Class –XII ORGANIC CONVERSIONS

Ascent of Series Descent of Series

alc. KCN LiAlH 4
R X R CN R CH 2 NH2 NH 3 Br 2
RCOOH RCONH 2 R NH 2
Reduction
Alky l halide Nitrile Primary amine Carboxy lic acid  Acid amide KOH Amine

HNO 2 HNO 2
( NaNO 2 & HCl )
Hy droly sis
( NaNO 2 & HCl )
+
H3O
Oxidation R OH
Carboxy lic acid
RCOOH R CH 2 OH or aldehy de Primary alcohol
Oxidation
Organic compound Carboxy lic acid Organic compound Primary alcohol

For aromatic conversion take the help of benzenediazonium chloride

Ethyne into benzene
Red-Hot-Cu Tube
3 CH CH
Polymerisation

Ethene into benzene Br Br

Br 2 Alc. KOH Red-Hot-Cu Tube
H2C CH2 H2C CH 2 HC CH
Polymerisation

Hexane into benzene CH3

H 2C CH3 Cr2O7 / V2O5 / Mo2O3 Aromatisation
H 2C CH2 773 K / 10 -20 atm. ( - H2 )  3 H2
Hexane CH2
Cyclohexane Benzene

Benzene into p-nitrobromobenzene

Br 2 / FeBr3 HNO 3 / H2SO 4
Br O 2N Br

Benzene into m-nitrochlorobenzene

NO 2 NO 2

HNO 3 / H2SO 4 Cl2 / FeCl3

Cl

Benzene into p-nitrotoluene

CH 3Cl / anhy. AlCl HNO 3 / H2SO 4
3 O 2N CH3
CH3

Benzene into Acetophenone O

O C
Anhy. AlCl 3 CH3
+ H3C C Cl

Ethanol into but-1-yne SOCl 2 HC CNa

CH 3CH 2OH CH 3CH 2Cl HC CCH 2CH 3
( Pyridine )  NaCl
Ethane to Bromoethene Br Br
Br 2 Alc. KOH Br 2 Alc. KOH
H3C CH3 CH 3CH 2Br H2C CH2 H2 C CH 2 H2C CH Br

Propene into 1-nitropropane

HBr AgNO 2
H3C CH CH2 H3C CH 2 CH 2 Br H3C CH 2 CH 2 NO 2
( Peroxide )  AgBr
Ethanoic acid into Benzene
aq NaOH Sodalime Cl 2 / h Na / Dryether
H3C COOH H3C COONa CH4 H3C Cl H3C CH3

Red hot iron tube Cl 2 / h
873 K
Br Br Cl
NaNH 2 Alc. KOH Br 2 Alc. KOH CH 2 CH3
HC CH H2C CH Br H2 C CH 2 H2C CH2
Class –XII ORGANIC CONVERSIONS
Toluene into Benzyl alcohol
Cl OH
CH3
Cl 2 / Boil Aq. KOH
CH2 CH2
 HCl
Propene into Propyne Br Br
Br 2 alc. KOH
H3C CH CH2 H3C HC CH 2 H3C C CH
CCl 4 NaNH 2

Ethanol into Fluoroethane

SOCl 2 Hg 2F 2
H3C CH 2 OH H3C CH 2 Cl H3C CH 2 F
( Pyridine )  Hg 2Cl 2
Bromomethane into Propanone CH3 CH3
+
Alc. KCN CH 3MgBr H2 O / H
CH 3Br CH 3CN H3C C NMgBr H3C C O
 KBr ( ether )

But-1-ene into But-2-ene Br

HBr alc. KOH
H3C CH 2 CH CH2 H3C CH 2 HC CH3 H3C CH CH CH3

1- Chlorobutane into n- Octane Dry ether

H3C CH 2 CH 2 CH 2 Cl + 2 Na
( Wurtz reaction )
H3C ( CH 2 ) 6 CH3

Benzene into Biphenyl Br 2 / FeBr 3

2 Br
Na / Dryether

Propene into Propan-1-ol H3C CH CH2

HBr
H3C CH 2 CH 2 Br
Aq. KOH
H3C CH 2 CH 2 OH
Peroxide
1- Bromopropane into 2-Bromopropane Br
alc. KOH HBr H3C CH CH3
H3C CH 2 CH 2 Br H3C CH CH2

Benzyl alcohol into 2-Phenylethanoic acid

OH SOCl 2 KCN +
CH2 Cl CN H2O / H
CH2 CH2 CH2COOH

Ethanol into Propanenitrile SOCl 2 KCN

H3C CH 2 OH H3C CH 2 Cl H3C CH 2 CN
( Pyridine )

Aniline into Chlorobenzene NaNO2 / HCl + - CuCl / HCl

NH2 N2 Cl Cl

2-Chlorobutane into 3,4-Dimethylhexane CH3

CH3
Na / Dryether
2 H3C CH 2 CH Cl H3C CH 2 CH CH CH 2 CH3
CH3

2-Methylpropene into 2-Chloro- 2-methylpropane Cl

HCl
H3C C CH2 H3C C CH3
CH3 CH3

Ethylchloride into Propanoic acid H2 O / H

+
KCN H3C CH 2 COOH
H3C CH 2 Cl H3C CH 2 CN

But-1-ene into n-butyliodide

HBr NaI
H3C CH 2 CH CH2 H3C CH 2 CH 2 CH 2 Br H3C CH 2 CH 2 CH 2 I
Peroxide Acetone
2-Chloropropane into Propan-1-ol Cl
alc. KOH
B2H6
H2O 2 / OH
H 3C CH CH2 H3C CH2 CH2 OH
H3C CH CH3

Isopropyl alcohol into Idoform OH I 2 / Na 2CO 3

CHI 3
H3C CH CH3
 CH3COONa
Chlorobenzene into p-nitrophenol NaOH
HNO3 / H2SO 4
O 2N OH
Cl OH
623 K / 300 atm.
Class –XII ORGANIC CONVERSIONS
2- Bromopropane into 1-Bromopropane alc. KOH HBr
H3C CH CH3 H 3C CH CH2 H3C CH2 CH2 Br
Peroxide
Br
tert.butyl bromide into Isobutyl bromide
CH3 CH3
alc. KOH HBr
H3C C CH3 H3C C CH2 H3C CH CH2 Br
Peroxide
Br CH3

Aniline into Phenylisocyanide ( w arm )

NH2
+ CHCl 3
+ 3 KOH NC + 3 KCl + 3 H 2O

Propene into Propan-2-ol HBr

Br
aq. KOH
HO
H3C CH CH2 H3C CH CH3 H3C CH CH3

Benzyl chloride into Benzyl alcohol CH2 Cl

aq. KOH
CH2 OH

Ethylmagnesium chloride into Propan-1-ol

O +
H2 O / H
H3C CH 2 MgCl + H C H H3C CH 2 CH 2 OM gCl H3C CH 2 CH 2 OH

Methylmagnesium bromide into 2-Methylpropan-2-ol

O OMgBr + OH
H2 O / H
CH 3MgBr + H3C C CH3 H3C C CH3 H3C C CH3
H3C H3C

Butan-1-ol into Butanoic acid CH 3CH 2CH 2CH 2OH Jones reagent ( CrO 3 - H 2SO 4 ) CH 3CH 2CH 2COOH

Benzyl alcohol into phenylethanoic acid

+
HBr KCN H 3O
CH2 OH CH2 Br CH2 CN CH2 COOH

3-Nitrobromobenzene into 3-Nitrobenzoic acid
+
Mg CO2 H 3O
Br Mg Br COOMgBr COOH
Ether ( Dry ice )

O 2N O 2N O 2N O 2N

4-Methylacetophenone into Benzene-1,4-dicarboxylic acid

KMnO 4 / KOH dil. H2SO4
H 3C COCH 3 KOOC COOK HOOC COOH

Cyclohexene into Hexane-1,6-dioic acid KM nO4 - H2SO4 COOH

Heat COOH Adipic acid

Butanal into Butanoic acid H C CH 2 CH 2 CHO Tollen's reagent

H3C CH 2 CH 2 COOH
3

Ethylbenzene into Benzoic acid

+
KMnO 4 / KOH H 3O
CH2CH3 COOK COOH

Acetophenone into Benzoic acid KMnO 4 / KOH H 3O

+
COCH 3 COOK COOH

Bromobenzene into Benzoic acid O

O
Br
Mg C O H2O
Mg Br C COOH
OMg Br

Phenylethene ( Styrene ) CH2

H 3O
+
KMnO 4 / KOH
into Benzoic acid CH COOK COOH

Ethanal into Butane-1,3-diol OH OH OH

dil. NaOH LiAlH4
H3C CHO H3C HC CH2 CHO H 3C CH CH 2 CH 2
Class –XII ORGANIC CONVERSIONS
Ethanal into But-2-enal OH Heat
dil. NaOH H3C HC CH2 CHO H3C CH CH CHO
H3C CHO  H2O

Ethanal into But-2-enoic acid

dil. NaOH
OH
Heat Tollen's reagent
H3C CH CH CHO H3C CH CH COOH
H3C CHO H3C CH CH2 CHO
H2O
CH 3 COOH COOCH 3

Benzene into methylbenzoate
CH 3Cl
KM nO4 / OH CH3OH
Anhy. AlCl3
( H2SO 4 )

CH 3 COOH COOH

KM nO4 / OH
CH 3Cl
Benzene into m-Nitrobenzoic acid HNO 3
Anhy. AlCl3 H2 SO 4
NO2

Benzene into CH 3Cl

CH 3 HNO 3
KM nO4 / OH HOOC
H 3C NO 2
p-Nitrobenzoic acid
NO 2
Anhy. AlCl3 H2 SO 4

Benzene into p-Nitrobenzaldehyde

CH 3Cl HNO 3 CrO2Cl2 / CS2
CH 3 H 3C NO 2 OHC NO 2
Anhy. AlCl3 H2 SO 4 +
H3O

Benzene into Phenylacetic acid

CH 3 CH 2 Cl CH 2CN CH 2COOH
+
H2O / H
CH 3Cl Cl 2 / Boil KCN

Anhy. AlCl3

Propanone into propene O OH

LiAlH4 H2SO4 (conc.)
H3C C CH3 H3C HC CH3 H3C CH CH2
Heat
Propanal into butanone OH O
CH 3MgBr K2Cr 2O7 / H2SO4
CH 3CH 2CHO + H3C CH 2 CH CH3 H3C CH 2 C CH3
H2O / H

Ethanol into 3-hydroxybutanal Anhydrous CrO 3 Dil. NaOH

OH
CH 3CH 2OH CH 3CHO H3C HC CH 2 CHO
OR Cu / 573 K Aldolcondensation
Benzaldehyde into benzophenone CHO COOH
O
K2Cr 2O7 / H2SO4 Ca(OH) 2 C
Heat

Benzaldehyde into 3-phenylpropan-1-ol

CHO CH CH CHO CH 2 CH 2 CH 2 OH
dil.NaOH H2 / Ni
+ CH3CHO
( Cross aldolcondensation )

Benzaldehyde into 3-phenylprop-2-en-1-ol

CHO CH CH CHO CH CH CH 2 OH
dil.NaOH NaBH4 / CH3OH
+ CH3CHO
( Cross aldolcondensation )

Benzaldehyde into -Hydroxyphenylacetic acid HO HO

O CN + COOH
CH CH
H2O / H
C
H
+ HCN

Benzoic acid into m-Nitrobenzyl alcohol COOH COOH CH 2 OH

+
HNO 3 / H2SO4 B 2H 6 / H3O

NO 2 NO 2

Benzoic acid into Benzaldehyde COOH COCl

Pd / BaSO4
CHO
SOCl2
Rosenmund reduction
Class –XII ORGANIC CONVERSIONS
Benzene into m-Nitroacetophenone O
O 2N
O
CH 3COCl / AlCl3 HNO3 / H2SO4
C CH 3 C CH3

Bromobenzene into 1-Phenylethanol O -

O MgBr
+
HO
+
Mg H3C C H H 3O
Br Mg Br CH CH3 CH CH3

Chloroethane into propan-1-amine Ethanolic NaCN LiAlH 4

H3C CH 2 Cl H3C CH 2 C N H3C CH 2 CH 2 NH2
Reduction

Chlorophenylmethane into 2-Phenylethanamine

H 2 / Ni
Ethanolic NaCN CH 2 C N CH 2 CH 2 NH2
CH 2 Cl
Reduction

Benzene into Aniline HNO3 / H2 SO 4 Sn / HCl NH2

NO 2
Reduction

Benzene into N,N-dimethylaniline CH3

CH3 Br
HNO3 / H2 SO 4 Sn / HCl NH2 N
NO 2
Reduction CH3

1,6-Dichlorobutane into hexane-1,6-diamine

LiAlH 4
Cl ( CH 2 ) 4 Cl KCN NC ( CH 2 ) 4 CN H2NH 2C ( CH 2 ) 4 CH 2NH 2

4-Nitrotoluene into 2- bromobenzoic acid

CH 3 CH3 CH 3 CH 3 CH 3 COOH
Br Br Br Br Br
Br 2 Sn / HCl NaNO2 / HCl H3PO2 KMnO 4
OH
273-278 K H2O

NO 2 NO2 NH 2 N N Cl

+

+ -
3-Methylaniline into 3-nitrotoluene NH 2 + - N 2BF 4
NO2
N 2 Cl
NaNO2
NaNO2 + HCl HBF 4
Cu 
CH3
CH3
CH 3 CH3
NH2 + -
N 2 Cl
Aniline into 1,3,5-tribromobenzene Br Br
Br Br Br Br H3PO2
NH2
aq. Br2 NaNO2 + HCl
Br
Br Br
Hexanenitrile into 1-aminopentane
-
H3C ( CH 2)4
H2O / HO
C N H3C ( CH 2)4 CONH 2
Br 2 + 4 KOH
H3C ( CH2)3 CH 2 NH2
H 2O 2

Methanol into ethanoic acid H3C OH

SOCl2
H3C Cl
KCN
H3C CN
H2O / H +
CH 3COOH

Etahnamine into methanamine

CH3CH2NH2
NaNO 2 + HCl
CH3CH2OH
KMnO 4
CH3COOH
NH3
CH 3CONH 2
Br 2 + 4 KOH
CH 3NH 2
( HNO 2 ) OH 
Methanamine into ethanamine LiAlH 4
KCN
CH 3NH 2 NaNO 2 + HCl
H3C OH
SOCl2
H3C Cl H3C CN CH3CH2NH2
( HNO 2 )

Ethanoic acid into Propanoic acid

+
B 2H 6 / H3O SOCl2 KCN H2O / H +
CH3COOH CH3CH2OH CH3CH2Cl CH3CH2CN CH3 CH2 COOH

Propanoic acid into ethanoic acid

CH3CH2COOH
NH3
CH3CH2 CONH2
Br 2 + 4 KOH NaNO 2 + HCl KMnO 4
CH3COOH
OH 
CH3CH2NH2 CH3CH2OH
 ( HNO 2 )
Class –XII ORGANIC CONVERSIONS
Nitromethane into dimethylamine CH3 NO2
Sn / HCl
CH3NH2
CH3 Cl
(CH3) 2NH
6 [H]

Ethanoic acid into methanamine

CH 3COOH
NH3
CH 3CONH 2
Br2 + 4 KOH
CH 3NH 2 + K2CO 3 + 2 KBr + 2 H 2O

Nitrobenzene into benzoic acid
Sn / HCl NaNO2 / HCl +  CuCN H2O / H +
NO2 NH2 N2 Cl C N COOH
273-278 K

Benzoic acid into aniline NH3

COOH CONH2
Br2 + 4 KOH

NH2

Benzamide into toluene

Br2 / KOH NaNO2 / HCl +  H3PO2 / H2O CH3Cl
CONH2 NH2 N2 Cl CH3
273-278 K Anhyd. AlCl
3

Aniline into p-Bromoaniline O O

HO / H
Br2 - +
( CH3CO )2O
NH2 NH C CH3 Br NH C CH3 Br NH2
Pyrid ine CH3COOH

+  + 
Aniline into 2,4,6-tribromofluorobenzene N2 Cl N2 BF 4 F
NH2 NH2 Br Br Br Br Br Br
Br Br NaNO2 / HCl HBF4 NaNO2
aq. Br2
273-278 K Cu 
Br Br Br
Br

Aniline into benzyl alcohol

NaNO2 / HCl +  CuCN LiAlH4 NaNO2 / HCl
NH2 N2 Cl CN CH2NH2 CH2OH
273-278 K

Chlorobenzene into p-Chloroaniline Cl

HNO 3
Cl NO2
Sn/ HCl Cl NH2
H 2SO4

Benzene into m-bromophenol + 

N 2 Cl OH
NO2 NO2 NH2

Br2 Boil H2O

HNO 3 Sn/ HCl NaNO2 / HCl
H 2SO4 FeBr3 273-278 K
Br Br
Br Br

Benzyl chloride into 2- Phenylethanamine CH2 Cl

KCN CH2 CN
LiAlH4
CH 2CH 2NH 2

m-Nitroaniline into m-Chloroiodobenzene + 

N 2 Cl I
NO2 NO2 NO 2 NH2

NaNO2 / HCl CuCl Sn/ HCl NaNO2 / HCl KI / Heat

273-278 K 273-278 K
+  Cl Cl
NH2 N2 Cl Cl Cl

Aniline into Benzoic acid

+
NaNO2 / HCl +  CuCN H2 O / H
NH2 N2 Cl CN COOH
273-278 K

p-Chloroaniline into p-Chlorobenzylamine

NaNO2 / HCl +  CuCN LiAlH4
Cl NH2 Cl N 2 Cl Cl CN Cl CH2 NH2
273-278 K

Toluene into m-Bromotoluene CH3

CH3 CH3
CH3 CH3 CH3
CH3
Br2 + (i) Diazotisation
( CH3CO )2 O H2 O / H
HNO 3 LiAlH4 (ii) H3PO2 / H2O
CH 3COOH
H 2SO4 Pyridine Br Br Br
NO 2 NHCOCH3 NH2
NH2 NHCOCH 3
NO 2 NH2 +  Cl
m- Dinitrobenzene into m-Dichlorobenzene N Cl2

NaNO2 / HCl CuCl

Sn/ HCl
273-278 K
NO 2 NH2 +  Cl
N 2 Cl
Class –XII ORGANIC CONVERSIONS
Class –XII ORGANIC CONVERSIONS