1.
Reaction of Alkane 1 Iodoform Test 24
Mechanism of Free Radical Substitution of Alkane 2 Preparation of Carboxylic Acid 25
Reactions of Alkene 3 - 4 Reactions of Carboxylic Acid 26
Mechanism of Dehydration of Alcohol to form Alkene 5 Methanoic Acid as a Reducing Agent 27
Mechanism of Hydration of Alkene 6 Preparation of Amine 28
Mechanism of Hydrohalogenation of Alkene 7 Reactions of Amine 29
Reactions of Benzene 8 Hinsberg Test 30
Mechanism of Electrophilic Aromatic Substitution 9 - 11 Nitrous Acid Test 31
Reactions of Haloalkane 12 Formation of Azo Compounds via Coupling Reaction 32
SN1 and SN2 13 Reactions of Amino Acid 33
Reactions of Alcohol 14 Addition Polymerisation 34
Oxidation of Alcohol 15 Condensation Polymerisation 35
Preparation of Alcohol using Grignard Reagent 16
Identification Test for 1o
, 2o
and 3o
Alcohol
(Lucas Test and Oxidation)
17
Reaction of Phenol 18
Preparation of Aldehyde and Ketone 19
Reaction of Aldehyde 20
Reaction of Ketone 21
Identification Test for Carbonyl Compounds
(Brady’s Test and Fehling’s Test)
22
Identification Test for Carbonyl Compounds
(Tollen’s Test and Schiff’s Test)
23

2.
Page 1 of 35
- Rimau -
REACTIONS OF ALKANE
COMBUSTION HALOGENATION
Type of Reaction: Free Radical Substitution
Excess oxygen
CH4 + 2O2 → CO2 + 2H2O
Limited oxygen
CH4 +
3
2
O2 → CO + 2H2O
Extreme lack of oxygen
CH4 + O2 → C + 2H2O
NOTE: Needs the presence
of UV light or high
temperature and an inert
organic solvent (e.g. CH2Cl2)
PRODUCTS: Haloalkanes
with a side product of acid
(the acid formed depends on
the halogen used)
CH4 + Cl2 CH3Cl + HCl
UV
CH2Cl2
REACTION
MECHANISM: Chain
initiation, chain propagation,
chain termination
NOTE: For alkanes with more than
2 C atoms (n>2), more than one
haloalkane will be formed
(major product and minor products)

3.
Page 2 of 35
- Rimau -
MECHANISM OF FREE RADICAL SUBSTITUTION OF ALKANE
STEP
1
(CHAIN
INITIATION
STEP)
STEP
2
(CHAIN
PROPAGATION
STEP)
STEP
3
(CHAIN
TERMINATION
STEP)
Br Br +
CH2Cl2
UV
C C
H H
H H
H
H +
+
+
+ Br
H
C C
H H
H H
H
H
Br Br C C
H H
H Br
H
H +
Br Br
+ C
H
H
H C
H
H
C
C
H
H
H H
H

4.
Page 3 of 35
- Rimau -
REACTIONS OF ALKENE
(RCH=CH2)
Hydrogenation (+H2)
Catalyst: Platinum, Pt,
Nickel, Ni or Palladium, Pd
Product(s): Alkane
RCHCH2
Halogenation in inert solvent
(+X2 in CH2Cl2)
Product(s): Vicinal dihalide
RCHCH2
Halogenation in water
(+X2 in H2O)
Product(s): Halohydrin
RCHCH2
Hydrohalogenation (+HX)
Product(s): Haloalkane
RCHCH2
Hydrohalogenation in the
presence of peroxides (+HBr
in ROOR)
Product(s): Haloalkane
RCHCH2
Hydration (+ acidified H2O)
Catalyst: Dilute H2SO4 or H3PO4
Product(s): Alcohol
RCHCH2
Oxidation - Baeyer’s Test
(+dilute cold alkaline KMnO4)
Catalyst: Platinum, Pt, Nickel,
Ni or Palladium, Pd
Product(s): Diols
RCHCH2
Oxidation (+conc. hot
acidified KMnO4)
Product(s): Carboxylic acid,
CO2 and H2O
RCOOH + CO2 + H2O
Ozonolysis (+ O3 followed by
Zn or H2O)
Product(s): Aldehyde/ketone
X
_
_
_
H
X
HO
_
X
_
= _
HO
X
H
Br
_
C
HO
H
_
_
_
_
_
OH
_
H
_
H
H
H
R
H
C O
O + =
Markovnikov
Hydration, halogenation,
hydrohalogenation,
hydrohalogenation (HCl) in
peroxide
Anti-Markovnikov
Hydrohalogenation (HBr) in
peroxide

5.
Page 4 of 35
- Rimau -
RCHCH2
_
_
_
_
OH
H H
H
2
,
Pt/Ni/Pd
Hydrogenation
RC
RCH=CHR´
RCHCH2
RCHCH2
_
_
Br
Br
_
HO Br
RCHCH2
RCHCH2
_
_
HO
Br H
RCHCH2
_
OH
H
Hydration
H
2
O,
dilute
H
2
SO
4
_
_
_
H
RCHCH2
_
_
HO OH
RC
_
_
OH
O
R
R´
H2O
CO2
+
+
C=CHR´´
_
_
_
R´C
OH
O
+
_
_
O
_ C
O
C_
_
R
R´
+
_
_
_
OH
R´´
O
_
_
R C
_
_
H
O
+ H
H
H
Cl
H
Markovnikov
Hydration
Halogenation
Hydrohalogenation
Hydrohalogenation (HCl) in
peroxide
Anti-Markovnikov
Hydrohalogenation (HBr) in
peroxide
Anti-Markovnikov
Hydrohalogenation (HBr) in
peroxide

6.
Page 5 of 35
- Rimau -
MECHANISM OF DEHYDRATION OF ALCOHOL TO FORM ALKENE
STEP
1
(PROTONATION
OF
ALCOHOL)
STEP
2
(FORMATION
OF
CARBOCATION)
STEP
3
(FORMATION
OF
ALKENE)
O
H
H
H
C
H3 C
CH3
CH3
C
CH3
OH
C2H5 +
+
+
+
+
C
H3 C
CH3
CH3
C
CH3
O
C2H5
H
H
O
H H
+
+
1,2-methyl shift
H
H
H
H
H
C
H3 C
CH3
C
H
C2H5
CH3
H
+
If necessary and when
possible, a more stable
carbocation will be formed
C
H3 C
CH3
C
H
C2H5
CH3
H
+
+
O
H
H
H
C
H3 C
CH3
C C2H5
CH3
+

7.
Page 6 of 35
- Rimau -
MECHANISM OF HYDRATION OF ALKENE
STEP
1
STEP
2
STEP
3
C
H3 C
CH3
C CH3
H
H
O
H
H
O
H
H
H
+
+
+
+
O
H H
+
+
+ O
H
H
H
+
C
H3 C
CH3
C CH3
H
C
H3 C
CH3
C CH3
H
H
H
+
C
H3 C
CH3
C CH3
H
H
H
+
C
H3 C
CH3
C CH3
H
H
OH

8.
Page 7 of 35
- Rimau -
H Br
MECHANISM OF HYDROHALOGENATION OF ALKENE
STEP
1
STEP
2
+ +
+
C
H3 C
CH3
C CH3
H
C
H3 C
CH3
C CH3
H
H
H
+
C
H3 C
CH3
C CH3
H
H
H
+
Br
-
slow
fast
Br
- C
H3 C
CH3
C CH3
H
H
Br

9.
Page 8 of 35
- Rimau -
H
O
C
R
_
_
_
NO2
COOH
R
Halogenation
X
2
,
UV
RX
X
R → alkyl group
X → halogen

10.
Page 9 of 35
- Rimau -
MECHANISM OF ELECTROPHILIC AROMATIC SUBSTITUTION
STEP
1
–
Formation
of
electrophile
Nitration Halogenation Friedel-Crafts
Alkylation
Friedel-Crafts
Acylation
H
O
+
H
NO
2
_
_
_
_
_
+
O
NO
2
+
H
H
OSO
3
H
+
HSO
4
-
_
+
δ
+
FeX
3
X
X
+
FeX
4
-
δ
_
X
+
Electrophile
X → halogen
+
Cl
R
+
AlCl
3
R
Cl
AlCl
3
AlCl
4
-
+
R
+
+
Acylium
ion
resonance
structure
R → alkyl group

11.
Page 10 of 35
- Rimau -
STEP
2
–
Formation
of
arenium
ion
H
H
H
H
H
H
E
+
+
+
+
E+
+
H
H
H
H
H
H
E
H
H
H
H
H
H
E
H
H
H
H
H
H
E
Arenium ion resonance structure
E+
Electrophile

12.
Page 11 of 35
- Rimau -
STEP
3
–
Loss
of
proton
(regeneration
of
catalyst) Nitration Halogenation Friedel-Crafts
Alkylation
Friedel-Crafts
Acylation
H
H
H
H
H
H
E
+
+
NO
2
HSO
4
-
NO
2
H
2
SO4
+
FeX
4
-
X
+
HX
+
FeX
3
X
AlX
4
-
R
R
AlX
3
+
+
HX
AlX
3
AlX
4
-

13.
Page 12 of 35
- Rimau -
C C OH
H
H
H
H
H
C C
H
H H
H
KOH,
EtOH
Δ
C C CN
H
H
H
H
H
C C NH2
H
H
H
H
H
excess NH3
Δ
C C O
H
H
H
H
H
R
R
C
O
O
-
A
g
+
R C
O
O C C H
H
H
H
H
REACTIONS OF
HALOALKANE
C C Cl
H
H
H
H
H
Mg
dry
ether
Cl
C C
H
H
H
H
H
Mg
H2O, H+
(i) CO2
(ii) H2O, H+
C C
H
H
H
H
H
H
C C
H
H
H
H
H
C
O
OH
(i) dry ether
(ii) H2O, H+
C C
H
H
H
H
H
C
O
H
H
H
H
C
O
H H
C C
H
H
H
H
H
C
O
H
R
H
H
(i) dry ether
(ii) H2O, H+
C
O
H R
(i) dry ether
(ii) H2O, H+
C C
H
H
H
H
H
C
O
R'
R
H
H
C
O
R' R

14.
Page 13 of 35
- Rimau -
C
H3 CH2 C CH3
CH3
Nu
-
SN1 Mechanism SN2 Mechanism
Unimolecular Nucleophilic Substitution Bimolecular Nucleophilic Substitution
Carbocation as the intermediate Has transition stage
𝑅𝑎𝑡𝑒 = 𝑘[𝑅𝑋]
- First order reaction
𝑅𝑎𝑡𝑒 = 𝑘[𝑅𝑋][𝑁𝑢−]
- Second order reaction
Two-step mechanism One-step mechanism
Order of reactivity
Methyl halide < 1o
< 2o
< 3o
Order of reactivity
3o
< 2o
< 1o
< Methyl halide
Nuˉ
is nucleophile
fast
+ Nuˉ
Brˉ
+
+
Brˉ
fast
C
Nu
H
H
H

15.
Page 14 of 35
- Rimau -
Na
+
C C C
O
-
H
H H H
H
H H
REACTIONS OF
ALCOHOL
C C C
OH
H
H H H
H
H H
H2O, H+
C C C
H H H
H
H H
NaOH
C C C
O
H
H H
H
H H
C
H3
C
O
OH
C C C
O
H
H H H
H
H H
C
CH3
O
C C C
H
H H H
H H
C C C
Cl
H
H H H
H
H H Δ
C C C
Cl
H
H H H
H
H H C C C
Br
H
H H H
H
H H

16.
Page 15 of 35
- Rimau -
1o
alcohol
2o
alcohol
3o
alcohol No reaction
* Oxidation of primary alcohols using strong oxidising agents (e.g. KMnO4) first produces aldehydes. The aldehyde is then further oxidised into
carboxylic acid.
OXIDATION OF ALCOHOL
C C
H
H
H
OH
H
H
C C
H
H
H
O
OH
C C
H
H
H
O
H
PCC
Δ
KMnO4, H+
CH2Cl2
C C
H
H
H
C
OH
H
H
H
H C C
H
H
H
C
O H
H
H
KMnO4, H+
Δ

17.
Page 16 of 35
- Rimau -
1o
alcohol
2o
alcohol
3o
alcohol
PREPARATION OF ALCOHOL USING GRIGNARD REAGENT
C
H H
O C MgBr
H
H
H
C C
H
H
H
O
H
H
H
(ii) H3O+
(i)
(ii) H3O+
(i)
C MgBr
H
H
H
C
H CH3
O
C C
H
H
H
O
H
C
H H
H
H
C
C
H3 CH3
O (i) C MgBr
H
H
H
(ii) H3O+
C C
H
H
H
O
CH3
C
H H
H
H

18.
Page 17 of 35
- Rimau -
LUCAS TEST OXIDATION
1o
alcohol
* refer pg. 15
For 1o
an 2o
alcohols;
Observation using KMnO4: Purple colour of solution
decolourises
Observation using K2Cr2O7: Orange colour of
solution turns green
For 3o
alcohols;
Observation: No observable changes
2o
alcohol
3o
alcohol
IDENTIFICATION TESTS FOR ALCOHOL
HCl
ZnCl2
C
OH
R'
R''
R C
Cl
R'
R''
R
Obs: Cloudy solution forms immediately
C
OH
H
H
R
Obs: No cloudy solution formed after 15 minutes
No observable changes
ZnCl2
HCl
C
OH
R'
H
R
HCl
ZnCl2
C
Cl
R'
H
R
Obs: Cloudy solution forms within 15 minutes

19.
Page 18 of 35
- Rimau -
REACTIONS OF
PHENOL
OH
IDENTIFICATION TESTS
CHEMICAL REACTIONS
O
-
Na
+
O
-
Na
+
NaOH
1
2
H2 +
H2O +
Phenol can undergo reactions of benzene as
well
Example:
OH
Br2, FeBr3
OH
Br
Purple complex
OH
FeCl3
Br
OH
Br
Br
White precipitate

20.
Page 19 of 35
- Rimau -
PREPARATION OF
ALDEHYDE
C
H3 C
O
H
C C H
OH
H
H
H
H CH2Cl2
PCC C C C C
H
H
H
H H H
H
H
Oxidation of 1o
alcohol
(ii) Zn, H2O
(i) O3
PREPARATION OF
KETONE
C
H3 C CH3
O
Ozonolysis of alkene
C C C
OH
H
H
H
H
H
H
H
Δ
KMnO4, H+
Oxidation of 2o
alcohol
C C C C
H
H
H
CH3 CH3 H
H
H
(i) O3
(ii) Zn, H2O
Ozonolysis of alkene
C
H3 C CH2
CH3
Oxidation
of
alkene
KMnO
4
,
H
+
Δ
Friedel-Craft Acylation can be used to
prepare aromatic ketones
C CH3
Cl
O
AlCl3
+
C CH3
O There are other
alkenes that can also
be used

21.
Page 20 of 35
- Rimau -
REACTIONS OF
ALDEHYDE
C
O
R H
C
OH
R H
H
Δ
H3O+
LiAlH4
CH3OH
Pt @ Pd @ Ni
H2
NaBH4
C
OH
R H
CN
HCN @ KCN, H+
C
OH
R H
SO3
-Na+
C
OH
R H
OH
C
OH
R H
OR'
KMnO
4
,
H
+
C
OR'
R H
OR'
C
N
R H
R'
N
H
2
R'
C
O
R OH
Reaction of carbonyl compounds (aldehyde/ketone) with
Grignard reagent is to prepare alcohol
*refer preparation of alcohol using Grignard reagent (pg. 16)

22.
Page 21 of 35
- Rimau -
REACTIONS OF
KETONE
C
O
R R'
Δ
H3O+
LiAlH4
CH3OH
Pt
H2
NaBH4
HCN @ KCN, H+
KMnO
4
,
H
+
C
OH
R R'
H
No reaction
C
OR''
R R'
OR''
C
OH
R R'
OH
C
OH
R R'
CN
C
OH
R R'
SO3
-
Na
+
C
OH
R R'
OR''
C
N
R R'
R''
N
H
2
R''
Reaction of carbonyl compounds (aldehyde/ketone) with
Grignard reagent is to prepare alcohol
*refer preparation of alcohol using Grignard reagent (pg. 16)

23.
Page 22 of 35
- Rimau -
Brady’s Test
(2,4-dinitrophenylhydrazine)
FUNCTION: To test for carbonyl compounds
Example:
Obs: Orange/yellow precipitate forms
Fehling’s Test
FUNCTION: To test for aliphatic aldehydes
Example:
Obs: Brick-red precipitate forms
IDENTIFICATION TESTS FOR CARBONYL COMPOUNDS
NH
N
H2
O2N
NO2
C
H3 C
O
CH3
Cu2O ↓
Cu2+
complex, OHˉ
H2O
+
+
NH
N
H2
O2N
NO2
NH
N
O2N
NO2
C
CH3
C
H3
C
H3 C
O
H C
H3 C
O
O
- +

24.
Page 23 of 35
- Rimau -
Tollen’s Test
FUNCTION: To test for aldehydes
Example:
Obs: Silver mirror forms
Schiff’s Test
FUNCTION: To test for aldehydes and propanone
REAGENT: Schiff’s reagent (Fuchsin, NaHSO3, HCl)
OBSERVATION: Magenta-pink colour solution forms
Ag ↓
[Ag(NH3)2]+
, OHˉ
C
H3 C
O
H C
H3 C
O
O
- +

25.
Page 24 of 35
- Rimau -
IODOFORM TEST
To test for methyl carbinol and methyl carbonyl
C
H3 C
OH
R
H
C
H3 C
O
R
methyl carbonyl
methyl carbinol
Example:
C
H3 C
OH
H
H
I2, OHˉ
+
H C
O
O
-
H
CHI3 ↓
Obs: Yellow precipitate forms
Example:
C
H3 C
O
H
I2, OHˉ
H C
O
O
-
H
+ CHI3 ↓
Obs: Yellow precipitate forms

26.
Page 25 of 35
- Rimau -
PREPARATION OF
CARBOXYLIC ACID
Oxidation of 1o alcohol
C
OH
R
H
H
C
O
R OH
Δ
KMnO4, H+
Oxidation of aldehyde
C
O
R H
KMnO4, H+
Δ C
O
R OH
Hydrolysis of nitriles
CN
R C
O
R OH
H2O, H+
Carboxylation of Grignard reagents
MgX
R
(i) CO2
(ii) H2O, H+
C
O
R OH
Hydrolysis of acyl chloride
C
O
R Cl
H2O, H+
C
O
R OH
Oxidation of alkyl benzene
R
KMnO4, H+
Δ
HOOC
*R group must contain benzylic
hydrogen

27.
Page 26 of 35
- Rimau -
C
O
R O C
O
R'
C
O
R O-Na+
,
conc.
H
2
SO
4
Δ
Na
NaOH
Na2CO3
C
H
R OH
H
OH
R'
C
O
R O R'
Δ
C
O
R'
OH
N
R''
R'
H
C
O
R N
R''
R'
N
R''
R'
H
C
O
R Cl
C
O
R' OH
REACTIONS OF
CARBOXYLIC ACID
C
O
R OH
OH
R'

28.
Page 27 of 35
- Rimau -
Using KMnO4 Using Tollen’s Test
C
H OH
O
C
H OH
O
Ag ↓
Δ
KMnO4, H+ [Ag(NH3)2]+
, OHˉ
H2O
+
CO2 ↑ CO2 ↑ +
+ H2O
METHANOIC ACID AS
A REDUCING AGENT
C
H OH
O

29.
Page 28 of 35
- Rimau -
Hofmann Degradation of Amides
Example:
PREPARATION OF
AMINE
Reduction of Nitro Compounds
Example:
NO2 HCl
Zn @ Fe @ SnCl2
NH2
Reduction of Nitrile Compounds
Example:
* NaBH4 in CH3OH @ H2 with Pt
catalyst can also be used
CN
R
LiAlH4
H2O, H+
C
R N
H
H
H
H
Reduction of Amides
Example:
(1o
amide → 1o
amine)
(2o
amide → 2o
amine)
(3o
amide → 3o
amine)
* NaBH4 in CH3OH can also be used
C
R NH2
O
4NaOH
H2O, H+
H2O, H+
H2O, H+
LiAlH4
LiAlH4
X2
LiAlH4
C
R NH2
H
H
C
R NH
O R'
C
R NH
H
H
R'
C
R N
O R'
R''
C
R N
H
H
R'
R''
C
O
NH2
R
NH2
R 2H2O
+
Na2CO3
+
2NaX
+

30.
Page 29 of 35
- Rimau -
Reaction with Carboxylic Acid
Reaction with Acid Chloride
NH2
R +
+
+ C
O
R' Cl C
O
R' NH R
NH
R
R'
C
O
R'' Cl C
R'' N
R'
R
O
C
O
R'' OH
C
O
R' OH
Δ
Δ
NH3 C
O
R OH C
O
R N
H
H
Δ
Bromine Water Test (to identify aniline)
C
O
R Cl
NH2
Br2 (aq) @ Br2, H2O
NH2
Br
Br
Br
Obs: 1) Brown colour of solution decolourises
2) White precipitate forms
REACTIONS OF
AMINE

31.
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1
O
amine
2
O
amine
3
O
amine HINSBERG TEST
S
O
O
Cl
S
O
O
Cl
S
O
O
Cl
NH2
R
+
HCl
HCl
+
+
HCl
excess KOH
S
O
O
N
-
R
K
+
S
O
O
N
R
H
No observable changes
Obs: Clear solution is
formed
No observable changes
Obs: White precipitate
is formed
Obs: White precipitate
is formed
Obs: Clear solution is
formed
NH
R
R'
excess KOH
S
O
O
N
R'
R
N
R
R'
R''
excess KOH
N
+
R
R'
R''
H
Cl
-
R,
R’
and
R’’
can
either
be
alkyl
group
or
aryl
group

32.
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N N Cl
-
ALIPHATIC AMINES AROMATIC AMINES
1
O
amine
2
O
amine
3
O
amine NITROUS ACID TEST Nitrous acid, HNO2 is prepared in-situ
using NaNO2 and HCl
C
H3 CH2 NH2
NaNO2, HCl
0 – 5 o
C
NaNO2, HCl
NaNO2, HCl
NaNO2, HCl
0 – 5 o
C
0 – 5 o
C
0 – 5 o
C
0 – 5 o
C
0 – 5 o
C
NaNO2, HCl
NaNO2, HCl
C
H2 CH2
C
H3 CH2OH
C
H3 CH2Cl
+
+
+
+
+
N2 ↑
Obs: Colourless gas bubbles are released
NH2
Obs: No release of colourless gas bubbles
C
H3 NH
CH3
C
H3 N
CH3
N O
Obs: Yellow oil is formed
NH
CH3
N
CH3
N O
Obs: Yellow oil is formed
C
H3 N
CH3
CH3
HCl
-
C
H3 N
+
CH3
CH3
NOCl
-
C
H3 N
+
CH3
CH3
Obs: Colourless solution
remains
N
CH3
CH3 N
CH3
CH3
N
O
Obs: Yellow precipitate is formed
Nitroso (-N=O) will be substituted at
the para position of the benzene ring

33.
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N NCl
-
+
OH
+
NaOH
N N OH
Obs: Yellow/orange precipitate (dye) is formed
Azo group (-N=N-) will bond at the para
position of phenol
FORMATION OF AZO COMPOUNDS
(COUPLING REACTION)

34.
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C COOH
H
R
N
H3
+
Cl
-
, conc. H2SO4
C COO
-
Na
+
H
R
N
H2
R' OH
C COOR'
H
R
N
H2 0 – 5 o
C
NaNO2, HCl
N2 ↑
Δ
C COOH
H
R
O
H
C COOH
H
R
Cl
C COOH
H
R
+
+
+
+
C
N
H2 COOH
H
R' C C
N
H2
H
R
O
HN C
H
R'
COOH
REACTIONS OF
AMINO ACIDS
C
N
H2 COOH
H
R
O
H H

35.
Page 34 of 35
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C C
H
H
Cl
H
ADDITION POLYMERISATION
C C
R
R''
R'
R'''
n
n C C
R
R''
R'
R'''
H H
Requires organic peroxides
(e.g. benzoyl peroxide) as
initiator
n
n
n
n C C
H
H
Cl
H
H H C
H2 C C CH2
CH3
H
CH2 C C CH2
CH3
H
H H

36.
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CONDENSATION POLYMERISATION
Monomers must each have
at least two functional
groups
Example:
+
C C
O O
O
H OH
n
Example:
+ C
O
CH3O C
O
CH3O
CH2 CH2
O
H OH C
O
C
O
O
O
CH2
CH2
O
H
n
+
+
O
H H
N
H2 NH2 NH NH
H C
O
C
O
O H
CH3OH