°, 3° Alcohol
(ii) 1°, 2°, 3° Alkyl halide
(iii) 1°, 2°, 3° Nitro Alkane

(11) Test of Methanol

OH OH O
COOH 
C–OMe
MeOH
 /H
 (Oil of winter green)

(12) Test for carboxylic acids :

(i) Litmus test
(ii) With Na Metal
(iii) Reaction with NaOH
(iv) With NaHCO3

(13) Test of Phenol :

(i) With Na Metal (ii) With NaOH (iii) With aqueous FeCl3

Page No.7
 ORGANIC REAGENTS

REAGENTS THEIR USES

(1) X2/CCl4/CS2/CHCl3/CH2Cl2 Anti addition of X2 on multiple bond.

X2 = Br2, Cl2

OH OH

(2) Br2 + CCl4 / CS2/CH3COOH 

Br

(3) Br2/CCl4,  HUNSDIECKER REACTION

O
R – C – O – Ag  R – Br
(one ‘C’ less product)

(4) I2 / CCl4 BIRNBAUM SIMONINI REACTION

O O
R – C – O – Ag  R – C – O – R

(5) Br2/KOH or NaOH / / NaOX HOFFMANN BROMAMIDE DEGRADATION

O
R – C – NH2  R–NH2
Amide into Amine with one ‘C’ less

(6) X2 + NaOH or NaOX HALOFORM REACTION

(7) Br2 / h; Cl2/h ; I2 / HgO or HIO3 /  Halogenation of alkane

R – H  R – X
Cl
Cl Cl
* h
+ Cl2(excess) 
Cl Cl
Cl
(8) X2 / red P ; X2 = Br2, Cl2 HVZ REACTION
CH3–COOH  CH 2  COOH
|
X
ONLY  HYDROGENS ARE REPLACED

Page No.1
 REAGENTS THEIR USES

(9) Cl2 / FeCl3 ; Br2 / FeCl3 ; I2 / HIO3 ; Halogenation of aromatic compound

X

Br2 / Fe ; HOCl ; Br2 + H2O 

M
M Br Br

* Br
2 
H 2O

Br
M = –OH , –NH2

(10) Br2 + H2O ; Interhalogen compound ; Anti addition on alkene

Br2 / aq. Brine solution;
NOCl (Tilden reagent); HOCl

(11) HOCl Addition on alkyne

Alkyne  Enol to Carbonyl compound
* HOCl oxidises aldehyde into
carboxylic acid

(12) HBr, HCl, HI Hydrohalogenation of alkene and alkynes

according to Markovnikov’s rule

(13) HBr / peroxide; CBrCl3, CIBr3, CBrF3, Addition of alkene and alkyne according
CHCl3, CHI3, RSH, COCl2 to Antimarkovnikov’s rule

(14) (i) O3 ; (ii) Zn / H2O ; Me2S ; Ph3P Reductive ozonolysis of alkene and alkyne

(15) O3 / H2O or O3 / H2O2 Oxidative ozonolysis of alkene and alkyne

(16) Cold dilute alkaline KMnO4 or Hydroxylation of alkene

dil.KMnO4 or Bayer’s reagent ; (preparation of syndiol on alkene)
OsO4 / NaHSO3

(17) Peroxy acids ; RCO3H; mcpba; H2S2O8; Epoxydation of alkene (Prielshavie reaction)
H2SO5 (Carro’s acid)

(18) Hydrolysis of epoxide in acidic and Anti-diol formation

basic medium

(19) Conc. H2SO4; H3PO4/; Al2O3/; Dehydration of alcohol into alkene

POCl3 / ; ThO2 / 

Page No.2
 REAGENTS THEIR USES
(20) N-Bromo succinimide (NBS) Allylic substitution

N-Chloro succinimide (NCS) CH 2  CH  CH 2  CH 2  CH  CH 2

| |
Br2 at low concentration H X
X2 at high concentration
t-Butyloxy chloride (Me3COCl) / h or 
SO2Cl2 / h or 

(21) H / H2O or H3O or dil. H2SO4 HYDRATION OF ALKENE

(i) (CH3COO)2 Hg / H2O MARKOVNIKOFF ADDITION OF

(ii) NaBH4 WATER WITH REAARRANGEMENT

(i) B2H6 / THF ADD WATER BY ANTIMARKOVNIKOV

(ii) H2O2 / OH¯ RULE NO REARRANGEMENT

(I) Hg (OAc) 2 / H 2O ADD WATER BY MARKOVNIKOV RULE

(II) NaBH 4 / OH  NO REARRANGEMENT
(i) (Sia)2BH / THF
(ii) (H2O2/OH¯) HYDRATION OF ALKYNE

(i) 9-BBN / THF

(ii) H2O2 / OH¯

(22) HgSO4 / dil. H2SO4 or Hg2+ Hydration of alkyne (Kucherov reaction)

(23) Mg Hg + H2O ; Zn–Hg + H2O Vicinal diol (Pinacol) formation by

Na – Hg + H2O compound having ketone group
* Pinacol conc
 .H 2SO 4
 Pinacolone
or H 3PO 4 / 

(24) Conc. H2SO4 Sulphonation of aromatic compound

(25) HNO3 + HClO4 ; conc. HNO3 ; Nitration of aromatic compound

solid N2O5 ; NO2F + BF3 ; AcONO2 ;
HNO2 / HNO3

(26) Anhydrous AlCl3 (i) Isomerisation of alkane

Alkane  Branched alkane

(ii) Friedal craft’s alkylation

Page No.3
 REAGENTS THEIR USES

+ RX  + HX

(iii) FRIEDEL CRAFT ACYLATION

OH OH
O
COR
+ R – C – Cl  +

COR
(iv) FRIES REARRANGEMENT

OCOR OH OH
COR
AlCl3 +


COR

(27) SbCl5 / , H;AlCl3 / , H SEMIPINACOL PINACOLONE REARRANGEMENT

AgNO3 / , H

(28) CHCl3 + NaOH /  ; H3O RIEMER TIEMANN REACTION

OH OH

CHO
+ CHCl3 + NaOH 
H3O

(29) CHCl3 + NaOH ,  CARBYLAMINE OF ISOCYANIDE TEST


R–NH2+CHCl3+ NaOH R–N  C +NaCl+H2O

OH OH
COOH
(30) CCl4 + NaOH, H3O + CCl4 + NaOH 

H 3O

(31) CO2 + NaOH , H3O KOLBE SCHMIDT REACTION

OH OH
COOH
H3O
+ CO2 + NaOH

(32) NaOH + CaO,  DECARBOXYLATION

Page No.4
 REAGENTS THEIR USES
O
(3 : 1) R – C – OH  R–H + CaCO3 

(33) N3H + conc. H2SO4 SCHMIDT REACTION

O
conc.H SO
R–C–OH +N3H  2
4
R–NH2+CO2+H2O+N2

O O
(34) CH2N2 (diazomethane) R–C–OH + CH2N2  R–C–OCH3 + N2

(35) Fused NaOH, high temperature, Dow process

Cl OH

high pressure 

(36) NaNO2 / HCl or HNO2 Diazotisation of Amine

(37) NaNO2 / HCl,  Aniline into diazonium chloride

(38) CuCl, CuBr, CuCN, H2O, H3PO2 Diazonium chloride into chlorobenzene,
Bromobenzene, Benzonitrile, Phenol, Benzene
respectively.

(39) Na /dry ether Wurtz reaction

2R – X  R – R
Fittig reaction

2 X
Wurtz-fittig reaction

X + RX + R + R–R

(40) Cu /  Ulmann’s reaction

2 I

(41) Ag /  CHCl3  HC  CH

(42) Zn dust Phenol to Benzene

(43) Zn dust,  ; NaI / Acetone Dehalogenation of Antivicinal dihalide

Page No.5
 REAGENTS THEIR USES

Cl
|
H 2 C  CH 2  H2C = CH2
|
Cl

(44) Alc. KOH; NaNH2 Dehydrohalogenation

(45) Aq. KOH Alkyl halide into Alcohol

(46) PCl5 / P2O5 / P4O10 / POCl3 /  Dehydration of amides into nitriles

(47) PCl5 R–OH  R–Cl

R–O–R’  R–Cl + R’–Cl + POCl3
OH

 Ph3PO4 (major)

R R Cl
O 
R R Cl

(48) SOCl2 Darzon method

Alkyl alcohol  Alkyl chloride

(49) HI Ether convert into alcohol and ALkyl halide

(50) HCN Carbonyl compound into cyanohydrin

(51) Aq. KCN R–X + aq. KCN  R–CN (cyanide)


(52) AgCN R–X + AgCN  R  N  C (isocyanide)

(53) KNO 2 R–X + KNO2  R–O–N=O (Alkyl nitrite)

(54) AgNO2 R–X + AgNO2  R–NO2 (Nitro Alkane)

(55) Moist Ag2O R–X + Moist Ag2O  R–OH

Page No.6
 REAGENTS THEIR USES

DISTINGUISHING TESTS

(1) HCl + anhydrous ZnCl2 Lucas test (To distinguish 1°,2°,3° alcohols)

(2) AgNO3 + NH4OH (Tollen’s reagent) Tollen’s test to identify aldehyde

(3) Fehling solution Fehling test

Only aliphatic aldehyde gives this test (red ppt.)

(4) Benedict solution Benedict test

Only Aliphatic aldehyde gives this test

(5) 2,4-DNP 2,4-DNP test

Test for ketone and aldehyde

(6) Hinsberg reagent Hinsberg test

C6H5SO2Cl to differentiate 1°, 2°, 3° amine

(7) CHCl3 + NaOH Carbylamine or Isocyanide test

(for primary amine)

(8) NaNO2 + HCl Libermann’s Nitroso test for phenol

(9) Beilstein test / Flame test Test of alkyl halide

Alkyl halide give blue green colour flame when
heated with Cu wire

(10) Victor Mayer test To differentiate

(i) 1°, 2°, 3° Alcohol
(ii) 1°, 2°, 3° Alkyl halide
(iii) 1°, 2°, 3° Nitro Alkane

(11) Test of Methanol

OH OH O
COOH 
C–OMe
MeOH
 /H
 (Oil of winter green)

(12) Test for carboxylic acids :

(i) Litmus test
(ii) With Na Metal
(iii) Reaction with NaOH
(iv) With NaHCO3

(13) Test of Phenol :

(i) With Na Metal (ii) With NaOH (iii) With aqueous FeCl3

Page No.7
 ORGANIC REAGENTS

REAGENTS THEIR USES

(1) X2/CCl4/CS2/CHCl3/CH2Cl2 Anti addition of X2 on multiple bond.

X2 = Br2, Cl2

OH OH

(2) Br2 + CCl4 / CS2/CH3COOH 

Br

(3) Br2/CCl4,  HUNSDIECKER REACTION

O
R – C – O – Ag  R – Br
(one ‘C’ less product)

(4) I2 / CCl4 BIRNBAUM SIMONINI REACTION

O O
R – C – O – Ag  R – C – O – R

(5) Br2/KOH or NaOH / / NaOX HOFFMANN BROMAMIDE DEGRADATION

O
R – C – NH2  R–NH2
Amide into Amine with one ‘C’ less

(6) X2 + NaOH or NaOX HALOFORM REACTION

(7) Br2 / h; Cl2/h ; I2 / HgO or HIO3 /  Halogenation of alkane

R – H  R – X
Cl
Cl Cl
* h
+ Cl2(excess) 
Cl Cl
Cl
(8) X2 / red P ; X2 = Br2, Cl2 HVZ REACTION
CH3–COOH  CH 2  COOH
|
X
ONLY  HYDROGENS ARE REPLACED

Page No.1
 REAGENTS THEIR USES

(9) Cl2 / FeCl3 ; Br2 / FeCl3 ; I2 / HIO3 ; Halogenation of aromatic compound

X

Br2 / Fe ; HOCl ; Br2 + H2O 

M
M Br Br

* Br
2 
H 2O

Br
M = –OH , –NH2

(10) Br2 + H2O ; Interhalogen compound ; Anti addition on alkene

Br2 / aq. Brine solution;
NOCl (Tilden reagent); HOCl

(11) HOCl Addition on alkyne

Alkyne  Enol to Carbonyl compound
* HOCl oxidises aldehyde into
carboxylic acid

(12) HBr, HCl, HI Hydrohalogenation of alkene and alkynes

according to Markovnikov’s rule

(13) HBr / peroxide; CBrCl3, CIBr3, CBrF3, Addition of alkene and alkyne according
CHCl3, CHI3, RSH, COCl2 to Antimarkovnikov’s rule

(14) (i) O3 ; (ii) Zn / H2O ; Me2S ; Ph3P Reductive ozonolysis of alkene and alkyne

(15) O3 / H2O or O3 / H2O2 Oxidative ozonolysis of alkene and alkyne

(16) Cold dilute alkaline KMnO4 or Hydroxylation of alkene

dil.KMnO4 or Bayer’s reagent ; (preparation of syndiol on alkene)
OsO4 / NaHSO3

(17) Peroxy acids ; RCO3H; mcpba; H2S2O8; Epoxydation of alkene (Prielshavie reaction)
H2SO5 (Carro’s acid)

(18) Hydrolysis of epoxide in acidic and Anti-diol formation

basic medium

(19) Conc. H2SO4; H3PO4/; Al2O3/; Dehydration of alcohol into alkene

POCl3 / ; ThO2 / 

Page No.2
 REAGENTS THEIR USES
(20) N-Bromo succinimide (NBS) Allylic substitution

N-Chloro succinimide (NCS) CH 2  CH  CH 2  CH 2  CH  CH 2

| |
Br2 at low concentration H X
X2 at high concentration
t-Butyloxy chloride (Me3COCl) / h or 
SO2Cl2 / h or 

(21) H / H2O or H3O or dil. H2SO4 HYDRATION OF ALKENE

(i) (CH3COO)2 Hg / H2O MARKOVNIKOFF ADDITION OF

(ii) NaBH4 WATER WITH REAARRANGEMENT

(i) B2H6 / THF ADD WATER BY ANTIMARKOVNIKOV

(ii) H2O2 / OH¯ RULE NO REARRANGEMENT

(I) Hg (OAc) 2 / H 2O ADD WATER BY MARKOVNIKOV RULE

(II) NaBH 4 / OH  NO REARRANGEMENT
(i) (Sia)2BH / THF
(ii) (H2O2/OH¯) HYDRATION OF ALKYNE

(i) 9-BBN / THF

(ii) H2O2 / OH¯

(22) HgSO4 / dil. H2SO4 or Hg2+ Hydration of alkyne (Kucherov reaction)

(23) Mg Hg + H2O ; Zn–Hg + H2O Vicinal diol (Pinacol) formation by

Na – Hg + H2O compound having ketone group
* Pinacol conc
 .H 2SO 4
 Pinacolone
or H 3PO 4 / 

(24) Conc. H2SO4 Sulphonation of aromatic compound

(25) HNO3 + HClO4 ; conc. HNO3 ; Nitration of aromatic compound

solid N2O5 ; NO2F + BF3 ; AcONO2 ;
HNO2 / HNO3

(26) Anhydrous AlCl3 (i) Isomerisation of alkane

Alkane  Branched alkane

(ii) Friedal craft’s alkylation

Page No.3
 REAGENTS THEIR USES

+ RX  + HX

(iii) FRIEDEL CRAFT ACYLATION

OH OH
O
COR
+ R – C – Cl  +

COR
(iv) FRIES REARRANGEMENT

OCOR OH OH
COR
AlCl3 +


COR

(27) SbCl5 / , H;AlCl3 / , H SEMIPINACOL PINACOLONE REARRANGEMENT

AgNO3 / , H

(28) CHCl3 + NaOH /  ; H3O RIEMER TIEMANN REACTION

OH OH

CHO
+ CHCl3 + NaOH 
H3O

(29) CHCl3 + NaOH ,  CARBYLAMINE OF ISOCYANIDE TEST


R–NH2+CHCl3+ NaOH R–N  C +NaCl+H2O

OH OH
COOH
(30) CCl4 + NaOH, H3O + CCl4 + NaOH 

H 3O

(31) CO2 + NaOH , H3O KOLBE SCHMIDT REACTION

OH OH
COOH
H3O
+ CO2 + NaOH

(32) NaOH + CaO,  DECARBOXYLATION

Page No.4
 REAGENTS THEIR USES
O
(3 : 1) R – C – OH  R–H + CaCO3 

(33) N3H + conc. H2SO4 SCHMIDT REACTION

O
conc.H SO
R–C–OH +N3H  2
4
R–NH2+CO2+H2O+N2

O O
(34) CH2N2 (diazomethane) R–C–OH + CH2N2  R–C–OCH3 + N2

(35) Fused NaOH, high temperature, Dow process

Cl OH

high pressure 

(36) NaNO2 / HCl or HNO2 Diazotisation of Amine

(37) NaNO2 / HCl,  Aniline into diazonium chloride

(38) CuCl, CuBr, CuCN, H2O, H3PO2 Diazonium chloride into chlorobenzene,
Bromobenzene, Benzonitrile, Phenol, Benzene
respectively.

(39) Na /dry ether Wurtz reaction

2R – X  R – R
Fittig reaction

2 X
Wurtz-fittig reaction

X + RX + R + R–R

(40) Cu /  Ulmann’s reaction

2 I

(41) Ag /  CHCl3  HC  CH

(42) Zn dust Phenol to Benzene

(43) Zn dust,  ; NaI / Acetone Dehalogenation of Antivicinal dihalide

Page No.5
 REAGENTS THEIR USES

Cl
|
H 2 C  CH 2  H2C = CH2
|
Cl

(44) Alc. KOH; NaNH2 Dehydrohalogenation

(45) Aq. KOH Alkyl halide into Alcohol

(46) PCl5 / P2O5 / P4O10 / POCl3 /  Dehydration of amides into nitriles

(47) PCl5 R–OH  R–Cl

R–O–R’  R–Cl + R’–Cl + POCl3
OH

 Ph3PO4 (major)

R R Cl
O 
R R Cl

(48) SOCl2 Darzon method

Alkyl alcohol  Alkyl chloride

(49) HI Ether convert into alcohol and ALkyl halide

(50) HCN Carbonyl compound into cyanohydrin

(51) Aq. KCN R–X + aq. KCN  R–CN (cyanide)


(52) AgCN R–X + AgCN  R  N  C (isocyanide)

(53) KNO 2 R–X + KNO2  R–O–N=O (Alkyl nitrite)

(54) AgNO2 R–X + AgNO2  R–NO2 (Nitro Alkane)

(55) Moist Ag2O R–X + Moist Ag2O  R–OH

Page No.6
 REAGENTS THEIR USES

DISTINGUISHING TESTS

(1) HCl + anhydrous ZnCl2 Lucas test (To distinguish 1°,2°,3° alcohols)

(2) AgNO3 + NH4OH (Tollen’s reagent) Tollen’s test to identify aldehyde

(3) Fehling solution Fehling test

Only aliphatic aldehyde gives this test (red ppt.)

(4) Benedict solution Benedict test

Only Aliphatic aldehyde gives this test

(5) 2,4-DNP 2,4-DNP test

Test for ketone and aldehyde

(6) Hinsberg reagent Hinsberg test

C6H5SO2Cl to differentiate 1°, 2°, 3° amine

(7) CHCl3 + NaOH Carbylamine or Isocyanide test

(for primary amine)

(8) NaNO2 + HCl Libermann’s Nitroso test for phenol

(9) Beilstein test / Flame test Test of alkyl halide

Alkyl halide give blue green colour flame when
heated with Cu wire

(10) Victor Mayer test To differentiate

(i) 1°, 2°, 3° Alcohol
(ii) 1°, 2°, 3° Alkyl halide
(iii) 1°, 2°, 3° Nitro Alkane

(11) Test of Methanol

OH OH O
COOH 
C–OMe
MeOH
 /H
 (Oil of winter green)

(12) Test for carboxylic acids :

(i) Litmus test
(ii) With Na Metal
(iii) Reaction with NaOH
(iv) With NaHCO3

(13) Test of Phenol :

(i) With Na Metal (ii) With NaOH (iii) With aqueous FeCl3

Page No.7