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2025 JC2 H2 CHEMISTRY 9729

ORGANIC CHEMISTRY
CONCEPT MAPS
 TMJC JC2 H2 Organic Chemistry Concept Maps

ALKANES
General Formula: CnH2n+2
Functional Group: NA
Mechanism: Free Radical Substitution

CH2=CH2 Alkene

(1) H2 gas, Ni catalyst, high T & P or

(2) H2 gas, Pd or Pt catalyst
Reduction

excess O2 limited O2
CO2 + H2O Complete Combustion CH3CH3 Incomplete Combustion CO + H2O
Limited Cl2 or Br2
UV light / hv
Free Radical Substitution

CH3CH2Cl or
Halogenoalkane
CH3CH2Br

Note:
Assuming the alkane is in excess,
thus the monosubstituted product
Preparation is the main product
Reaction

2
 TMJC JC2 H2 Organic Chemistry Concept Maps

General Formula: CnH2n

ALKENES
Functional Group: Alkene H H H H H H
Mechanism: Electrophilic Addition H C C C H or H C C C H
H H H H H H
X H H H X H
CH3CO2H + CO2 + H2O Halogenoalkane
H C C C H or H C C C H
Alcoholic KOH, heat OH H H H OH H
Alcohol
(or NaOH in ethanol, heat)
Steps to obtain product of strong oxidation Hot acidified KMnO4
Elimination
(Strong) Oxidation (Apply Saytzeff’s Rule) (1) Excess conc. H2SO4, heat or
 cleave to form  add O to H directly bonded
C C C O (2) Excess conc. H3PO4, heat or
OH
(3) Al2O3 catalyst, heat
to C=C  O C
is unstable  forms CO2 + H2O Elimination (Apply Saytzeff’s Rule)
OH

(1) Steam, high T & P, conc. H3PO4 cat.

H H (1) cold alkaline KMnO4 H H or (2) cold conc. H2SO4 followed by H H
(Mild) Oxidation hot water
H C C CH3 C C H C C CH3
OH OH Diol H CH3 Electrophilic Addition
(Apply Markovnikov’s Rule) H OH
Alcohol

(1) X2 in CCl4, HX(g)

H H in the dark or
(2) X2 (g or l), Electrophilic Addition
Aqueous X2 (Apply Markovnikov’s Rule)
H C C CH3 (1) H2 gas, Ni catalyst, high in the dark Electrophilic Addition
T & P or Electrophilic (Apply Markovnikov’s Rule)
H H (2) H2 gas, Pd or Pt catalyst, Addition
Alkane
Reduction
H H H H
H H
H C C CH3 H C C CH3 H C C CH3
Preparation X X X OH H X
Halogenoalkane
Reaction Halogenoalkane

3
 TMJC JC2 H2 Organic Chemistry Concept Maps

BENZENE & METHYLBENZENE

Structural Formula: C6H6 (Benzene), C6H5CH3 (Methylbenzene)
Mechanisms: 1. Electrophilic Substitution (of benzene ring) 2. Free Radical Substitution (of alkyl side-chain) Halogenoarene

X
Benzene

NO2 Conc. HNO3 and conc. H2SO4,

55C
Electrophilic Substitution Alkylbenzene
R

Nitrobenzene

Methylbenzene

CH3 CH3
CH3
CH3 Conc. HNO3 and conc. H2SO4, X2 with CH3
30C Anhydrous FeX3 / AlX3 catalyst.
NO2 X
and Electrophilic Substitution Electrophilic Substitution and
Note: X = Cl or Br
NO2 X
Limited Cl2 (g) or Br2(g)
KMnO4 in dilute H2SO4, heat UV light
(Side chain) Oxidation Free Radical Substitution
Note: X = Cl or Br
COOH CH2X

Preparation
Reaction

Benzoic acid 4
 TMJC JC2 H2 Organic Chemistry Concept Maps

HALOGEN DERIVATIVES
General Formula: CnH2n+1X (for aliphatic halogenoalkanes) H H
Functional Group: Primary (1), Secondary (2), or Tertiary (3o) Halogenoalkane
H C C H
Mechanism: Nucleophilic Substitution

H H H OH Alcohol

C C 1. HX gas (X = Cl or Br), heat

CH3CH3 H H a. HCl(g), heat
b. NaBr, conc. H2SO4, heat
Alkene 2. Anhydrous PCl3 / PBr3 or
HX(g) I2 with red phosphorus, heat
Alkane X2, UV light Electrophilic 3. Anhydrous PCl5
Free Radical Substitution Addition 4. Anhydrous SOCl2
Note: X = Cl or Br Nucleophilic Substitution

Nitrile H H H H
(Note: 1 additional
Ethanolic KCN, heat under reflux
H H
C atom compared Alcoholic KOH, heat
with starting
H C C H
Nucleophilic Substitution
H C C H C C
halogenoalkane)
Elimination
H H
H CN H X
HCl(aq) or H2SO4(aq), Alkene
1. LiAlH4 in dry ether or
heat under reflux 2. H2 with Ni catalyst, high T & P or NaOH(aq) or KOH(aq), heat
Acidic Hydrolysis 3. H2 with Pd or Pt catalyst Nucleophilic Substitution
Reduction Excess concentrated NH3 in ethanol,
H H heat in a sealed tube H H
H H Nucleophilic Substitution
H C C H H H H C C H
H C C H
H COOH H C C H H OH
Carboxylic acid
H CH2NH2
Alcohol
(Note: 1 additional C atom Amine H NH2
compared with starting (Note: 1 additional C atom
halogenoalkane) compared with starting Amine
Preparation halogenoalkane) (Note: Same no. of C atom as starting halogenoalkane)
Reaction 5
 TMJC JC2 H2 Organic Chemistry Concept Maps
Secondary
alcohol
ALCOHOLS Ketone
R
R reduced
General Formula: CnH2n+1OH Carbonyl compound C O R' C OH
(Ketone / Aldehyde) R'
Functional Group: primary, secondary or tertiary alcohol
H

C O R
reduced
C O RCH2OH
H Primary
Halogenoalkane alcohol
Aldehyde
1. LiAlH4 in dry ether or (also obtained from
C C R X 2. NaBH4 in ethanol or reduction of RCOOH)
Alkene 3. H2 with Ni catalyst, high T and P or
NaOH(aq) or KOH(aq), 4. H2 with Pd or Pt catalyst
1. Steam, conc. H3PO4, high T and P or heat Reduction K Cr O or KMnO ,
2 2 7 4
2. Cold conc. H2SO4 followed by hot water Nucleophilic
Electrophilic Addition Substitution K2Cr2O7, dil H2SO4 R C H dil H2SO4 R C OH
(Apply Markovnikov’s Rule) RCH2OH Heat
heat with immediate O O
1o alcohol distillation Aldehyde Carboxylic
1. Excess conc. H2SO4, heat or acid
2. Al2O3 catalyst, heat or R' Acidified K2Cr2O7 or KMnO4, heat
3. Excess conc. H3PO4, heat Oxidation R C R'
C C Elimination (Apply Saytzeff’s Rule) R OH R
CH OH
O
R'' Ketone
2o alcohol Resistant
Alkene R' C OH to
R' C OH R' C Cl R oxidation

O O 3o
Alkaline I2(aq), alcohol R−COO−
Reactive metal
Oxidation of CH3CH(OH)−R alcohols +
RO−Na+ + ½ H2 (e.g. Na or K) Conc. H2SO4,
CHI3
Acid-metal heat 1. HX gas (X = Cl or Br), heat
Condensation
Displacement Condensation a. HCl, anhydrous ZnCl2, heat (yellow ppt)
Alkoxide (Salt) b. NaBr, conc. H2SO4, heat
2. Anhydrous PCl3 / PBr3 or
R' C OR R' C OR I2 with red phosphorus, heat
3. Anhydrous PCl5
Preparation O O 4. Anhydrous SOCl2
Reaction Ester Ester Nucleophilic Substitution
R X
+ H2O + HCl Halogenoalkane
6
 TMJC JC2 H2 Organic Chemistry Concept Maps
General Formula: C6H5OH OH
PHENOLS
Functional Group: phenol,

OH
Mechanism: Electrophilic Substitution
X X
OH OH
OH
O 2N NO2
X
and X

X2 (aq)
X Electrophilic NO2
Substitution
X2 in organic solvent Conc. HNO3
Electrophilic Substitution Electrophilic Substitution

OH
- + OH OH
O Na Reactive metals
(e.g. Na or K) Dilute HNO3 NO2
+ ½ H2 and
Acid-metal Electrophilic Substitution
Displacement

R' C Cl NO2
Note: If K was used, then the O
potassium salt would be obtained Condensation

NaOH(aq) Aqueous neutral

O-Na+ Neutralisation FeCl3 solution
Complex Formation R' C O
O
Violet Complex*
Preparation
Reaction Note: KOH(aq) can be used instead + HCl
to obtain the potassium salt *structure:
not in syllabus
7
 TMJC JC2 H2 Organic Chemistry Concept Maps

CARBONYL COMPOUNDS
General Formula: RCHO (aldehydes),
RR’CO (ketones)
Functional Group: Aldehyde or Ketone H R'
Mechanism: Nucleophilic Addition
R C H R C H
Primary Secondary
alcohol OH OH alcohol
R−COO−
K2Cr2O7, dil H2SO4, K2Cr2O7 or KMnO4,
+
CHI3
heat with immediate distillation dil H2SO4, heat R C OH
Oxidation Oxidation
(yellow ppt) O
Aldehydes Ketones (only for aldehydes)
R C H R C R'
Cyanohydrin K2Cr2O7 or KMnO4
O O
/ dil H2SO4, heat
Oxidation
HCN, trace amounts of NaOH
(or NaCN) as catalyst, cold Tollens’ reagent, heat Ag + RCOO-
C OH Nucleophilic Addition C O Oxidation
(only for aldehydes)
CN 1. LiAlH4 in dry ether or
Fehling’s reagent, heat
2. H2 with Ni catalyst, high temperature and pressure or
Oxidation
HCl(aq) or H2SO4(aq), 3. H2 with Pd or Pt catalyst
heat under reflux Reduction Cu2O + RCOO-
Acidic Hydrolysis 1. LiAlH4 in dry ether or
2. NaBH4 in ethanol or (only for aliphatic aldehydes)
3. H2 with Ni catalyst, high
2,4-DNPH,
temperature and pressure or
heat H
4. H2 with Pd or Pt catalyst
C OH C OH Reduction
Condensation
C N N NO2

COOH CH2NH 2 H R' O2N

R C H R C H (for all ketones & aldehydes)
Preparation From From
Reaction Aldehydes OH Ketones OH
8
 TMJC JC2 H2 Organic Chemistry Concept Maps

CARBOXYLIC ACIDS & DERIVATIVES

General Formula: RCOOH (carboxylic acids), RCOCl (acyl chlorides), RCOOR’ (esters), RCONR’R’’ (amides)
Mechanism: Nucleophilic Acyl Substitution

R-COO- R-CN
Primary HCl(aq) or H2SO4(aq),
1. Reactive metals (e.g. Na or K)
Secondary amide
Acid-metal Displacement Heat under reflux
amide
Acidic Hydrolysis
R-CONH2 2. NaOH(aq) or KOH(aq) R-CHO
R-CONHR’ Neutralisation

3. Na2CO3(aq) or NaHCO3(aq)
NH3(g) Neutralisation K2Cr2O7 or KMnO4,
Condensation dil H2SO4, heat
H2O(l) Oxidation
NH2R’
Condensation
R C Cl Nucleophilic Acyl
Substitution / Hydrolysis
1. PCl5 or
R-COOH LiAlH4 in dry ether, r.t.p.
R-CH2OH
NHR’R’’ O 2. PCl3, heat or
3. Anhydrous SOCl2 Reduction
Condensation Nucleophilic Acyl Substitution
1. Hot acidified KMnO4 or
HO R’-OH 2. Hot alkaline KMnO4 followed by
conc.H2SO4 catalyst,
H2SO4(aq) / HCl(aq)
R-CONR’R’’ R’-OH, heat
(Strong) Oxidation
in aq. NaOH Condensation
Condensation
Tertiary Condensation
amide R C O R'
+ H2O (for RCOOH) R-CH=CH2
R C O O
HCl (for RCOCl)
O
Note: The esters and amides can be hydrolysed to obtain the carboxylic acids
Preparation + HCl The ester can be reduced using LiAlH4 to the corresponding two alcohols
The amide can be reduced using LiAlH4 to the corresponding amines
Reaction 9
 TMJC JC2 H2 Organic Chemistry Concept Maps

ALIPHATIC AMINES
General Formula: RNH2 (primary amines)
Reactions: 1. Neutralisation 2. Nucleophilic Substitution

Note: R = R’CH2
R’-CN
1. LiAlH4 in dry ether or
2. H2 with Ni catalyst, heat or
3. H2 with Pd or Pt catalyst
Reduction

Excess concentrated NH3

HCl(aq) or H2SO4(aq) in ethanol, heat in sealed tube
R-NH3+ Neutralisation R-NH2 Nucleophilic Substitution
R-X
R' C Cl
O

Condensation

R' C N R
O H
Preparation
Reaction + HCl

10
 TMJC JC2 H2 Organic Chemistry Concept Maps

PHENYLAMINES
General Formula: C6H5NH2
Mechanism: Electrophilic Substitution
Br

Br NH2

Br

Aqueous Br2
Electrophilic
Substitution

Sn in conc. HCl, heat

HCl(aq) or H2SO4(aq) followed by NaOH(aq).
NH3+ Neutralisation
NH2 Reduction
NO2

R' C Cl
O

Condensation

R' C N
Preparation
O H
Reaction

11
 TMJC JC2 H2 Organic Chemistry Concept Maps

AMINO ACIDS
General Formula: RCH(NH2)COOH (for -amino acids)

Functional Groups: Carboxylic acid and (primary) amine

H
- +
R C COO Na
NH2

NaOH(aq)
Neutralisation

H H H
Na2CO3(aq) or
HCl(aq) or H2SO4(aq) NaHCO3(aq) - +
R C COOH R C COOH R C COO Na
Neutralisation Neutralisation
+
NH3 NH2 NH2
H
R' C COOH
NH2
Condensation, formation of peptide bond

H O H H H O H H
Preparation R C C N C COOH and R' C C N C COOH *Only possible for amino acid
Reaction
NH2 R' NH2 R
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 TMJC JC2 H2 Organic Chemistry Concept Maps

SUMMARY OF HYDROLYSIS OF ESTERS & AMIDES

Esters Amides

R C O R' R C NH2 R C N R' R C N R'

O O O H O R"

HCl(aq) or
H2SO4(aq), R-COOH R-COOH R-COOH R-COOH
heat under reflux H H
H N R'
+ NH4+
H N R'
Acidic Hydrolysis
+ R’-OH + +
H R"

R-COO- R-COO- R-COO- R-COO-

NaOH(aq) or
KOH(aq),
heat under reflux
H N R' H N R'
Basic Hydrolysis + R’-OH + NH3 + + R"
H
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 TMJC JC2 H2 Organic Chemistry Concept Maps

REDUCTION OF ESTERS & AMIDES

Esters Amides

R C O R' R C NH2 R C N R' R C N R'

O O O H O R"

R-CH2OH R-CH2NH2
LiAlH4 in dry ether

+ R’-OH

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