FHSC1124 ORGANIC CHEMISTRY

TUTORIAL E-BOOK Qs

TABLE OF CONTENTS
Tutorial
Title Question Scopes
No.
1 Introduction to 1.1 Naming of functional groups / homologous series
Organic 1.2 Definition / Types of isomerism
Chemistry 1.3 Chain / Position / Functional Group Isomerism
1.4 Geometric Isomerism
1.5 Optical Isomerism
1.6 Effect of geometric isomerism on physical properties
2 Alkanes 2.1 IUPAC Nomenclature – Naming of alkanes
2.2 Drawing of alkanes
2.3 Physical Properties
2.4 Combustion / oxidation reaction
2.5 Free-radical substitution reaction and mechanism
2.6 Isomerism of alkanes / Crude oil / Petroleum
3 Alkenes 3.1 IUPAC nomenclature - Naming of alkenes
3.2 Drawing of alkenes
3.3 Addition reactions – conditions, catalyst
3.4 Addition reactions – reactants / products
3.5 Electrophilic addition mechanism
3.6 Markovnikov’s rule
4 Alkenes + 4.1 Oxidation of Alkenes
Arenes 4.2 Chemical tests for the presence of C-C double bond /
(Aromatic Differentiate alkanes and alkenes
Hydrocarbons) 4.3 IUPAC Nomenclature – Naming of arenes
4.4 Drawing of arenes
4.5 Physical Properties of Benzene
4.6 Physical Properties of Benzene – Comparison with
alkanes / alkenes / etc
5 Arenes 5.1 Draw suitable products for electrophillic substitution
(Aromatic reactions of benzene
Hydrocarbons) 5.2 Reactions / conditions for electrophillic substitution
5.3 EArS Mechanism
5.4 Reaction scheme – synthesis of derivative of benzene
5.5 Electrophillic addition reaction / Side chain oxidation
5.6 Tests to differentiate benzene with other compounds
6 Haloalkanes/ 6.1 IUPAC Nomenclature - Naming of haloalkane /
Alkyl Halides halogenoarene
6.2 Drawing of haloalkane / halogenoarene
6.3 Preparation of alkyl halides / halogenoarenes
6.4 Carbon-halogen bond strength
6.5 SN1 / SN2 mechanism
6.6 Differences between SN1 and SN2
7 Haloalkanes/ 7.1 E1 / E2 mechanism
Alkyl Halides 7.2 Formation of nitriles and primary amines
+ 7.3 Reactions of Grignard reagents with CO2 / carbonyl
 Hydroxyl 7.4 IUPAC Nomenclature - Naming of alcohol / phenol
Compounds 7.5 Drawing of alcohol / phenol
7.6 Physical properties
8 Hydroxyl 8.1 Synthesis of alcohols
Compounds 8.2 Grignard Reagent
8.3 Reactions of alcohols
8.4 Zaitsev’s Rule
8.5 Tests to differentiate alcohols / phenols,
Triiodomethane reaction
8.6 Reaction of phenols
9 Carbonyl 9.1 IUPAC Nomenclature - Naming of aldehyde / ketone
Compounds 9.2 Drawing aldehyde / ketone
9.3 Physical properties
9.4 Write chemical equations
9.5 Mechanism – Nucleophilic addition reaction
9.6 Predict reactants / products
10 Carbonyl 10.1 Synthesis / conversion – reagents, conditions,
Compounds + equations
Carboxylic 10.2 Mechanism – Carbonyl condensation reaction
Acids and 10.3 Chemical Test
their 10.4 IUPAC Nomenclature - Naming of carboxylic acid /
Derivatives acid halides
10.5 Drawing carboxylic acid / acid halides
10.6 Physical property – acidity
11 Carboxylic 11.1 IUPAC Nomenclature - Naming of Ester / carboxylic
Acids and salt / anhydride
their 11.2 Drawing Ester / carboxylic salt / anhydride
Derivatives 11.3 Physical properties
11.4 Write chemical equations
11.5 Suggest reagents / conditions
11.6 Reaction scheme – predict reactants / products
12 Amines and 12.1 IUPAC Nomenclature - Naming of amines / amide
Amides 12.2 Drawing of amines / amide
12.3 Physical property – basicity
12.4 Synthesis / writing chemical equations
12.5 Chemical tests
12.6 Reaction scheme / predict reactants / products
UNIVERSITI TUNKU ABDUL RAHMAN

Centre : Centre for Foundation Studies Course Code : FHSC1124

Programme : Foundation in Science Course Title : Organic Chemistry
Year/ : Session :
Trimester
Lecturer :

Tutorial 1: Topic 1 Introduction to Organic Chemistry

1.1 NAMING OF FUNCTIONAL GROUPS / HOMOLOGOUS SERIES

1.1.1 Identify ALL the functional groups in the following compounds:

(a) Aspirin (b) Testosterone

O
OH

O
H

H H

OH O

(c) Acetaminophen (d) Methyl anthranilate

H2N

O
OH
O

O
N
H

(e) Procaine (f) Cinnamil

O O

N C
O

NH2
 (g) Ascorbic Acid (h) Asparagine
OH HO
O
HO
NH2
HO

O OH
O NH2 O

1.2 DEFINITION / TYPES OF ISOMERISM

1.2.1 (a) Define the term ‘structural isomerism’.

(b) List out the types of stereoisomerism.

(c) Define the term ‘position isomerism’.

1.3 CHAIN / POSITION / FUNCTIONAL GROUP ISOMERISM

1.3.1 Draw FOUR (4) possible tertiary alcohols with a molecular formula of C5H10O.
[Sept 2018]

1.3.2 Draw FOUR (4) functional group isomers with the molecular formulae C2H4O2 and
name the main functional group for each of these structures. [Dec 2015]

1.3.3 Draw TWO (2) possible structural isomers that contain a four-carbon ring with
molecular formula of C5H5N. [May 2021]

1.3.4 Draw TWO (2) possible cyclic functional group isomers with the molecular formula
of C3H4O. [April 2017]

1.3.5 Sketch TWO (2) functional group isomers with a molecular formula of C4H8O.
[Oct 2021]

1.4 GEOMETRIC ISOMERISM

1.4.1 Draw TWO (2) possible pairs of geometric isomers for the cyclic compound C6H8O2.
[April 2019]

1.4.2 Draw FOUR (4) possible geometric isomers with the molecular formula C3H6O2.
[Sept 2014]
1.4.3 Draw TWO (2) possible pairs of geometric isomers for the cyclic compound C6H12.
[Dec 2017]

1.4.4 Draw TWO (2) possible pairs of cyclopentene geometric isomers with the molecular
formula of C5H6Cl2. [May 2022]

1.5 OPTICAL ISOMERISM

1.5.1 Do the following compounds show chirality? If yes, draw the optical isomers. Mark
the chiral centre with an asterisk (*).

(a) C6H5CH(COOH)CH2CCl3 [May 2022]

(b) C6H5CH2CH2CH(OH)Cl

(c) (CH3)2C=CHCH2CH(OH)CH3

(d) CH2=CHC(NO2)2CH(CH3)COOH [Sept 2018]

(e)
NO2

CHCH2CH2CH3
[Sept 2015]

(f)
OH H

HO N

HO [Apr 2021]

1.6 EFFECT OF GEOMETRIC ISOMERISM ON PHYSICAL PROPERTIES

1.6.1 Compare the boiling points of cis and trans isomers of 1,2-dibromopropene. Explain
your answer.

1.6.2 For the compound 1,2-difluoroethene, explain the following observations:

(a) Cis isomer has a higher boiling point than trans isomer.

(b) Trans isomer has a higher melting point than cis isomer.
1.6.3 Pent-2-ene exists as geometric isomers. Identify the isomer with the highest melting
point and explain your answers. [Apr 2017]
Tutorial 2: Topic 2 Alkanes
2.1 IUPAC NOMENCLATURE – NAMING OF ALKANES

2.1.1 Give the IUPAC name for the following compounds.

(a) (b)
H Br CH2CH3
H H

H3C C C C CH3

H H CH3 H3C CH3

[Dec 2015]

(c) (d)
Cl
Br

[Dec 2011]

(e) (f)

(g) (h)
CH3

Cl
I

(i) (j)
H

CH2CH3
CH3

H
2.2 DRAWING OF ALKANES

2.2.1 Draw the structure for the following compounds.

(a) 1,5-dichloro-1,5-difluorohexane

(b) trans-1-methyl-3-propylcyclobutane

(c) 4,5-dibromo-4-ethyl-2,3-dimethyloctane

(d) cis-1-bromo-1,3-diethylcyclohexane

(e) 5-ethyl-2,3,3,4-tetramethylnonane

(f) 1-bromo-1-pentylcyclooctane

(g) 2-chloro-3,3-dimethylhexane [Dec 2017]

(h) cis-1,2-difluorocyclobutane

(i) 3-ethyl-5-propyloctane

(j) trans-3-chloro-1,1,4-trimethylcyclopentane

2.3 PHYSICAL PROPERTIES

2.3.1 Arrange the non-polar compounds P and Q below in ascending order of boiling
points. Explain your answer.

CH3C(CH3)2C(CH3)3 , CH3(CH2)3C(CH3)3
P Q

2.3.2 Boiling points of some alkanes are shown in the table below.

Alkane, X Boiling point of X Isomer of X Boiling point of

(C) isomer (C)
Ethane - 88.5 - -
Butane -1 2-methylpropane - 12
Hexane 68.7 2,3-dimethylbutane 58

(a) Explain the change in boiling points of X, from ethane to hexane.

(b) Explain why the boiling points of the X differ than that of their corresponding
isomers.

2.3.3 Compare the boiling points of hexane and 2,2-dimethylbutane. Explain your answer.
[Sep 2018]
2.3.4 Arrange the following alkanes in order of increasing boiling point. Explain your
answer.
Pentane, 2,2-dimethylpropane, propane

2.4 COMBUSTION / OXIDATION REACTIONS

2.4.1 Provide a balanced chemical equation for the following reactions:

(a) Thermal cracking of C21H44 produces 2 moles of butene, 5 moles of X and 1

mole of Y. Given that X and Y are alkene and alkane respectively.

(b) Complete combustion of 1-methylcyclobutane.

(c) Monochlorination of 1,1-dimethylcyclopropane in the presence of UV light.

2.4.2 By using the appropriate molecular formula, write a balanced equation for the
complete combustion of nonane.

2.4.3 Write a balanced equation for the complete combustion of 2,2-dimethylheptane.

2.5 FREE RADICAL SUBSTITUTION REACTION AND MECHANISM

2.5.1 Mono-chlorination of an alkane with molecular formula C5H12 in the presence of UV

light forms tertiary alkyl halide compound A and white fume.

(a) Draw the structure of compound A and name the white fume.

(b) Show the mechanism of initiation step when compound A reacts with chlorine.
2.5.2 When compound A reacts with chlorine, monochlorination takes place at the tertiary
carbon of compound A.

CH3

H3C C CH2CH3

H
Compound A

(a) State the type of bond cleavage that occurs in the reaction.

(b) State the type of mechanism involved in the reaction.

(c) Draw the mechanism involved for the monochlorination of compound A.

Show all the steps clearly.

2.5.3 Mono-chlorination of 3-methylpentane in the presence of UV light forms a chiral

compound A and white fume. Catalytic cracking of 3-methylpentane produces 1 mol
of B, one mol of C and one mol of methane gas. Given that B is an alkene and C is a
cycloalkane.

(a) Draw the structure of compound A and name the white fume.

(b) Show the mechanism of initiation step when 3-methylpentane reacts with
chlorine.

(c) Write the chemical equation for catalytic cracking of 3-methylpentane.

(d) Compare the boiling points of 3-methylpentane and 2,2,3-trimethylpentane.

Explain your answer.

2.5.4 Under the influence of ultraviolet light, 2-chloropropane is produced when propane
reacts with chlorine. Outline the mechanism for the formation of 2-chloropropane in
the propagation step. [May 2022]

2.6 ISOMERISM OF ALKANES / CRUDE OIL / PETROLEUM

2.6.1 Hexane and isomer D share the same molecular formula of C6H14. Isomer D has a
lower boiling point than hexane. Given that the isomer D is symmetrical in shape and
optically inactive.

(a) Write a balanced equation for the complete combustion of hexane.

(b) Draw the structure of isomer D.

 (c) Explain why isomer D has a lower boiling point than hexane.

(d) Isomer D undergoes dibromination at the same carbon in the presence of

sunlight. Write the balanced chemical equation involved.

2.6.2 (a) Briefly explain the term ‘catalytic cracking’.

(b) Cracking of a straight-chain compound B, C6H14, produced unsaturated

compound C and saturated compound D, which has an approximate molecular
mass of 44 g molˉ1. Write a balanced equation for the cracking of compound B
and label compounds C and D.

2.6.3 Decane is one of the compounds isolated from distillation. It further undergoes
cracking process to form one mole of compound P as shown below. Compound P
which is a branched chain molecule reacts with chlorine in the presence of UV light to
produce monochloro-substituted product Q.

C10H22 → 2 C3H6 + P

(a) Identify the structure of compound P.

(b) State the alternative of UV light.

(c) Draw the TWO possible structures for Q.

(a) State the expected observation for the reaction between compound P and
bromine in the presence of UV light.
Tutorial 3: Topic 3 Alkenes
3.1 IUPAC NOMENCLATURE – NAMING OF ALKENES

3.1.1 Give the IUPAC name for the following compounds.

(a) (b)

[May 2021]

(c) (d)
Cl

H3CH2C(H3C)2C H

H CH2CH3

(e) (f)

H H
H Br
C C
H3C C C C CH2CH3

CH3 H CH3 Br Br

(g) (h)
CH2CH3
CH3

CH2 Cl
 (i) (j)
CH3 Br

H3CH2CH2C CH2CHCH2CH3

H H Cl

3.2 DRAWING OF ALKENES

3.2.1 Draw the structure for the following compounds.

(a) trans-2,2-dichlorohex-3-ene [Sept 2015]

(b) trans-2-bromo-3,5-dimethylhex-2-ene [Apr 2021]

(c) 1,2-dimethylcyclopenta-1,3-diene

(d) 6-chloro-1-ethylcycloocta-1,3-diene

(e) trans-3,4-dichlorocyclopentene [Dec 2018]

(f) trans-3-ethyl-1,5-dimethylcyclopent-1-ene

(g) cis-1,5-diiodopent-2-ene

(h) 1-bromo-2-chlorocyclohexa-1,4-diene

(i) 3-Chloro-3-ethylcyclopentene [May 2022]

(j) 2,2-dimethylhex-3-ene

3.3 ADDITION REACTIONS – CONDITIONS, CATALYSTS

3.3.1 Write the equation(s) for the following conversion(s) by stating the reagent(s) and
condition(s) for the reaction(s).

(a) Hydration of 3-methylpent-2-ene

(b) Hydration of 1-methylcyclopentene

(c) Bromination of 4-methylcyclohexa-1-diene

(d) Chlorination of 2,5-dimethylhex-2-ene

(e) Hydroxylation of 2-methylbut-2-ene

(f) Hydroxylation of 1,3-dimethylcyclohex-1-ene

 (g) Hydrogenation of 2,3-dimethylbut-2-ene

(h) Hydrogenation of 1,2-dimethylcyclopropene

3.4 ADDITION REACTIONS – REACTANTS / PRODUCTS

3.4.1 Based on the reactions schemes below, draw the structural formula of S, T and U.

Br2 in ether
at room
temperature
Hot KMnO4
C C CH3 T + U
H3O+

H H

3.4.2 Complete the following equation(s). Label the major and minor product(s), if any.

(a)
KMnO4 / H+

Heat

(b)
Ni
+ 2H2

(c)

+ HCl
ether

(d)
KMnO4 / H+

heat
 (e)

H3PO4
+ H2O
heat

3.4.3 The structure of phenylethene, often called styrene is shown below. It can be used to
make poly(styrene). Draw a section of the polymer chain formed from two units of
monomer.
H C C H

[Dec 2013]

3.5 ELECTROPHILIC ADDITION MECHANISM

3.5.1 Draw the mechanism involved when 3,3-dimethylbutene is added with bromine in
diethyl ether at room temperature.

3.5.2 Compound P undergo hydration to form organic compounds, S and T. S is optically

active whereas T is optically inactive.

H H H CH3 H

H C C C C C H

H H H
Compound P

(a) Suggest the structural formula of S and T.

(b) State TWO (2) conditions for the formation of compound S and T.

(c) Propose a reaction mechanism between compound P and hydrogen iodide to

form major product.

(d) Name the type of mechanism for (c).

3.5.3 The structure of compound Z is shown below:

CH3 CH2CH2CH3

H3CH2C C C H

(a) State the expected observation and draw the product formed when compound
Z is shaken with few drops of bromine in tetrachloromethane in a test tube at
room temperature.

(b) Give the condition and reagent(s) to convert compound Z to the structure
below.

CH3 CH2CH2CH3

H3CH2C C C H

OH OH

(c) Propose a mechanism for the electophilic addition of compound Z with

hydrogen bromide to form major product.

3.5.4 Hexane and hexene react with halogens to produce haloalkanes via different
mechanisms. The differences between the two reactions are shown below:

Compound Hexane Hexene

Type of mechanism P Q
Type of product Mixture of haloalkanes Haloalkane
Temperature R S

(a) Based on the table above, state the type of mechanism P.

(b) State the temperature R required for the reaction. [Dec 2013]

3.5.5 The following electrophilic addition reaction occurs at room temperature. Propose a
complete mechanism for the reaction.

CH2Br

ether
Compound C + Br2 Br
3.5.6 1-Phenylbut-2-ene reacts with bromine in diethyl ether at room temperature to form
dibromoalkane and no white fume is released. Outline the mechanism for the reaction.

3.5.7 Polypropylene is a thermoplastic made from the combination of propylene monomers.

H H H H

* C C C C *

CH3 H CH3 H
n

Polypropylene

Write the mechanism when propylene reacts with Br2. [Oct 2021]

3.6 MARKOVNIKOV’S RULE

3.6.1 An alkene with molecular formula C4H8 reacts with steam to form major product E
which consist of tertiary carbon.

(a) Name the mechanism for the reaction.

(b) Explain why alkenes tend to react with electrophiles.

(c) State the rule used to identify the major product.

(d) Draw the structural formula of the major product E.

3.6.2 1-Ethylcyclopentene reacts with HBr to form major product.

(a) Explain Markovnikov’s rule.

(b) Draw and name the major product formed.

3.6.3 Compound D reacts with HCl to form major and minor products – compound E and
compound F respectively.

+ HCl Compound E Compound F

(major) +
(minor)

Compound D

(a) State the rule applied for predicting the major product.

(b) Explain the rule stated in (a).

(c) Draw the structures of compound E and compound F.

3.6.4 Name two reactions that are most useful to predict the major product for
Markovnikov’s rule.
Tutorial 4: Topic 3 Alkenes & Topic 4 Arenes
4.1 OXIDATION OF ALKENES

4.1.1 1-Methylcyclohexene can undergo addition and oxidation reactions.

(a) State the condition(s) and reagent(s) required when 1-methylcyclohexene

undergo oxidation reaction to produce a diol compound.

(b) Draw TWO (2) products formed when 1-methylcyclohexene reacts with
phosphoric acid in water when it undergoes addition reaction. Label the major
and minor products, if any.

4.1.2 Complete the following equation(s).

(a)
O
acidified KMnO4
Q +
O
hot

(b)
H3C CH3
acidified KMnO4 R
room temperature

(c)
OH
+
KMnO4 / H
S
cold

OH

(d)

KMnO4 / H+
T + U
heat
 (e)
CH3 CH3 CH3 CH3
Radical
V * C C C C *
initiator

CH3 H CH3 H n

(f)
radical
W
initiator

4.1.3 Propene is treated with hot acidified KMnO4 solution, producing two products.

(a) Name the reaction above.

(b) Draw a balanced chemical equation for the reaction above.

(c) In industry, propene can be further polymerised into poly(proprene) which is

one of the most versatile thermoplastic polymers. Draw the structural formula
of the poly(propene) by showing two monomers.

4.2 CHEMICAL TESTS FOR PRESENCE OF C-C DOUBLE BOND /

DIFFERENTIATE ALKANES AND ALKENES

4.2.1 Alkene F is an unbranched cyclic compound which contains six carbons. The reaction
between alkene F and hydrogen is highly exothermic.

(a) Write a balanced equation for the reaction above.

(b) Suggest a chemical test which would show that the reaction above has reacted
completely. State clearly the reagent, condition and observation of the test.

4.2.2 The structure of compound J is shown below:

CH3

CH2
Compound J

State the expected observation and draw the product formed when compound J is
shaken with few drops of acidified potassium manganate(VII) in a test tube at room
temperature.
4.2.3 Suggest how you would differentiate between 1-methylcyclohexane and
1-methylcyclohexene. State the reagent(s) and condition(s) used and the expected
observations. Write equation(s) where appropriate by showing the stereochemistry of
the products, if any.

4.2.4 Suggest a chemical test to differentiate 2-methylbutane from 2-methylbutene. Write

the chemical equation and state the observation involved.

4.3 IUPAC NOMENCLATURE – NAMING OF ARENES

4.3.1 Give the IUPAC name for the following compounds.

(a) (b)

H2N

O2N CN

Br

(c) (d)
NH2

NO2
[Sept 2015]

(e) (f)
CHO
Cl
NH2

H3C
 (g) (h)
NH2

COOH

H3C I
[Dec 2018] [Oct 2021]

(i) (j)
O

C NH2

HOOC COOH

NH2
[Sept 2022]

4.4 DRAWING OF ARENES

4.4.1 Draw the structure for the following compounds.

(a) p-diethylbenzene

(b) m-nitrobenzenesulphonic acid [April 2015]

(c) 2-bromo-3,4-dichlorophenol

(d) 2-bromo-4-phenylhexane

(e) 3-benzyl-2-bromo-5-phenylhexane

(f) 4-bromobenzaldehyde

(g) 3,4-dibromotoluene

(h) m-propylnitrobenzene

(i) 3-amino-5-nitrobenzonitrile [Oct 2021]

(j) 3-nitrobenzoic acid

4.5 PHYSICAL PROPERTIES OF BENZENE

4.5.1 Comment on the solubility of biphenyl in water. Justify your answer.

Biphenyl

4.5.2 Table 1 shows the boiling point of benzene and toluene.

CH3

Compounds

Benzene
Toluene
Boiling Points 80°C 111°C

Explain why the boiling point of benzene is lower than toluene.

4.5.3 Naphthalene is a bicyclic aromatic hydrocarbon, consisting of a fused pair of benzene

rings.

Naphthalene

(a) Would you use water as a solvent for naphthalene? Justify your answer.

(b) Naphthalene tends to undergo substitution reaction, instead of addition

reaction. Explain this statement.

4.6 PHYSICAL PROPERTIES OF BENZENE – COMPARISON WITH ALKANES

/ ALKENES / ETC

4.6.1 You were given three organic compounds: benzene, methylbenzene and hexane.
Arrange the boiling points of these compounds in ascending order. Explain your
answer in terms of structure and bonding.
Tutorial 5: Topic 4 Arenes
5.1 DRAW SUITABLE PRODUCTS FOR ELECTROPHILIC SUBSTITUTION
REACTION OF BENZENE

5.1.1 Complete the following equation(s).

(a)

SO3
CH2CH3
H2SO4

(b)
O
AlCl3
COOH + H3CH2C C Cl

(c)

CH3Cl / AlCl3
Cl

(d)

conc. HNO3
SO3H
conc. H2SO4

5.2 REACTIONS / CONDITIONS FOR ELECTROPHILIC SUBSTITUTION

5.2.1 State the reagent(s) and condition(s) for the following conversion(s).

(a) Methylbenzene → 2-nitromethylbenzene

(b) Nitrobenzene → 3-chloronitrobenzene

(c) Benzene → benzenesulphonic acid

(d) Toluene → 1-ethyl-4-methylbenzene

5.2.2 State the reactant(s) and condition(s) for the following conversion(s).

(a)
OH

Reactant B
Reactant A + HCl
Condition C

(b)
O

Reactant E
Reactant D + HCl
Condition F

5.3 EArS MECHANISM

5.3.1 Benzene undergoes Friedal-Crafts acylation to produce compound A and white fumes,
HBr.
O

Compound A

(a) Identify the reactant and catalyst required for this reaction.

(b) Outline the mechanism for this reaction. [Sept 2016]

5.3.2 Phenol can undergo nitration to form a mixture of ortho and para isomers.

(a) Outline the mechanism for this reaction to form the p-isomer.

(b) Outline the mechanism for this reaction to form the o-isomer.

5.3.3 Benzaldehyde can be nitrated by reaction with a mixture of concentrated nitric acid
and sulphuric acid to form m-nitrobenzaldehye. Outline the mechanism for the
nitration of benzaldehyde.
5.3.4 Benzoic acid undergoes halogenation reaction to form compound E.

COOH

Br
Compound E

Outline the mechanism for this reaction.

5.3.5 The following reaction scheme show some reactions of ethylbenzene.

CH2CH3

A B
Cl2 / AlCl3 Cl2 / UV
?? ??

(a) Draw the mechanism for reaction A.

(b) Name the product(s) formed for reaction B.

5.3.6 An exothermic reaction occurs when benzoic acid is converted to 3-nitrobenzoic acid.
The reaction of electrophile with benzoic acid is a slow step, however the reaction
speeds up during deprotonation.

(a) Name the electrophile.

(b) Explain why the reaction between electrophile and benzoic acid is slow step.

(c) Outline the mechanism for this reaction. [Sept 2019]

5.3.7 Sulphonation is the introduction of a sulphonic acid group into an organic compound,
leading to the production of an aromatic sulphonic acid.

(a) Outline the mechanism of ethylbenzene undergoing sulphonation to produce

an ortho substituted product.

(b) Name the product formed.

5.3.8 Phenol is an aromatic compound with the formula of C6H6O. It undergoes
sulphonation in the presence of concentrated sulphuric acid to form a para-oriented
product.

(a) Write the complete mechanism for the reaction.

(b) Name the product formed. [Oct 2021]

5.4 REACTION SCHEME – SYNTHESIS OF DERIVATIVE OF BENZENE

5.4.1 Show the reaction scheme to form the following compound by using benzene as a
starting material.

COOH

NO2

5.4.2 Show the reaction scheme to synthesize II from I. Given that –Cl is ortho-para-
directing while –COOH is meta-directing.

Cl COOH

???

I II

5.4.3 Show the reaction scheme to form the following compound by using benzene as a
starting material.

HO3S
5.5 ELECTROPHILIC ADDITION REACTION / SIDE CHAIN OXIDATION

5.5.1 State the reagent(s) and condition(s) for the following conversion.

benzene → cyclohexane

5.5.2 Identify the unknown compound(s) in the following reactions.

(a)
H CH3

+ A C CHCH3 + HBr

(b)
(i) alkaline KMnO4
(ii) dilute H2SO4
CH2CH3 B + C + D
heat

5.5.3 When a monosubstituted compound A is refluxed with acidified potassium

permanganate, compound B is formed. The molecular formulae of A and B are C8H10
and C8H6O4 respectively. Given that compound A and B consist of benzene ring.
Predict the structural formulae of compounds A and B.

5.6 TESTS TO DIFFERENTIATE BENZENE WITH OTHER COMPOUNDS

5.6.1 Suggest a chemical test to differentiate 4-methylbenzenesulfonic acid and

4-nitrobenzenesulphonic acid. State the reagent(s), condition(s) and expected
observation(s).

5.6.2 Suggest a chemical test to differentiate o-chlorotoluene and chlorobenzene. State the
reagent(s), condition(s) and expected observation(s). [Sept 2012]
Tutorial 6: Topic 5 Haloalkanes / Alkyl Halides
6.1 IUPAC NOMENCLATURE – NAMING OF HALOALKANE /
HALOGENOARENE

6.1.1 Give the IUPAC name for the following compounds.

(a) (b)

Cl

Cl F

(c) (d)
F
H2
Cl H3C C C CH3

C C
H
I H H

(e) (f)
H3CH2C I

C C

F CH3 Cl Br

(g) (h)

Cl

(i) (j)

CH3 H

H Br

Cl Br

[Sept 2022]
6. 2 DRAWING OF HALOALKANE / HALOGENOARENE

6.2.1 Draw the structure for the following compounds.

(a) 1-chloro-1,2-diphenylethane

(b) cis-1-bromo-2-propylcyclopentane

(c) trans-3,4-dichloropenta-1,3-diene

(d) 1-fluoro-1-methylcyclopentane

(e) m-dibromobenzene

(f) 1-iodocyclobuta-1,3-diene

(g) 3-chloro-3,4-diphenylhexane

(h) o-bromobenzenesulphonic acid

(i) 3-fluoro-1-methylcyclobutene

(j) 1-bromo-2-methylbut-2-ene

6.3 PREPARATION OF ALKYL HALIDE / HALOGENOARENE

6.3.1 Give the suitable reagent(s) and condition(s) for the following reactions:

(a) CH2=CHCH2 CH2ClCH(Cl)CH2

(b) C6H6 C6H5Br

6.3.2 Complete the following equation(s).

(a)
OH
ether
+ SOCl2 A + B + C

(b)
ether
CH3CH2CH2OH + PBr3 D
 (c)

AlCl3
E + F Cl + HCl

(d)

N N + KI G + H

6.3.3 Based on the reaction scheme below:

HBr I
H3CH2C C C CH3 Major compound B Alcohol C
HBr
CH3 H

Cl2

(a) Draw the structures of compounds A, B and C.

(b) State the reagent and condition required for reaction I.

6.3.4 Draw a three-step reaction scheme for the following conversion.

CH2OH

6.4 CARBON-HALOGEN BOND STRENGTH

6.4.1 An alkanonitrile was produced when a haloalkane with the molecular formula of
C5H11I was refluxed with potassium cyanide in alcohol. The reaction occurs via a
unimolecular process.

(a) Deduce the rate law of the reaction.

(b) Predict what would happen to the rate of reaction if the reactant C5H11I is
replaced with 2-chloro-2-methylbutane. Explain your answer. [Dec 2014]
6.4.2 2-Iodo-2-methylbutane, 2-chlorohexane and 1-bromobutane are different classes of
alkyl halides. Which alkyl halide will react the fastest towards SN2 reaction. Explain
your answer.

6.4.3 Briefly explain why it is easier for 1-iodohexane than 1-chlorohexane to undergo
nucleophilic substitution. [Oct 2021]

6.5 SN1 / SN2 MECHANISM

6.5.1 2-bromo-2-phenylbutane is hydrolysed in water through SN1 reaction.

(a) State the rate equation for the above reaction.

(b) Outline the mechanism for the reaction. [Apr 2016]

6.5.2 2-Bromobutane is hydrolysed in water through S 1 reaction.

N

(a) State the rate law for the above reaction.

(b) Outline the mechanism for the reaction. [May 2022]

6.5.3 In SN2 mechanism, the hydroxide ion attacks the partially positive carbon of
1-chloropentane from the opposite side with respect to the leaving group to reach a
transition state.

(a) Describe what would happen during the transition state of this reaction.

(b) Explain why hydroxide ion attacks the partially positive carbon of
1-chloropentane from the opposite side with respect to the leaving group.

(c) Outline the mechanism for this reaction. [Sept 2016]

6.5.4 Compound X and Y are branch-chain isomers with a molecular formula of C4H9Cl. X
reacts with ethanol to form carbocation, P while Y reacts with OH− to form Z.

(a) Illustrate the structure of compounds X and Y.

(b) Analyze the isomer that undergoes SN1 mechanism.

(c) Illustrate the structure of the compound P.

(d) Write the rate expression for both SN1 and SN2 reactions. [Oct 2021]
6.6 DIFFERENCES BETWEEN SN1 AND SN2

6.6.1 Complete the following table on the SN1 and SN2 mechanisms of haloalkanes (R-X).

Mechanism SN1 SN2

Rate equation
Number of step(s)
Reactivity of 1/ 2/ 3 R-X
Formation of carbocation

6.6.2 Complete the following table on the SN1 and SN2 mechanisms based on the
haloalkane given.

Haloalkane CH2Cl

C(CH3)2(Cl)CH2CH(CH3)2

Mechanism
Formation of carbocation
Rate Equation
Tutorial 7: Topic 5 Haloalkanes + Topic 6 Hydroxyl Compounds
7.1 E1 / E2 MECHANISM

7.1.1 2-Bromo-2,3-dimethylbutane is refluxed with water in ethanol in elimination process

to form alkenes and other side products. The rate law for this reaction is as follows:

Rate = k [2-bromo-2,3-dimethylbutane]

(a) Outline the mechanism of the reaction that leads to the formation of the minor
product, an alkene.

(b) Predict the change in the rate of reaction if the concentration of

2-bromo-2,3-dimethylbutane is tripled. [Dec 2016]

7.1.2 2-Chlorobutane is refluxed with sodium hydroxide in ethanol. A major product is

formed through the E2 mechanism.

(a) State the rules involved and briefly explain the rule.

(b) Draw the mechanism for the formation of the major product. [Apr 2015]

7.1.3 2-Bromo-2-methylbutane undergoes E1 reaction when refluxed with water in ethanol.

(a) Name the major product.

(b) Outline the mechanism to form the major product.

7.1.4 Compound G reacts with water in ethanol and ethanoyl chloride respectively to form
different products H and I as shown in Table 4.1.

H CH3

C C Cl

H CH3

Compound G

Table 4.1
Reaction V Reaction VI
Reagent Water in ethanol Ethanoyl chloride
Type of Mechanism E1 EaRS
Compound H Compound I
Product
= Major product = Ortho product
 (a) State the rate law that occurs in Reaction V.

(b) Draw compounds H.

(c) Draw the mechanism for the reaction of compound G with water in ethanol
that occurs in Reaction V.

(d) Draw the expected product formed when compound H reacts with hot
acidified potassium permanganate given that the expected product gives a
positive iodoform result. [Apr 2019]

7.1.5 The rate law shows the elimination reaction of 3-chloro-4-methylhexane.

Rate = k [3-chloro-4-methylhexane] [OH-]

(a) Outline the mechanism for the formation of the major product.

(b) State the class of alkyl halide that reacts most readily through this reaction and
the rule applied. [Dec 2017]

7.1.6 Compound A with the molecular formula of C5H11Cl is a branched and optically
active secondary haloalkane. It undergoes elimination when it is refluxed with a
solution of potassium hydroxide in ethanol to form major product. Write the
mechanism for the formation of the major product. [Oct 2021]

7.1.7 Ethene, hydronium ion and iodide ion are formed when compound B is refluxed with
ethanolic water. Write the mechanism of the reaction. [Oct 2021]

7.2 FORMATION OF NITRILES AND PRIMARY AMINES

7.2.1 Write a balanced chemical equation for the reaction between:

(a) 2-chloropentane and potassium cyanide

(b) 2-methylpentanenitrile and lithium aluminium hydride

7.2.2 Write a balanced chemical equation for the reaction between chloropropane and
ammonia.
7.2.3 Identify compounds A, B, and C in the following reactions.

1. LiAlH4 / ether
KCN
A B
2. H2O
Cl

NH3

7.2.4 Show the reaction scheme for the following conversion. State the reagent(s) and
condition(s) if any, for each step.

[Sept 2014]

7.3 REACTIONS OF GRIGNARD REAGENTS WITH CO2 / CARBONYL

7.3.1 Write the respective complete equations to form the following compounds, starting
from phenylmagnesium bromide.

(a) 2-Phenylbutan-2-ol

(b) Benzoic acid

7.3.2 Complete the following equation(s).

(a)
H2O / H3O+
CH3CHO + CH3MgBr A + B

(b)
H2O / H3O+
CH3COCH3 + CH3MgBr
C + D

(c)
O

H2O
MgBr + C E + F
H3O+
H3C
 (d)
O

H2O
C + CH3CH2CH(MgBr)CH3 G + H
H3C CH2CH2CH3 H3O+

7.3.3 Grignard reagent is used to make complicated alcohols easily. In a reaction, a

Grignard reagent, C6H5MgBr reacts with acetone through acidic hydrolysis.
O

C
H3C CH3
(Acetone)

(a) Write a complete equation for the above reaction.

(b) Name the product formed in this reaction.

7.4 NAMING OF ALCOHOL / PHENOL

7.4.1 Give the IUPAC name for the following compounds.

(a) (b)
HO OH

OH

(c) (d)
I

H OH H H OH
F NO2
H C C C C C H

H HO
 (e) (f)
CH3 H OH H
F
H3C C C C C H

H CH3 H HO

HO

(g) (h)
OH

Br

OH

Cl
[Oct 2021]

(i) (j)

OH

OH OH
[Sept 2019] [Sept 2014]

7.5 DRAWING OF ALCOHOL / PHENOL

7.5.1 Draw the structure for the following compounds.

(a) 5-ethylcyclohex-3-en-1-ol

(b) m-chlorophenol

(c) trans-2-bromocyclopentanol

(d) cyclobuta-1,3-dienol [Sept 2016]

 (e) cis-2-methylcyclopentanol

(f) 7,7-dimethyloct-2-ene-2,3,6-triol

(g) 1,2,4-hexanetriol

(h) 3-chlorocyclobutan-1-ol

(i) 2-aminocyclohex-2-enol [Sept 2018]

(j) 5-ethylcyclohex-2-enol [Sept 2022]

7.6 PHYSICAL PROPERTIES

7.6.1 Arrange the following compounds in increasing order of acidity. Explain your answer.

HO
H3C OH Br OH

I II III
[Apr 2017]

7.6.2 4-Chlorophenol is more acidic than 2-methylpentan-1-ol. Explain why. [Apr 2015]

7.6.3 Suggest a chemical test to distinguish each of the following pairs of compounds by
stating the reagent(s) used, condition and expected observation(s). For reactions that
show positive results, write a balanced chemical equation.

(a) Benzene and phenol

(b) Butan-2-ol and pentan-3-ol [Apr 2013]

(c) 2-Methylpropan-2-ol and propanol [Dec2017]

7.6.4 Compare the acid strength of compounds I and II. Explain your answer.

OH OH

NO2

I II
[Dec 2018]

7.6.5 Explain why 1-bromo-1-phenylmethanol is more acidic than 1-cyclohexylethanol.

[Sep 2018]

7.6.6 Arrange following compounds in increasing order of acidity. Explain your answer.

[Apr 2018]
Tutorial 8: Topic 6 Hydroxyl Compounds
8.1 SYNTHESIS OF ALCOHOLS

8.1.1 Complete the following equation(s).

(a)
H O
H2O
MgBr + H3C C C H A + B
H3O+

(b)
OH H
H2SO4
H3C C C CH3 C + D +E
heat
H H

(c)
OH CH3

H2O
H3C MgBr + F H3C C C CH3 + Mg(OH)Br
H3O+
CH3 H

(d)
Cl

CH3CH2CHCH3 + NaOH G + H
reflux

8.2 GRIGNARD REAGENT

8.2.1 The reaction between 2-methyl-3-pentanone and ethyl magnesium bromide in

ether/water will produce a tertiary alcohol, A.

(a) Write the reaction scheme (including the reagent) to produce ethyl magnesium
bromide.

(b) Draw and name the tertiary alcohol A.

(c) Show the synthesis pathway to produce 2-methylpent-2-ene using

2-methyl-3-pentanone as a starting materials. State clearly the reagent(s) and
condition(s) for each steps. [Dec 2015]
8.2.2 Complete the following equations by drawing the product(s) formed.

O
+ H2O/ H+
CH3CH2C H
BrMg [Dec 2017]

8.2.3 Ethane reacts with bromine in the presence of UV-light to form a monosubstituted
product B. When B reacts with magnesium in ether, followed by propanone, an
intermediate product C is formed. C undergoes hydrolysis to form D which reacts
with ethanoyl chloride to produce a pleasant-smelling product E and white fume.
Draw the structures of B, C, D and E. [Dec 2016]

8.2.4. Polystyrene is a synthetic aromatic hydrocarbon polymer made from the monomer
known as styrene.

H H H H

* C C C C *

H H

n
Polystyrene

Show the reaction scheme for the conversion of styrene to 2-phenylpropanoic acid.
Predict clearly the reagent(s) and the condition(s) involved in each step. [Oct 2021]

8.3 REACTIONS OF ALCOHOLS

8.3.1 An organic compound with molecular formula, C4H10O, has four structural isomers of
F, G, H and I in which H and I are branched chain isomers. All the four F, G, H and
I can react with hot concentrated sulphuric acid to produce compounds with
molecular formula of C4H8. F, G and I can decolourise acidified potassium
permanganate. Only G will give yellow precipitate when reacts with aqueous alkaline
iodine at room temperature.

(a) Draw the structures of F, G, H and I respectively.

(b) Write a chemical equation when H reacts with hot concentrated sulphuric acid.
8.3.2 Hydrogenation of compound J, C5H10, gives 2-methylbutane. Compound J also reacts
with hydrogen bromide to give an alkyl halide. When this alkyl halide is hydrolysed,
alcohol K, C5H12O, is produced. Oxidation of compound K by potassium
dichromate(IV) produces compound L, C5H10O, which shows positive iodoform test.
Draw the structures of J, K and L respectively.

8.3.3 Compound M (C4H10O) produced yellow precipitate when heated with iodine and
aqueous solution of sodium hydroxide. Based on the statement, write the structural
formula of M. [Dec 2013]

8.3.4 The following diagram shows the conversion of compound N into compound O.

Show the steps to obtain compound O from compound N, stating clearly the
reagent(s) and reaction condition(s) (if any) in each step.

8.3.5 Write the reaction scheme for the following transformation. State the reagent(s) and
condition(s) for each step.

H3C C CH3 H3C C CH3

Cl O

8.3.6 Show the complete reaction scheme for the following conversion. State the reagent(s)
and condition(s) involved.

2-methylpropanol → 2-methylpropan-2-ol [Dec 2018]

8.3.7 A straight-chain compound P with a molecular formula of C4H10O forms a yellow

precipitate when it undergoes iodoform test. Compound P reacts with ethanoic acid to
produce compound Q and water in the presence of concentrated sulphuric acid.
Compound P also produces compound R (major product) when it is passed over hot
aluminium oxide. In addition, compound R can decolourise the brown colour of
bromine water. Draw the structures for P, Q and R. [Apr 2017]
8.3.8 Compound S is a branched-chain secondary alcohol. It reacts with PBr3 to form
compound T that is optically active. Compound T is further refluxed with water in
ethanol to yield major product U with molecular formula of C5H10. Deduce the
structures of compounds S, T and U. [Sep 2018]

8.3.9 1-Bromoethyl 3-oxobutanoate can be synthesised using 2-methylcyclopropanol. Show

a three-step reaction scheme for the conversion and state the reagent(s) and
condition(s) (if any), for each step.

Br O

O O
1-bromoethyl 3-oxobutanoate [Apr 2021]

8.4 ZAITSEV’S RULE

8.4.1 (a) Draw the structure of product(s) formed from the dehydration of
3-methylpentan-2-ol when it is heated with excess concentrated sulphuric acid.
Label the major and minor products.

(b) Explain Zaitsev’s rule. [Dec 2010]

8.4.2 Draw the structure of product(s) formed from the dehydration of

2,3-dimethylbutan-2-ol when it is heated with concentrated phosphoric acid. Label the
major and minor products.

8.4.3 Complete the following equation(s). Label the major and minor product(s), if any.

(a)
CH2CH3

OH
hot conc. H3PO4

(b)

hot Al2O3

OH
 (c)
OH

hot conc. H2SO4

(d)

hot Al2O3

OH

(e)
OH

hot Al2O3

OH

8.5 TESTS TO DIFFERENTIATE ALCOHOLS / PHENOLS,

TRIIODOMETHANE REACTION

8.5.1 Suggest suitable reagent(s) and condition(s) to differentiate the following pairs of
organic compounds. State the observation(s) for each of the compounds and provide
chemical equation for the reactions that show positive results.

(a) Benzene and phenol

(b) Butan-2-ol and pentan-3-ol [Apr 2013]

(c) 2-Methylbutan-2-ol and 2-methylbutan-1-ol

(d) Methylbenzene and phenol

(e) 1-Methylcyclohexanol and phenol [Apr 2016]

8.6 REACTIONS OF PHENOLS

8.6.1 Complete the following equation(s).

(a)
O

ONa A + B
Cl

(b)
Br

C + D Br OH + 3 HBr

Br

(c)

OH + Na E + F

(d)
O

G + H C O CH2CH3 + HCl

(e)
OH

3 + FeCl3 I + J
Tutorial 9: Topic 7 Carbonyl Compounds
9.1 NAMING OF ALDEHYDE / KETONE

9.1.1 Give the IUPAC name for the following compounds.

(a) (b)
CH2CH3
H

Br
O Cl

H
Br O

(c) (d)
O

CH2CHO

(e) (f)
O

H3C CH3

H O

(g) (h)
O

NH2 H O

H3C C C C H

H2N CH3
[Dec 2016]
 (i) (j)
O

[Sept 2016]

9.2 DRAWING OF ALDEHYDE / KETONE

9.2.1 Draw the structure for the following compounds.

(a) 2,4-dimethylhex-2-enedial

(b) 5-cyclobutyl-5-hydroxypent-3-enal

(c) pentanedial

(d) 2,3-dichloro-3-iodobutanal

(e) 2,2-dimethylhexanedial

(f) trans-2-ethyl-5-methylcyclohex-3-enone

(g) 1,4-diphenylbut-2-ene-1,4-dione

(h) 4-phenylhexan-3-one [Sept 2019]

(i) 3-methylcyclohexa-2,5-dienone

(j) 3,4-diaminohexan-2-one

9.3 PHYSICAL PROPERTIES

9.3.1 You were given three organic compounds with roughly the same molecular mass:

2-methylpentanol, 4-methylpentan-2-one and heptane

Arrange the boiling points of these compounds in ascending order. Explain this trend.
[Apr 2014]

9.3.2 State which compound has the higher boiling point in the following pairs and briefly
explains why.

(a) Pentanal and hexane

(b) Pentanal and 1-pentanol

9.3.3 The boiling points of 2-methylpropene, propanone, and propan-2-ol are −7 °C, 57 °C
and 82 °C respectively. Compare and explain the trend of the boiling points for these
three compounds.

9.4 WRITE CHEMICAL EQUATIONS

9.4.1 Write the balanced chemical equation(s) for the following reaction(s).

(a) 1-Methylcyclobutane-1,3-diol reacts with acidified potassium dichromate

(b) 3-Heptanone reacts with sodium borohydride in ethanol, in the presence of

acid

(c) Butanol reacts with acidified potassium permanganate under reflux

(d) Pentanal reacts with lithium aluminium hydride in ether, in the presence of
acid

9.4.2 Butan-2-ol undergoes oxidation to form compound X which gives positive iodorm
test. Compound X reacts with phyenylmagnesium bromide, followed by hydrolysis to
form compound Y and Mg(OH)Br.

(a) State the expected observation(s) for positive iodoform test.

(b) Write the chemical equation(s) for the formation of compounds X and Y.

(c) Give the IUPAC name for compounds X and Y.

9.4.3 Show the reaction scheme for the following conversion. State clearly the reagent(s)
and the condition(s) involved in each step.

[Sep 2016]
9.5 MECHANISM – NUCLEOPHILIC ADDITION REACTION

9.5.1 Outline the mechanism for the reaction of compound A with hydrogen cyanide, HCN.

H3CH2CH2C C CH3

Compound A
[Apr 2012]

9.5.2 Propanone undergoes reaction with hydrogen cyanide, HCN.

H3C C CH3

(a) Name the type of mechanism for this reaction.

(b) State the main purpose of this reaction.

(c) Show the mechanism for this reaction. [Apr 2015]

9.5.3 Show the complete mechanisms for the base-catalysed hydration of 2-propanone.

9.5.4 An experiment was carried out by reacting cyclopentanone and water in the presence
of potassium hydroxide.
O

Cyclopentanone

(a) Outline the complete reaction mechanism and name the product formed.

(b) State the type of intermediate product formed. [Sep 2019]

9.5.5 Benzaldehyde reacts with hydrogen cyanide to produce a cyanohydrin. Write the
mechanism of the reaction. [Sep 2021]
9.6 PREDICT REACTANTS / PRODUCTS

9.6.1 Complete the following equation(s).

(a)
K2Cr2O7 / H+ OH
A
reflux

(b)
O
H2O / OH−
B

(c)
OH
HCN
C

9.6.2 State the reaction(s), reagent(s) and condition(s) for the following conversion(s).

(a)
OH

O O

(b)
O OH

OH
9.6.3 Identify structures B, C, D and E.

NaBH4
in ethanol
O

KMnO4 / H+ O +
Alkene B
heat

K2Cr2O7 /H+
MgBr

H2O / H+

D E

9.6.4 Identify the structures F, G, H and I.

NaBH4
in
ethanol

H O

KMnO4 / H+ K2Cr2O7 / H+
G H3C C C H H
heat heat
(symmetrical
alkene) H

MgBr H2O / H+

I + Mg(OH)Br

9.6.5 Two compounds, J and K, have similar molecular formula of C3H6O. Both the
compounds give positive results when tested with Brady's reagent. Compound A can
be easily oxidised into L, C3H6O2, whereas compound K can hardly be oxidised.
However, compound K can be reduced to M, C3H8O. Identify the structural formulae
of compounds J, K, L and M, and name them all.
9.6.6 Compound N (C2H4O) which gives positive results for Brady’s test undergo carbonyl
condensation reaction in the presence of NaOH to form O. The optically active
compound O reacts with sodium to produce P and gas Q.

(a) State the condition and observation of positive Brady’s test.

(b) Draw the structures of N, O, P and Q [Apr 2015]

9.6.7 The vapour of 2,4-dimethylpentan-2-ol reacts with hot Al2O3 to form major
compound R. Compound R reacts with hot acidified potassium manganate(VII) to
produce compound S and compound T. Compound T can be further oxidized to
compound U. Deduce the structures of R, S, T and U. [Dec 2017]

9.6.8 Based on the reaction scheme below, draw the structures of V, W, X, Y and Z.

V + NaI + CHI3 + H2O

I2 in NaOH

O
+
KMnO4/H
H3C C C + W
heat
CH3 CH3 CH3CH2MgCl

H2O/H+

OH

H3C C + Y

CH2CH3 O

H
H3C C C Cl

CH3

Z + HCl
[Apr 2018]
9.6.9 The reaction scheme of acetophenone with several reagents is shown below:

OH

(i) Reagent II
(ii) H3O+

O
Reagent I
AlCl3

I2, NaOH
HCN

T R + S + NaI + H2O

(a) Illustrate the structures of R, S and T.

(b) Write the reagents of I and II. [Sep 2021]

Tutorial 10: Topic 7 Carbonyl Compounds + Topic 8 Carboxylic Acid and
Their Derivatives
10.1 SYNTHESIS / CONVERSION – REAGENTS, CONDITIONS, EQUATIONS

10.1.1 An alkene, C6H12, with a methyl branch, produced compounds A and B through
oxidative cleavage whereby both compounds contain 3 carbon atoms each. Both A
and B produced orange precipitates when tested with 2,4-dinitrophenylhydrazine.
Only A decolourized purple colour of acidified potassium permanganate, producing
compound C. B showed positive result for iodoform test. When C is mixed with
ethanol, it produced a sweet-smelling substance, D. Draw the structures of A, B, C
and D. [Sep 2013]

10.1.2 Compound E (molecular formula of C5H10O) reacts with 2,4-dinitrophenylhydrazine

but has no effect on Tollens’ reagent. E reacts with alkaline iodine to give a yellow
precipitate.

(a) State the functional group that is present in E.

(b) Draw all the possible structure(s) of E.

10.1.3 Compound F, C4H8, reacts with hydrogen bromide to form only one product,
compound G, C4H9Br. When aqueous sodium hydroxide is added to G, compound H,
C4H9OH, is formed. Compound H reacts with hot acidified potassium manganate(VII)
to form compound I, C4H8O. Compound I forms orange precipitate with Brady’s
reagent and yellow precipitate with aqueous alkaline iodine. Draw the structural
formulae of F, G, H and I.

10.1.4 In the lab, a test tube containing pentan-2-one and iodine solution is added with
sodium hydroxide solution.

(a) Write a complete equation for the reaction.

(b) State the observation of the reaction.

10.1.5 C, D and E are acyclic isomers with a molecular formula of C4H8O. When
compounds C, D and E react with 2,4-dinitrophenylhydrazine, a yellow precipitate is
formed. Compound D and E give a positive result with silver nitrate in aqueous
ammonia. Sketch the structures of C, D and E. [Sep 2021]
10.2 MECHANISM – CARBONYL CONDENSATION REACTION

10.2.1 Give a chemical equation for the NaOH-catalysed aldol condensation reaction of
2-phenylethanal.

10.2.2 Write a chemical equation for the NaOH-catalysed aldol condensation reaction of
butanal.

10.2.3 Give the chemical equation for NaOH-catalyzed aldol condensation of

3-methylbutanal.

10.2.4 Outline the mechanism for KOH-catalysed carbonyl condensation reaction of

prop-2-enal.
H O

H C C C H

Prop-2-enal [Sep 2014]

10.2.5 Butanal undergoes carbonyl condensation in the presence of sodium hydroxide,

NaOH. Outline the mechanism for the reaction. [Dec 2018]

10.2.6 Outline the mechanism for NaOH-catalysed carbonyl condensation reaction of

pentan-3-one. [Apr 2017]

10.3 CHEMICAL TEST

10.3.1 Suggest suitable reagent(s) and condition(s) to differentiate the following pairs of
compounds. State the observation(s) for each of the compounds.

(a) 3-pentanone and 3-methylpentan-3-ol

(b) pentanal and pentan-3-one

(c) 2-methyl-3-hexanone and 2-methylhexan-1-ol

(d) Pentan-2-one and pentan-3-one [Dec 2014]

(e) Pent-1-en-3-one and pent-3-en-2-one [Dec 2018]

(f) Heptan-3-one and heptan-2-one [Sep 2019]

10.4 NAMING OF CARBOXYLIC ACID / ACID HALIDE

10.4.1 Give the IUPAC name for the following compounds.

(a) (b)
O
O

OH OH
HO

(c) (d)
NH2

HOOC
HOOC

HO OH

(e) (f)

HOOC COOH Cl COCl

(g) (h)
O
OH O
Br C Br
F
H H F

(i) (j)
Br O

OH C I
O
10.5 DRAWING OF CARBOXYLIC ACID / ACID HALIDE

10.5.1 Draw the structure for the following compounds.

(a) 3-iodo-2-methylbutanoic acid

(b) 4-ethylhexa-2,4-dienoic acid

(c) 3-methylcyclobut-2-enecarboxylic acid

(d) 3-chloro-6-hydroxycyclohexane-1,2-dicarboxylic acid

(e) 4-ethyl-4-phenylhexanoic acid [Apr 2014]

(f) cis-2-chlorocyclopropanecarbonyl chloride

(g) Hexanoyl bromide

(h) 4-aminobut-2-enoyl chloride

(i) cis-cyclopent-4-ene-1,3-dicarbonyl dichloride

(j) 3-cyclopropyl-2,4-diiodopentanoyl bromide

10.6 PHYSICAL PROPERTY - ACIDITY

10.6.1 4-Methylbenzoic acid is more acidic than butanoic acid. Explain why.

OH
O

O OH
4-methylbenzoic acid butanoic acid [Apr 2014]

10.6.2 4-Chlorobenzoic acid is more acidic than 2-methylpentan-1-ol. Explain why.

OH

Cl

O HO

4-chlorobenzoic acid 2-methylpentan-1ol [Apr 2015]

10.6.3 You are given two carboxylic acids, ethanoic acid and butanoic acid. State which
compound is more acidic. Explain.
10.6.4 2-Bromo-2-phenylethanoic acid is more acidic than 2-methyl-2-phenylpropanoic acid.
Explain this statement. [Sep 2016]

10.6.5 Compare the boiling points of the compounds below and briefly explain your
answers.
2,3-Dimethylpentanoic acid and 2,3-dimethylpentanol
[Sep 2021]
Tutorial 11: Topic 8 Carboxylic Acid and Their Derivatives
11.1 NAMING OF ESTER / CARBOXYLIC SALT / ANHYDRIDE

11.1.1 Give the IUPAC name for the following compounds.

(a) (b)
O
O OH

O
O

[Sept 2018] [Sept 2021]

(c) (d)
O Br

O Cl
O

O Cl Br

(e) (f)
CH3 O
O
C C O-K+

CH3 HO O-K+

(g) (h)
H3C Cl

O
O-Na+

C ONa

(i) (j)
O O
O

O
O

O
 (k) (l)

O
O

O O O
[Sept 2021]

11.2 DRAWING OF ESTER / CARBOXYLIC SALT / ANHYDRIDE

11.2.1 Draw the structure for the following compounds.

(a) 3-aminocyclopentyl 3-aminopropanoate

(b) phenyl 2-phenylethanoate

(c) 2-methylbutyl 3-hydroxyproponoate

(d) butyl 3-bromobenzoate [Apr 2019]

(e) sodium 2-bromopent-2-enoate

(f) potassium 2-phenylethanoate

(g) potassium 3-chlorohexanoate

(h) sodium 4-methylpenta-2,4-dienoate

(i) ethanoic propanoic anhydride [Apr 2016]

(j) benzoic anhydride

(k) but-2-enoic anhydride

(l) 2-methylbutanoic 2-methylcyclobutanecarboxylic anhydride

11.3 PHYSICAL PROPERTIES

11.3.1 Boiling point of sodium butanoate is higher than butanol. Explain why. [Dec 2016]
11.3.2 Arrange the boiling points of the following compounds in increasing order. Explain
your answer.
O O O

H3CH2CH2C C O-Na H3CH2C C O CH3 H3CH2CH2C C OH

Sodium butanoate Methyl propanoate Butanoic acid
[Sept 2013]

11.3.3 The following temperatures are the boiling points for the organic compounds in table
below.

117.7 °C, 163.5 °C, −1°C

Organic compound Boiling point (°C)

Butanol
Butane
Butanoic acid

(a) Copy and complete the table by matching the boiling points to the organic
compounds.

(b) Explain your answer in (a) in terms of intermolecular forces of the

compounds.

(c) Compare and explain the solubility of butanoic acid and butanol in water.
[Apr 2019]

11.4 WRITE CHEMICAL EQUATIONS

11.4.1 Write a chemical equation for the reaction of propanoic anhydride with water.

11.4.2 Write an equation for the preparation of propyl butanoate using acid chloride.

11.4.3 Write the equations for the preparation of the following esters using an acid chloride.

(a) methyl propanoate

(b) cyclopentyl benzoate

11.4.4 Give the balanced equations for the hydrolysis of ethyl benzoate, using:

(a) NaOH

(b) H2O / HCl

11.4.5 Write the chemical equations for the reaction of compound A with:

H3CH2CH2CH2C C O CH3
Compound A

(a) Diluted acid, H+(aq), and

(b) Sodium hydroxide.

(c) Name the type of reaction in (a) and (b). [Apr 2014]

11.4.6 Ethanoyl chloride produces sweet-smelling compound D when reacts with propanol.
Write a balanced chemical equation for the reaction and name compound D.
[Dec 2018]

11.5 SUGGEST REAGENTS / CONDITIONS

11.5.1 Suggest suitable reagent(s) and condition(s) to differentiate the following pairs of
organic compounds. State the observation for each of the compounds and provide a
chemical equation for the reaction that shows positive result.

(a) Propanoyl chloride and propanoic acid [Dec 2010]

(b) 2-methyl-3-pentanone and 2-methylpentanoic acid [Dec 2016]

(c) Hexanoic acid and hexanoyl bromide [Sep 2015]

11.5.2 Structural formula shown below is cinnamic acid, which is found in cinnamon bark.

HO

Cinnamic acid
(a) Draw the structure of the product formed when cinnamic acid is refluxed with
propanol in the presence of concentrated acid.

(b) In an experiment, a chemist added cinnamic acid to the aqueous sodium

carbonate in a beaker. Predict weather any reaction will occur between these
two substances. State the observation (if any) and explain your answer.
[Sep, 2021]
11.6 REACTION SCHEME – PREDICT REACTANTS / PRODUCTS

11.6.1 Complete the following equation(s).

(a)
O

A + B H3CH2C C N CH3 + CH3CH2OH

(b)
O CH3
Conc. H2SO4
C+ D H3CH2C C O C C2H5 + H2O
heat

CH3

(c)
O
O
E+ F H C O +
HO C H

(d)

CH3CH2NH2
O G + H
(Neutral) (Amphoteric)
O
[Dec 2015]

(e)
O

+ HCl I + J
- +
O Na

(f)
O

+ CH3NH2 K + L

Cl
 (g)
O
H2O
M + HCl

OH

(h)
O
NH3
N + CH3OH
NH2

11.6.2 Based on the reaction scheme below,

NaOH CH3NH2 + CH3CH2OH

CH3CH2OH + M L N

(i) CH3CH2OH
(ii) conc H2SO4 heat
COOH

O
Reagent I
Alcohol J CH2CH3 C OH K + H2O

Reagent II

(a) identify the reagents I and II.

(b) draw the structures of J, K, L, M and N.

11.6.3 Compound R C2H3OCl, forms a yellow precipitate when tested with alkaline iodine
solution. When compound R reacts with water, it forms compound S and a white
fume is released. When ethanamine, CH3CH2NH2, is mixed with compound R, it
forms compound T, which forms an acidic substance, U when boiled in hydrochloric
acid, HCl. Draw the structures of R, S, T and U. [Sept 2014]

11.6.4 An acyl halide, C2H3OBr reacts with compound V to form an ester, W. Compound V
forms purple colouration when tested with iron(III) chloride, FeCl3 solution.
Compound W reacts with ammonia, NH3 to produce nitrogen-containing compound
X. Draw the structures of V, W and X. [Dec 2016]
Tutorial 12: Topic 9 Amines and Amides
12.1 NAMING OF AMINE / AMIDE

12.1.1 Give the IUPAC name for the following compounds.

(a) (b)
NH2
H
N

O
Br
[Dec 2012]

(c) (d)
H N(CH3)(Cl)

N
Cl O

(e) (f)
CON(CH3)2

N
H

(g) (h)

NH2
N

Cl Cl
[Dec 2019] [Sept 2016]

(i) (j)
O
NH2

NH2 N
H

[April 2016]
12.2 DRAWING OF AMINE / AMIDE

12.2.1 Draw the structure for the following compounds.

(a) 2-ethyl-N,N,4-trimethylcyclobutanamine

(b) 3-iodo-5-methylhex-4-en-2-amine

(c) N,N,3-trimethyl-5-propylcyclohexanamine

(d) Pentane-3,3-diamine

(e) N,4-dimethylpent-3-en-2-amine

(f) N-cyclopropylpenta-2,4-dienamide

(g) N,3-dimethylbenzamide

(h) N,3-dimethylpent-2-enamide

(i) 4-nitrobenzamide

(j) N-methylpent-3-enamide [Sept 2022]

12.3 PHYSICAL PROPERTY – BASICITY

12.3.1 Rank the following compounds in decreasing order of basicity. Explain your answer.

NH2

CH3

CH3CH2NH2 H3CH2C N H

I II III [Dec 2016]

12.3.2 Based on the compounds below, arrange them in the order of increasing basicity and
explain your answer.

Butanamine l-bromobutanamine heptanamine

12.3.3 Based on the compounds below, arrange them in the order of increasing basicity and
explain your answer.

Ethanamine l-fluoroethanamine propanamine

12.3.4 Rank the following compounds in decreasing order of basicity. Explain your answer.

NH2 NH2

H C N H

H H

OH NO2
I II III
[Sept 2013]

12.4 SYNTHESIS / WRITING CHEMICAL EQUATIONS

12.4.1 Show the synthesis pathway to convert benzene into benzamide.

12.4.2 Phenylamine is an aromatic amine. It has the reactions of the amine group and the
benzene ring. The structural formula of phenylamine is shown as below:

NH2

Write the equations for the reactions between phenylamine and the following
compounds:

(a) Hydrochloric acid

(b) Aqueous bromine [Sept 2011]

12.4.3 Write chemical equation(s) for the following reactions:

(a) Synthesis of propanamine from propanoic acid

(b) Synthesis of pentanamide from pentanoyl chloride

12.4.4 Show the synthesis pathway needed to produce 2-phenylethanamine using

methylbenzene as starting material, state clearly the reagent(s) and reaction
condition(s) for each step. [Sept 2014]
12.4.5 Show the reaction scheme for the following conversion. State the reagent(s) and
condition(s) (if any) for each step.
CH2NH2

[Dec 2018]

12.4.6 2,2–Dimethylbutan-1-amine can be prepared from 2-methylbut-2-ene in three steps.

Predict clearly the reagent(s) and reaction condition(s) for each step. [Sept, 2021]

12.5 CHEMICAL TESTS

12.5.1 Suggest suitable reagent(s) and condition(s) to differentiate the following pairs of
compounds and state the expected observation(s).

(a) 2-Aminobutanol and 2-methylbutanol

(b) Phenylamine and 1-phenylmethanamine

(c) Propan-1-amine and propanone

(d) Cyclohexene and cyclohex-1-enamine [Dec 2018]

(e) Pentanamide and pentanamine

12.5.2 Suggest ONE (1) suitable chemical test to differentiate these two compounds. State
the reagent(s), condition(s) and expected observation(s) for each compound. Provide
the chemical equation for the reaction that shows positive result.

[Sep 2020]
12.6 REACTION SCHEME / PREDICT REACTANTS / PRODUCTS

12.6.1 Based on the diagram below, draw the structures of P, Q, R and S.

dilute HCl
C NH2 R + NH4Cl

1. LiAlH4 / ether S
2. H3O+

O
Q P
HCl
C N CH2CH3 + H2O

12.6.2 An acyl bromide, J and compound K reacts to produce 2-methylpropanamide as

shown below. Compound L and salt M are formed when 2-methylpropanamide is
boiled with hydrochloric acid.

NH2

2-methylpropanamide

(a) Draw the structures of compounds J, K and L.

(b) Name the salt M. [Dec 2014]

12.6.3 Compound X which has a molecular formula of C3H9N reacts with nitrous acid to
produce compound Y and nitrogen gas. Y on oxidation produces Z, which reacts with
2,4- dinitrophenylhydrazine but not with Tollen’s reagent. Give structural formulae
for X, Y and Z.

12.6.4 Compound X, molecular formula, C8H9NO, heated with dilute sodium hydroxide, an
oily compound Y and sodium ethanoate are formed. Y decolorizes aqueous bromine at
room temperature and forms a white precipitate Z. Suggest a possible structure of
compounds X to Z. Write down the equations involved.
12.6.5 Identify A and B.

O
SOCl2/ NH3 1. LiAlH4/ether
C OH A B
2. H2O

12.6.6 Compound M is a monosubstituted benzene with molecular formula of C7H9N. It

reacts with hydrocholic acid to form compound N which is a white crystalline salt.
Compound M aslo reacts with nitrous acid to yield compound O, nitrogen gas and
water. Deduce the structures of compounds M, N and O. [Sep 2019]

12.6.7 Based on the diagram below:

NH3
1. LiAlH4/ether C
U V NH2
2. H2O
H
Boiled
H2O with HCl

HNO2

W + NH4Cl

O
X + Y + H2O

C
+ HCl
OH

O
H CH3
C
N C C CH3 + H2O

H H H

(a) Identify Y which is a colourless, odourless and tasteless diatomic gas.

(b) Draw the structures of U, V, W, X and Z. [Apr 2016]

12.6.8 Based on the reaction scheme below, sketch the structure of K, L, M, N and O.

AlCl3
+ K
Cl
O

NH

M + HCl + L + HCl

Boiled with HCl

N + O
[Sept 2021]