SUMMARY OF ORGANIC REACTIONS CHEM II

COMPOUND NAME OF REAGENT CONDITION PRODUCT TYPE OF

PROCESS REACTION
1. ALKANE Halogenation halogen, X2 uv or sunlight Haloalkane + HCl Free radical
substitution
2. ALKENE Halogenation X2 RT Dihalide
C C
C C X X

Hydrogenation H2 RT Alkane
C C
H H Electrophilic
Hydration H 2O H2SO4 Alcohol addition
Apply
C C
Markovnikov’s OH H
Rule to
Hydrohalogenation HX RT Haloalkane
Unsymmetrical
alkene C C
X H
Mild oxidation KMnO4/OH- RT or below Diol
C C
OHOH

Strong oxidation KMnO4/H+ Heat Carbonyl or Oxidation

C O +O C

carboxylic acid

Page 1 of 6 FAB/ESM 1324/CHEM 2/ENGINEERING 8/6/2009

 COMPOUND NAME OF REAGENT CONDITION PRODUCT TYPE OF
PROCESS REACTION
3 (i) BENZENE Nitration Conc. HNO3 + T: 500C – C6H5NO2 + H2O
conc. H2SO4 600C
Electrophilic
Halogenation X2 AlCl3 or FeCl3 C6H5Cl + HCl
substitution
(if X is Cl2)
Alkylation CH3Cl AlCl3 or FeCl3 C6H5CH3 + HCl
Halogenation Excess X2 Uv or C6H6X6
sunlight, heat
Addition
Hydrogenation Excess H2 Ni as catalyst C6H12
High T, high P
Ring reaction:
3 (ii) Nitration Conc. HNO3 + T: 300C CH3 + O2N CH3
METHYLBENZENE conc. H2SO4
NO2 Electrophilic
Halogenation X2 AlCl3 or FeCl3 CH3 + Cl CH3 substitution
(if X is Cl2)
Cl
Side chain
reaction:
Halogenation X2 Uv or sunlight CH2Cl
Free radical
substitution

Oxidation KMnO4/H+ Heat COOH

Oxidation

Page 2 of 6 FAB/ESM 1324/CHEM 2/ENGINEERING 8/6/2009

COMPOUND NAME OF REAGENT CONDITION PRODUCT TYPE OF
PROCESS REACTION
4. Hydrolysis H2O or alkaline Heat Alcohol
(i)HALOALKANE (aq) (eg. NaOH or
C C
KOH) H OH
C C
H X With NH3 NH3 Heat strongly Amines (mixtures)
C C Nucleophilic
H NH2 substitution

With CN- KCN in ethanol Heat Nitrile

C C
H CN
dehydrohalogenation Alkaline (in Heat Alkene
ethanol)
(eg. NaOH in C C Elimination
ethanol or KOH in
ethanol)
(ii) NITRILE Hydrolysis Dilute sulphuric Boil Carboxylic acid
acid Oxidation
C C C C
H CN H COOH
Reduction LiAlH4 RT Amines

C C Reduction
CH2NH2

Page 3 of 6 FAB/ESM 1324/CHEM 2/ENGINEERING 8/6/2009

 COMPOUND NAME OF REAGENT CONDITION PRODUCT TYPE OF
PROCESS REACTION
5. (i) ALCOHOL Halogenation HX or RT Haloalkane
NaX + conc. H2SO4 Nucleophilic
C C C C
H OH or H X substitution
PCl5 or PCl3 or PBr3
Salt formation Na RT Sodium alkoxide
and H2 acid base
C C reaction
H ONa
Iodoform reaction I2 and NaOH(aq) Warm CHI3 (yellow
*only +ve for precipitate)
C2H5OH and 20 and sodium
with structure: alkanoate salt
H
CH3 C OH
Esterification RCOOH H+, heat Ester – RCOOR
Or (pleasant smelling)
RCOCl RT
C C Substitution
H O C R
O
+ H2O or HCl
Oxidation K2Cr2O7/H+ Warm 20
Ketone
*only 10 and 20 10
Aldehyde
Alcohol can be
oxidised K2Cr2O7/H+ Heat 20
Ketone Oxidation
10
RCOOH

KMnO4/H+ 10
Carboxylic acid

Page 4 of 6 FAB/ESM 1324/CHEM 2/ENGINEERING 8/6/2009

 Dehydration Conc. H2SO4 T > 1700C Alkene Elimination

COMPOUND NAME OF REAGENT CONDITION PRODUCT TYPE OF

PROCESS REACTION
(ii) PHENOL Ring reaction
OH Halogenation Br2(aq) RT OH
Br Br
+ 3HBr
Br
white ppt. Electrophilic
Nitration Dilute HNO3 RT OH OH substitution
NO2
*FeCl3 is +
another
distinguishing NO2
test for Side chain
phenol. Salt Na RT C6H5ONa + H2 Acid base
formation NaOH RT C6H5ONa + H2O reaction
Esterification RCOCl only!! (for your RT O
syllabus) O C R
Substitution

Page 5 of 6 FAB/ESM 1324/CHEM 2/ENGINEERING 8/6/2009

 COMPOUND NAME OF REAGENT CONDITION PRODUCT TYPE OF
PROCESS REACTION
6. CARBONYL With HCN HCN RT Cyanohydrin
Nucleophilic
O OH CN
C C addition
Oxidation (i) Tollen’s reagent Silver mirror
* only (i) Fehling’s reagent. Red brown ppt
aldehydes (iii) K2Cr2O7/H+ Orange
green Oxidation
can be (iv) KMnO4/H+ Purple
colourless
oxidised (v) KMnO4/OH- Purple
brown ppt.
Reduction LiAlH4 or NaBH4 RT Ald
10 alcohol
Reduction
Ketone
20 alcohol
Condensation 2,4-DNP RT -2,4-
H dintrophenylhydrazone
O2N N NH2 H Addition-
NO2 O2N N N C elimination
NO2
Orange ppt
Iodoform I2 and NaOH(aq) warm CHI3 (yellow
*Only ethanal precipitate)
And ketones and sodium alkanoate
with –CH3 gp. salt
7.CARBOXYLIC Salt Na RT Salt + H2
Acid base
ACID formation NaOH RT Salt + H2O
reaction
O Na2CO3 RT Salt + H2O + CO2
C Esterification R-OH H+, heat Ester (RCOOR) Substitution
OH
Formation of PCl5 , SOCl2 RT Acyl chloride
acyl chloride O Substitution
C
Cl

Page 6 of 6 FAB/ESM 1324/CHEM 2/ENGINEERING 8/6/2009