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(1)
1. Hydrohalogenation
2. Hydration
H 3C
3. Oxymercuration demercuration
CH 3
CH 2
CH 3
CH 3
HO
Alcohol without rearrangement
following Markownikoff rule
BH 3 or B 2H 6
H 3C
CH 3
OH
H 2O 2 /OH
CH 2
Alcohol without rearrangement
Unsymmetrical Alkene
following MR but resemble Anti-MR
X2
H 3C
Unsymmetrical Alkene
(2)
H 3C
Hg(OAc) 2 /H 2O
Na BH 4
CH 3
CH3
5. Halogenation
HX
Unsymmetrical Alkene
H 3C
4. Hydroboration oxidation
CH 3
CH3 X
H 3C
X
Alkyl dihalide without rearrangement
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6. Addition of alcohol
ROH/H +
H 3C
Unsymmetrical Alkene
H 3C
H 3 C OR
Ether with rearrangement
Br
NBS
CH 2
Allyl or benzyl group
7. NBS
CH3
Na/Ether
8. Wurtz reaction
R X
Primary or secondary Alkyl halide
R X
Alkyl
halide
Li
CH 2
R R
Alkane
RLi CuI
R2CuLi R'X R R'
Alkyl
Lithium dialkyl
Alkane
lithium
cuprate
Electrolysis
R COONa
R R
Salt of mono carboxylic acid
Alkane
COONa
Electrolysis
COONa
Salt of dicarboxylic acid with single bond
COONa
Electrolysis
COONa
Salt of dicarboxylic acid with double bond
H2C CH2
Alkene
HC CH
Alkyne
(3)
H3 C
CH3
CH2
CH 3
HBr
Peroxide
Br
H 3C
Unsymmetrical Alkene
13. Hydrogenation
2
RC CR or RCH=CHR or Pd or Pt RCH2 CH2 R
Alkyne
Alkene
2
RC CR BaSO
4
Alkyne
RC CR
Alkyne
H /Pd
(4)
cis-alkene
R
Na/liq NH 3
R
trans-alkene
ZnHg/HCl
R1
R2
Aldehyde or ketone
R1
R2
Alkane
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NH 2NH 2 /KOH
R1
R2
Any aldehyde or ketone
18. LiAlH 4
OH
RCH/R
O
LiAlH 4
RCH/R
RCX/OCR/OR/OH
RC N
R1
R2
Alkane
LiAlH 4
LiAlH 4
RCH 2 OH
RCH 2 NH2
O
RCNH2
LiAlH 4
19. NaBH 4
RCH/X
RCH 2 NH2
OH
NaBH 4
RCHR , RCR
O
RCOR/RC
20. DIBAL-H
OH
NaBH 4
RCHR
O
N
DIBAL-H
78C
RCH
DIBAL-H
room T
RCH2 OH
(5)
21. Ozonolysis
22. Hydroxylation
RCH=CHR'
(i) O 3
(ii) Zn/(CH 3) 2S
RCH + R'CH
OH OH
RCH=CHR'
dil KMnO 4
RCHCHR
23. PCC
RCH 2 OH
OH
RCHR
24. KMnO4
PCC
PCC
RCH 2 OH
RCR
KMnO 4
OH
RCOOH
O
RCHR
RCH
O
KMnO 4
RCR
COOH
KMnO 4
25. Cu/
(6)
RCOH
CH 3
3 alc
Cu/
RC=CH 2
R
Alkene
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mcpba
R'
OR'
Ester
RCH
RC
Tollen's reagent
CH
Tollen's reagent
R1
OR2
Ester
O
O
R
H
Aldehyde
Na/ROH
R 1 CH2 OH + R 2 OH
Alcohol
R
H/R
Alcohol
Alcohol
OH
Aluminium complex
R
H/R
Aldehyde or ketone
OH
C Ag + (White ppt)
RC
H 2 /Pd-Ba SO 4
R
Cl
Acid halide
O
Aluminium complex
R
H/R
Alcohol
O
R
H/R
Any aldehyde or ketone
(7)
32. Halogenation
X2 /AlCl 3
Aromatic compound
NO 2
33. Nitration
conc.
HNO 3 /H 2SO 4
Aromatic compound
34. Sulphonation
conc.H 2SO 4
Aromatic compound
RX/AlCl 3
Aromatic compound
COR
RCOX/AlCl 3
Aromatic compound
(8)
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37. Protonation
OH
HNO 2
38. Nitrosation
Phenol
Aromatic compound
N
R
HNO2
OH
NH 2
PhN 2Cl
pH 1 0
Phenol
KOH
Phenol
N 2 Ph
p-diazophenylaniline
OH
OH
CHCl 3
NH 2
PhN 2Cl
pH 5
, Aniline
N2 Ph
p-diazophenylphenol
OH
,
NO
N,N-dialkyl aniline
NO
p-nitrosophenol
p-nitroso-N,N-dialkyl aniline
OH
CHO
o-Hydroxybenzene , Phenol
carbaldehyde
OH
CCl 4
COOH
KOH
o-Hydroxybenzene
carboxylic acid
(9)
OH
COOH
1. CO 2 /KOH
2. H +
Phenol
CHO
HCN/HCl
Aromatic compound
CHO
CO / HCl / AlCl 3
Aromatic compound
CH 2 Cl
CH 2O/HCl
44. Chloromethylation
Aromatic compound
NH 2
45. Diazotization
N 2 Cl
NaNO 2 /HCl
0-5C
(10)
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X
CuX/HX
X
Cu powder/HX
N 2 Cl
NaBF4 /Heat
CH 3 CBr
1
49. SN reaction
CH 3
Alkyl halide
CH 3 COH
CH 3
alcohol with rearrangement
KOH/Acetone
50. SN reaction
CH 3 Br
Alkyl halide
CH3 OH
Alcohol without rearrangement
(11)
CH 3 CH 2 OH
Alcohol
CH 3 Cl
KOH
CH3
CH 3
CH 3 CBr EtOH
52. E1 reaction
CH3
Alkyl halide
CH 3 C=CH 2
Alkene with rearrangement
CH 3
CH 3
alc. KOH
CH 3 CBr
53. E2 reaction
CH 3 C=CH 2
Alkene without rearrangement with Anti elimination
CH 3
Alkyl halide
CH3 CH 3
Pinacol-pinacolone
54. rearrangement
CH 3 C
CCH 3
CH 3 COH
(12)
H+
OH OH
1,2-diol
CH3
CH 3 CH2 OCH 3
Ether via SN 2
CH 3
Alcohol
anhydrous
ZnCl 2 /HCl
O CH 3
CH 3 CCCH 3
CH 3
Aldehyde Ketone
CH3
CH 3 CCl
CH3
Alkyl chloride & test of alcohol
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CH 3
Gabril-phthalimide amine
57. synthesis
CH 3 COH
HBr
CH3 CBr
CH 3
Alkyl halide with rearrangement
CH 3
Alcohol
O
NH
O
Phthalimide
O
(i) KOH
(ii) RX
(iii) H2 O/H+
OH
HCN
RCH/R
RCH/R
Aldehyde/ketone
ROH/H
RCH/R
Aldehyde/ketone
O
H 2O/H +
CN
Cyanohydrin
OH
RNH2
1 amine (Preparation of 1 amine)
RCH/R
D 2O/D + or D 2O/OD
H/R
H 3C
Aldehyde or ketone with alpha H
RCH/R
COOH
- Hydroxycarboxylic acid
OR
ROH/H
OR
Hemiacetal
OH
RCH/R
OR
Acetal
O
H/R
DH 2 C
Replacement of alpha H with D
(13)
OH O
Ba se
H
H 3C
Aldehyde or ketones
with H
H
H 3C
-Hydroxy aldehyde
or ketone
NaOH
H
H
Aldehyde without H
Base
OH
H 3C
Br2 /P
OH
(14)
X 2 /NaOH
R
R
CH3
CH 3
Alcohol or aldehyde or ketone with
following skeleton
+ H 3C OH
H
O Na +
Salt of carboxylic acid Alcohol
Ph
OH
unsaturated
carboxylic
acid
-
or
Ph
H
Aromatic aldehyde
H
H 3C
- unsaturated
aldehyde or ketone
ONa
R
Salt of
carboxylic acid
O
CHX 3
Haloform
OH
Br
Replacement of H with Br
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NaOH /CaO
Alkane
Br2 /NaOH
NH 2
R
Amide
NH 2
Amine
R
OH
Carboxylic acid
OH
(i) RMgX
(i) RMgX
OH
RCX/OCR/OR
(i) RMgX
(ii) H 2O
RCR
R
RC
H 2 O/H +
O
RCOH
Br 2
R
OAg
Silver salt of carboxylic acid
R Br + CO 2 + AgBr
Alkyl
bromide
(15)
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