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Conversions(ORGANIC)
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Abir Dutta
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Class –XII
ORGANIC CONVERSIONS
Ascent of Series R
alc. KCN
X
R
Alky l halide
Descent of Series
LiAlH 4
CN
R
Reduction
Nitrile
CH 2 NH2
Primary amine
Organic compound
RCONH 2 Acid amide
Br 2
R NH 2 Amine
KOH
( NaNO 2 & HCl )
HNO 2
( NaNO 2 & HCl )
+
R
RCOOH
NH 3
HNO 2
Hy droly sis H3O
RCOOH Carboxy lic acid
Carboxy lic acid or aldehy de
CH 2 OH
Oxidation
Oxidation
R OH Primary alcohol
Organic compound For aromatic conversion take the help of benzenediazonium chloride Ethyne into benzene Primary alcohol
Carboxy lic acid
3 CH
Ethene into benzene H2C
Br
Br 2
CH2
Br
H2C
Hexane into benzene
Red-Hot-Cu Tube Polymerisation
CH
Alc. KOH
CH 2
HC
CH
Red-Hot-Cu Tube Polymerisation
CH3
H 2C
CH3
H 2C
3 H2
773 K / 10 -20 atm. ( - H2 )
CH2
Hexane
Aromatisation
Cr2O7 / V2O5 / Mo2O3
CH2
Cyclohexane
Benzene
Benzene into p-nitrobromobenzene Br 2 / FeBr3
HNO 3 / H2SO 4
Br
Benzene into m-nitrochlorobenzene
O 2N
NO 2
Br NO 2
HNO 3 / H2SO 4
Cl2 / FeCl3
Cl
Benzene into p-nitrotoluene CH 3Cl / anhy. AlCl
3
HNO 3 / H2SO 4
CH3
Benzene into Acetophenone H3C
C
SOCl 2
CH 3CH 2OH
CH 3CH 2Cl
( Pyridine )
H3C
CH3
HC
CH 3CH 2Br
H2C
CH2
Br 2
CNa
HC
NaCl Br
Alc. KOH
C
Anhy. AlCl 3
Cl
Ethane to Bromoethene Br 2
CH3
O
O
+ Ethanol into but-1-yne
O 2N
H2 C
CH3
CCH 2CH 3
Br CH 2
Alc. KOH
H2C
CH
Propene into 1-nitropropane H3C
CH
CH2
HBr ( Peroxide )
H3C
CH 2
Ethanoic acid into Benzene H3C
COOH
aq NaOH
H3C
COONa
CH 2 Br
Sodalime
AgNO 2
AgBr CH4
Cl 2 / h
H3C
CH 2
H3C
Cl
CH 2 NO 2
Na / Dryether
H3C
Cl 2 / h
Red hot iron tube 873 K Br
HC
CH
NaNH 2
H2C
CH3
CH
Br
Alc. KOH
H2 C
Br CH 2
Br 2
H2C
CH2
Alc. KOH
Cl CH 2 CH3
Br
Class –XII
ORGANIC CONVERSIONS
Toluene into Benzyl alcohol Cl
Cl 2 / Boil HCl
CH3
Propene into Propyne H3C
CH
OH
Aq. KOH
CH2
CH2
Br
Br 2 CCl 4
CH2
H3C
Br
HC
alc. KOH
CH 2
Ethanol into Fluoroethane H3C
SOCl 2
CH 2 OH
H3C
( Pyridine )
Alc. KCN
CH 3Br
H3C
( ether )
But-1-ene into But-2-ene H3C
CH 2
CH
CH
CH 2 F CH3
+
C
H2 O / H
NMgBr
H3C
C
O
Br HBr
CH2
C
H3C
Hg 2Cl 2
CH3 CH 3MgBr
CH 3CN
KBr
Hg 2F 2
CH 2 Cl
Bromomethane into Propanone
H3C
NaNH 2
H3C
1- Chlorobutane into n- Octane
H3C
Benzene into Biphenyl
CH 2 HC
CH3
CH 2 CH 2 CH 2 Cl
+
Br 2 / FeBr 3
Propene into Propan-1-ol H3C
CH
2 H3C
Peroxide
1- Bromopropane into 2-Bromopropane H3C
H3C
Dry ether ( Wurtz reaction )
2 Na
CH
CH
CH3
H3C
( CH 2 ) 6
CH3
Na / Dryether
Br
HBr
CH2
alc. KOH
Aq. KOH
CH 2 CH 2 Br
H3C
CH 2 CH 2 OH Br
alc. KOH
CH 2 CH 2 Br
H3C
CH
HBr
CH2
H3C
CH
CH3
Benzyl alcohol into 2-Phenylethanoic acid CH2
OH
SOCl 2
CH2
KCN
Cl
Ethanol into Propanenitrile H3C
SOCl 2
CH 2 OH
Aniline into Chlorobenzene
H3C
( Pyridine )
2-Chlorobutane into 3,4-Dimethylhexane 2 H3C
CH 2
+
N2 Cl
CH3 CH Cl
H2O / H
CH2COOH
KCN
CH 2 Cl
NaNO2 / HCl
NH2
+
CN
CH2
-
H3C
CH 2 CN
CuCl / HCl
Cl
CH3
Na / Dryether
H3C
CH 2
CH
CH CH 2 CH3
CH3
2-Methylpropene into 2-Chloro- 2-methylpropane
Cl
H3C
Ethylchloride into Propanoic acid H3C
H3C
CH 2
CH
HBr Peroxide
CH2
2-Chloropropane into Propan-1-ol H3C
Isopropyl alcohol into Idoform H3C
Chlorobenzene into p-nitrophenol
HCl
CH2
H3C
C CH3
CH3
+
KCN
CH 2 Cl
But-1-ene into n-butyliodide
C CH3
H3C
Cl CH
H3C
CH3
CH 2
CH
CH 2
CH 2 Br
H 3C
CH
I 2 / Na 2CO 3 CH3 Cl
NaI Acetone
H3C
H3C
B2H6
alc. KOH
OH
H2 O / H
CH 2 CN
CH3COONa NaOH 623 K / 300 atm.
H2O 2 / OH
CH2
CH 2 COOH
CH 2
CH 2
H3C
CH2
CH 2 I
CH2
OH
CHI 3 OH
HNO3 / H2SO 4
O 2N
OH
Class –XII
ORGANIC CONVERSIONS
2- Bromopropane into 1-Bromopropane H3C
CH
alc. KOH
HBr
CH3
CH
H 3C
CH2
tert.butyl bromide into Isobutyl bromide
CH3
CH3 H3C
C
alc. KOH
CH3
H3C
H3C
Peroxide
Br
CH2
CH2
Br
HBr
C
CH2
H3C
Peroxide
CH
CH2
Br
+
3 H 2O
CH3
Br
Aniline into Phenylisocyanide
+
NH2
Propene into Propan-2-ol
+
CHCl 3
( w arm )
3 KOH
+
NC
3 KCl
Br
H3C
CH
HBr
CH2
Benzyl chloride into Benzyl alcohol
H3C
CH2
HO
aq. KOH
CH CH3
H3C
aq. KOH
Cl
CH2
CH CH3
OH
Ethylmagnesium chloride into Propan-1-ol O H3C
+
CH 2 MgCl
H
C
+
H3C
H
H2 O / H
OM gCl
CH 2 CH 2
H3C
CH 2 CH 2
OH
Methylmagnesium bromide into 2-Methylpropan-2-ol OMgBr
O
+
CH 3MgBr
H3C
C
H3C
CH3
C
OH
+
H2 O / H
CH3
H3C
H3C
Butan-1-ol into Butanoic acid
C
CH3
H3C
CH 3CH 2CH 2CH 2OH Jones reagent ( CrO 3 - H 2SO 4 )
CH 3CH 2CH 2COOH
Benzyl alcohol into phenylethanoic acid HBr
CH2 OH
KCN
CH2 Br
H 3O
CH2 CN
Mg Ether
O 2N
CO2
Mg Br
CH2 COOH
3-Nitrobromobenzene into 3-Nitrobenzoic acid Br
+
H 3O
COOMgBr
( Dry ice )
+
COOH
O 2N
O 2N
O 2N
4-Methylacetophenone into Benzene-1,4-dicarboxylic acid H 3C
COCH 3
KMnO 4 / KOH
KOOC
COOK
Cyclohexene into Hexane-1,6-dioic acid
dil. H2SO4
HOOC
COOH
COOH
KM nO4 - H2SO4 Heat
Butanal into Butanoic acid H C 3
CH 2
CH 2
Ethylbenzene into Benzoic acid
Mg
dil. NaOH
O
C
COOK
H3C
OH HC
CH 2
CH 2 H 3O
H 3O
COOH
+
COOH
+
COOH
H2O
COOH
OMg Br
CH2 CH
Ethanal into Butane-1,3-diol CHO
COOK
Adipic acid
O
C
Phenylethene ( Styrene ) into Benzoic acid H3C
KMnO 4 / KOH
O
Mg Br
H3C
KMnO 4 / KOH
COCH 3
Bromobenzene into Benzoic acid Br
Tollen's reagent
CHO CH2CH3
Acetophenone into Benzoic acid
COOH
CH2
CHO
KMnO 4 / KOH
LiAlH4
COOK
H 3O
CH
COOH
OH
OH H 3C
+
CH 2
CH 2
Class –XII
ORGANIC CONVERSIONS
Ethanal into But-2-enal H3C
dil. NaOH
CHO
OH H3C
Heat
HC
CH2
CHO
Ethanal into But-2-enoic acid H3C
dil. NaOH
CHO
OH H3C
CH
CH2
Heat
H3C
H2O
CHO
Benzene into methylbenzoate
H3C
H2O
CH
CH
CHO
CH
CH
Tollen's reagent
CH 3
Anhy. AlCl3
H3C
CH
COOH COOCH 3
CH3OH ( H2SO 4 )
CH 3
Anhy. AlCl3
COOH
COOH
KM nO4 / OH
CH 3Cl
Benzene into m-Nitrobenzoic acid
CH
COOH
KM nO4 / OH
CH 3Cl
CHO
HNO 3
H2 SO 4 NO2
Benzene into p-Nitrobenzoic acid
CH 3Cl
HNO 3
CH 3
Anhy. AlCl3
H2 SO 4
H 3C
KM nO4 / OH HOOC
NO 2
NO 2
Benzene into p-Nitrobenzaldehyde CH 3Cl
HNO 3
CH 3
Anhy. AlCl3
H 3C
H2 SO 4
NO 2
CrO2Cl2 / CS2
OHC
+
NO 2
H3O
Benzene into Phenylacetic acid CH 2 Cl
CH 3
Cl 2 / Boil
CH 3Cl
CH 2CN
KCN
H2O / H
CH 2COOH
+
Anhy. AlCl3
Propanone into propene
O H3C
Propanal into butanone CH 3CH 2CHO
C
LiAlH4
CH3
OH H3C
HC
H2SO4 (conc.)
CH3
H3C
Heat
H2O / H
+
H3C
Ethanol into 3-hydroxybutanal CH 3CH 2OH
CH 2
CH
Anhydrous CrO 3 OR Cu / 573 K
Benzaldehyde into benzophenone
CHO
CH2
O
OH
CH 3MgBr
CH
CH3
K2Cr 2O7 / H2SO4
CH 3CHO
H3C
CH 2
CH3
OH
Dil. NaOH Aldolcondensation
H3C
HC
CH 2
CHO
O
COOH
K2Cr 2O7 / H2SO4
C
Ca(OH) 2
C
Heat
Benzaldehyde into 3-phenylpropan-1-ol CH
CHO
+
CH
CHO
dil.NaOH CH3CHO ( Cross aldolcondensation )
H2 / Ni
CH 2
CH 2
CH 2 OH
CH
CH
CH 2 OH
Benzaldehyde into 3-phenylprop-2-en-1-ol CH
CHO
+
dil.NaOH CH3CHO ( Cross aldolcondensation )
CH
CHO
NaBH4 / CH3OH
Benzaldehyde into -Hydroxyphenylacetic acid
HO
O
HO
CH
+
C H
Benzoic acid into m-Nitrobenzyl alcohol
CN
HCN
+
H2O / H
COOH
COOH
+
NO 2
Benzoic acid into Benzaldehyde
COOH
SOCl2
COCl
COOH
CH 2 OH
B 2H 6 / H3O
HNO 3 / H2SO4
CH
Pd / BaSO4
Rosenmund reduction
NO 2 CHO
Class –XII
ORGANIC CONVERSIONS
Benzene into m-Nitroacetophenone
Bromobenzene into 1-Phenylethanol Mg
Br
C
H3C
Chloroethane into propan-1-amine CH 2
H
H3C
CH 2
CH
LiAlH 4
N
C
+
H3C
Reduction
CH 2
C
CH 2
Benzene into Aniline
N
CH 2
NH2
CH 2
NH2
CH 2
Reduction
HNO3 / H2 SO 4
Sn / HCl
NO 2
NH2
Reduction
Benzene into N,N-dimethylaniline HNO3 / H2 SO 4
CH3
H 2 / Ni
Ethanolic NaCN
Cl
H 3O
CH3
Chlorophenylmethane into 2-Phenylethanamine CH 2
CH3
HO
CH
Ethanolic NaCN
Cl
C
+
-
O MgBr
C
O
HNO3 / H2SO4
CH 3
O
Mg Br
H3C
O 2N
O
CH 3COCl / AlCl3
Sn / HCl
NO 2
Reduction
CH3
CH3 Br
NH2
N CH3
1,6-Dichlorobutane into hexane-1,6-diamine Cl
( CH 2 ) 4
KCN
Cl
NC
LiAlH 4
( 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 Br
Br 2
Sn / HCl
NO2
NO 2
CH 3
H3PO2
273-278 K
H2O
OH
+ N 2BF 4
+ N 2 Cl
NH 2
+ HCl
NaNO2
+ N 2 Cl
NH2 Br
Br NaNO2
( CH 2)4
C
N
H3C
H 2O 2
Methanol into ethanoic acid
H3C
OH
Br
+ HCl
Br
H3C
CONH
Br 2 2
KCN
Cl
+
4 KOH
H3C
H3C
NaNO 2
+
HCl
( HNO 2 )
Methanamine into ethanamine CH 3NH 2
NaNO 2
+
HCl
( HNO 2 )
H3C
KMnO 4
CH3CH2OH
OH
SOCl2
OH
CH3COOH
H3C
Cl
KCN
NH3
CH 3CONH 2
H3C
CN
( CH2)3 H2O / H +
CN
Etahnamine into methanamine CH3CH2NH2
Br
H3PO2
Br
( CH 2)4
SOCl2
CH3
Br
Br
Br
H3C
Cu CH3
CH3
aq. Br2
Hexanenitrile into 1-aminopentane H2O / HO
NO2
HBF 4
CH 3
Aniline into 1,3,5-tribromobenzene
Br
KMnO 4
N Cl
N +
NaNO2
NH2
Br
NaNO2 / HCl
NH 2
3-Methylaniline into 3-nitrotoluene
COOH
Br
Br
Br 2
LiAlH 4
+
4 KOH
CH 2
NH2
CH 3COOH
CH 3NH 2
CH3CH2NH2
Ethanoic acid into Propanoic acid CH3COOH
B 2H 6 / H3O
+
CH3CH2OH
SOCl2
Propanoic acid into ethanoic acid CH3CH2COOH
NH3
CH3CH2 CONH2
Br 2
CH3CH2Cl
+
4 KOH
KCN
CH3CH2NH2
CH3CH2CN
NaNO 2
+
( HNO 2 )
HCl
H2O / H +
CH3CH2OH
CH3 CH2 COOH KMnO 4 OH
CH3COOH
Class –XII
ORGANIC CONVERSIONS
Nitromethane into dimethylamine Ethanoic acid into methanamine NH3
CH 3COOH
CH 3CONH
Nitrobenzene into benzoic acid NO2
Sn / HCl
Sn / HCl
CH3 NO2
+
Br2 2
4 KOH
+
Benzoic acid into aniline
NH3
COOH
Br2 / KOH
NH2
Aniline into p-Bromoaniline
C
CH3
NH2
CH3
CH3
+
Br
NH2
+
N2 BF 4 Br
Br
F Br
Br
Cu
273-278 K Br
Br
NaNO2
HBF4
NaNO2 / HCl
Br
C
N2 Cl
Br
Br
aq. Br2
NH
+
NH2
HO / H -
Br
CH3COOH
Aniline into 2,4,6-tribromofluorobenzene
NH2
CH3Cl Anhyd. AlCl 3
O
Br2 NH
COOH
4 KOH
H3PO2 / H2O
N2 Cl
273-278 K
O
( CH3CO )2O Pyrid ine
NH2
+
NaNO2 / HCl
2 H 2O
H2O / H +
N
+
Br2
+
2 KBr
C
CONH2
Benzamide into toluene CONH2
+
CuCN
N2 Cl
273-278 K
(CH3) 2NH
K2CO 3
+
CH 3NH 2
NaNO2 / HCl
NH2
CH3 Cl
CH3NH2
6 [H]
Br
Br
Br
Aniline into benzyl alcohol NH2
+ CuCN
NaNO2 / HCl
N2 Cl
273-278 K
LiAlH4
CN
Chlorobenzene into p-Chloroaniline
CH2NH2
HNO 3
Cl
Cl
+
Benzene into m-bromophenol NO2
Br2
H 2SO4
FeBr3
273-278 K
CuCl
NaNO2 / HCl
273-278 K
CH 2CH 2NH 2
+ N 2 Cl
I
KI / Heat
NaNO2 / HCl
Sn/ HCl
273-278 K
+
NH2
LiAlH4
CH2 CN
NH2
NO 2
NO2
KCN
CH2 Cl
m-Nitroaniline into m-Chloroiodobenzene
Br
Br
Br
Benzyl chloride into 2- Phenylethanamine
NH2
Boil H2O
NaNO2 / HCl
Sn/ HCl
Cl
OH
N 2 Cl
NH2
NO2
Br
NO2
CH2OH
Sn/ HCl
NO2
H 2SO4
HNO 3
NaNO2 / HCl
Aniline into Benzoic acid
NH2
Cl
Cl
Cl
N2 Cl
+
+ CuCN
NaNO2 / HCl
N2 Cl
273-278 K
Cl
H2 O / H
CN
COOH
p-Chloroaniline into p-Chlorobenzylamine Cl
NH2
NaNO2 / HCl
273-278 K
+
Cl
N 2 Cl
CuCN
Toluene into m-Bromotoluene CH3
CH3
NO 2
m- Dinitrobenzene into m-Dichlorobenzene
Cl
CH2 NH2
CH3
NHCOCH 3
Sn/ HCl
(ii) H3PO2 / H2O
Br NHCOCH3
NH2
Cl
2
CuCl
NaNO2 / HCl NH2
Br
Br
+ N Cl 273-278 K
NO 2
(i) Diazotisation
H2 O / H
NH2
NO 2
CH3
CH3 +
CH 3COOH
Pyridine NH2
LiAlH4
Br2
( CH3CO )2 O
H 2SO4
CN
CH3
CH3
LiAlH4
HNO 3
Cl
+
N 2 Cl
Cl
Class –XII
ORGANIC CONVERSIONS
Class –XII
ORGANIC CONVERSIONS
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