2023 JC2 H1 CHEMISTRY (8873)

Revision: Introduction to Organic Chemistry, Alkanes, Alkenes

Name: ___________________________________________ Civics Group: _________

Learning Outcomes
Students should be able to:
(a) interpret, and use the nomenclature, general formulae and structural formulae (including displayed
formulae) of the following classes of compounds: (i) hydrocarbons (alkanes, alkenes and benzene) (ii)
halogenoalkanes (iii) alcohols (including primary, secondary and tertiary) (iv) aldehydes and ketones (v)
carboxylic acids (vi) esters (vii) amines (viii) amides
(b) interpret, and use the following terminology associated with organic reactions:
(i) functional group
(ii) addition, substitution, elimination
(iii) condensation, hydrolysis
(iv) oxidation and reduction [in equations for organic redox reactions, the symbols [O] and [H] are
acceptable]
(c) describe constitutional (structural) isomerism
(d) describe cis-trans isomerism in alkenes, and explain its origin in terms of restricted rotation due to the
presence of π bonds [use of E, Z nomenclature is not required]
(e) deduce the possible isomers for an organic molecule of known molecular formula
(f) (i) describe the shapes of the ethane, ethene and benzene molecules
(ii) explain the shapes of, and bond angles, in the ethane, ethene and benzene molecules in relation to σ
and π carbon-carbon bonds
(iii) predict the shapes of, and bond angles in, molecules analogous to those specified in (f)(ii)
(g) describe the chemistry of the following classes of compounds:
(i) alkanes (exemplified by ethane) as being generally unreactive except in terms of combustion and
substitution by chlorine
(ii) alkenes (exemplified by ethene) in terms of combustion and addition reactions with bromine (in CCl4)
and hydrogen
 H1 Revision : Introduction to Organic Chemistry

1. Bonding in Organic Molecules 3. Common Functional Groups

Around each C atom… Shape Angle Functional
Structure Prefix Suffix
Group
4 single bonds 4  bonds Alkane ─ ─ -ane
Ethane Tetrahedral 109.5o
No double bond No  bond
Alkene ─ -ene

Arene -phenyl -benzene

2 single bonds 3  bonds Trigonal
Ethene 120o
1 double bond 1  bond planar fluoro-;
chloro-
Halogenoalkane ─
1 single bond bromo-
3  bonds Trigonal
Benzene 2 partial double 120o where X = F, Cl, Br, I iodo-
2  bonds planar
bonds
Alcohol hydroxy- -ol
2. Representing Organic Compounds
Type of formula Representation of lactic acid
Aldehyde formyl- -al
Empirical Formula
CH2O
(shows simplest ratio of atoms of each element)
Molecular Formula Ketone oxo- -one
C3H6O3
(shows actual number of atoms of each element

Structural Formula Amine amino- -amine

OR CH3CH(OH)CO2H
(shows how atoms are bonded to one another

Full Structural or Displayed Formula

(shows in detail how atoms are bonded to one Amide ─ -amide
another)

Carboxylic acid ─ -oic acid

Skeletal Formula
(shows only carbon skeleton and functional
Ester ─ -oate
groups

4. Naming Organic Compounds 1. Find the longest carbon chain and name this as an alkane. This is the parent name.
2. Identify the major functional group. Replace –ane (in the alkane) with a suffix
3. Number the atoms in the main chain. Begin at the end nearer the major functional group and give this the lowest number. For
alkanes, begin at the end nearer the first branch point.
4. Identify the substituents (e.g. minor functional groups) on the main chain and their number. The substituent name and position is
the prefix

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 H1 Revision : Introduction to Organic Chemistry

5. Organic Reactions

(a) Addition: A + B → A−B (d) Condensation: A−H + B−OH → A + B + H2O

e.g. Addition of alkenes e.g. Esterification

(b) Substitution: A−B + C−D → A−C + B−D (e) Hydrolysis: A−B + H2O → A−H + B−OH
e.g. Substitution of halogenoalkanes e.g. Hydrolysis of esters

(c) Elimination: A−B → A + B

e.g. Elimination of halogenoalkanes (f) Oxidation: Increase in oxygen and/or decrease in hydrogen
e.g. Oxidation of aldehydes

(g) Reduction: Decrease in oxygen and/or increase in hydrogen

e.g. Reduction of aldehydes

6. Isomerism
Isomers are molecules that have the same molecular formula but different arrangement of the atoms in space.
(a) Constitutional (structural) isomers are isomers with the same molecular formula but different structural formula.

(b) Cis-trans isomers are isomers that arise when there are 2 different substituents attached to each of the two carbon atoms of a C=C bond, due to its restricted rotation.
Note: cis-trans isomerism is not possible for cycloalkenes with ring size smaller than eight carbon atoms.

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 H1 Revision : Introduction to Organic Chemistry

1 Plastic food containers that are safe to use in the microwave oven are often made of poly(propene).
Poly(propene) is a polymer made up of many monomers called propene. Propene, C3H6, has the structure
shown below.

Which of the following correctly describes the numbers of σ and π bonds present in a molecule of propene?

𝛔 𝛑
A 2 1
B 1 8
C 1 2
D 8 1

CJC/20/1/11

2 The C2H2 molecule is linear.

What can be deduced from this about the numbers of σ and π bonds present in the molecule?

σ π
A 2 2
B 2 3
C 3 1
D 3 2
NJC18/1/6

3 Which compound does not have the same bond angle about all of its carbon atoms?

A benzene
B methanoic acid
C 2-ethylpentan-2-ol
D 2-bromopropene
NYJC18/1/23

4 Which of the following statements about prop-1,2-diene, H2C=C=CH2, is not correct?

A Only two of the carbon atoms have the shape of trigonal planar.
B The two π-bonds in prop-1,2-diene are perpendicular to each other.
C There are only six σ-bonds in a prop-1,2-diene molecule.
D Prop-1,2-diene is a planar molecule.
VJC18/1/10

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 H1 Revision : Introduction to Organic Chemistry

5 Progesterone is a hormone which is involved in menstrual cycle and pregnancy. The following structure
shows one molecule of progesterone.

What is the molecular formula for the progesterone hormone?

A C19H14O2 B C19H22O2 C C20H30O2 D C21H30O2

CJC18/1/28

6 Which structure correctly represents 4-chloro-3-hydroxybutanoic acid?

A B

C D

IJC18/1/22

7 What is the skeletal formula of 2,4,4-trimethylhexane?

A B

C D

RI18/1/21

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 H1 Revision : Introduction to Organic Chemistry

8 Terfenadine is an antihistamine formerly used for the treatment of allergic conditions.

The structure of terfenadine is shown below:

Which functional group is not present in terfenadine?

A amine
B tertiary alcohol
C secondary alcohol
D phenol
CJC18/1/27
9 Compound E has a straight−chain structure with a molecular formula of C5H8O.

Which functional groups may be present in any of the isomers of compound E?

1 Alcohol
2 Aldehyde
3 Ester

A 1, 2 and 3
B 1 and 2 only
C 1 only
D 2 only
NYJC18/1/21

10 How many structural isomers can C4H9Cl form?

A 3 B 4 C 5 D 6
NJC/18/1/23

11 Which one of the following structural formulae exists in both cis and trans forms?
A CH2=CHCl
B cyclohexene
C CHCl=C(CH2CH3)2
D CH3CH=CHCl
CJC/21/1/24

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 H1 Revision : Introduction to Organic Chemistry

12 Ethene can be formed from bromoethane in two steps.

C2H5Br C2H5OH C2H4

Which statements about these steps are not correct?

1 Step R involves substitution.

2 Step S involves elimination.
3 C2H4 is able to exhibit cis-trans isomerism.

A 1 only C 1 and 2 only

B 3 only D 1, 2 and 3

ACJC/21/1/28 (modified)

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 H1 Revision : Alkanes

1. Introduction 2. Reactions of alkanes

• Alkanes are saturated
hydrocarbons
• General formula:
▪ Straight chained alkanes:
CnH2n+2
▪ Cycloalkanes: CnH2n
Alkanes are generally unreactive because:
• C–C bond and C–H bond are strong (i.e. requires a lot of energy to break) and non-polar (i.e. does not attract nucleophiles or
electrophiles)
• No lone pairs in alkane molecules; all valence electrons and orbitals of carbon (i.e. 2s and 2p) are used in bonding no empty low
lying orbitals available to form dative bonds with molecules and ions
(a) Combustion
Complete Combustion Incomplete combustion
Occurs in excess oxygen or normal air Occurs in a limited supply of oxygen
CO2(g) and H2O(l) produced CO(g), H2O(l) and sometimes, C (soot) is produced
General equation: CnH2n+2 + 3n + 1 O2 → nCO2 + (n+1)H2O
No general equation
2
Non-sooty flame Sooty flame

(b) Free Radical Substitution (Halogenation)

R1 R1
uv light
R2 C H + X2 R2 C X + HX

R3 R3
• Reagents and conditions: Cl2(g) or Br2(l), in the presence of UV light
• Reactivity of halogens with alkanes decrease down Group 17
o Hr =  B.E. ( bonds broken ) −  B.E.(bonds formed ) = B.E.(C - H) + B.E.( X - X) − B.E.(C - X) − B.E.(H - X )
Halogen, X2 Hr / kJ mol 1 Description of FRS reaction rate
F2 −479 Highly exothermic and difficult to control.
Cl2 −117
Exothermic with the reactivity of Cl2 being more than that of Br2.
Br2 −43
Endothermic and generally unreactive
I2 +22
(due to weak C−I and H−I bonds formed)

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 H1 Revision : Alkanes

1 Which statement is correct regarding alkanes?

A They undergo substitution reactions.

B The carbon atoms in alkanes are sp2 hybridised.
C They are generally unreactive due to the polar C–H bond.
D Propane reacts with chlorine gas to give three different mono–substituted products.
DHS18/1/18

2 2-phenylethylamine is the 'feel-good' factor in chocolate. It can be synthesised from benzene in the
following sequence.

Which set of information is true of the steps in the sequence?

I II III IV
Type of reaction Reagents and conditions Type of reaction Type of reaction
A substitution Br2, uv light substitution reduction
B substitution HBr, heat addition addition
C addition Br2, uv light substitution reduction
D addition HBr, heat addition addition

CJC/21/1/23

3 (CH3CH2)3CH can react with chlorine under UV light to produce monochloro-compounds.

How many possible constitutional isomers of monochloro-compounds can it produce?

A 2 B 3 C 6 D 7
NYJC18/1/24

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 H1 Revision : Alkanes

4 An alkane Z is reacted with chlorine gas in the presence of ultraviolet light to form two monochlorinated
alkanes in an approximate molar ratio of 3 : 1.

Which of the following is a possible structure for Z?

CH3 CH3

A H C CH3 C H C CH3

H CH3

CH3 CH3 CH3 CH3

B H3C C C CH3 D H C C CH3

H H H H
NJC17/1/20

5 Compound E, C4H10, reacts with chlorine gas in the presence of light to form two monochlorinated alkanes,
F and G, in an approximate molar ratio of 2 : 3.

What are the structures of E and F?

E F

A CH3CH(CH3)CH3 CH3CH(CH3)CH2Cl

B CH3CH(CH3)CH3 CH3CCl(CH3)CH3

C CH3CH2CH2CH3 CH3CH2CHClCH3

D CH3CH2CH2CH3 CH3CH2CH2CH2Cl
IJC18/1/24

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 H1 Revision : Alkenes

1. Introduction 3. Reactions of alkenes

• Alkenes are unsaturated hydrocarbons (a) Combustion
• General formula: CnH2n 3n
Cn H2 n + O 2 → nCO 2 + nH2 O
2

2. Preparation of alkenes (b) Reduction (Catalytic Hydrogenation)

(a) Cracking of alkanes (industrial method)

(b) Elimination of H2O

(c) Electrophilic addition of X2 in inert solvent (e.g. CCl4)

(c) Elimination of HX ▪ Can be used as test for unsaturation (i.e. presence of C=C)
o Test: Bubble compound into Br2 in CCl4 at room temperature (no light or in the dark)
o Observation: Orange-red colour of Br2 in CCl4 is rapidly decolourised

(d) Electrophilic addition of HX

▪ Markovnikov’s Rule: The + positive end of the reagent (e.g. H of H–Br or I of I-Cl) adds to the C of the
C=C in the unsymmetrical alkene that has a greater number of hydrogen atoms directly attached.
▪ Order of reactivity of HX is HI > HBr > HCl as H–X bond becomes weaker down the group

(e) Electrophilic addition of X2(aq)

▪ Markovnikov’s Rule: The Br adds to the C of the C=C in the unsymmetrical alkene that has a greater
number of hydrogen atoms directly attached.
▪ Can be used as test for unsaturation (i.e. presence of C=C)
o Test: Bubble compound into Br2(aq) at room temperature (no light or in the dark)
o Observation: Orange colour of Br2(aq) is rapidly decolourised

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 H1 Revision : Alkenes

Summary of Alkene Reactions

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 H1 Revision : Alkenes

1 When one ethene molecule reacts with one bromine molecule by electrophilic addition, how many bonds
are broken and formed?

number of 𝜎 bonds number of 𝜋 bonds number of 𝜎 bonds number of 𝜋 bonds

broken broken formed formed
A 1 1 2 0
B 0 1 2 0

C 1 0 0 2
D 1 1 0 2
DHS18/1/30

2 Which compound could not be formed by the action of bromine on an alkene of molecular formula C5H10?

Br

A C

Br
Br Br
Br

B D
Br Br
Br
NJC17/1/18

3 How many different alkenes, including cis-trans isomers, could be produced when 3-methylpentan-2-ol
reacts with excess concentrated sulfuric acid at 170 oC?

A 2
B 3
C 4
D 5
IJC/18/25

4 How many different alkenes, including cis-trans isomers, could be produced when
CH3CH2C(CH3)BrCH2CH2CH3 is treated with hot ethanolic KOH?

A 2 C 4
B 3 D 5
RI18/1/23

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 H1 Revision : Alkenes

5 Limonene is an oil formed in the peel of citrus fruits.

Which product is formed when an excess of bromine, Br2(l) reacts with limonene at room temperature in
the dark?

NJC18/1/25

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