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(minor) SO3H
(major)
Cl Cl
Friedel Crafts alkylation CH3
CH 3Cl + Anhyd AlCl3 +
(minor) CH3
(major)
Cl Cl
Friedel Crafts acylation COCH3
CH 3COCl or (CH3CO)2O +
Anhydrous AlCl 3
(minor) COCH3
(major)
+ Mg, dry ether ArMgX
(Grignard's reagent)
+ Na + RX ,dry ether Ar _ R
WURTZ FITTIG REACTION (eg: C6H5.CH3)
Cleavage of O_H bond
RCHO (aldehydes) Active Metals RONa + H2
Cleavage of C_ O bond
OF H 2 O 1o alc. Aldehyde
o
Dehydrogenation 2 alc. Ketone
Tert > Sec > Pri
o
Cu, 573 K 3 alc. Alkene
RCOCl (Acyl Chloride) REDUCTION Dehydration
( to pri. Alcohol) LiAlH4 or NaBH4
1o alc. Aldehyde Acid
(containing same (containing same
+ HCHO + H2O 1o alcohol no. of C - atoms)
Benzoylation C6H5OCOC6H5
C6H5COCl , Schotten-Bauman reaction
OH OH
dil HNO3 NO2
298 K +
Nitration
NO2
Aromatic
OH
conc. HNO3
Substitution
O2 N NO2
+ conc. H2SO4
Picric acid
Electrophilic
NO2
Cl2 water OH
Br Br
Br2 water
(polar solvent)
SO3H SO3Na Halogenation Br
NaOH H + / HCl (white ppt)
570 - 620 K
OH OH
Benzene sulphonic Br2 in CS2 Br
acid 273 K +
(non-polar solvent)
Br
OH OH
Cl ONa Friedel Crafts Alkylation R
NaOH H + / HCl RX / Anhyd. AlCl3 +
623 K, 320 atm
R
conc. H2SO4 OH
288 K SO3H
Sulphonation
NH2 N2 +Cl-
Cumene
C6H5N2+Cl- , alkali OH
N N
Coupling reaction
ONa OH
NaOH (i) CO2, 398 K, 4-7atmos. COOH
(ii) H+ / H2O Salicylic acid
Kolbe's reaction
Cleavage of C - O bond
Zn dust
O
Oxidation
Na2Cr2O7 / conc. H2SO4 Benzoquinone
O
RCH2OH Oxidation Na
RCOONa + H2 (g)
(Primary alcohol) (i)KMnO4 in acidic/ alkaline/
neutral medium OR NaOH
RCOONa + H2O
(ii)K2Cr2O7/H+ OR Acidic
(iii)CrO3 / H+ Nature NaHCO3 or
RCOONa + H2O + CO2 (g)
Na2CO3
(RCO)2O + H2O
Anhydride Reduction
RCH2OH
(i)LAH/ether OR
(alcohol)
(ii)B2H6
+NH3
RCOONH4
,P2O5
RCONH2 RCN
(amide) (nitrile)
RCONH2
Br2 + NaOH Alkyl H2O
[RN2+Cl-] ROH + N2
[Hoffmann's Bromamide NaNO2/HCl amine
degradation reaction] 273-278 K [ QUANTITATIVE ESTIMATION]
Diazotisation
Aryl
CO [C6H5N2]+Cl-
Gabriel's Pthalimide synthesis amine Diazonium salt
NH (i) KOH
CO (ii) RX
(iii) OH
- Pri. RNHSO2C6H5 (soluble in KOH)
C6H5SO2Cl2 Sec.
R2NSO2C6H5 (insoluble in KOH)
Hinsberg's reagent
Tert. No reaction
C6H5NO2 REDUCTION
(nitrobenzene) (i)H2+Ni or Pd or Pt
(ii)Sn + conc. HCl
(preferred)(iii)Fe + conc. HCl
(iv)H2 + Pd (ethanol)
(v)SnCl2 + conc. HCl
H2SO4
[C6H5NH3]2+S042-
Alkylation
C6H5NHR C6H5NR2 [C6H5NR3]+X-
(RX)
CH3COCl
C6H5NHCOCH3 + HCl
NUCLEOPHILIC Pyridine
SUBSTITUTION Acylation
(CH3CO)2O
C6H5NHCOCH3 + CH3COOH
conc. H2SO4
Benzoylation
C6H5NHCOC6H5 + HCl
C6H5COCl,
NaOH [Schotten Baumann Reaction]
Carbylamine reaction
C6H5NC + KCl + H2O
CHCl3+alc. KOH + heat
REACTION OF -NH2 GROUP
Diazotization
C6H5N2+Cl- + NaCl + H2O
NaNO2 + HCl [273-278K]
NH2
Bromination Br Br
Br2 + H2O + 3HBr
(bromine water)
Br
2,4,6-Tribromoaniline
[white ppt]
ELECTROPHILIC
SUBSTITUTION NH2 NH2 NH2
Nitration NO2
conc.HNO3 + conc H2SO4 + +
(288 K) NO2
NO2 47% 2%
51%
H3PO2 + H2O
C6H6 + N2 + H3PO3 + HCl
C2H5OH
C6H6 + N2 + CH3CHO + HCl
H2O , 283 K
C6H5OH + N2 + HCl
C6H5OH CuCl/HCl
N N OH n
C6H5Cl + N2
OH Sandmayer's react
p-Hydroxyazo benzene + Cl + H2O
Orange Dye
Cu/HCl
C6H5Cl + N2 + CuCl
[TEST FOR PHENOL] Gatterman reactn
Cu/HBr
C6H5Br + N2 + CuBr
Gatterman reactn
C6H5NH2
N N NH2
OH
p- Aminoazobenzene KI ,
+ Cl + H2O C6H5I + N2 + KCl
Yellow dye
CuCN ,
or Cu/KCN C6H5CN + N2 + CuCl
Na + C2H5OH or LAH
C6H5CH2NH2
OXIDATION
CrO3 in anhydrous medium or
PCC (Pyridinium chloro chromate)
o
1 Alcohol CrO3 o
2 Alcohol
ROH Chromic anhydride R
DEHYDROGENATION CH_OH
R
Cu or Ag at 573K
HC = CH HCHO
HC CH CH3CHO
o
HCHO 1 Alcohol
o
(i) Grignard's reagent RCHO 2 Alcohol
(ii) H2O / H+ Other aldehydes
Ketone 3o Alcohol
Nucleophilic
Addition
OR' OR'
Aldehyde RCH R'OH RCH
H+ / H2O OH OR'
hemiacetal acetal
Alcohol + dry HCl
CH2OH
+ Ketone R O-CH2
CH2OH + H2O
C
R O-CH2
H+ / H2O
Ketal
C = N _ NHCONH2 (semicarbazone)
(Semicarbazide)
(NH2NHCONH2)
Aldehydes 1o Alcohol
NaBH4 or LiAlH4
o
or H2 + Ni/Pd/Pt Ketones 2 alcohol
Ketones No reaction
HCHO No effect