H2 CHEMISTRY 9729

Organic Chemistry Notes

FEBRUARY 23, 2020

By Marcus Soh
Victoria Junior College
2018-2019
Table of Contents
ALKANES ................................................................................................................................................................................................. 4
ALKENES ................................................................................................................................................................................................. 5
HALOGENOALKANES ............................................................................................................................................................................... 8
ARENES ................................................................................................................................................................................................. 12
HALOGENOARENES ............................................................................................................................................................................... 16
HYDROXYLS (ALIPHATIC) ....................................................................................................................................................................... 18
HYDROXYLS (AROMATIC) ...................................................................................................................................................................... 22
CARBONYLS (ALDEHYDES) ..................................................................................................................................................................... 25
CARBONYLS (KETONES) ......................................................................................................................................................................... 28
CARBONYLS (CARBOXYLIC ACIDS) ......................................................................................................................................................... 30
CARBONYLS (ACYL CHLORIDES)............................................................................................................................................................. 33
CARBONYLS (ESTERS) ............................................................................................................................................................................ 35
AMINES (ALIPHATIC) ............................................................................................................................................................................. 36
AMINES (AROMATIC) ............................................................................................................................................................................ 38
AMIDES ................................................................................................................................................................................................. 40
AMINO ACIDS ....................................................................................................................................................................................... 41
PROTEINS .............................................................................................................................................................................................. 42
DISTINGUISHING TESTS (by functional group)....................................................................................................................................... 43
DISTINGUISHING TESTS (by reagent) .................................................................................................................................................... 45
REDUCING AGENTS ............................................................................................................................................................................... 47
OXIDISING AGENTS ............................................................................................................................................................................... 47
REACTION MECHANISMS ...................................................................................................................................................................... 48

Page | 2
 Hydroxyls Carbonyls
Halogeno-
Alkanes Alkenes Alcohols Aldehydes Ketones Carboxylic acids Acyl chloride Ester
alkanes
O O O
H O
C C C C R X R OH R C R C R C
R C O R C R' O R'
OH Cl
Free radical Combustion Elimination Acid-metal Nucleophilic Nucleophilic Acid-metal Hydrolysis Acid hydrolysis
substitution Reduction Nucleophilic Nucleophilic addition addition Acid-base Condensation Alkaline hydrolysis
Combustion Oxidation substitution substitution Condensation Condensation Condensation
Electrophilic addition Condensation Reduction Reduction Conversion to acyl
(elimination) Oxidation Iodoform test chloride
Oxidation Iodoform test Reduction
De-carboxylation

Arenes Halogenoarenes Phenols Amines Phenylamines Amides Proteins

X OH NH2
O H
H O H H
N
R R'' C N NH2 C C N C CO2H

R' R R
R R'

Addition Hydrolysis Acid-metal Neutralisation Neutralisation Acid hydrolysis Acid-base catalysed hydrolysis
Electrophilic Nucleophilic Acid-base Nucleophilic Nucleophilic Alkaline hydrolysis Enzymatic hydrolysis
substitution substitution Nucleophilic substitution substitution Reduction
substitution Condensation Condensation
Electrophilic Electrophilic
substitution substitution
Markonikov’s rule: For unsymmetrical alkenes, the electrophile will go to the carbon with the greater number of hydrogen bonded to it. This is to produce a more stable
carbocation.

Functional groups attached to benzylic carbons (the first carbon bonded directly to the benzene ring) can undergo the same reactions as if they were not bonded to a
benzene ring.

Phenol (-OH) and Phenylamine (-NH2) groups are very activating groups. Hence, reactions that used to need a catalyst do not need a catalyst anymore.

Methanoic acid (HCOOH) and ethandioic acid (HO2C-CO2H) are unstable in the presence of acidified KMnO4 and will be oxidised to CO2 and H2O.

Note: Always specify the medium and the reactants.

Note: Nu refers to Nucleophile, E refers to Electrophile and X is a Halogen.
Page | 3
 ALKANES
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION
H H H2 gas, Ni catalyst,
C C
heat
Reduction Produces
OR CH3CH3 C2H4 + H2 → C2H6
(alkene) alkanes C-C
H H H2 gas, Pt or Pd
ethene catalyst, r.t.p.

cyclohexane
Addition H2, Ni, 150°C, high + 3H Produces
C6H12 2
(benzene) pressure cyclohexane

benzene
REACTIONS
H H
Limited O2, heat CO (g) + H2O (g) C2H6 + 5/2O2 → 2CO + 3H2O
H C C H
Combustion
H H Excess O2, heat CO2 (g) + H2O (g) C2H6 + 7/2O2 → 2CO + 3H2O
ethane
H

H Limited Cl2 (g) or Br2 H C Cl

(g), UV light
H C H H Produces
Free Radical
chloroethane halogenoalkanes
Substitution
Cl R-X
H
CH4 + Cl2 → CH3Cl + HCl
methane
Excess Cl2 (g) or Br2 Cl C Cl CH3Cl + Cl2 → CH2Cl2 + HCl
(g), UV light CH2Cl2 + Cl2 → CHCl3 + HCl
Cl
CHCl3 + Cl2 → CCl4 + HCl
tetrachloromethane

Previous: -- | Current: Alkanes | Next: Alkenes Page | 4

 ALKENES
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION
H H
H H
Elimination H C C Cl C C
NaOH in ethanol, Produces
(halogeno- CH3CH2Cl → CH2=CH2 + HCl
heat H H
alkenes
alkane)
H H ethane (major product)
chloroethane
H H
Condensation H H
or H C C OH Excess conc. H2SO4, C C
elimination C2H5OH → CH2=CH2 + H2O Produces alkenes
heat H H
(alcohol)
H H
ethene
ethanol
REACTIONS
H H
Limited O2, heat CO (g) + H2O (g) C2H4 + 2O2 → 2CO + 2H2O
C C
Combustion
H H
Excess O2, heat CO2 (g) + H2O (g) C2H4 + 3O2 → 2CO2 + 2H2O
ethene
H H H2 gas, Ni catalyst,
C C
heat
Produces
Reduction OR CH3CH3 C2H4 + H2 → C2H6
H H
alkanes
H2 gas, Pt or Pd
ethene catalyst, r.t.p.

Previous: Alkanes | Current: Alkenes | Next: Halogenoalkanes Page | 5

 CO2 (g) + H2O (g)
H H KMnO4 in acidic
medium, heat
C C

H H
ethene
=CH2 group

Oxidation
KMnO4 in alkaline
CO32- + H2O
medium, heat

H3C CH3
KMnO4 in H2SO4,
CH3COOH
C C heat
Produces
H H
KMnO4 in H2SO4, carboxylic acids
but-2-ene CH3COO-Na+
heat
=CHR group

H3C CH3
KMnO4 in H2SO4,
CH3COCH3
C C heat
Produces
H3C CH3 ketones
dimethylbut-2-ene KMnO4 in NaOH,
=CRR’ group CH3COCH3
heat

Previous: Alkanes | Current: Alkenes | Next: Halogenoalkanes Page | 6

 Cold conc. H2SO4,
followed by water CH3 H
with heating
H C C H Produces
Steam, high CH2=CH2 + H2O → CH3CH2OH
alcohols
temperature, high
pressure, acid H OH
catalyst
CH3 H
CH3CH=CH2 + Br2 + H2O → CH3CHBrCH2OH
H3C H (major)
Br2 in water, r.t.p. H C C H

C C CH3CH=CH2 + Br2 → CH3CHBrCH2Br

Electrophilic
Br OH (minor)
addition CH3 H
H H CH3 H
H3C H
δ+
+ Cl
δ− -
C C Cl H C C H + Cl
prop-2-ene H H
H

X2 in CCl4, r.t.p. H C C H CH3 H CH3 H

-
H C C H + Cl H C C H

Cl Cl Cl Cl Cl

CH3 H

Produces
HX in water, r.t.p. H C C H CH3CH=CH2 + HCl → CH3CH2CH2Cl
halogenoalkanes
H Cl

Previous: Alkanes | Current: Alkenes | Next: Halogenoalkanes Page | 7

 HALOGENOALKANES
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION
H H H H
HCl or HBr, heat C2H5OH + HCl → C2H5Cl + H2O
Nucleophilic H C C OH SOCl2, heat H C C Cl C2H5OH + SOCl2 → C2H5Cl + SO2 + HCl
substitution
(alcohol) PX3, heat 3C2H5OH + PCl3 → 3C2H5Cl + H3PO4
H H H H
ethanol PCl5, r.t.p. chloroethane C2H5OH + PCl5 → C2H5Cl + POCl3 + HCl
H H
H H
Electrophilic C C H C C Cl
addition HX in water, r.t.p. CH2=CH2 + HCl → CH3CH2Cl
(alkene) H H
H H
ethene
chloroethane

H H

Free Radical H C H H
Limited Cl2 (g) or Br2 C Cl Produces
Substitution
(g), UV light halogenoalkanes
(alkane)
H H
methane chloromethane

Previous: Alkenes | Current: Halogenoalkanes | Next: Arenes Page | 8

 REACTIONS
H H

C C Produces
H H CH3CH2Cl → CH2=CH2 + HCl
H H
alkenes
ethene (major product)
H C C Cl NaOH in ethanol, H H
Elimination
heat H H
H H H C C OH δ+
+ OH
-
+ Cl
- Produces
chloroethane δ−
Cl C C OH
alcohols
H
H3C H CH3
H H
CH3CH2OH (minor product)
H H SN2 mechanism
1° carbocation
H
C C H
δ+
+ OH
-
+ -
Cl
H H δ−
Cl C C OH
H
ethene (minor product) H3C H CH3
H H Produces alcohols
SN1 mechanism
3° carbocation Distinguishing
Nucleophilic H C C Cl H H CH3CH2CH2 test for halogen:
NaOH in water, heat CH3CH2CH2
substitution δ+ δ− slow -
Acidify with HNO3
+ + Cl
H H H C C OH
H3C C Cl H3C C (aq), followed by
chloroethane CH2CH3 CH2CH3
AgNO3 (aq)
H H CH3CH2CH2 CH3CH2CH2
CH3CH2OH (major product) - fast
H3C C
+ + OH H3C C OH

CH2CH3 CH2CH3
H H H H
H
excess NH3 in H H
Nucleophilic H C C Cl ethanol, heat under H C C N δ+
+ +
Cl C NH3 C NH2 HCl
substitution pressure in a sealed δ−
H
H H CH3
H H tube H H H3C

chloroethane CH3CH2NH2

Previous: Alkenes | Current: Halogenoalkanes | Next: Arenes Page | 9

 H H
H
H H
H C C N
δ+
Cl C + NH3 + HCl
C NH2
H δ−
H
H H H3C H CH3
CH3CH2NH2
H H primary amine Produces amines.
secondary Multiple
limited NH3 in
H C C Cl amine substitution
Nucleophilic ethanol, heat under CH3CH2Cl + CH3CH2NH2 → (CH3CH2)2N + HCl
occurs because
substitution pressure in a sealed
the product is
H H tube (CH3CH2)3N
CH3CH2Cl + (CH3CH2)2N → (CH3CH2)3N + HCl also a
chloroethane tertiary amine nucleophile.
CH2CH3
CH2CH3

CH3CH2Cl + (CH3CH2)3N + HCl

N CH2CH3 N CH2CH3
CH2CH3
H3CH2C
CH2CH3
H3CH2C

H H H H
H H
Produces
H C C Cl H C C C N nitriles
Nucleophilic NaCN in ethanol, δ+
+ -
+ -
Cl C CN C CN Cl for further
substitution heat δ−
H
H3C H CH3 reactions: see
H H H H
below
chloroethane CH3CH2C≡N
H H H
H
LiAlH4 in dry ether, H C C C N Produces
Reduction followed by water, CH3CH2CN + 4[H] → CH3CH2CH2NH2
H H H amines
r.t.p. H H H
CH3CH2CH2NH2
H C C C N
H H
O
H H
Acid propane nitrile H C C C 2CH3CH2CN + 4H2O + H2SO4 → 2CH3CH2COOH + Produces
H2SO4 in water, heat
hydrolysis (NH4)2SO4 carboxylic acids
OH
H H
CH3CH2COOH

Previous: Alkenes | Current: Halogenoalkanes | Next: Arenes Page | 10

 H H
O

Alkaline H C C C CH3CH2CN + H2O + NaOH → CH3CH2COO-Na+ +

NaOH in water, heat
hydrolysis - + NH3
O Na
H H
CH3CH2COO-Na+

Previous: Alkenes | Current: Halogenoalkanes | Next: Arenes Page | 11

 ARENES
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
Na+ PREPARATION
CO2
Na+
CO2

De- + NaOH + Na2CO3

NaOH, heat
carboxylation

sodium benzoate
OH
OH

Reduction + Zn + ZnO
Zn metal, heat
(phenol)

phenol
REACTIONS

cyclohexane
H2, Ni, 150°C, high + 3H Produces
Addition 2
pressure cyclohexane

benzene

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 Cl Cl FeCl3 Cl
+ + FeCl4-
H
Cl
X Prolonged
+ Cl+ conditions
Br2 or Cl2, halogenoarene produce 1,2-
Electrophilic
anhydrous FeBr3 or dihalide and 1,4-
substitution
FeCl3, r.t.p. H
Cl
Cl
dihalide
Produces
benzene
+ + HCl
halogenoarenes
FeCl3

2H2SO4 + HNO +
NO2 + H O+ +
-
2HSO4
3 3

H
NO2
NO2
+ NO + Excessive
2
nitrobenzene temperatures
Electrophilic conc. HNO3, conc.
lead to multiple
substitution H2SO4, heat at 60°C H
NO2
NO2 substitution of
NO2+
benzene
+ HSO4
- + H2SO4

R Cl AlCl3 R
+ + AlCl4-
H
R
R
+ R+ Produces
RCl or RBr, alkyl-substituted methylbenzene
Electrophilic
anhydrous AlCl3 or benzene for further
substitution
BF3, r.t.p. H
R
R
reactions: see
below
benzene
+ AlCl4- + AlCl3 + HCl

Previous: Halogenoalkanes | Current: Arenes | Next: Halogenoarenes Page | 13

 CH3
CH3
CH3

Br2 or Cl2, X
Electrophilic
anhydrous FeBr3 or Similar to benzene
substitution
FeCl3, r.t.p.

methylbenzene X
CH3
CH3
CH3
Temperature
NO2 needed is
Electrophilic conc. HNO3, conc.
Similar to benzene reduced as CH3 is
substitution H2SO4, heat at 30°C
an activating
group.
methylbenzene NO2
CH3
CH3
CH3

RCl or RBr, R
Electrophilic
anhydrous AlCl3 or Similar to benzene
substitution
BF3, r.t.p.

methylbenzene R
CH3
CH3 CH3 CH3
methylcyclohexane
H2, Ni, 150°C, high
Ring addition
pressure + 3H
2

methylbenzene

Previous: Halogenoalkanes | Current: Arenes | Next: Halogenoarenes Page | 14

 CH3
CH2Cl
chloromethylbenzene
Side-chain
substitution
Cl2 or Br2, UV light Similar to alkanes
(free radical
substitution)

methylbenzene
CH3
CHO
benzaldehyde
Side-chain
CrO2Cl2 or MnO2, *temperature is
oxidation -
65% H2SO4 not given in notes
(weak)

methylbenzene
CH3
COOH Reaction only
benzoic acid occurs on
Side-chain KMnO4 (aq), H2SO4 presence of
oxidation (aq), heat under - benzylic
(strong) reflux hydrogen
Produces benzoic
acid
methylbenzene

Previous: Halogenoalkanes | Current: Arenes | Next: Halogenoarenes Page | 15

 HALOGENOARENES
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION
Cl Cl FeCl3 Cl
+ + FeCl4-
H
Cl
X
+ Cl+
Electrophilic Br2 or Cl2, halogenoarene
substitution anhydrous FeBr3 or
H
(benzene) FeCl3, r.t.p. Cl
Cl

benzene
+ FeCl3 + HCl

REACTIONS
Cl
OH phenol Na+
Cl O OH

NaOH (aq), 360°C,

NaOH (aq) dil HCl Produces
Hydrolysis 150 atm followed heat
phenols
by dilute HCl

chlorobenzene
CH2Cl
CH2OH

Does not occur

Nucleophilic with chlorine
NaOH in water, heat Similar to halogenoalkanes
substitution directly bonded
to benzene ring

chloromethylbenzene

Previous: Arenes | Current: Halogenoarenes | Next: Hydroxyls (Aliphatic) Page | 16

 CH2Cl
CH2NH2

excess NH3 in Does not occur

Nucleophilic ethanol, heat under with chlorine
Similar to halogenoalkanes
substitution pressure in a sealed directly bonded
tube to benzene ring

chloromethylbenzene
CH2Cl Does not occur
CH2CN with chlorine
directly bonded
to benzene ring
Nucleophilic NaCN in ethanol,
Similar to halogenoalkanes
substitution heat
Undergoes the
same step-up
reactions as
chloromethylbenzene
halogenoalkanes

Previous: Arenes | Current: Halogenoarenes | Next: Hydroxyls (Aliphatic) Page | 17

 HYDROXYLS (ALIPHATIC)
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION
H H
H H
Electrophilic C C
Cold conc. H2SO4, H C C OH
addition followed by water CH2=CH2 + H2O → CH3CH2OH
(alkene) H H with heating
H H
ethene
CH3CH2OH
SN2 mechanism
1° carbocation
H H
δ+
Cl C + OH
-
+ -
Cl
δ− C OH
H
H3C H CH3
H H H H
SN1 mechanism
Nucleophilic 3° carbocation
substitution H C C Cl NaOH in water, H C C OH CH3CH2CH2 CH3CH2CH2
(halogeno- heat δ+ δ− slow -
+ + Cl
alkane) H H H H H3C C Cl H3C C

chloroethane CH3CH2OH (major product) CH2CH3 CH2CH3

CH3CH2CH2 CH3CH2CH2

- fast
H3C C
+ + OH H3C C OH

CH2CH3 CH2CH3
H H
H H
O
Reduction LiAlH4 in dry ether, H C C OH
H C C C Produces primary
(carboxylic followed by CH3CO2H + 4[H] → CH3CH2OH + H2O
OH alcohols
acid) H H hydrolysis, r.t.p.
H H
ethanoic acid
ethanol

Previous: Halogenarenes | Current: Hydroxyls (Aliphatic) | Next: Hydroxyls (Aromatic) Page | 18

 H
H
Reduction LiAlH4 in dry ether CH2OH
C O Produces primary
(aldehyde) followed by C O + 2[H] CH2OH
alcohols
hydrolysis, r.t.p.
benzyaldehyde phenylmethanol
CH3
CH3 CH3
CH3
Reduction LiAlH4 in dry ether Produces
(ketone) C O followed by C OH C O + 2[H] C OH secondary
hydrolysis, r.t.p. H
alcohol
H
REACTIONS
H H H H

- +
Acid-metal or H C C OH H C C O Na Effervescence of
Na metal, r.t.p. 2C2H5OH + 2Na → 2C2H5O-Na+ + H2
redox H2 observed
H H H H
ethanol
H H
O

Nucleophilic H C C OH R-CO2H, conc H2SO4, Produces

R C C2H5OH + RCO2H ⇌ RCO2CH2CH3 + H2O
substitution heat esters
H H O CH2CH3
ethanol
H H
O
H C C OH
Produces
Nucleophilic R C
R-COCl, r.t.p. C2H5OH + RCOCl → RCO2CH2CH3 + HCl esters (favoured
substitution
method)
H H O CH2CH3
ethanol
H H H H
HCl or HBr, heat C2H5OH + HCl → CH3CH2Cl + H2O

Nucleophilic H C C OH SOCl2, heat H C C Cl C2H5OH + SOCl2 → CH3CH2Cl + SO2 + HCl Produces

substitution PX3, heat 3C2H5OH + PCl3 → 3 CH3CH2Cl + H3PO4 halogenoalkanes
H H H H
ethanol PCl5, r.t.p. chloroethane C2H5OH + PCl5 → CH3CH2Cl + POCl3 + HCl

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 H H
H H

Condensation H C C OH Excess conc. H2SO4, C C

C2H5OH → CH2=CH2 + H2O Produces alkenes
or elimination heat
H H
H H
ethene
ethanol
H H
H Must write distil
O
H C C OH in exam.
Oxidation Acidified K2Cr2O7 H C C Produces
CH3CH2OH + [O] → CH3CHO + H2O
(mild) distil aldehyde. Can be
H H H
H further oxidised:
ethanol see below
CH3CHO
1° alcohol
H H
O O Must write reflux
H C C H C C
in exam.
Oxidation Acidified K2Cr2O7,
CH3CHO + [O] → CH3COOH Produces
(mild) reflux
H OH carboxylic acid
H H
ethanal CH3COOH
H H
H
O
H C C OH Produces
Oxidation Acidified KMnO4, H C C
CH3CH2OH + 2[O] → CH3COOH + H2O carboxylic acid
(strong) heat
H H OH
H
ethanol
CH3COOH
1° alcohol
H OH H H O H

H C C C H
Oxidation Acidified KMnO4, H C C C H
CH3CH(OH)CH3 + [O] → CH3COCH3 + H2O Produces ketones
(strong) H H H heat
propan-2-ol H H
2° alcohol CH3COCH

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 CH3 O
Ethanol is the
H C OH
Iodine and aqueous CH3CH2OH + 4I2 + 6OH → CH3COO + 5I + 5H2O
- - -
only 1° alcohol to
Iodoform test C
NaOH, warm + CHI3 give positive
- + iodoform test.
R R O Na

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 HYDROXYLS (AROMATIC)
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION
Cl
OH phenol Na+
Cl O OH

Hydrolysis NaOH (aq), 360°C, dil HCl

NaOH (aq)
(halogeno- 150atm followed by heat
arene) dilute HCl

chlorobenzene
REACTIONS
OH Na+
O Na+
OH O

Acid-metal or
Na metal, r.t.p. + 2Na
redox 2 2 + H2

phenol
OH Na+
O Na+
OH O
Alcohols do not
react with NaOH,
only phenols do
Acid-base NaOH (aq), r.t.p. + NaOH + H2O Reason: phenol
salt is more
stable
phenol

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 O
OH
O
O C - Na+
OH O O C
Nucleophilic R R
substitution R-COCl in NaOH Produces
or (aq), r.t.p. NaOH RCOCl esters
condensation

phenol
OH
OH
OH
OH
OH
NO2
Electrophilic + HNO3 + H2O Mono-
Dilute HNO3, r.t.p.
substitution substitution

NO2
phenol NO2
OH
OH
OH
NO2 NO2
OH
O2N NO2

Electrophilic Concentrated + 3HNO3 + 3H2O

tri-substitution
substitution HNO3, r.t.p.

NO2
phenol
NO2
OH
OH
OH OH
OH
Br
Electrophilic Liquid Cl2 or Br2, + Br2 + HBr Mono-
substitution r.t.p. substitution

Br
phenol
Br

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 OH
OH
OH
Br Br
OH
Br Br

Electrophilic Aqueous Cl2 or Br2, + 3Br2 + 3HBr

tri-substitution
substitution r.t.p.

Br
phenol
Br

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 CARBONYLS (ALDEHYDES)
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION
H H
H
O
Oxidation H C C OH
(mild) Acidified K2Cr2O7 H C C
CH3CH2OH + [O] → CH3CHO + H2O
(primary distil
H H H
alcohol) H
ethanol
CH3CHO
1° alcohol
REACTIONS
O δ− O Produces racemic
H H OH
O CN , r.t.p.
- δ+
+ - mixture
H3C C CN H3C C CN

Nucleophilic H C C H C C C N H H Produces
-
addition HCN with trace
O OH nitriles
H
H amounts of base, H H H3C C CN + H
δ−
CN H3C C CN + -
CN for further
δ+
ethanal r.t.p. CH3CH(OH)CN reactions: see
H H
below
H

Acid HO C COOH
H2SO4 in H2O, heat -
hydrolysis
CH3
H OH 2-hydroxypropanoic acid
H
H C C C N
Base - +
NaOH in H2O, heat HO C COO Na
hydrolysis H H
2- CH3
hydroxypropanenitrile H

LiAlH4 in dry ether, HO C CH2NH2

Reduction followed by water, -
r.t.p. CH3
amino-propan-2-ol

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 H
Hydrazine
CH3CHO + H2N-NH2 → CH3CH=N-NH2 + H2O
H2N-NH2, r.t.p. H3C C N NH2
H
H
Brady’s reagent
H H3C C N N
O (2,4-DNPH) gives
Phenylhydrazine CH3CHO + H2N-NHC6H5 → CH3CH=N-NHC6H5 +
orange ppt. Can
H C C H2N-NHC6H5, r.t.p. H2O
Condensation be used to
H identify carbonyl
H compounds.
ethanal (2,4-DoNotPeeHere -
2,4-dinitrophenyl H H
Goh Wei Ren 18S411)
Hydrazine, r.t.p.
H3C C N N NO2
CH3CHO + H2N-NHC6H3(NO2)2 →
2,4-DNPH, r.t.p.
CH3CH=N-NHC6H3(NO2) + H2O
Bradys’ reagent, O2N
r.t.p.
LiAlH4 in dry ether
H
followed by H
Reduction hydrolysis, r.t.p. CH2OH Produces primary
C O
NaBH4 in ethanol, C O + 2[H] CH2OH
alcohols
r.t.p.
benzyaldehyde phenylmethanol
H2, Pt catalyst, r.t.p.

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 Purple solution is
acidified KMnO4,
- - decolorised to
heat
colorless
Distinguishing
tests for
acidified K2Cr2O7, aldehyde vs
- -
heat ketone.
H
O Orange solution
turns green
H C C H
Oxidation O
H Tollens’ reagent,
H H C C
CH3CHO + 2[Ag(NH3)2]+ + 3OH- → Silver mirror
Ag(NH3)2+ solution,
ethanal CH3CO2- + 4NH3 + 2Ag + 2H2O precipitated
warm -
O
H
H
Fehling’s solution, O
Alkaline CuSO4and
H C C
CH3CHO + 2Cu2+ + 5OH- → Brick red ppt
potassium sodium
CH3CO2- + Cu2O + 3H2O produced
tartrate, warm -
O
(KNaC4H4O6·4H2O) H
CH3CHO + 3I2 + 4NaOH → CH3CO2-Na+ + CHI3 + R-COCH3 gives
H 3NaI + 3H2O positive iodoform
O H O O
O test.
H C C C
+ 3I2 + 3NaOH
C
+ 3NaI + 3H2O Note: for
Iodine and aqueous H C C
Iodoform test H CH3 H CI3 aldehydes, only
NaOH, warm
H - ethanal gives
H O O O
H positive test
ethanal C
+ NaOH CHI3 + C Pale yellow ppt
-
H CI3 H O Na
+
produced

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 CARBONYLS (KETONES)
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION
H O H
H OH H

Oxidation H C C C H
H C C C H K2Cr2O7 in H2SO4,
(secondary CH3CH(OH)CH3 + [O] →CH3COCH3 + H2O
reflux
alcohol) H H H
H H
propan-2-ol
propan-2-one
REACTIONS
O δ− O Produces racemic
OH mixture
H O H H3C
δ+
C + -
CN H3C C CN
HCN with trace
CH3
Nucleophilic H C C C H amounts of base H3C C CH3 CH3 Produces
-
addition (NaOH or NaCN), O OH nitriles
H H
r.t.p. C N H3C C CN + H
δ−
CN H3C C CN + CN- for further
propan-2-one δ+
reactions: see
CH3CH(OH)CNCH3
CH3 CH3
below
OH
OH

H3C C CN
Hydrolysis H2SO4 in H2O, heat H3C C COOH -
CH3
CH3

OH OH

H3C C CN LiAlH4 in dry ether, H3C C CH2NH2

Reduction -
r.t.p.
CH3 CH3

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 CH3
Hydrazine
CH3COCH3 + H2N-NH2 → (CH3)2C=N-NH2 + H2O
H2N-NH2, r.t.p. H3C N NH2
C
CH3
H

H3C C N N
Phenylhydrazine CH3COCH3 + H2N-NHC6H5 → (CH3)2C=N-NHC6H5
H O H H2N-NHC6H5, r.t.p. + H2O
Brady’s reagent
H C C C H
gives orange ppt.
Condensation Can be used to
H H identify carbonyl
propan-2-one 2,4-dinitrophenyl compounds
Hydrazine, r.t.p.
CH3 H

H3C C N N NO2 CH3COCH3 + H2N-NHC6H3(NO2)2 →

2,4-DNPH, r.t.p.
(CH3)2C=N-NHC6H3(NO2)3 + H2O
O2N

Bradys’ reagent,
r.t.p.
CH3
CH3 CH3 CH3
LiAlH4 in dry ether Produces
Reduction
C O followed by C OH C O + 2[H] C OH secondary
hydrolysis, r.t.p. H
alcohol
H

RCOCH3 + 3I2 + 4NaOH → RCO2-Na+ + CHI3 + 3NaI

O + 3H2O
O
O O
C Iodine and aqueous + 3I2 + 3NaOH + 3NaI + 3H2O
C C
Iodoform test C
R CH3 NaOH, warm R CH3 R CI3
- +
Any ketone with R O Na O O

-COCH3 group (pink) + NaOH +

C CHI3 C
- +
R CI3 R O Na

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 CARBONYLS (CARBOXYLIC ACIDS)
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION
H H
H
O Must write distil
H C C OH
in exam.
Oxidation H C C
Acidified K2Cr2O7 Produces
(mild) CH3CH2OH + [O] → CH3CHO + H2O
distil aldehyde. Can be
(alcohol) H H H
H further oxidised:
ethanol see below
CH3CHO
1° alcohol
H H
O O Must write reflux
Oxidation H C C H C C
in exam.
Acidified K2Cr2O7,
(mild) CH3CHO + [O] → CH3COOH Produces
reflux
(aldehyde) H OH carboxylic acid
H H
ethanal CH3COOH
H H
H
O
Oxidation H C C OH Produces
Acidified KMnO4, H C C
(strong) CH3CH2OH + 2[O] → CH3COOH + H2O carboxylic acid
heat
(alcohol) H H OH
H
ethanol
CH3COOH
1° alcohol
H H
H H O
Acid H C C C
H C C C N 2CH3CH2CN + 4H2O + H2SO4 → 2CH3CH2COOH + Produces
hydrolysis H2SO4 in water, heat
(NH4)2SO4 carboxylic acids
(nitrile) H H OH
H H
propane nitrile
CH3CH2COOH

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 CH3
COOH benzoic acid
Side-chain
oxidation KMnO4 (aq), H2SO4
(strong) (aq), heat under -
(methylbenze reflux
ne)
methylbenzene
H H
O O

Hydrolysis H C C H C C Produces
water, r.t.p. CH3COCl + H2O → CH3CO2H + HCl
(acyl chloride) carboxylic acids
Cl OH
H H
ethanoyl chloride ethanoic acid
REACTIONS

Acid-metal Na metal, r.t.p. CH3CO2H + Na → CH3CO2-Na+ + ½ H2

H H
O O
NaOH, r.t.p. CH3CO2H + NaOH → CH3CO2-Na+ + H2O
H C C H C C
- +
OH O Na Distinguishing
Acid-base H NaHCO3, r.t.p. H CH3CO2H + NaHCO3 → CH3CO2-Na+ + H2O + CO2
test for carboxylic
ethanoic acid sodium ethanoate
acids
(alcohols/phenols
Na2CO3, r.t.p. 2CH3CO2H + Na2CO3 → 2CH3CO2-Na+ + H2O + CO2
do not react)

H H
O O
H
Esterification H C C
R-OH (e.g. CH3OH), H C C
/ concentrated H2SO4 CH3CO2H + CH3OH ⇌ CH3CO2CH3 + H2O Produces esters
O C H
condensation OH catalyst, reflux H
H
ethanoic acid H
methyl ethanoate

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 H PCl5, r.t.p. 3CH3CO2H + PCl3 → 3CH3COCl + H3PO4
O H
O
Conversion to H C C
PCl3, reflux H C C CH3CO2H + PCl5 → CH3COCl + HCl (g) + POCl3
acyl chloride
OH
H Cl
H
ethanoic acid Preferred
SOCl2, reflux ethanoyl chloride CH3CO2H + SOCl2 → 3CH3COCl + HCl (g) + SO2 (g)
reaction

H
O H H

H C C LiAlH4 in dry ether, Produces primary

Reduction H C C OH CH3CO2H + 4[H] → CH3CH2OH + H2O
r.t.p. alcohols
OH
H
H H
ethanoic acid
ethanol
H H
O
CH3CO2H + NaOH → CH3CO2-Na+ + H2O
H C C
Soda lime (CaO / H C H
De- CH3CO2-Na+ + NaOH → CH4 + Na2CO3
NaOH mixture), Produces alkanes
carboxylation Overall:
OH reflux
H H CH3CO2H + 2NaOH → CH4 + Na2CO3 + H2O
ethanoic acid methane
Excess
Dehydration O
concentrated - HCO2H → H2O + CO
(special) H C H2SO4, reflux
Oxidation OH H2SO4 (aq), KMnO4
methanoic acid - HCO2H + [O] → H2O + CO2
(special) (aq), reflux Unstable in
presence of hot
Excess
Dehydration O O KMnO4
concentrated - H2C2O4 → H2O + CO + CO2
(special)
C C H2SO4, reflux
Oxidation HO OH H2SO4 (aq), KMnO4
ethanedioic acid - H2C2O4 + [O] → H2O + 2CO2
(special) (aq), reflux

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 CARBONYLS (ACYL CHLORIDES)
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION

PCl5, r.t.p. 3CH3CO2H + PCl3 → 3CH3COCl + H3PO4

H H
O O
Conversion to
acyl chloride H C C PCl3, reflux H C C CH3CO2H + PCl5 → CH3COCl + HCl (g) + POCl3
(carboxylic
OH Cl
acid) H H Preferred
ethanoic acid ethanoyl chloride reaction as the 2
SOCl2, reflux CH3CO2H + SOCl2 → 3CH3COCl + HCl (g) + SO2 (g)
gases are easily
removed
REACTIONS
H H
O O

H C C H C C Produces
Hydrolysis water, r.t.p. CH3COCl + H2O → CH3CO2H + HCl
carboxylic acids
Cl OH
H H
ethanoyl chloride ethanoic acid
H
O
H
H C C
H R-OH (e.g. CH3OH),
Condensation O C H CH3COCl + CH3OH → CH3COOCH3 + HCl Produces esters
O r.t.p. H
H C C H
methyl ethanoate
Cl
H Produces esters
ethanoyl chloride O NaOH produces
C6H5OH, NaOH (aq), C6H5OH + NaOH → C6H5O-Na+ + H2O
Condensation the stronger
r.t.p. H3C C CH3COCl + C6H5O-Na+ → CH3COOC6H5 + NaCl
nucleophile
O C6H5O-Na+

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 O H CH3COCl + NH3 → CH3CO-NH2 + HCl
H
Condensation O NH3, r.t.p. Produces amides
H3C C N H
Excess ammonia: CH3COCl + 2NH3 → CH3CO-NH2
H C C + NH4Cl
O H CH3COCl + CH3NH2 → CH3CO-NHCH3 + HCl
Cl
H R-NH2 (e.g. CH3NH2),
Condensation Produces amides
ethanoyl chloride r.t.p. H3C C N CH3
Excess amine: CH3COCl + 2CH3NH2 → CH3CO-
NHCH3 + CH3NH3Cl

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 CARBONYLS (ESTERS)
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION
H
O
H
H C C
H R-OH (e.g. CH3OH),
O C H CH3COCl + CH3OH → CH3COOCH3 + HCl Produces esters
O r.t.p. H

Condensation H C C H
(acyl chloride) methyl ethanoate
Cl
H Produces esters
ethanoyl chloride O NaOH produces
C6H5OH, NaOH (aq), C6H5OH + NaOH → C6H5O-Na+ + H2O
the stronger
r.t.p. H3C C CH3COCl + C6H5O-Na+ → CH3COOC6H5 + NaCl
nucleophile
O C6H5O-Na+
REACTIONS
H H
O O
H
H C C
Acid H C C
O C H H2SO4 (aq), reflux CH3COOCH3 + H2O ⇌ CH3COOH + CH3OH reversible
hydrolysis H
OH
H H
methyl ethanoate ethanoic acid
H H
O O
H C C
H not reversible as
Alkaline H C C CH3COO- is
O C H NaOH (aq), reflux CH3COOCH3 + NaOH → CH3COO-Na+ + CH3OH
hydrolysis H - + resonance
O Na
H H stabilized
methyl ethanoate sodium ethanoate

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 AMINES (ALIPHATIC)
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION
H H
H
H H
H C C N
δ+
Cl C + NH3 + HCl
C NH2
H δ−
H
H H H3C H CH3
CH3CH2NH2
H H primary amine
Nucleophilic secondary
excess NH3 in
substitution H C C Cl ethanol, heat under amine CH3CH2Cl + CH3CH2NH2 → (CH3CH2)2NH + HCl
(halogen- pressure in a sealed
alkane) H H tube (CH3CH2)3N
chloroethane CH3CH2Cl + (CH3CH2)2N → (CH3CH2)3N + HCl
tertiary amine

CH2CH3
CH2CH3

CH3CH2Cl + (CH3CH2)3N + HCl

N CH2CH3 N CH2CH3
CH2CH3
H3CH2C
CH2CH3
H3CH2C

H
O H H
LiAlH4 in dry ether,
Reduction H3C N
Produces primary
H3C C N H followed by C CH3CONH2 + 4[H] → CH3CH2NH2
(amides) amines
ethanamide hydrolysis, r.t.p.
H
H
H H H H H
H
H C C C N
LiAlH4 in dry ether, H C C C N
Reduction
H H followed by water, CH3CH2CN + 4[H] → CH3CH2CH2NH2
(nitriles) H
propane nitrile r.t.p. H H H
CH3CH2CH2NH2

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 REACTIONS
H H H H

H C N Any acid (e.g. HCl), H C N H

Neutralisation CH3NH2 + HCl → CH3NH3+Cl-
r.t.p.
H H H H
methylamine methylammonium chloride
H H
Nucleophilic RX (e.g. CH3CH2Cl), H H
H H H
substitution H C N heat under δ+
H3C C N CH3 + CH3NH2 CH2 + HCl
(amine acting pressure in a sealed Cl
δ−
C C N Produces amines
H
as attacking tube H3C H CH3
species) H H (alcoholic amine) H
methylamine
H H

O H CH3COCl + CH3NH2 → CH3CO-NHCH3 + HCl

H C N R-COCl (e.g.
Condensation Produces amides
CH3COCl), r.t.p. H3C C N CH3
Excess amine: CH3COCl + 2CH3NH2 → CH3CO-
H H NHCH3 + CH3NH3Cl
methylamine

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 AMINES (AROMATIC)
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION
NO2 NH2
NO2 NH2

Sn and + 6[H] + H2O

Reduction concentrated HCl,
(nitro- heat, followed by
benzene) addition of alkali
at r.t.p.
nitrobenzene C6H5NO2 + 6H+ + 3Sn → C6H5NH2 + 2H2O + 3Sn2+
phenylamine
REACTIONS
+
NH2 NH3 CH3CO2

Any acid
Neutralisation (e.g. CH3CO2H), C6H5NH2 + CH3CO2H → C6H5NH3+CH3CO2-
r.t.p.

phenylamine phenylammonium ethanoate

H
NH2
N CH2CH3
Nucleophilic
RX (e.g. CH3CH2Cl),
substitution
heat under
(amine acting C6H5NH2 + CH3CH2Cl → C6H5NH(CH2CH3) + HCl
pressure in a sealed
as attacking
tube
species)

phenylamine
ethylphenylamine

Previous: Amines (Aliphatic) | Current: Amines (Aromatic) | Next: Amides Page | 38

 NH2
O

R-COCl (e.g. C
Condensation H3C N C6H5NH2 + CH3COCl → CH3CONHC6H5 + HCl Produces amides
CH3COCl), r.t.p.

H
phenylamine N-phenylethanamide
NH2
NH2 NH2 Distinguishing
Br Br NH2 test for
Br Br
phenylamine.
Electrophilic + + 3HBr Observation:
Br2 (aq), r.t.p. 3Br2
substitution orange bromine
decolorises with
formation of a
Br white ppt.
phenylamine Br
2,4,6-tribromophenylamine

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 AMIDES
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION
H H

O H CH3COCl + CH3NH2 → CH3CO-NHCH3 + HCl

Condensation H C N R-COCl (e.g.
Produces amides
(amine) CH3COCl), r.t.p. H3C C N CH3
Excess amine: CH3COCl + 2CH3NH2 → CH3CO-
H H NHCH3 + CH3NH3Cl
methylamine
REACTIONS
O H O
Acid HCl (aq) / H2SO4 Produces
CH3CONHCH3 + H2O + H+ → CH3CO2H + CH3NH3+
hydrolysis H3C C N CH3 (aq), heat H3C C OH carboxylic acid

H
Test for primary
O O
Alkaline amide
NaOH (aq), heat CH3CONH2 + OH- → CH3CO2- + NH3
hydrolysis H3C C N H H3C C
-
O Na
+ Pungent NH3 gas
produced
H H
H
O H LiAlH4 in dry ether,
H C C N Produces primary
Reduction followed by CH3CONH2 + 4[H] → CH3CH2NH2
H3C C N H amines
hydrolysis, r.t.p.
H
H H

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 AMINO ACIDS
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
REACTIONS
H

H H +
NH3 C CO2H

Adding acid to +
NH2
-
NH3 C CO2H C CO2 R
protonated Any acid
amino acid
R R
High pH Low pH Order of
H deprotonation:
α-carboxylic acid
+ -
NH3 C CO2 R-carboxylic acid
α-amino acid
H H R R-amino acid

Adding alkali - +
to fully NH2 C CO2 NH3 C CO2H
Any base H
deprotonated
amino acid R R -
Low pH High pH H2N C CO2

Previous: Amides | Current: Amino acids | Next: Proteins Page | 41

 PROTEINS
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
PREPARATION
H H H O H H
H O H H

Condensation NH2 C CO2H NH2 C CO2H NH2 C C N C CO2H NH2 C C N C CO2H

Dipeptide
(amino acid) formation
R R
R R R R
REACTIONS
H O H

+
H H H
Dilute acid, heat C C NH3 C - -
O
Acid-base OH
R R
catalysed C C N C
H O H
hydrolysis R R
Dilute alkali, heat C C H2N C - -
-
O
R R
H O H H

Enzymatic Enzymes cleave at either the carboxylic end or amino acid end. The resulting fragment depends on the
C C N C Enzyme, r.t.p.
hydrolysis action of the enzyme.
R R

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 DISTINGUISHING TESTS (by functional group)
Reaction Reagents and
Test for Observations (for X = …) Notes
name Conditions
X2 in water, r.t.p. Cl2: Pale yellow solution decolorises
Electrophilic
Alkene Br2: Orange solution decolorises
addition
I2: Brown solution decolorises
KMnO4 (aq) in H2SO4
Oxidative (aq), heat Purple KMnO4 decolorises
Alkene
cleavage [Terminal alkene: Effevescene of CO2 gas that gives a
white ppt with limewater]
Add NaOH (aq), heat.
Acidify with dilute
HNO3, followed by
AgNO3 (aq). Cl: White ppt produced
Halogeno- Nucleophilic Br: Pale yellow ppt produced
alkane R-X substitution I: Yellow ppt produced

Add NH3 (aq) Cl: White ppt dissolves to form colorless solution
Br: Cream ppt insoluble in dilute NH3, soluble in
concentrated NH3 to form colorless solution
K2Cr2O7 (aq) in H2SO4
(aq), distill 1° and 2° alcohol: Orange solution turns green
K2Cr2O7 (aq) in H2SO4 3° alcohol: No observation
Alcohol
Oxidation (aq), reflux
(1° and 2°)
KMnO4 (aq) in H2SO4
(aq), heat 1° and 2° alcohol: Purple solution decolorises
3° alcohol: No observation
Na metal, r.t.p. Effeverscene of H2 observed
Alcohol
Acid-metal
(1°, 2° and 3°)
Brady’s reagent (2,4-
DNPH) Orange ppt produced
Aldehyde Condensation

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 K2Cr2O7 (aq) in H2SO4 Orange solution turns green
(aq), reflux
Aldehyde Oxidation
KMnO4 (aq) in H2SO4 Purple solution decolorises
(aq), heat
Tollen’s reagent
Aldehyde Oxidation [Ag(NH3)2]+, warm Silver mirror precipitated

Fehling’s solution, Brick red ppt produced

Aldehyde Oxidation warm Blue solution decolorises

Brady’s reagent (2,4-

Ketone Condensation DNPH) Orange ppt produced

Aldehyde / I2 in NaOH (aq),

ketone with Iodoform warm Pale yellow ppt produced Only ethanal gives positive iodoform test
RCOCH3
Carboxylic Na2CO3 Effevescene of CO2 gas which produces a white ppt with Distinguish between carboxylic acid and alcohol /
Acid-base limewater
acid NaHCO3 phenol
Alkaline NaOH (aq), heat Pungent NH3 gas produced
Amide (1°)
hydrolysis

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 DISTINGUISHING TESTS (by reagent)
Reagent Reaction name Positive test for Observations (for X = …) to copy down Notes
Oxidative Alkenes
cleavage
KMnO4 (aq) in H2SO4 (aq), heat Purple solution decolorises
1° and 2° alcohols
or
Aldehydes
KMnO4 (aq) in NaOH (aq), heat Oxidation
Purple solution decolorises, white ppt
Reagents reactant with more than 1 functional group

Benzene with side chain

produced
K2Cr2O7 (aq) in H2SO4 (aq), heat
1° and 2° alcohols
or Oxidation Orange solution turns green
Aldehydes
KMnO4 (aq) in NaOH (aq), heat
Alcohol
Effevescene of H2 which “pops” a lighted
Na metal / any metal Acid-metal Phenol
splint
Carboxylic acid
Electrophilic
Alkene Cl2: Pale yellow solution decolorises
addition
X2 (aq) Br2: Orange solution decolorises
Electrophilic Phenol
I2: Brown solution decolorises
substitution Phenylamine
Aldehyde
Brady’s reagent Condensation Orange ppt produced
Ketone
R-COCH3
O

I2 in NaOH, warm Iodoform Pale yellow ppt formed

C

R CH3
Aliphatic aldehyde
Tollens’ reagent [Ag(NH3)2+], warm Oxidation Silver mirror formed
Aromatic aldehyde

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 Fehling’s solution, warm Oxidation Aliphatic aldehyde Brick red ppt formed
Effervescene of CO2 which produces a white
Na2CO3 Acid-base Carboxylic acid
ppt with limewater
NaOH (aq), heat, followed by Nucleophilic
Dilute HNO3, followed by substitution
AgNO3 (aq), Cl: White ppt produced
Br: Pale yellow ppt produced
followed by I: Yellow ppt produced

NH3 (aq) or conc. NH3 Halogenoalkanes Cl: White ppt dissolves to form colorless
solution
Br: Cream ppt insoluble in dilute NH3, soluble
in concentrated NH3 to form colorless
solution
I: Yellow ppt insoluble in both dilute and
concentrated NH3

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 REDUCING AGENTS
Resulting compound from…
Reagent
Alkene Aldehyde Ketone Carboxylic acid Acyl chloride Ester Amide Nitrile
H2, Ni
catalyst, heat
Yes Yes Yes Yes
H2, Pt or Pd
catalyst, r.t.p.

NaBH4 in
Yes Yes
methanol

LiAlH4 in dry
Yes Yes Yes Yes Yes Yes Yes
ether

…produces… alkane 1° alcohol 2° alcohol 1° alcohol 1° alcohol 2 1° alcohols 1° amine 1° amine

OXIDISING AGENTS
Resulting compound from…
Reagent
Alkene Phenol Alkylbenzene 1° and 2° alcohol Aldehyde Benzaldehyde Methanoic acid Ethanedioic acid
KMnO4 (aq) in
H2SO4 (aq), Yes
cold
KMnO4 (aq) in
H2SO4 (aq), Yes Yes Yes Yes Yes Yes Yes
heat
K2Cr2O7 (aq)
in H2SO4 (aq), Yes Yes Yes
heat
Tollen’s
reagent
Yes Yes
[Ag(NH3)2]+,
warm
Fehling’s
solution, Yes
warm

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 REACTION MECHANISMS
Name of Reagents and
Starting compound Products Reaction Mechanism / Chemical Equation Notes
Reaction Conditions
REACTIONS
H
Cold conc. H2SO4,
CH3
H3C H
CH3 H δ+ δ− -
followed by water C C + E Nu H C C H + Nu

with heating
H H E = electrophilic
Electrophilic H H
E
Alkenes C C CH3 H H Nu = nucleophile
Br2 in water, r.t.p.
CH3
addition -
H + Nu
X2 in CCl4, r.t.p.
H C C H C C H

N E
HX in water, r.t.p. E Nu E

Br2 or Cl2, -
E Nu + + A Nu
anhydrous FeBr3 or A E

FeCl3, r.t.p. E H
E

Arenes and benzene conc. HNO3, conc.

+ E+
Electrophilic derivatives H2SO4, heat at 60°C A = acid catalyst
substitution (alkylbenzene, phenol,
phenylamine) H
E
E

RCl or RBr,
anhydrous AlCl3 or + A + H Nu
BF3, r.t.p.

O δ− O

OH δ+
+ -
H3C C CN H3C C CN R group = H
Aldehydes HCN with trace R
Nucleophilic H3C C CN
R
/ amounts of base, -
addition O OH
Ketone r.t.p. δ−
R H3C C CN + H
δ+
CN H3C C CN + CN- R group = alkyl
R R

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 Halogenalkanes SN2
NaCN in ethanol, SN2
/ H H
heat
Halogenoarenes H δ+
+ + -
X C Nu C Nu X
R-CO2H, conc H2SO4, δ−
H
heat R C Nu R H R
R-COCl, r.t.p. SN1
R R
HCl or HBr, heat H slow
Alcohols SOCl2, heat R X + X-
SN1 C R C
/ PX3, heat
Nucleophilic R R
Phenols R
substitution R R
R C Nu fast
PCl5, r.t.p. + Nu
R C R C Nu

R
R R

RX (e.g. CH3CH2Cl), H H
H H H
Amines heat under δ+
H3C C N CH3 + CH3NH2 CH2 + HCl
/ pressure in a sealed δ−
Cl C C N
H
Phenylamines tube H3C H CH3
(alcoholic amine) H

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