SEMESTER 3

CHEMISTRY
ORGANIC CHEMISTRY
Alkane
Alkene
Haloalkane
Hydroxyl compound
Carbonyl compound
Carboxyl compound
Amino compound
a) Alkane with halogen (X2)
General Equation : RCH2CH3 + X2 (g) → RCHXCH3 + HX
Reagent /Condition : chlorine or bromine gas ;
under ultraviolet light (UV)
Type of reaction : Free radical substitution reaction
Note :
1. The rate of reaction is slow, therefore cannot be use as a test
to distinguish alkane from other compounds.
2. As long as it’s a saturated carbon, it can be halogenated via
free radical reaction. For example :
CH3NH2 + Br2 → BrCH2NH2 + HBr
b) i.Alkene with halogen (X2)
General equation : RCH=CH2 + X2 (g or l) → RCHXCH2X
Reagent /Condition : chlorine or bromine gas ;
under organic solvent CH2Cl2 or CCl4
Type of reaction : electrophilic additional reaction
Note : 1. The rate of reaction is high, and therefore suitable to
be use to distinguish alkene from other functioning group.
2. Reaction is slightly different when halogen its reacted as
aqueous solution. For example, when react with bromine water,
the following reaction take place :
RCH=CH2 + Br2 (aq) →
RCH(OH)CH2Br (major) + RCHBrCH2Br (minor)
*Note from the reaction, -OH is added to C with more substituent / Br is added
to C with more H
b) ii. Alkene with hydrogen halide (HX)
General equation :RCH=CH2 + HX (g) →
RCHXCH3 (major) + RCH2CH2X (minor)
Reagent /Condition : hydrogen chloride, HCl, hydrogen bromide,
HBr / room temperature
Type of reaction : electrophilic additional reaction
Note : 1. The reaction follows Markovnikoff rules - In addition of
hydrogen halide to unsaturated hydrocarbon, C=C, hydrogen is
preferable to be added to carbon with greater hydrogen in it.
c) Alcohol with PCl5 or thionyl chloride SOCl2
General equation : RCH2OH + PCl5 → RCH2Cl POCl3 + HCl (g)
RCH2OH + SOCl2 → RCH2Cl + SO2 (g) + HCl (g)
Reagent /Condition : PCl5 in room temperature or
SOCl2 under reflux
Type of reaction : nucleophilic substitution reaction.
Note :1. Usually the reaction using thionyl chloride is more
preferable since the side products produces are gas, hence the
main organic product is easily isolated.
d) Carboxylic acid with PCl5 or SOCl2
Equation : RCH2COOH + PCl5 → RCH2COCl + POCl3 + HCl (g)
RCH2COOH + SOCl2 → RCH2COCl + SO2 (g) + HCl (g)
Reagent /Condition : PCl5 in room temperature or
SOCl2 under reflux
Type of reaction : nucleophilic substitution reaction.
Note : 1. Usually the reaction using thionyl chloride is more
preferable since the side products produces are gas, hence the
main organic product is easily isolated.
e) Benzene (or any derivatives) with halogen

General equation :

Reagent /Condition : chlorine(Cl2) in AlCl3 at room temperature

bromine(Br2) in FeBr3 under reflux
Type of reaction : electrophilic aromatic substitution reaction.
Note :1. The reaction uses AlCl3 or FeBr3 as catalyst in the
reaction
f) Phenol with bromine water

General equation :

Reagent /Condition : bromine water, Br2 (aq) under room temp

Type of reaction : electrophilic aromatic substitution reaction.
Note : 1. Observation of the reaction - brown solution
decolourised and turned to white precipitate when bromine water
is added to phenol
2. The reaction occur almost immediately since -OH in phenol is
ring activate, which caused all Br to substituted at all ortho and
para position.
g) Aniline with bromine water

General equation :

Reagent /Condition : bromine water, Br2 (aq) under room temperature

Type of reaction : electrophilic aromatic substitution reaction.
Note : 1. Observation of the reaction - brown solution decolourised and
turned to white precipitate when bromine water is added to aniline
2. The reaction occur almost immediately since -NH2 in aniline is ring
activate, which caused all Br to substituted at all ortho and para
position.
Homolog
Chemical Tests
ous series

a)To distinguish alkene from other functioning group

i. Reagent / Condition : bromine in CCl4
Observation : Brown colour of bromine decolourised while
the other will not
Equation :

ii. Reagent / Condition : hot acidified KMnO4

Alkene Observation : Purple colour of KMnO4/H+ decolourised
-C=C- while the other will not
Equation :

(Note : This test is also suitable to distinguish alk-1-ene with

other alkene. Both alkene will decolourised purple colour of
KMnO4 but alk-1-ene will further give effervescence that
turned line water chalky)
 a) To distinguish 1o, 2o alcohol from tertiary alcohol
i. Reagent : acidified KMnO4 ; under reflux
Observation : purple colour of KMnO4/H+ decolourised
when added to 10 or 2o alcohol, but no observable
changes to 3o alcohol.
Equation

ii. Reagent :acidified K2Cr2O7 under reflux

Observation : green colour of K2Cr2O7/H+ turned orange
when added to 10 or 2o alcohol, but no observable
Alcohol
changes to 3o alcohol.
-C-OH
Equation :

b) ~ Iodoform test.
i. Reagent : I2 /OH- under reflux
Observation : brown colour decolourised and give yellow
crystal precipitate when added to alcohol with -
CH(OH)CH3, while compound without methyl alcohol
shows no observable changes
Equation :
 a)Distinguish carbonyl compound & other functioning group
i. Reagent / Condition : 2,4-dinitrophenylhydrazine
Observation : Orange precipitate is formed when carbonyl
compound is added to 2,4-dinitrophenylhydrazine.
Equation :

Carbonyl
compoun b) To distinguish between aldehyde and ketone
d i. Reagent : Fehling solution [solution of complex of Cu2+]
C=O Positive Test : only works for aldehyde (except benzaldehyde)
Observation : blue solution turns to red precipitate of Cu2O
Equation : red ppt.
ii. Tollens' reagent [solution of complex Ag(NH3)2]+]
Positive test : only work for aldehyde (except glucose)
Observation : colourless solution turn silver mirror
Equation : silver mirror

c) To distinguish between ethanal and other aldehyde /

alkan-2-one with other ketone. Reagent : (I2 + NaOH) Iodine in
sodium hydroxide
Only work for ethanal as it has methyl-carbonyl group
Observation : a yellow crystal of triiodomethane is observed
Equation :
CH3CH=O + 3 I2 + NaOH
CHI3 + HCOO–Na+ + 3 HIHI
 a) To distinguish between carboxylic acid and other
functioning group
Reagent : sodium carbonate, Na2CO3 or sodium
Carboxyli bicarbonate, NaHCO3
c acid Observation : effervescence occur, colourless gas evolved
-COOH turn lime water chalky
Equation : 2 R-COOH + Na2CO3

2 R-COONa + CO2 (g) + H2O
R-COOH + NaHCO3
R-COONa + CO2 (g) + H2O

a) To distinguish between primary amine and other class of

amine / functioning group
Amine Reagent : NaNO2 + HCl / 0-5oC
R-NH2 Observation : effervescence occur, colourless gas evolved.
Equation : R-NH2 + NaNO2 + HCl

R-OH + N2 + H2O + NaCl
a) To distinguish between benzene and cycloalkane
Reagent / Condition : conc. HNO3 catalysed by conc H2SO4 under reflux
Observation : Yellow oily liquid is observed when mixed with benzene
Equation : NO2
conc. H2SO4
+ HNO3 + H 2O

b) To distinguish between phenol and alkyl alcohol

Reagent / Condition : bromine water
Observation : brown colour decolourised and white precipitate is
formed almost immediately after the reaction
Equation :
c) To distinguish between phenylamine and alkyl amine
Reagent / Condition : bromine water
Observation : brown colour decolourised and white precipitate is
formed almost immediately after the reaction
a) CH3CH2CH2OH to CH3CH2CH2CH2NH2

b) CH3CH2CH2Br to CH3CH2CH(OH)COOH
c) CH3CH2COOH to CH3CH2CH2COOH

d) CH3CH2OH to CH3CH(OH)CH3
e) CH3CH2OH to CH3CH2CH2CH2CONHCH2CH3
CH3
Sn, HCl

NO2
CH3 CH2Cl ethanolic CH2CN
Cl2, UV KCN 1. LiAlH4
2. H3O+
OH OH OH
CH2CH2NH2

OH