Flow Chart of organic reactions in CHM096

o
Cl2 or Br2/ hv or high heat (300-400 C) Free radical substitution
Alkyl halides/NaOH
3o Amines Quaternary ammonium salt
+
Alkyl halides/NaOH o Con NH3/ NaOH
Mg/dry ether Grignard Dilute H
o 1 Amines
2 Amines e.g CH3CHNH2CH3
Reagent
Alkyl halides/NaOH Nucleophilic
substitution HBr or HCl in ether or H2O
Alkynes 2 mol H2/Pt/Ni/Pd

NaCN/H
+
Nucleophilic hydrohalogenation
Alkyl Halides
Alkane Nitrile OR HCN substitution
e.g CH3CHBrCH3 (major) NaOH/EtOH Elimination 1 mol H2/Pt/Ni/Pd
e.g CH3CHCNCH3 (major) CH3CH2CHBr (minor)
CH3CH2CHCN (minor)
Nucleophilic Alkanes
NaOH/H2O substitution Free redical substitution
Alkoxide e.g CH3CH2CH3
e.g CH3ONa
Metal e.g Na Nucleophilic Alkenes
Carboxylic acid Cold, dil alkaline
+ H2SO4
substitution eg. CH3CH=CH2 hydrogenation
Ester Alcohols PCl3 or PCl5 or PBr3 or SOCl2 SN2 KMnO4  Electrophilic addition
 Oxidation 1 mol H2/Pt/Ni/Pd
CH3OH Diol Hot,
1 o 1o eg. CH3CHOHCHOH acidified Br2 or Cl2/CCl4
Nucleophilic HBr or HI / heat
2o substitution
KMnO4
2o HCl/ZnCl2/heat (Lucas reagent)
C=C bond cleavage
Halogenation
3o SN1
3o =C  ketoneI
Alcohols Elimination =CH  carboxylic acid
e.g Alcohols
CH3CHOHCHBr (major) Conc. H2SO4. (Dehydration)
CH3CHBrCHOH (minor) =CH2  CO2 + H2O
(Elimina Dihalide alkanes
e.g CH3CHBrCHBr
+
H /H2O Hydration
+ + Br2 or Cl2/H2O
Hot KMnO4/H or Hot K2Cr2O7/H
Oxidation
Oxidation Hot KMnO4/H+ or Halohydrin
H2/Pt or LiAlH4 Hot K2Cr2O7/H+ Alcohols + con H2SO4 e.g CH3CHOHCHBr (major)
Aldehydes Carboxylic Acid Ester CH3CHBrCHOH (minor)
H2/Pt or LiAlH4 Tollens reagent +
e.g CH3COOH Dil H /Reflux
Formaldehyde -
Dil OH /Reflux
Reduction
+ Metal e.g Na or alkali e.g NaOH Eg. NaOH
HCN or NaCN/H
H2/Pt or LiAlH4 +
HCN or NaCN/H Alkanoate (salt of
Ketones Cyanohydrin carboxylic acid)
Hot KMnO4/H+ or Oxidation
e.g CH3COONa
Hot K2Cr2O7/H+
Oxidation Iodoform Test : 1) Alcohol with CH3CHOH-
No Reaction 2) Etanal CH3CH=O
3) Ketone with CH3C=O
T. Syed Illah and Dr LHSim