O3/Zn

(Ozonolysis)
CHO [O]
COOH OQR [Oragnic Quick Revision] (ALIPHATIC) (1) CH 3MgBr OH

COOH (2) H2O

CHO
O Zn-Hg
Fe-tube Oxidation KOH OCH (Clemmenson reduction)
CHºCH C6H6 O Conc. HCl
500°C V2O5, 500°C O O OCH3
Benzene (Acetal) NH2-NH2
O CH3–C–C–H (Wolf-Kishner reduction)
OH OH CHCOOK + KOH, D
H |CH3OH (Hunsdiecker reaction)
CH3–CH2–CH2 CH3–CH–CH3 CHºCH OH I2 Å
(1) AgOH
Acetylene Kolbe's O KOH Å H CH3–Br
CHCOOK OCH3 CHl3+CH3CO2Na
C + H2 Electrolysis reaction D NaOH (2) Br2/CCl4
(Hemiacetal) (Iodoform reaction)
(Aldol-condensation)
O
Å CH3–CO2H
Br2/H NH2–CH3 CaO/D
N–CH2
(Cold.) CH2–Br 1° amine
CH2OH (Schiff-base) O
CH4 conc. dil. Alk. KMnO4 (pH=4-5)
Methane CH3–CH=CH2 CH2=CH2 I OH Al(OCHMe2)3
Å
H2SO4 (Baeyer's reagent) H P+I2 H O (CH3CO)2 Ca
–
Ethylene CH2OH
(Syn) CH3CH(OH)CH3 NH2OH OH
Glycol D

)
N
(pH=4-5)

am
CH2OH D Conc. H2SO 4 Acetone
CH3Br OH mCPBA
+
H 3O O
OH l–CH2–CO2H +CaCO3
CH3–CH–CH3 CH3–CH2 O CH2OH CH3–C–H OH O
CH3CH3 (Anti) Glycol Å
O CH2N2
H

gr
OSO3H O
(Diazotization) HNO2 Ethane Cyclic ketal
PCl5 O
Cl OH O

le
CH3–CH2–CH2–NH2 Cl D2O/DO
CH3–CH F
CH3CH3 Propanamine Cl + SO2 + HCl CD3–C–CD3
CH3–CH2Br Prolonged

Te
Ethane D Zn/D MCPBA
Ethyl bromide heating
H2/Ni LiAlH4 CH3–CH=CH–CH3 PhCHO, KOH O H O

s(
Br2/CCl4 HBr/H2O2 Ph Et
Br2/CCl4 Br Cross aldol
CH3–CH2Br KCN CH2–CH2CN O

er
Ethyl bromide Propane nitrile CH2=CH2 CH2BrCH2Br (Anti-markonikov rule) OH Å
OH
Br HCN H3O
Ethylene CN CO2H
CH3–CH–CH–CH3 D

ap
Cyanohydrin
Br (Anti add)
CH2CNCH2CN Cl2+Ca(OH)2 O
Alc KOH CHCl3+(CH3COO)2Ca

hP
SOCl2 Ethylene Cyanide Br O–C
CH3CH2OH CH2Br–CH2Br HBr Ag heat D
Ethyl alcohol CH3–CºC–CH3 C–O
CH3CH2COOH Ethylene bromide
(Markonikov rule) HCºCH O O
Propanoic acid
CH2COOH
as O
+CaCO3 (Lactide)
ak
CH3CH2–Cl D
O Red, Orange CHO CH2OH
CH3–CHO CH2COOH Conc. - KOH (i) SOCl2 (ii) CH2N2 (iii) Ag2O/D (iv) H3O
+

CH2=CHBr or yellow ppt CH3CH2COOH

Acetaldehyde Succinic acid O Intramolecular Å
Arndt Eistert reaction
A

Vinyl bromide Succinic CHO CO2K

CH3CH2COCl Cannizaro O
Propanoyl chloride anhydride reaction H2
@

CH3–C–Cl CH3CHO
Pd-BaSO4
CHBrCOOH AgOH CHOHCOOH (Rossenmund reduction) PCC or
2NaNH2
CH3–COOH CHºCH OH SeO2/D Cu/573
CH3CH2CONH2 2CH3l
CHBrCOOH
Acetic acid Acetylene CHOHCOOH
Propanamide Dibromo Dihydroxy succinic
Å
NaHSO3 Ag2O (Tollen's reagent) LiAlH4
H3CH–SO3Na CH3CHO CH3–CO2H CH3–CH2–OH
Succinic acid acid or (Silver mirror test)
Tartaric acid Ag (i) C2H5OH Na
CH3CºCCH3
(ii) DIBAL-H CH3CH2ONa
CH3COONa Red ppt SN
2

Sodium acetate (Cu2O) CH3–CHO

CH3CH2NH2
HI
Ethyl amine CH3–CH2–O–CH 3 CH3–CH2–OH + CH3I
CH3CHO [Zeisel method] HI
Ethanal
Br2 CH3CH2I
cis-2-butene trans-2-butene Meso EtOEt
OH OH CH3–CH–CH3
CCl4 OH OH
140°C HCHO HO
CH4 CH3–CH2–O–CH2–CH3 H
conc. Continues ether synthesis OH
–
OH CH3–CH–O–CH2–CH3
Methane CH3CH2N = C CH3CH2OH
H2SO4 HO Ether peroxide
Ethylisonitrile Ethyl alcohol 170° CH2=CH2 OH O O–OH
 OQR [Oragnic Quick Revision] (Aromatic)
SO2NH–CH3
NH2 CH3–NH2
SO2Cl KOH
(1) HNO3/H2SO4 OH Soluble OH OH OH
Å Br Br Br Br2/CS2
(2) H SO2N–(CH3)2 2
NO2 (CH3)2–NH H2O 273K
O NH2 Hinsberg KOH
O (1) Br2/CH 3COOH NO2 reagent Insoluble Br2 (White ppt) Br
CH3–C–Cl NH–C–CH2 (CH3)3–N
(Acetanilide) (2) OH No reaction Br2/H 2O (loso)
Pyridine Br
(Acetylation reaction) (D.D.T.) Å
OH O(COCH2)
H
+
NH3 ONa CO2/high press
SO3Na dil. HCl
COOH CH3COCl COOH
NH2 NH2 NH2
Br2/CS2 Koble's Schmidt
Br Br Acetyl Salicylic acid
Cl Sod. Phenolate
reaction Salicylic acid
or NO2 SO3 or Aspirin (drug)
Aniline Br2 /H2O Br Selective red. Zwitter ion Soda lime Heat
Tribromo Anline Na HO N O

)
NO2

am
OH Indophenol
LiAlH4 O
Ph–CH2–NH2 SO3H NH2 O
CH2Cl
NO2 Cl
Phenol

gr
Cl Benzene
CONH2 CHO Benzene Acetophenone
Benzyl chloride NO2 SO3H
POCl3

le
Ph–CºN m-Dinitro Benzene Sulphanilic acid
or P2O5
Benzamides or PCl

Te
5 Ph–N=N–NH–Ph Cl
(N–N coupling)
Ph–C–CH3
Na (birch red.)

s(
Cl
COONH4 COOH CH3Cl in presence
CH3 liq. NH3 NO2 NH2 N2Cl CN COOH

er
Sandmeyer's
NH3 [O] of AlCl3 HNO3+H2SO4 Sn + HCl Diazo reaction reaction dil. HCl
alk. KMnO4 Friedal Craft's reduction 0°-5°C CuCN/HCN H2O
50°C

ap
Ammonium Benzoic acid Toluene or reaction Nitro Benzene Aniline NaNO2/HCl
Benzene Cyno Benzene Benzoic acid
Benzoate Methyl Benzene Ph–CºCH
Diazoniumchloride [Benzonitile]
R–Cl/AlCl3

hP
Cl No reaction
Cl Cl
3Cl2/hv BENZENE Cl
COCl
Cl
Cl
Cl
COONa as O
O
Chloro Benzene
O
ak
Benzene Hexachloride OH
(BHC) or O Benzoyl chloride
Sod. Benzoate HO N=N Cl
Gammaxine maleic
(C6H6Cl6 or 666)
A

insecticide anhydride (C-N coupling)

CH3
Cl O2N NO2 OH O Chloro Benzene
@

Cl Cl 6Cl2 CHO (1) O2

+ OH
AlCl3 NO2 (2) H2O
+
CHO
Cl Cl Cumene CH2
Cl Trinitro Toluence
Benzene (Industrial preparation of Phenol)
Hexachloro benzene (Explosive) Benzaldehyde Phenol
O NH2 Benzaldehyde
(HCB) (TNT) O (Wittig reaction)
(C6Cl6) Ph–C–Cl / Benzoylation
Ph–NH–C–Ph
3H2/Ni Schotton baumann Rxn
Aniline
high temp/pressure
OH NaHCO3 O
Cyclo Hexane PhCOONa
dil HNO 3 Conc.HNO3 Br
O
OH OH CH3
O NO2 CH=CHCOOH COOH C–O–Et O CHO
O2N NO2 OH OH EtOH
KMnO4/D (Benzoquinone)
+ O2N NO2
Conc.HNO3 (Better method for preparation H
+

of Picric acid) Salicylaldehyde Toluene

O NO2 Cinnamic acid Benzoic acid (Esterification)
Phenol NO2 (Clemmenson reduction)
(Major) Picric acid reaction
Picric acid
(i) Conc. H 2SO4 (ii) HNO3