Class XII

ORGANIC CONVERSIONS

Ascent of Series
R X alc. KCN R CN LiAlH 4 Reduction R CH 2 NH2 Alky l halide Nitrile Primary amine HNO 2 ( NaNO 2 & HCl ) R Oxidation CH 2 OH Primary alcohol

Descent of Series
RCOOH Carboxy lic acid NH 3

RCONH 2 Acid amide

Br 2 KOH

R NH 2 Amine HNO 2

Hy droly sis H3O

+

( NaNO 2 & HCl )

Organic compound

RCOOH Carboxy lic acid

Carboxy lic acid or aldehy de

Oxidation

R OH Primary alcohol

Organic compound For aromatic conversion take the help of benzenediazonium chloride Ethyne into benzene
3 CH CH Br CH 2 Alc. KOH HC CH Red-Hot-Cu Tube Polymerisation Aromatisation Red-Hot-Cu Tube Polymerisation

Ethene into benzene

H2C CH2 Br 2

Br H2C
CH3

Hexane into benzene

H 2C H 2C

CH3
CH2

Cr2O7 / V2O5 / Mo2O3

773 K / 10 -20 atm. ( - H2 )

3 H2
Cyclohexane Benzene

Hexane

CH2

Benzene into p-nitrobromobenzene

Br 2 / FeBr3

Br NO 2

HNO 3 / H2SO 4

O 2N NO 2

Br

Benzene into m-nitrochlorobenzene

HNO 3 / H2SO 4

Cl2 / FeCl3

Cl

Benzene into p-nitrotoluene

CH 3Cl / anhy. AlCl
3

CH3

HNO 3 / H2SO 4

O 2N

CH3

Benzene into Acetophenone

+
Ethanol into but-1-yne Ethane to Bromoethene
H3C CH3 Br 2 CH 3CH 2Br Alc. KOH CH 3CH 2OH

H3C

Cl

Anhy. AlCl 3

CH3

SOCl 2 ( Pyridine )

CH 3CH 2Cl

HC

CNa

NaCl
Br Br CH 2

HC

CCH 2CH 3

H2C

CH2

Br 2

H2 C

Alc. KOH

H2C

CH

Br

Propene into 1-nitropropane

H3C CH CH2 HBr ( Peroxide ) H3C CH 2 CH 2 Br AgNO 2

AgBr
CH4 Cl 2 / h

H3C

CH 2

CH 2 NO 2

Ethanoic acid into Benzene

H3C COOH aq NaOH H3C COONa Red hot iron tube 873 K

Sodalime

H3C

Cl

Na / Dryether

H3C

CH3

Cl 2 / h
Br Br CH 2

HC

CH

NaNH 2

H2C

CH

Br

Alc. KOH

H2 C

Br 2

H2C

CH2

Alc. KOH

Cl CH 2 CH3

Class XII

ORGANIC CONVERSIONS
Cl 2 / Boil HCl
Cl CH2

Toluene into Benzyl alcohol

CH3

Aq. KOH

OH CH2

Propene into Propyne

H3C CH CH2 Br 2 CCl 4 SOCl 2 ( Pyridine )
CH 3MgBr H3C

Br HC

Br CH 2

alc. KOH NaNH 2 Hg 2F 2

H3C

CH

Ethanol into Fluoroethane

H3C CH 2 OH H3C CH 2 Cl
CH3

Hg 2Cl 2
H2 O / H
+

H3C

CH 2 F
CH3

Bromomethane into Propanone

CH 3Br
Alc. KCN

KBr

CH 3CN

( ether ) Br

H3C

NMgBr

H3C

But-1-ene into But-2-ene

H3C CH 2 CH CH2 HBr H3C

CH 2 HC

CH3

alc. KOH

H3C

CH

CH

CH3 CH3

1- Chlorobutane into n- Octane Benzene into Biphenyl Propene into Propan-1-ol H3C

H3C

CH 2 CH 2 CH 2 Cl 2 HBr Peroxide

2 Na

Dry ether ( Wurtz reaction ) Na / Dryether

H3C

( CH 2 ) 6

Br 2 / FeBr 3

Br

CH

CH2

H3C

CH 2 CH 2 Br

Aq. KOH

H3C HBr

CH 2 CH 2 OH Br

1- Bromopropane into 2-Bromopropane

H3C CH 2 CH 2 Br

alc. KOH

H3C

CH

CH2

H3C

CH

CH3

Benzyl alcohol into 2-Phenylethanoic acid

CH2 OH

SOCl 2

CH2

Cl

KCN

CH2

CN

H2O / H

CH2COOH

Ethanol into Propanenitrile

H3C CH 2 OH

SOCl 2 ( Pyridine )
NaNO2 / HCl

H3C

CH 2 Cl

KCN

H3C

CH 2 CN

Aniline into Chlorobenzene

NH2

N2 Cl

CuCl / HCl

Cl

2-Chlorobutane into 3,4-Dimethylhexane

2 H3C
CH 2

CH3 CH Cl

Na / Dryether

CH3 H3C CH 2 CH CH3 CH CH 2 CH3

2-Methylpropene into 2-Chloro- 2-methylpropane

H3C C CH3 CH2

Cl

HCl

H3C

C CH3

CH3

Ethylchloride into Propanoic acid

H3C CH 2 Cl HBr Peroxide
Cl CH

KCN

H3C

CH 2 CN

H2 O / H

H3C

CH 2 COOH

But-1-ene into n-butyliodide

H3C CH 2 CH CH2

H3C

CH 2 alc. KOH

CH 2

CH 2 Br

NaI Acetone
B2H6
CH2

H3C

CH 2

CH 2

CH 2 I

2-Chloropropane into Propan-1-ol

H3C

CH3 OH CH

H 3C

CH

H2O 2 / OH

H3C

CH2

CH2

OH

Isopropyl alcohol into Idoform

H3C

I 2 / Na 2CO 3
CH3
Cl

CH3COONa
NaOH 623 K / 300 atm.

CHI 3
OH

Chlorobenzene into p-nitrophenol

HNO3 / H2SO 4

O 2N

OH

Class XII

ORGANIC CONVERSIONS
alc. KOH
H 3C CH CH2

2- Bromopropane into 1-Bromopropane

H3C CH Br CH3

HBr

Peroxide

H3C

CH2

CH2

Br

tert.butyl bromide into Isobutyl bromide

CH3 H3C C Br CH3

CH3 H3C C CH2

alc. KOH

HBr

Peroxide

H3C

CH CH3

CH2

Br

Aniline into Phenylisocyanide

NH2

CHCl 3

3 KOH

( w arm )
Br

NC

+
H3C

3 KCl
HO

3 H 2O

Propene into Propan-2-ol

H3C CH CH2

HBr

H3C
Cl

CH CH3 aq. KOH

aq. KOH

CH CH3

Benzyl chloride into Benzyl alcohol Ethylmagnesium chloride into Propan-1-ol

O H3C CH 2 MgCl

CH2

CH2

OH

+
H3C

H3C

CH 2 CH 2

OM gCl

H2 O / H

H3C

CH 2 CH 2

OH

Methylmagnesium bromide into 2-Methylpropan-2-ol

O CH 3MgBr
OMgBr

CH3

H3C

C H3C

CH3

H2 O / H

OH H3C C H3C CH3

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

CH2 OH

HBr

CH2 Br

KCN

CH2 CN

H 3O

H 3O
+

CH2 COOH

3-Nitrobromobenzene into 3-Nitrobenzoic acid

Br O 2N

Mg Ether
O 2N

Mg Br

CO2 ( Dry ice )

O 2N

COOMgBr

COOH O 2N

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

H 3C COCH 3

KMnO 4 / KOH

KOOC

COOK

dil. H2SO4

HOOC

COOH

Cyclohexene into Hexane-1,6-dioic acid

KM nO4 - H2SO4 Heat

COOH COOH H3C

COOK

Adipic acid CH 2 COOH

COOH

Butanal into Butanoic acid H C 3 Ethylbenzene into Benzoic acid

CH 2

CH 2

CHO
CH2CH3

Tollen's reagent
KMnO 4 / KOH

CH 2

H 3O

Acetophenone into Benzoic acid Bromobenzene into Benzoic acid

Br

COCH 3

KMnO 4 / KOH

COOK

H 3O

COOH

O C O

O C

Mg

Mg Br

H2O
OMg Br

COOH

Phenylethene ( Styrene ) into Benzoic acid Ethanal into Butane-1,3-diol

H3C CHO
dil. NaOH

CH2 CH

KMnO 4 / KOH

COOK

H 3O

COOH

OH HC CH2 CHO

H3C

LiAlH4

OH H 3C CH CH 2

OH CH 2

Class XII

ORGANIC CONVERSIONS
OH H3C
OH H3C CH CH2 CHO

Ethanal into But-2-enal Ethanal into But-2-enoic acid

H3C CHO
dil. NaOH

H3C

CHO

dil. NaOH

Heat
CH2 CHO

HC

CH

H2O

H3C

CH

CH

CHO

H2O
CH 3Cl

Heat

H3C

CH CH 3

CHO

Tollen's reagent

H3C

CH

CH

COOH COOCH 3

Benzene into methylbenzoate

Anhy. AlCl3
CH 3Cl

KM nO4 / OH

COOH

CH3OH
( H2SO 4 ) COOH

CH 3

Benzene into m-Nitrobenzoic acid Benzene into p-Nitrobenzoic acid

CH 3Cl

Anhy. AlCl3
HNO 3

KM nO4 / OH

COOH
HNO 3

H2 SO 4 NO2

Anhy. AlCl3

CH 3

H2 SO 4

H 3C

NO 2

KM nO4 / OH HOOC

NO 2

Benzene into p-Nitrobenzaldehyde

CH 3Cl

Anhy. AlCl3

CH 3

HNO 3

H2 SO 4

H 3C

NO 2

CrO2Cl2 / CS2

H3O

OHC

NO 2

Benzene into Phenylacetic acid

CH 3 CH 2 Cl

CH 3Cl

Cl 2 / Boil
O

KCN

CH 2CN

H2O / H

CH 2COOH

Anhy. AlCl3

Propanone into propene

H3C

CH3

LiAlH4
OH

OH H3C HC CH3

H2SO4 (conc.)

Heat

H3C

CH
O

CH2

Propanal into butanone

CH 3CH 2CHO

CH 3MgBr
H2O / H
+

H3C

CH 2

CH

CH3

K2Cr 2O7 / H2SO4

H3C

CH 2 OH

CH3

Ethanol into 3-hydroxybutanal

CH 3CH 2OH

Anhydrous CrO 3
OR Cu / 573 K
CHO

CH 3CHO

Dil. NaOH Aldolcondensation

COOH

H3C

HC

CH 2
O

CHO

Benzaldehyde into benzophenone

K2Cr 2O7 / H2SO4

Ca(OH) 2

Heat

Benzaldehyde into 3-phenylpropan-1-ol

CHO CH CH CHO

+
CHO

dil.NaOH CH3CHO ( Cross aldolcondensation )

H2 / Ni

CH 2

CH 2

CH 2 OH

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

CH CH CHO

dil.NaOH CH3CHO ( Cross aldolcondensation )

CH

CH

NaBH4 / CH3OH

CH 2 OH

Benzaldehyde into -Hydroxyphenylacetic acid

O C H

HO CH CN

HO

HCN
COOH COOH

H2O / H

CH

COOH

Benzoic acid into m-Nitrobenzyl alcohol

CH 2 OH

HNO 3 / H2SO4

B 2H 6 / H3O
NO 2

NO 2 CHO

Benzoic acid into Benzaldehyde

COOH

SOCl2

COCl

Pd / BaSO4

Rosenmund reduction

Class XII

ORGANIC CONVERSIONS
O C CH 3
O 2N

Benzene into m-Nitroacetophenone

CH 3COCl / AlCl3

HNO3 / H2SO4

O C CH3

Bromobenzene into 1-Phenylethanol

Br

O H3C C H

O MgBr CH CH3 H 3O

+
HO
+

Mg

Mg Br

CH

CH3

Chloroethane into propan-1-amine

H3C CH 2 Cl

Ethanolic NaCN

H3C

CH 2

LiAlH 4

Reduction
H 2 / Ni

H3C

CH 2

CH 2

NH2

Chlorophenylmethane into 2-Phenylethanamine

CH 2 Cl

Ethanolic NaCN

CH 2

Reduction
Sn / HCl

CH 2

CH 2

NH2

Benzene into Aniline Benzene into N,N-dimethylaniline

HNO3 / H2 SO 4
NO 2

HNO3 / H2 SO 4

NO 2

Reduction
CH3 N CH3

NH2

Sn / HCl

Reduction
LiAlH 4

NH2

CH3 Br

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

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 Br 2 CH3 Br CH 3 Br CH 3 Br CH 3 Br COOH Br

Sn / HCl

NaNO2 / HCl

H3PO2 H2O
N + N Cl + N 2BF 4

273-278 K
NO 2 NO2 NH 2

KMnO 4 OH

3-Methylaniline into 3-nitrotoluene

NH 2 NaNO2 CH 3

+ N 2 Cl

NO2 NaNO2

+ HCl
NH2

HBF 4
CH3 + N 2 Cl Br NaNO2 Br

Cu
CH3

CH3

Aniline into 1,3,5-tribromobenzene

NH2

Br

Br Br

Br

aq. Br2

+ HCl
Br

H3PO2
Br

Br

H3C

Hexanenitrile into 1-aminopentane H2O / HO

( CH 2)4 C N
H 2O 2

H3C
OH
SOCl2

( CH 2)4 H3C

CONH Cl

Br 2
2

4 KOH

H3C

( CH2)3
H2O / H +

CH 2

NH2

Methanol into ethanoic acid

NaNO 2

H3C

KCN

H3C

CN

CH 3COOH

Etahnamine into methanamine

CH3CH2NH2

HCl

( HNO 2 )

CH3CH2OH

KMnO 4 OH

CH3COOH

NH3

H3C

CH 3CONH 2

Br 2

4 KOH

CH 3NH 2

Methanamine into ethanamine

CH 3NH 2
NaNO 2

HCl

( HNO 2 )

H3C

OH

SOCl2

H3C

Cl

KCN

CN

LiAlH 4

CH3CH2NH2

Ethanoic acid into Propanoic acid

CH3COOH B 2H 6 / H3O
+

CH3CH2OH

SOCl2

CH3CH2Cl

KCN

CH3CH2CN

H2O / H +

CH3 CH2 COOH KMnO 4 OH

Propanoic acid into ethanoic acid

CH3CH2COOH
NH3

CH3CH2 CONH2

Br 2

4 KOH

CH3CH2NH2

NaNO 2

HCl

( HNO 2 )

CH3CH2OH

CH3COOH

Class XII

ORGANIC CONVERSIONS
CH3 NO2 Sn / HCl 6 [H] CH3NH2 CH3 Cl (CH3) 2NH

Nitromethane into dimethylamine Ethanoic acid into methanamine Nitrobenzene into benzoic acid
NO2

CH 3COOH

NH3

CH 3CONH

Br2
2

4 KOH

CH 3NH 2

K2CO 3

2 KBr

2 H 2O

Sn / HCl

NH2

NaNO2 / HCl

273-278 K
NH3

N2 Cl

CuCN

H2O / H +

COOH

Benzoic acid into aniline

COOH

CONH2

Br2

4 KOH

NH2

Benzamide into toluene

CONH2

Br2 / KOH

NH2

NaNO2 / HCl

273-278 K

N2 Cl

H3PO2 / H2O

CH3Cl Anhyd. AlCl 3

CH3

Aniline into p-Bromoaniline

NH2

( CH3CO )2O Pyrid ine

Br2
NH C CH3

CH3COOH

Br

NH

CH3

HO / H
-

Br

NH2

Aniline into 2,4,6-tribromofluorobenzene

NH2 NH2 Br Br

N2 Cl Br Br

N2 BF 4 Br Br

aq. Br 2

Br

NaNO2 / HCl

HBF4
Br Br

NaNO2 Cu

Br

273-278 K
Br

Br

Aniline into benzyl alcohol

NH2

NaNO2 / HCl

273-278 K

N2 Cl

+ CuCN

CN

LiAlH4

CH2NH2

NaNO2 / HCl

CH2OH

Chlorobenzene into p-Chloroaniline Benzene into m-bromophenol

NO2

Cl

HNO 3 H 2SO4

Cl

NO2

Sn/ HCl

Cl

NH2

+
NO2 NH2

N 2 Cl

OH

HNO 3 H 2SO4

Br2 FeBr3

Sn/ HCl
Br

NaNO2 / HCl

Boil H2O
Br

273-278 K
Br

Br

Benzyl chloride into 2- Phenylethanamine m-Nitroaniline into m-Chloroiodobenzene

NO2

CH2 Cl

KCN

CH2 CN

LiAlH4

CH 2CH 2NH 2

+
NH2
N 2 Cl

NO2

NO 2

NaNO2 / HCl

CuCl

Sn/ HCl
Cl

NaNO2 / HCl

KI / Heat
Cl
+

273-278 K
NH2

+
N2 Cl

273-278 K
Cl
Cl

Aniline into Benzoic acid

NH2

NaNO2 / HCl

273-278 K

N2 Cl

+ CuCN

CN

H2 O / H

COOH

p-Chloroaniline into p-Chlorobenzylamine

Cl NH2

NaNO2 / HCl

273-278 K
CH3

Cl

N 2 Cl

CuCN

Cl

CN

LiAlH4

Cl

CH2 NH2

Toluene into m-Bromotoluene

CH3

CH3

CH3

CH3

CH3

CH3

HNO 3 H 2SO4
NO 2

LiAlH4

( CH3CO )2 O

Br2
CH 3COOH
NHCOCH 3 NO 2

H2 O / H Br NHCOCH3
NH2

(i) Diazotisation
(ii) H3PO2 / H2O
Br NH2 Br

Pyridine
NH2

m- Dinitrobenzene into m-Dichlorobenzene

+ N Cl
2

Cl

Sn/ HCl
NO 2

NaNO2 / HCl

CuCl

273-278 K
NH2

N 2 Cl

Cl

Class XII

ORGANIC CONVERSIONS

Class XII

ORGANIC CONVERSIONS