2.
Haloalkane and Haloarene
Organic Chemistry
❑ Markovnikov’s rule
❑ Anti- Markovnikov’s rule (Peroxide effect)
SET A: ❑ Dehydrohalogenation
1. Identification of 10, 20 and 30 alcohols by Victor Meyer’s method. ❑ Saytzeff’s rule
2. Separation of 10, 20 and 30 amines by Hoffmann’s method. ❑ Wurtz reaction
3. Distinction of 10, 20 and 30 amines by Nitrous acid test ❑ Fittig reaction
4. Comparison of basic strength of 10, 20 and 30 amines. ❑ Wurtz- Fittig reaction
5. Oxidized product of 10, 20 and 30 alcohols. ❑ Diazotization reaction
6. Chemical properties of Grignard’s reagent. ❑ Sand Meyer's reaction
7. Reduction of Nitrobenzene in different medium. ❑ Gattermann reaction
❑ Reimer-Tiemann reaction
❑ Carbylamine reaction
SET B: Name reactions: 3. Alcohol and Phenol
1. Aromatic Hydrocarbon ❑ Oxo process
❑ Decarboxylation reaction ❑ Hydroboration
❑ Friedel- Craft’s alkylation ❑ Esterification reaction
❑ Friedel- Craft’s acylation ❑ Dow’s process
❑ Liebermann's Test
❑ Carboxylation reaction ( Kolbe’s reaction )
❑ Coupling reaction( preparation of azo dyes)
4. Ether
❑Williamson’s etherification reaction
5. Aldehyde and Ketone
❑Ozonolysis ❑2,4-DNP Test
❑Rosenmund reduction ❑ Action with ammonia
❑Clemmensen reduction ❑Action of Tollen’s reagent
❑Wolf- kishner reduction ❑Action with Fehling’s solution
❑Aldol condensation ❑ Iodoform Test
❑Cannizaro’s reaction
❑Gattermann Koch synthesis 7. Amine
❑Perkins condensation ❑(Hoffmann’s reaction) Bromamide reaction (
❑Benzoin condensation Decarbonylation )
6. Carboxylic acid ❑ Hoffmann’s Ammonolysis reaction
❑ Coupling Reaction
❑Hell- Volhard- Zelinsky (HVZ )
❑(Hoffmann’s reaction) Bromamide reaction ( Decarbonylation )
❑Claisen Condensation reaction.
Conversion
To increase Carbon number in chain
a. Wurtz reaction
b. Reaction with KCN
c. Reaction with Grignard reagent
d. Oxo-process
e. Carboxylation reaction
f. Carbonylation reaction
To decrease Carbon number in chain
a. Decarboxylation reaction [Sodalime (CaO + NaOH)]
b. Decarbonylation reaction [Hoffmann’s bromamide reaction]
3
Aliphatic Conversion
Cl2,hv Cl2,hv KCN
Na/dryether
CH4 CH3-Cl ∆ CH3-CH3 CH3-CH2-Cl CH3-CH2-CN
Alc. KOH [Link]
H2O/H+
Br2/CCl4
Br-CH2-CH2-Br CH2=CH2 CH3-CH2-OH
CH3-CH2-COOH
[Link] H2/Ni [O]
SOCl2
CH2=CH-Br CH3-CH3 CH3-CHO
CH3-CH2-COCl
[Link] Cl2,hv [O]
NH3
CH≡CH CH3-CH2-Cl CH3-COOH
CH3-CH2-CONH2
H2O 42% H2SO4, NaOH + CaO
1% HgSO4, Br2/KOH
CH3-CHO CH4 CH3-CH2-NH2
LiAlH4 HNO2
CH3-CH2-OH CH3-CH2-OH
LiAlH4 SOCl2 KCN
LiAlH4
HCHO CH3-OH CH3-Cl CH3-CN CH3-CH2-NH2
HNO2
CH3-CH2-OH
H H [O]
H2O/H+ KCN
CH3-C-OH CH3-C-OH CH3-CHO
COOH CN [O]
LiAlH4 SOCl2 KCN H2O/H+
(HCOO)2Ca Distill
HCHO CH3-OH CH3-Cl CH3-CN CH3-COOH
NH3
CaO CH3-COO-NH4+
-H2O ∆
[O] [O] HNO2 Br2/KOH
HCOOH HCHO CH3-OH CH3-NH2 CH3-CO-NH2
Aromatic Conversion NO2 NH2 COOH
N2+Cl- CN
COONa
Sn/HCl NaNO2 + HCl H2O/H+
CuCN/HCl
0-50C
Aniline
H2O,Boil
OH CaO+ NaOH Conc. HNO3, N=N NH2
Conc. H2SO4
Zn-Dust Cl OH
i. NaOH,
Cl2, FeCl3 3500C, 300atm BDC
N=N OH
Cl
ii. HCl CHCl3, OH
NaOH
CH3Cl , CHO
Anh. AlCl3 60-70 0C
CH3 CH2-Cl CH2-OH CHO COOH
CH≡CH Cl2,hv Aq. KOH [O] [O]
NO2 NH2 NC NH-CH3
Sn/HCl CN CH2 –NH2
CHCl3/alc. KOH LiAlH4
Warm LiAlH4
CH3 CHO
CeO2/H+ (CH3CO)2O
CH=CH-COOH
CH3 COONa,1800C
KMnO4
COOH COCl CONH2 NH2
SOCl2 NH3
Br2/KOH
NH3
COO-NH4+ CONH2 NH2
-H2O Br2/KOH
7
CuCN/HCl
CN
Cu2Cl2 /HCl
Cl
Or
Cu-powder /HCl
Cu2Br2 /HBr
Br
Or
Cu-powder /HBr
NaNO2 + HCl
NH2 N2+Cl- H2O,Boil
0-50C
OH
Aniline
N=N NH2
Phenol N=N OH
8
Conc. HNO3 Sn/HCl H2/Pd
CHCl3, KOH D
A B C
Conc. H2SO4 60-70 0C
CH3Cl/AlCl3 NH3
KMnO4/ H+ SOCl2 D
A B C
∆
NH2
NaNO2 + HCl NH3
CuCN H2O/H+ D E
A B C ∆
0-50C