Organic Chemistry Conversions

Broadly you can classify conversions into two types – aliphatic and aromatic.

Aliphatic Conversions
a). For stepping up the series:

Stepping up the series means that the product has one carbon more than that of reactant. For
such kind of a conversion, convert the given compound to an alkyl halide and then to a cyanide
and then to the required organic compound as asked in the question. This way, the product has
one carbon more than the reactant.

HX alc. KCN LiAlH 4

R OH R X R CN R CH 2 NH2
Anhydrous ZnCl 2 Reduction
Alcohol Alkyl halide Nitrile Primary amine

HNO 2
X2 / UV Hydrolysis
( NaNO 2 & HCl )
+
Hydrocarbon H3O
LiAlH 4
R CH 2 OH RCOOH R CH 2 OH
+ Oxidation
Primary alcohol H3O Primary alcohol
Carboxylic acid

b). For stepping down the series:

Stepping down the series means that the product has one carbon less than that of its reactant. For
such kind of a conversion, convert the given compound to an amide and then let it undergo
Hoffmann bromamide degradation reaction. Then you convert it to the required product as asked
in the question.
NH 3 Br 2 HNO 2
RCOOH RCONH 2 R NH 2
R OH
HX
R X
Carboxylic acid  Acid amide KOH Amine ( NaNO 2 & HCl )
Primary alcohol
Anhydrous ZnCl 2
Alkyl halide

Alkaline KMnO4 Aqueous KOH

R CH2 OH R CH2 X
Primary alcohol Alkyl halide

c). Reaction with Grignard’s reagent:

Grignard’s reagent is a versatile reagent and can be used for many conversions. Some of its
reactions are given below:

Dryether
R X + Mg RMgX

RMgX + CO 2 RCOOH

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 RMgX + HCHO Primary Alcohol

RMgX + RCHO Secondary Alcohol

O
RMgX + R C R Tertiary Alcohol
O
RMgX + R C N R C R

Aromatic Conversions
There are two types of conversions possible in this case:

a. When the functional group contains carbon atom:

Cl OH CH3

NaOH , 623 K, 300 atm Zn dust CH 3Cl

+ Anhydrous AlCl3
H

H2 / Pd , BaSO4 , S SOCl2 Alkaline KMnO4

OHC ClOC HOOC
Boiling Xylene

b. When the functional group does not contain carbon atom:

OH
Warm H2O

I
H3PO2
Zn dust

H2O
KI
+
N2 BF4- +
N2 Cl- Cl

HBF 4
CuCl
HCl

Conc. HNO 3
H2SO4 , 333 K

CuBr
2
NO

F Br
HBr
NaNO2
,
Na

HCl
Cu

NO 2 NH2
Sn / HCl

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

Ethene into benzene Br Br

Br2 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 CH 2 773 K / 10 -20 atm. ( - H 2 )  3 H2
Hexane CH2
Cyclohexane Benzene

Benzene into p-nitrobromobenzene

Br 2 / FeBr 3 HNO 3 / H 2SO 4
Br O 2N Br

Benzene into m-nitrochlorobenzene

NO 2 NO 2

HNO 3 / H 2SO 4 Cl2 / FeCl 3

Cl

Benzene into p-nitrotoluene

CH3Cl / anhy. AlCl3 HNO 3 / H 2SO 4
O 2N CH3
CH3

Benzene into Acetophenone O

O C
Anhy. AlCl3 CH3
+ H3C C Cl

Ethanol into but-1-yne

SOCl2 HC CNa
CH 3CH 2OH CH 3CH 2Cl HC CCH 2CH 3
( Pyridine ) NaCl

Ethane to Bromoethene
Br Br
Br2 Alc. KOH Br2 Alc. KOH
H3C CH3 CH 3CH 2Br H2C CH2 H2 C CH2 H2C CH Br

Propene into 1-nitropropane

HBr AgNO2
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
NaNH2 Alc. KOH Br2 Alc. KOH CH 2 CH3
HC CH H2C CH Br H2 C CH2 H2C CH2

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Toluene into Benzyl alcohol
Cl OH
Cl 2 / Boil Aq. KOH
CH3 CH 2 CH 2
 HCl
Propene into Propyne Br Br
Br2 alc. KOH
H3C CH CH2 H3C HC CH2 H3C C CH
CCl 4 NaNH2

Ethanol into Fluoroethane

SOCl2 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 CH3MgBr H2 O / H
CH 3Br CH 3CN H3C C NM gBr 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 Br2 / FeBr3

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 SOCl2 KCN +
CH 2 Cl CN H2O / H
CH 2 CH 2 CH 2COOH

Ethanol into Propanenitrile SOCl2 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 CH2 CH Cl H3C CH2 CH CH CH2 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
B2 H6
H2O 2 / OH
H 3C CH CH2 H3C CH2 CH2 OH
H3C CH CH3

Isopropyl alcohol into Idoform OH I 2 / Na2CO 3

CHI 3
H3C CH CH3
 CH3COONa
Chlorobenzene into p-nitrophenol NaOH
HNO3 / H 2SO 4
O 2N OH
Cl OH
623 K / 300 atm.
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 2- Bromopropane into 1-Bromopropane al c. KOH HBr
H3C CH CH3 H3C CH CH2 H3C CH2 CH2 Br
Peroxide
Br
tert.butyl bromide into Isobutyl bromide
CH3 CH3
al c. KOH HBr
H3C C CH3 H3C C CH2 H3C CH CH2 Br
Peroxide
Br CH3

Aniline into Phenylisocyanide ( warm )

NH2
+ CHCl3
+ 3 KOH NC + 3 KCl + 3 H2O

Propene into Propan-2-ol HBr

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

Benzyl chloride into Benzyl alcohol CH 2 Cl

aq. KOH
CH 2 OH

Ethylmagnesium chloride into Propan-1-ol

O +
H2 O / H
H3C CH 2 MgCl + H C H H3C CH 2 CH 2 OMgCl 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 ( CrO3 - H2SO 4 ) CH 3CH 2CH 2COOH

Benzyl alcohol into phenylethanoic acid

+
HBr KCN H 3O
CH 2 OH CH 2 Br CH 2 CN CH 2 COOH

3-Nitrobromobenzene into 3-Nitrobenzoic acid
+
Mg CO 2 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. H 2SO 4
H 3C COCH 3 KOOC COOK HOOC COOH

Cyclohexene into Hexane-1,6-dioic acid KMnO 4 - H 2SO 4 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
CH 2CH 3 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 Li AlH4
H3C CHO H3C HC CH2 CHO H 3C CH CH 2 CH 2

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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
KMnO 4 / OH CH3OH
Anhy . AlCl3 ( H 2SO 4 )

CH 3 COOH COOH

/ OH 
CH 3Cl
Benzene into m-Nitrobenzoic acid KMnO 4 HNO3
Anhy . AlCl3 H2 SO 4
NO2

Benzene into CH 3Cl

CH 3 HNO3
KMnO 4 / OH HOOC
H 3C NO 2
p-Nitrobenzoic acid
NO 2
Anhy . AlCl3 H2 SO 4

Benzene into p-Nitrobenzaldehyde

CH 3Cl HNO3 CrO2Cl2 / CS 2
CH 3 H 3C NO 2 OHC NO 2
Anhy . AlCl3 H2 SO 4 +
H3O

Benzene into Phenylacetic acid

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

Anhy . AlCl3

Propanone into propene O OH

Li AlH4 H2SO4 (conc.)
H3C C CH3 H3C HC CH3 H3C CH CH2
Heat
Propanal into butanone OH O
CH3M gBr K2Cr2O7 / H2SO4
CH 3CH 2CHO + H3C CH2 CH CH3 H3C CH2 C CH3
H2O / H

Ethanol into 3-hydroxybutanal Anhydrous CrO3 Dil. NaOH

OH
CH 3CH 2OH CH 3CHO H3C HC CH2 CHO
OR Cu /573 K Aldolcondensation
Benzaldehyde into benzophenone CHO COOH
O
K2Cr2O7 / 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 NaBH 4 / CH 3OH
+ 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 / H 2SO 4 B 2H 6 / H 3O

NO 2 NO 2

Benzoic acid into Benzaldehyde COOH COCl

Pd / BaSO4
CHO
SOCl 2
Rosenmund reduction

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 Benzene into m-Nitroacetophenone O
O 2N
O
CH 3COCl / AlCl 3 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 CH2 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 HNO 3 / H 2SO 4 Sn / HCl NH2

NO 2
Reduction

Benzene into N,N-dimethylaniline CH3

CH3 Br
HNO 3 / H 2 SO 4 Sn / HCl NH2 N
NO 2
Reduction CH3

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

LiAlH 4
Cl ( CH2 )4 Cl KCN NC ( CH2 )4 CN H2NH2C ( CH2 )4 CH2NH2

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 NaNO 2 / HCl H3PO 2 KMnO 4
OH
273-278 K H2O

NO 2 NO 2 NH 2 N N Cl

+

+ -
3-Methylaniline into 3-nitrotoluene NH 2 + - N 2BF 4
NO2
N 2 Cl
NaNO 2
NaNO 2 + HCl HBF4
Cu 
CH3
CH3
CH 3 CH3
NH2 + -
N 2 Cl
Aniline into 1,3,5-tribromobenzene Br Br
Br Br Br Br H3PO 2
NH2
aq. Br 2 NaNO 2 + 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 CH2 NH2
H 2O 2

Methanol into ethanoic acid H3C OH

SOCl 2
H3C Cl
KCN
H3C CN
H2O / H+
CH 3COOH

Etahnamine into methanamine

CH3CH2NH2
NaNO 2 + HCl
CH3CH2 OH
KMnO 4
CH3 COOH
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
SOCl 2
H3C Cl H3C CN CH3CH2 NH2
( HNO 2 )

Ethanoic acid into Propanoic acid

+
B 2H 6 / H 3O SOCl 2 KCN H2O / H +
CH3COOH CH3CH2OH CH3 CH2 Cl CH3 CH2CN CH3 CH2COOH

Propanoic acid into ethanoic acid

CH3CH2COOH
NH3
CH3CH2CONH 2
Br 2 + 4 KOH NaNO 2 + HCl KMnO 4
CH3COOH
OH 
CH3CH2 NH2 CH3 CH2OH
 ( HNO 2 )

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Nitromethane into dimethylamine CH3NO2
Sn / HCl
CH3NH2
CH3 Cl
(CH3) 2NH
6 [H]

Ethanoic acid into methanamine

CH 3COOH
NH3
CH 3CONH 2
Br 2 + 4 KOH
CH 3NH 2 + K2CO 3 + 2 KBr + 2 H2O

Nitrobenzene into benzoic acid
Sn / HCl NaNO 2 / HCl +  CuCN H2O / H +
NO 2 NH2 N2 Cl C N COOH
273-278 K

Benzoic acid into aniline NH3

COOH CONH 2
Br 2 + 4 KOH

NH2

Benzamide into toluene

Br 2 / KOH NaNO 2 / HCl +  H3PO 2 / H 2O CH3Cl
CONH 2 NH2 N2 Cl CH3
273-278 K Anhyd. AlCl 3

Aniline into p-Bromoaniline O O

HO / H
Br 2 - +
( CH 3CO ) 2O
NH2 NH C CH3 Br NH C CH3 Br NH2
Pyridine CH3COOH

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

Aniline into benzyl alcohol

NaNO 2 / HCl +  CuCN LiAlH 4 NaNO 2 / HCl
NH2 N2 Cl CN CH 2NH 2 CH 2OH
273-278 K

Chlorobenzene into p-Chloroaniline Cl

HNO 3
Cl NO 2
Sn/ HCl Cl NH2
H 2SO 4

Benzene into m-bromophenol +  OH

N 2 Cl
NO 2 NO 2 NH2

Br 2 Boil H2O
HNO 3 Sn/ HCl NaNO 2 / HCl
H 2SO 4 FeBr 3 273-278 K
Br Br
Br Br

Benzyl chloride into 2- Phenylethanamine CH 2 Cl

KCN CH 2 CN
LiAlH 4
CH 2CH 2NH 2

m-Nitroaniline into m-Chloroiodobenzene + 

N 2 Cl I
NO 2 NO2 NO 2 NH2

NaNO 2 / HCl CuCl Sn/ HCl NaNO 2 / HCl KI / Heat

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

Aniline into Benzoic acid

+
NaNO 2 / HCl +  CuCN H2 O / H
NH2 N2 Cl CN COOH
273-278 K

p-Chloroaniline into p-Chlorobenzylamine

NaNO 2 / HCl +  CuCN LiAlH 4
Cl NH2 Cl N 2 Cl Cl CN Cl CH 2 NH 2
273-278 K

Toluene into m-Bromotoluene CH3

CH3 CH3
CH3 CH3 CH3
CH3
Br 2 + (i) Diazotisation
( CH3CO ) 2 O H2 O / H
HNO 3 LiAlH 4 (ii) H 3PO 2 / H 2O
CH 3 COOH
H 2SO 4 Pyridine Br Br Br
NO 2 NHCOCH3 NH2
NH2 NHCOCH 3
NO 2 NH2 +  Cl
m- Dinitrobenzene into m-Dichlorobenzene N Cl2
NaNO 2 / HCl CuCl
Sn/ HCl
273-278 K
NO 2 NH2 +  Cl
N 2 Cl
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