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Flow Chart of organic reactions in CHM096

Cl 2 or Br 2 / hv or high heat (300-400 o C) Free radical
Cl 2 or Br 2 / hv or high heat (300-400 o C)
Free radical substitution
Alkyl halides/NaOH
3 o Amines
Quaternary ammonium salt
Mg/dry ether
Grignard
Dilute H +
Alkyl halides/NaOH
Con NH 3 / NaOH
2 o Amines
1 o Amines
e.g CH 3 CHNH 2 CH 3
Reagent
Alkyl halides/NaOH
Nucleophilic
HBr or HCl in ether or H 2 O
substitution
Alkynes
2 mol H 2 /Pt/Ni/Pd
hydrohalogenation
NaCN/H +
Nucleophilic
Alkyl Halides
Alkane Nitrile
OR HCN
substitution
NaOH/EtOH
Elimination
1 mol H 2 /Pt/Ni/Pd
e.g
e.g
CH 3 CHCNCH 3 (major)
CH 3 CH 2 CHCN (minor)
CH 3 CHBrCH 3 (major)
CH 3 CH 2 CHBr (minor)
Nucleophilic
Alkanes
NaOH/H 2 O
substitution
Alkoxide
e.g CH 3 ONa
Free redical substitution
e.g CH 3 CH 2 CH 3
Metal e.g Na
Nucleophilic
Alkenes
Carboxylic acid
+ H 2 SO 4
substitution
Cold, dil alkaline
eg.
CH 3 CH=CH 2
hydrogenation
PCl 3 or PCl 5 or PBr 3 or SOCl 2
S
KMnO 4
 Electrophilic addition
Ester
Alcohols
N 2
 Oxidation
1 mol H 2 /Pt/Ni/Pd
CH 3 OH Diol Hot, 1 o eg. CH 3 CHOHCHOH acidified Br 2 or
CH 3 OH
Diol
Hot,
1 o
eg. CH 3 CHOHCHOH
acidified
Br 2 or Cl 2 /CCl 4
1 o
Nucleophilic
HBr or HI / heat
HCl/ZnCl 2 /heat (Lucas reagent)
KMnO 4
2 o
substitution
2 o
Halogenation
C=C bond cleavage
3 o
S N 1
o
3
=C
 ketone
Alcohols
Elimination
=CH
 carboxylic acid
e.g
Alcohols
CH
CHOHCHBr (major)
Conc. H 2 SO 4 .
3
(Dehydration)
=CH 2
 CO 2 + H 2 O
CH 3 CHBrCHOH (minor)
e.g CH 3 CHBrCHBr
H + /H 2 O
Hydration
Br 2 or Cl 2 /H 2 O
Hot KMnO 4 /H + or Hot K 2 Cr 2 O 7 /H +
Oxidation
Halohydrin
H 2 /Pt or LiAlH 4
Hot KMnO 4 /H + or
Hot K 2 Cr 2 O 7 /H +
Alcohols + con H 2 SO 4
e.g
Carboxylic Acid
Aldehydes
Ester
H 2 /Pt or LiAlH 4
Tollens reagent
e.g CH 3 COOH
Dil H + /Reflux
Formaldehyde
Reduction
Dil OH - /Reflux
Eg. NaOH
Metal e.g Na or alkali e.g NaOH
HCN or NaCN/H +
H 2 /Pt or LiAlH 4
HCN or NaCN/H +
Ketones
Alkanoate (salt of
carboxylic acid)
Cyanohydrin
Oxidation
Hot KMnO 4 /H + or
Hot K 2 Cr 2 O 7 /H +
e.g CH 3 COONa
Oxidation
No Reaction
Iodoform Test : 1) Alcohol with CH 3 CHOH-
2) Etanal CH 3 CH=O
3) Ketone with CH 3 C=O
CH 3 CHOH- 2) Etanal CH 3 CH=O 3) Ketone with CH 3 C=O Dihalide alkanes

Dihalide alkanes

Oxidation

CH 3 CHOHCHBr (major) CH 3 CHBrCHOH (minor)

T. Syed Illah and Dr LHSim