Topic

Chemistry of Carbon
Compounds

Unit 29 An introduction to the chemistry of carbon

compounds
Unit 30 Isomerism
Unit 31 Typical reactions of selected functional
groups
Unit 32 Synthesis of carbon compounds
Unit 33 Important organic substances

Key

C o ncepts

An introduction to the chemistry

of carbon compounds
Homologous series
Systematic naming
Effects of functional groups and chain
length on physical properties

Chemistry of
Carbon Compounds

Isomerism
Structural isomerism chain
isomerism, position isomerism and
functional group isomerism
Stereoisomerism geometrical
isomerism and enantiomerism

Synthesis of carbon compounds

Synthetic routes for carbon
compounds
Preparation of simple carbon
compounds

Typical reactions of selected

functional groups
Reactions of alkanes, alkenes,
haloalkanes, alcohols, aldehydes,
ketones, carboxylic acids, esters and
amides

Important organic substances

Aspirin
Soaps and soapless detergents
Nylons and polyesters
Carbohydrates
Lipids
Proteins

Topic 8

Unit 29 An introduction to the chemistry of carbon compounds

Chemistry of Carbon Compounds

Unit 29

An introduction to the chemistry of carbon

compounds

29.1 29.12 & 29.21

Summary

29.1

The value of medicines: longer and healthier lives

29.2

Functional groups: centre of reactivity

29.3

Naming alkanes and alkenes

29.4

Naming carbon compounds with one type of functional

group

29.5

Naming haloalkanes

29.6

Naming alcohols

29.7

Naming aldehydes and ketones

29.8

Naming carboxylic acids

29.9

Naming esters

29.10 Naming amides

1 The following table summarizes the nomenclature of compounds in various

homologous series.
Homologous
series

General
formula

Functional
group it
contains

Alkanes

CnH2n+2

Alkenes

CnH2n

add appropriate
prefix to ane

X
Haloalkanes

RX

(X = F, Cl,
Br or I)

Alcohols

ROH

OH

Aldehydes

RCHO

Ketones

RCOR1

Carboxylic
acids

RCOOH

29.11 Naming amines

29.12 Naming compounds with more than one type of functional
group
29.13 Intermolecular forces and physical properties of carbon
compounds
29.14 Physical properties of haloalkanes
29.15 Physical properties of alcohols

29.17 Physical properties of carboxylic acids

29.18 Physical properties of esters

29.21 Common names of carbon compounds

O
C

OH

O
Esters

RCOOR1

Amides

RCONH2
(unsubstituted)

Amines

RNH2
(primary)

O
C

add the name

of halogeno
functional group
as prefix to the
corresponding
alkane

replace the last

letter e of the
corresponding
alkane with al
replace the last
letter e of the
corresponding
alkane with one

29.19 Physical properties of amides

29.20 Physical properties of amines

replace ane of
the corresponding
alkane with ene

Example
Structural formula

replace the last

letter e of the
corresponding
alkane with oic
acid
the name consists
of two separate
words, the first
word comes from
the alcohol, the
second word
comes from the
acid
replace the oic
acid ending of
the corresponding
acid by amide
replace the last
letter e of the
corresponding
alkane with
amine

IUPAC name

CH3
2-methylbutane

CH3CHCH2CH3

CH3CH

propene

CH2

Cl
CH3

replace the last

letter e of the
corresponding
alkane with ol

29.16 Physical properties of aldehydes and ketones

Nomenclature

CH

CH3

CH3CH2OH

2-chloropropane

ethanol

O
C

CH3CH2

propanal

O
C

CH3

propanone

CH3

O
OH

CH3CH2CH2

O
CH3

butanoic acid

methyl

CH3

ethanoate

O
CH3

CH3NH2

NH2

ethanamide

methanamine

Topic 8

Unit 29 An introduction to the chemistry of carbon compounds

Chemistry of Carbon Compounds

2 Sometimes there is more than one functional group in one compound. This kind
of compound should be named according to the following order of precedence of
functional groups:
COOH > COO > CONH2 > CHO > CO > OH > NH2 > C=C

Example
Give the IUPAC names of the following compounds.
a)

CH2COOH

(1 mark)

Exam tips

The longest continuous chain containing the carbon bearing the OH

group may NOT appear in a straight line. Questions often ask about
the names of such structures.

b)

O
CH3

(1 mark)

CH2CH(CH3)2

3,4

C2H5

H3C

CH3

OH
2-methylbutan-2-ol

c) CH3CH=CHCH2OH

(1 mark)

d) CH3CH(NH2)CH2COOH

(1 mark)

Answer
a) phenylethanoic acid

(1)

DO NOT spell amine as ammine.

b) 2-methylpropyl ethanoate

(1)

c) but-2-en-1-ol

(1)

DO NOT confuse amine and amide.

d) 3-aminobutanoic acid

(1)

The general formula of primary amine is RNH2, while that of amide is

(H or R)CONH2.
Students may need to identify the functional groups present in unfamiliar
compounds.
e.g.
O
CH2CH3

for (a), the

group is a phenyl group. It is attached to the ethanoic

acid.

O
C

Remarks*
Remarks

CH2CH3

(b)

O
CH3

CH
CH3CH2

O
O

NH2

CH3

C=C bond;
amide functional group;
amine functional group; and
ester functional group.

CH2CH(CH3)2

(c) The double bond takes the form -en-.

(d) COOH is the principle functional group. The NH2 group is named
as a prefix.

oseltamivir
Besides the ether linkage, functional groups present in oseltamivir
include:

this part comes

this part comes from
from ethanoic acid 2-methylpropan-1-ol

NH
C

29.13 29.20
Summary
1 The physical properties (e.g. the boiling point and water solubility) of a carbon
compound are affected by
a) the functional group it contains;
b) the length of the carbon chain in molecules.

Topic 8

Unit 29 An introduction to the chemistry of carbon compounds

Chemistry of Carbon Compounds

2 The following table summarizes the physical properties of members of some

homologous series.
Homologous
series

Intermolecular forces

Physical properties

permanent dipole-permanent dipole

attractions between molecules

boiling points higher than those of

alkanes of similar relative molecular
masses

CH3

Cl

+
+

Haloalkanes

CH3

CH3

Cl

Homologous
series

Intermolecular forces

Physical properties

permanent dipole-permanent dipole

attractions between molecules

boiling points higher than those of

alkanes of similar relative molecular
masses

CH3

CH3
+

Cl

CH3

polar molecules can interact with

water molecules

slightly soluble in water

hydrogen
molecules

boiling points much higher than

those of alkanes of similar relative
molecular masses

bonding

between

Aldehydes
and
ketones

CH3

hydrogen bonding between aldehyde

/ ketone molecules and water
molecules
H

aldehydes and ketones with less

carbon atoms show appreciable water
solubility

C
H3C

CH2CH3

CH3

key:

hydrogen bond

key:

hydrogen bonding between

molecules; more extensive than that
in alcohols

hydrogen bond
hydrogen bonding between alcohol
molecules and water molecules
H
H

alcohols with less carbon atoms

are miscible with water in all
proportions

O
CH3

alcohols with a long carbon chain in

their molecules are much less soluble
in water

C
O

boiling points higher than those of

alcohols of similar relative molecular
masses

CH3

key:
hydrogen bond

hydrogen bonding between acid

molecules and water molecules

H
O
H

hydrogen
bond

O
CH3

C
H

H
H

Carboxylic
acids

key:

O
CH3CH2

permanent dipole-permanent
dipole attraction

CH3CH2

key:

permanent dipole-permanent
dipole attraction

Alcohols

CH3

key:

CH3CH2

CH3

key:
hydrogen bond

the first four acids are miscible with

water in all proportions

Unit 29 An introduction to the chemistry of carbon compounds

Chemistry of Carbon Compounds

permanent dipole-permanent dipole

attractions between molecules

boiling points are about the same as

those of aldehydes and ketones of
similar molecular masses

hydrogen bonding between ester

molecules and water molecules

simple esters are very soluble in

water

Homologous
series

Intermolecular forces

Physical properties

hydrogen bonding between molecules

of primary amines; hydrogen bonding
less strong than that in alcohols

boiling points of primary amines

higher than those of alkanes but
generally lower than those of alcohols
of similar relative molecular masses

Physical properties

O
H

Intermolecular forces

Homologous
series

Topic 8

O
CH3CH2
O

CH2CH3

key:

bonding

between

key:

Amines

hydrogen bond
hydrogen
molecules

CH3

Esters

hydrogen bond
hydrogen bonding between
primary amine molecules and water
molecules

boiling points are high

primary amines with less carbon

atoms are very soluble in water

H
O

CH3

10

O
hydrogen bond

C
N

Exam tips

key:

Amides

key:

O
CH3

e.g.

hydrogen bond
hydrogen bonding between amide
molecules and water molecules
O
H

Questions may ask students to arrange carbon compounds in order of

increasing boiling point.

simple amides are very soluble in

water

CH3(CH2)2CH3 < CH3(CH2)3CH3 < CH3(CH2)3Cl < CH3(CH2)3OH

Attractions
between
molecules

weak instantaneous dipoleinduced dipole attractions

permanent dipolepermanent dipole

attractions

hydrogen
bonds

The following carbon compounds are miscible with water:

methanol, ethanol and propan-1-ol;

O
CH3

ethanal and propanone;

methanoic acid, ethanoic acid, propanoic acid and butanoic acid.

N

O
H

key:
hydrogen bond

11

12

Topic 8

Unit 30 Isomerism

Chemistry of Carbon Compounds

Example
Compounds W, X, Y and Z are all colourless liquids. Suggest how you would distinguish
the four compounds from each other.
CH3CH2OH

(CH3)3COH

CH3(CH2)2Br

CH3(CH2)7OH

(5 marks)

Answer
Distinguishing the liquids by water solubility
Add water to the liquids. Both CH3CH2OH and (CH3)3COH are miscible with
water.

(1)

Distinguishing the two liquids which are miscible with water

Warm each of these two liquids with acidified potassium dichromate solution.

(1)

Only CH3CH2OH turns the dichromate solution from orange to green.

(1)

Distinguishing the two liquids which are not miscible with water
Warm each of the two liquids which are not miscible with water with AgNO3(aq) in
ethanol.
(1)
Only CH3(CH2)2Br gives a creamy precipitate slowly.

Remarks*
Remarks
In questions of this type, it is common to distinguish the compounds by
their water solubility before other chemical tests.
Hydrocarbons such as cyclohexane and cyclohexene often appear in this
type of questions. They are insoluble in water.

(1)

Unit 30

Isomerism

30.1

Isomerism

30.2

Structural isomerism

30.3

Geometrical isomerism

30.4

Physical properties of geometrical isomers

30.5

Chirality

30.6

Enantiomers

30.7

Test for chirality plane of symmetry

30.8

Properties of enantiomers

13

14

Topic 8

Unit 30 Isomerism

Chemistry of Carbon Compounds

30.1 30.2

Exam tips

Summary

15

When ask about the type of isomerism, give the precise type, instead
of just stating structural isomerism.
e.g.

The following charts show the classification of isomers.

H3C

isomers
different compounds that have the
same molecular formula

OH

and

OCH3

The type of isomerism involved is functional group isomerism.

Questions often ask about methods for distinguishing between isomeric
compounds.
e.g.

structural isomers
atoms are linked in different orders

stereoisomers
atoms are linked in the same way but
with different spatial arrangements

H3C

OH

and

OCH3

can be distinguished by
a physical method
comparing their boiling points / melting points; H3C
has a higher boiling point / melting point.

structural isomers

OH

a spectroscopic method
comparing their IR spectra; H3C

OH has a broad and

1

chain isomers
isomers with the same
functional group but
different carbon skeletons
e.g.
CH3CH2CH2CH2CH3

position isomers
isomers with the same
carbon skeleton and
functional group, but the
position of the functional
group is different
e.g.

and

CH3CH2CH2CH2OH

CH3
CH3CHCH2CH3

functional group
isomers
isomers with the same
molecular formula but
different functional
groups
e.g.
O
CH3CH2C

and
OH
CH3CHCH2CH3

strong absorption at 3 230 3 670 cm .

Example
Consider the isomeric compounds X and Y shown below:
OH

OH
CHO

OH

and
O
CH3C

CHO
O

CH3

compound X

compound Y

a) Name the type of isomerism involved.

b) Which of the above compounds has a higher melting point? Explain.

(1 mark)
(3 marks)

Answer
a) Position isomerism

(1)

b) The melting point of compound Y is higher than that of compound X.

(1)

Only compound X can form intramolecular hydrogen bonds.

(1)

Compound Y forms more intermolecular hydrogen bonds than compound X does.

(1)

16

Topic 8

Unit 30 Isomerism

Chemistry of Carbon Compounds

Remarks*
Remarks

17

Example
Questions often ask students to compare the melting point / volatility of
isomeric compounds.

Consider the melting points and boiling points of cis-1,2-dichloroethene and trans1,2-dichloroethene.

Compound X forms intramolecular hydrogen bonds due to the close proximity

of the OH group and CHO group.
O
H

Compound

Melting point (C)

Boiling point (C)

cis-1,2-dichloroethene

80

60

trans-1,2-dichloroethene

50

48

hydrogen bond
Explain why

O
C

a) cis-1,2-dichloroethene has a higher boiling point;

(3 marks)

b) trans-1,2-dichloroethene has a higher melting point.

(2 marks)

Answer

a) The boiling point of a compound depends on its intermolecular attractions.

In a molecule of the cis isomer, the dipole moments of the two polar CCl bonds
reinforce each other. Thus, the molecule has a net dipole moment. Thus, these
molecules are held together by permanent dipole-permanent dipole attractions. (1)

30.3 30.4
Summary
1 Stereoisomers that have a different arrangement of their atoms in space due to the
restricted rotation about a carbon-carbon double bond are geometrical isomers.
2 Compounds with two different groups attached to each carbon of the double bond
have two alternative structures, which are geometrical isomers.
CH3
C

CH3
C

CH3
C

and
H

cis-isomer

In a molecule of the trans isomer, the dipole moments of the two polar CCl bonds
cancel each other. Thus, the molecule has no dipole moment. Thus, these molecules
are held together by weaker instantaneous dipole-induced dipole attractions.
(1)
b) In addition to intermolecular attractions, the melting point of a compound depends
also on the degree of compactness of molecules in the solid state.
(1)
The cis isomer has a lower degree of symmetry. It fits into a crystalline lattice
relatively poor and thus has a lower melting point.
(1)

Remarks*
Remarks

Questions often ask students to compare the melting points and boiling
points of geometrical isomers.

CH3

e.g.

trans-isomer

3 Geometrical isomers normally have similar chemical properties. However, their

physical properties are often quite different.

CH3OOC

H
C

H3C

Br
C

H3C

H3C
C

and
Cl

Cl

H3C

are NOT
Br

geometrical isomers. They are identical molecules.

One of the carbon atoms of the double bond has two methyl groups
attached to it.

H
C

COOCH3
m.p. 102 C

Exam tips

(1)

CH3OOC

COOCH3
m.p. 19 C

Their intermolecular attractions are van der Waals forces of comparable

strength.
The trans isomer has a higher melting point because it is more
symmetrical.

18

Topic 8

Unit 30 Isomerism

Chemistry of Carbon Compounds

30.5 30.8

Answer
a)

Summary
1 A chiral molecule is defined as one that is not superposable on its mirror image. A
chiral molecule and its mirror image are called a pair of enantiomers.
2 Most simple chiral molecules contain one carbon atom bonded to four different
atoms or groups of atoms. Such a carbon atom is called a chiral carbon.
3 A pair of enantiomers have the same physical property and chemical property,
except
a) their behaviour towards plane-polarized light; and

Questions may ask students to mark chiral carbons on the structures

of unfamiliar compounds.
e.g.
Tamiflu

Aspartame

CH2CH3
CH

O
C

CH3CH2

O
O

CH2CH3

NH

CH

O
NH

CH2

*
*

H2N

NH2

COOH
H

HOOC
(1)

(1)

b) They rotate the plane of polarization of a beam of plane-polarized light to opposite

directions.
(1)

Remarks*
Remarks

Questions often ask students to suggest a different physical property between

a pair of enantiomers. One of them turns the plane of polarization of a
beam of plane-polarized light clockwise, while the other anticlockwise.

Questions often ask about enantiomers.

CH3

Students need to give good drawings of three-dimensional structures. Use

the conventions commonly used in the representation of three-dimensional
structures.

b) their reactions with chiral reagents.

Exam tips

CH3

CH

OCH3

CH2

CO2H

C
CH3
DO NOT confuse the terms chiral and achiral.

Example
Compound X has the following structural formula:
CH(CH3)COOH
The above structural formula can represent two stereoisomers.
a) Draw three-dimensional structures of the two stereoisomers.
b) State a physical property which is different for the two stereoisomers.

(2 marks)
(1 mark)

19

20

Topic 8

Unit 31 Typical reactions of selected functional groups

Chemistry of Carbon Compounds

Unit 31

Typical reactions of selected functional groups

31.1 31.7
Summary

31.1

Introduction

31.2

Important reactions of alkanes

31.3

Addition reactions of alkenes

31.4

Addition of hydrogen to alkenes

31.5

Addition of halogens to alkenes

31.6

Addition of hydrogen halides to alkenes

31.7

Substitution reactions of haloalkanes

31.8

Reactions of alcohols

31.9

Reactions of aldehydes and ketones

1 The figure below summarizes the addition reactions of alkenes.

RCH2CH3
alkane

H2(g)
Pt catalyst

RCHCH2

RCH

OH OH
diol

31.10 Reactions of carboxylic acids

HBr(g)

31.12 Hydrolysis of amides

RCHCH3
Br
major product

RCHBrCH2Br

alkene

cold alkaline
dilute potassium
permanganate
solution

31.11 Hydrolysis of esters

CH2

Br2
(in organic
solvent)

RCH2CH2Br
minor product

dibromoalkane

Br2(aq)

RCHCH2Br
OH
bromoalcohol

RCHBrCH2Br
dibromoalkane

bromoalkanes
2 Markovnikovs rule for addition reaction of an asymmetric alkene:
When a molecule HA adds to an asymmetric alkene, the major product is the one
in which the hydrogen atom attaches itself to the carbon atom already carrying the
larger number of hydrogen atoms.
3 Substitution reactions of haloalkanes alkaline hydrolysis of haloalkanes
R

NaOH(aq)
reflux

OH

21

Topic 8

Unit 31 Typical reactions of selected functional groups

Chemistry of Carbon Compounds

Exam tips

Questions often ask students to predict the major product of an addition

reaction involving an asymmetrical alkene.
e.g.
CH3

CH3
C

CH3

C2H5

C2H5
C

CH3

HBr

Br

HBr

Br

3
3
Put about 2 cm of ethanol and 1 cm of silver nitrate solution in each of two test
tubes.
(1)

Place the test tube in a water bath at 60 C.

CH3 CH3

23

Answer

(1)

Add several drops of compounds X and Y separately to each test tube.

H

A yellow precipitate forms rapidly in the test tube containing compound Y.

(1)

CH3 H

A white precipitate forms slowly in the test tube containing compound X.

(1)

C2H5 C2H5

Remarks*
Remarks

Questions often ask about chemical tests for distinguishing haloalkanes.

H
CH3 H

31.8 31.9

I
HI

Summary
C3H7Cl

CH3CH

reflux
with NaBr +
conc. H2SO4; or
reflux with
red P + Br2

Deductions:
C3H7Br

re
co flu
re nc x w
flu . H it
x 3P h N
w O a
ith 4 ; I
+
re or
d
P
+
I2

C2H5

propan-1-ol
(1 alcohol)

C2H5
C
H2C=CH

H
CH3

H
H3C

CH3COOH +
conc. H2SO4

C
HC=CH2

Example

C3H7I

CH3COOC3H7

CH3CH2COOH

1-iodopropane

propyl ethanoate

propanoic acid

CH3CH(OH)CH3

Describe, by giving reagent(s) and stating observations, how you could distinguish
between the following two compounds using a simple test tube reaction.
CH3CH2CHCH3
Cl
compound X

and

CH3CH2CHCH3
I
compound Y

(4 marks)

K2Cr2O7 /
H3O+, heat

Structures of the compound:

C3H7OH

r
;o
ux
efl ux
+ ,r
fl
e
O + , re
an
3
th
/ H 3O
7
ye
H
ox
r 2O /
C O4
th
K 2 Mn
/e

K
H4

Al +
Li 3O
H

1-bromopropane

The compound should have a chiral carbon.

excess
conc. H2SO4,
180 C; or
Al2O3,
300 C

K
di 2 Cr
st 2 O
il 7
of / H
2 Li
ft 3
he O +
H AlH
3O
pr
+ 4
/e
op
th
an
ox
al
ye
th
an
e

It has a pair of enantiomers.

propanal

Molecular formula C6H12

It loses its chiral centre after hydrogenation.

CH3CH2CHO

CH2

propene

1-chloropropane

Given information:

The compound should be an alkene as it can undergo

hydrogenation.

l+
C
.H
nc r
co t; o r
ith ys ; o
w al l 5 l 2
x cat PC SOC
flu 2 h
re Cl it th
Zn x w wi
i x
m u
refl

Questions may ask students to deduce the structure of a compound

based on the type of isomerism it can exhibit and its reactions.

22

propan-2-ol
(2 alcohol)

K2Cr2O7 / H3O+
reflux
1 LiAlH4 / ethoxyethane
2 H3O+

(CH3)3COH

K2Cr2O7 / H3O+

methylpropan-2-ol

reflux

(3 alcohol)

CH3COCH3
propanone

no reaction

24

Topic 8

Unit 31 Typical reactions of selected functional groups

Chemistry of Carbon Compounds

31.10 31.12

The formation of hydrogen chloride fumes upon reaction with phosphorus

pentachloride is a test for the presence of a hydroxyl group in a
compound.

Exam tips

25

Summary

The relative ease with which alcohols undergo dehydration shows the
following order:

CH3CH2COOCH2CH3

CH3CH2COOH

CH3CH2OH + conc. H2SO4

ethyl propanoate

Ease of dehydration: 3 > 2 > 1 alcohol

Questions often ask about the oxidation of alcohols:

H 2O /
H3O+

the oxidizing agent required;

the name(s) of the product(s).
Remember that LiAlH4 will NOT act upon C=C bonds.
The transformation of COOH to CH2OH involves 2 steps: reduction
+
by LiAlH4, followed by treatment with H3O .

propanoic acid
1 LiAlH4 /
ethoxyethane
2 H3O+

NaOH
solution

aqueous
NH3

CH3CH2COOH

CH3CH2COO Na+

CH3CH2CH2OH

CH3CH2COO NH4+

propanoic acid

sodium propanoate

propan-1-ol

ammonium propanoate

CH3CH2OH

CH3CH2OH

ethanol

ethanol

heat

CH3CH2CONH2

Example

propanamide

Describe, by giving reagent(s) and stating observations, how you could distinguish
between the following two compounds using a simple test tube reaction.
OH
CH3

H2O /
+
H3O

NaOH
solution

CH2OH
and

compound X

(2 marks)

compound Y

CH3CH2COOH

CH3CH2COO Na+

propanoic acid

sodium propanoate

Answer
Warm each compound with acidified potassium dichromate solution.

(1)

Only compound Y turns the dichromate solution from orange to green.

(1)

The oxidation reaction is commonly used to distinguish

e.g.

a primary / secondary alcohol from a tertiary alcohol;

The active ingredient of a superglue has the following structure:

an aldehyde from a ketone.

Test

Warm with
K2Cr2O7 / H3O+

Alcohols
1 and 2 alcohols
clear orange
solution turns
green almost
immediately
3 alcohols no
observable change

When propan-1-ol and propanoic acid are heated under reflux to

produce an ester, the ester can be separated from the reaction mixture
by fractional distillation or using a separating funnel.
Given the structure of an ester, students should be able to analyze the
ester and deduce the alcohol and carboxylic acid forming the ester.

Remarks*
Remarks

Compound

Exam tips

Aldehydes

Ketones

clear
orange
solution
turns
green

no
observable
change

CN

OCH3

O
H
It is an ester formed from C
H

CN
C
COOH

and CH3OH.

Topic 8

26

Unit 32

Chemistry of Carbon Compounds

Unit 32

Questions often give carbon compounds with similar structures (such

O
O
as H

CH3 and CH3

OH ) and compare them.

Whether they have the same molecular formula / relative molecular

mass.

Introduction

32.2

Planning a synthesis

32.3

Problems in devising a synthesis

32.4

Laboratory preparation of simple carbon compounds

Whether they have the same boiling point.

32.5

Preparing 1-bromobutane in the laboratory

Example
Oil of wintergreen is a common ester. Salicylic acid can be obtained from it in two
steps.
COOCH3

Step 1

OH

a sodium salt of
salicylic acid
+
CH3OH

COOH

Step 2

OH

oil of wintergreen

salicylic acid

a) Give the reagent and condition used in Step 1.

(2 marks)

b) Suggest a structure for the sodium salt of salicylic acid formed in Step 1. (1 mark)
(1 mark)

c) Suggest a reagent that can be used in Step 2.

Answer
a) Sodium hydroxide solution

(1)

Heat under reflux

(1)

COO Na

(1)

OH
c) Dilute sulphuric acid / dilute hydrochloric acid

(1)

Remarks*
Remarks
To draw the structure of sodium salt of salicyclic acid in (b), just use the
general equation for the hydrolysis of an ester for deduction.
O
R

32.1

Whether they have the same odour.

To tackle these questions, first identify the homologous series to which

each compound belongs. Then answer according to the general properties
of the series concerned.

b)

Synthesis of carbon compounds

Whether they are soluble in water.

Whether they have the same chemical properties.

Synthesis of carbon compounds

O
O

R1 + NaOH

O Na+ + R1

Students may also work backwards from the structure of salicyclic acid to
deduce the structure of its sodium salt.

27

Topic 8

28

Unit 32

Chemistry of Carbon Compounds

32.1 32.3

c)

Cl

Synthesis of carbon compounds

OH

OH(aq)
heat

Summary

(1)

Steps for devising a synthesis:

a) identify an immediate precursor to the target molecule;

conc. H2SO4
heat

b) continue until the starting molecule is reached.

1st precursor

target molecule

(0.5)

2nd precurso

Br2 (in organic

or conc. H3PO4
heat

starting molecule

(1)

solvent)

(0.5)

Br
Br

(1)

Remarks*
Remarks
The syntheses discussed would NOT involve a change in the length of
the carbon chain.

Exam tips

Students should be familiar with the reactions of organic functional groups

in order to suggest workable synthetic routes for the transformations.

In part (a), the immediate precursor of the target molecule (an alcohol) may
be a carboxylic acid or a haloalkane. As a carboxylic acid can be obtained
from the starting molecule (an amide) via hydrolysis, so the synthesis can
be done in the two steps shown.
Many conversions involve
the hydrolysis of haloalkanes to alcohols;

Example

the oxidation of alcohols to ketones and carboxylic acids;

Outline a syntheticc route, in NOT MORE THAN THREE STEPS, to accomplish each of
the following conversions. For each step, give the reagent(s), the conditions and the
structure of the product.
a) CH3CH2CH2CONH2

CH3CH2CH2CH2OH

b)

COCH3

CH2CH3

(3 marks)

the reduction of aldehydes, ketones and carboxylic acids to alcohols.

32.4 32.5
Summary

(4 marks)
c)

Stage 1 planning the preparation;

Br

Cl

(4 marks)

Br
Answer
a) CH3CH2CH2CONH2

H2O / H3O+
heat (1)

CH2CH3

Stage 2 carrying out the reaction to produce the desired product;

Stage 3 separating the crude product from the reaction mixture;
Stage 4 purifying and drying the product;

CH3CH2CH2COOH (1)
1 LiAlH4 / ethoxyethane
2 H3O+
(1)

b)

The laboratory preparation of a carbon compound involves five main stages:

Stage 5 calculating the percentage yield of the product.

CH3CH2CH2CH2OH

Common separation and purification methods for products

Type of product

CHBrCH3

simple distillation

Br2

Liquid product

fractional distillation
liquid-liquid extraction

UV light or heat

(1)

Separation and purification method to employ

Solid product

(0.5)
CH(OH)CH3

COCH3

OH (aq)

K2Cr2O7 / H3O

heat

reflux

(1)

(0.5)

(1)

re-crystallization

29

30

Topic 8

Unit 32

Chemistry of Carbon Compounds

Exam tips

DO NOT confuse an experimental set-up for fractional distillation with

that for simple distillation.

Synthesis of carbon compounds

31

Answer
a)

Questions often ask students to describe the re-crystallization procedure

for the purification of a crude solid product.

organic layer

Example

aqueous layer

2-chloro-2-methylpropane can be prepared by reacting methylpropan-2-ol with

concentrated hydrochloric acid.
(CH3)3COH(l) + HCl(aq)

(CH3)3CCl(l) + H2O(l)

This preparation follows the steps outlined below:

Step 1

Shake excess concentrated hydrochloric acid with methylpropan-2-ol in a

separating funnel.

Step 2

Separate the organic layer from the aqueous layer.

Step 3

Wash the crude product with 10% sodium hydrogencarbonate solution.

Step 4

Dry the product with a suitable reagent.

Step 5

Purify the dried product to remove the remaining methylpropan-2-ol.

The table below lists some information of methylpropan-2-ol and 2-chloro-2methylpropane:

Compound

methylpropan-2-ol

2-chloro-2-methylpropane

3
Density (g cm )

0.78

0.84

Boiling point (C)

82

51

Water solubility

miscible

very slightly soluble

a) Draw a diagram of the separating funnel after the reaction has taken place in Step
1, labelling clearly the aqueous layer and organic layer.
(2 marks)
b) Suggest ONE advantage of using a separating funnel to carry out Step 1.

(1 mark)

(2)
b) Any one of the following:
Allow better mixing of the reactants by vigorous shaking of the separating
funnel.
(1)
Allow easy isolation of the product by draining out the lower aqueous layer from
the separating funnel.
(1)
c) Add slowly 10% sodium hydrogencarbonate solution. Wait until no effervescence
occurs.
(1)
Stopper and shake the separating funnel vigorously.

(1)

During shaking, open the tap of the separating funnel regularly to release the pressure
built inside the funnel.
(1)
Remove the aqueous layer. Repeat the washing procedure until no effervescence
occurs upon the addition of sodium hydrogencarbonate solution.
(1)
d) Anhydrous calcium chloride / sodium sulphate

(1)

e) Simple distillation / fractional distillation

(1)

Remarks*
Remarks

c) Outline the experimental procedure for washing the crude product in Step 3. Include
the necessary safety precautions.
(4 marks)

Questions often ask about the purposes of different steps in the preparations
of carbon compounds.

d) Suggest a suitable reagent for drying in Step 4.

(1 mark)

e) Name a method for purifying the dried product in Step 5.

(1 mark)

When giving a reagent for drying, remember to include the word

anhydrous.

32

Topic 8

Unit 33 Important organic substances

Chemistry of Carbon Compounds

Unit 33

Important organic substances

33.1 33.9 & 33.13

Summary

33.1

Introduction

33.2

Aspirin from herbal remedy to modern drug

33.3

Analyzing aspirin tablets by back titration

33.4

Detergents

33.5

How do detergents help water to clean?

33.6

The wetting and emulsifying properties of detergents in relation

to their structures

33.7

The cleaning action of detergents

33.8

Manufacture of soaps and soapless detergents

33.9

The cleaning abilities of soaps and soapless detergents in hard

water

33.10 Nylons
33.11 Polyesters
33.12 Carbohydrates

1 a) The structure of the active ingredient of aspirin tablets, acetylsalicylic acid, is

shown below. It contains two functional groups.
O

carboxyl group

OH

CH3

ester group

b) The percentage by mass of acetylsalicylic acid in aspirin tablets can be determined

by back titration.
2 a) There are two types of detergents:
i) soap made from natural fats and oils; and
ii) soapless detergents made from chemicals derived from petroleum.
b) The structure of a typical anionic detergent is shown below:

33.13 Lipids
33.14 Proteins and polypeptides
hydrophobic
hydrocarbon tail

hydrophilic anionic
head

c) A detergent helps water to remove dirt by

i) the ability to act as a wetting agent; and
ii) the emulsifying action.
3 Fats and oils are mixed triglycerides.
4 Soap is made by boiling natural oils or fats with a strong alkali, usually sodium
hydroxide or potassium hydroxide solution.

33

34

Topic 8

Unit 33 Important organic substances

Chemistry of Carbon Compounds

a) Animal fat is one of the raw materials in the production of detergent X.

Students should be able to draw the correct structure of the ester linkage
in a triglyceride (see the structure shown below). The three carboxylic
acids bearing long chains are attached to a glycerol backbone.

Exam tips

i) Name another raw material that is needed in the production of detergent X from
an animal fat.
(1 mark)
ii) Name the type of reaction that takes place in the production of detergent X.
(1 mark)

When fats and oils are heated with sodium hydroxide solution, they are
hydrolyzed first to form glycerol and carboxylic acids. The acids then
react with the alkali to form sodium carboxylates, which are soaps.
Such reactions are called saponification.
H
H

R
H

O
H

3NaOH
alkali

b) An oil tanker was wrecked and spilt a lot of crude oil in the sea. State whether
detergent X is suitable for treating the oil spill. Explain your answer.
(3 marks)

O
H

iii) Write a chemical equation for the reaction involved in the preparation.
(1 mark)

O
O

OH
OH
OH

Answer

+ 3RCOO Na

sodium
carboxylate
(soap)

a) i) Sodium hydroxide

iii)

H
C

Whether it is made from natural fats and oil or from hydrocarbons

obtained from petroleum.
Whether it forms scum in hard water / sea water.

(CH2)nCH3

O
H

C
H

(CH2)nCH3

3NaOH

(CH2)nCH3
H
H

+ 3CH3(CH2)nCOO Na+

(CH2)nCH3

(CH2)nCH3

(1)
(1)

Sea water contains a lot of metal ions, such as calcium ions and magnesium ions.
(1)
Detergent X will react with these metal ions to form scum.

O
H

b) Not suitable

O
C

The structure of the main chemical constituent of an animal fat is shown below:

(CH2)nCH3

Example

Hydrogenation of vegetable oils produces margarines.

Whether it is biodegradable.

(1)

glycerol

Questions often give the structure of a soap / soapless detergent and

ask about its properties.

(1)

ii) Saponification / alkaline hydrolysis

H
triglyceride in fat or oil

35

(1)

36

Topic 8

Unit 33 Important organic substances

Chemistry of Carbon Compounds

Remarks*
Remarks

c) The repeating unit of poly(ethylene terephthalate) is

Questions often ask about the purpose of adding concentrated sodium
chloride solution in soap preparation.
Concentrated sodium chloride solution is added to salt out the soap
produced.
Questions often ask students to give the products formed from the complete
hydrolysis of triglycerides existing in natural fats and oils.
e.g.

(CH2)16CH3

(CH2)7CH

complete

CH(CH2)7CH3

hydrolysis

O
CH2

CH2

CH2

from dicarboxylic acid

from diol

b) The open-chain form of glucose contains an aldehyde group and five hydroxyl
groups.

O
CH

3 a) Glucose can exist in open-chain and cyclic forms.

O

CH2

4 a) Fructose can exist in open-chain and cyclic forms.

CH2

OH

CH

OH

b) The open-chain form of fructose contains a keto group and five hydroxyl
groups.

CH2

OH

5 a) When two amino acid molecules undergo condensation reaction, a water molecule
is eliminated and a peptide link forms. The product is a dipeptide.

(CH2)16CH3

+ CH3(CH2)16COOH +

CH3(CH2)7

H
(CH2)7COOH

OH +

amino acid 1
+

CH3(CH2)7

b) Nylons are formed by condensation polymerization.

N
H

OH

amino acid 2

peptide link (or amide group)

Summary

(CH2)7COOH

33.10 33.12 & 33.14

1 a) Nylons are polyamides which contain the amide linkage

R1

R1

OH +

H2O

a dipeptide
.

b) The peptide links in peptides and proteins can be hydrolyzed to release the
individual amino acids.

c) The repeating unit of nylon-6,6 is

H
N

Exam tips

O
(CH2)6

(CH2)4

H
from diamine

O
from dicarboxylic acid
O

A condensation reaction is a reaction in which two or more molecules

react together to form a larger molecule with the elimination of a small
molecule such as water.
Nylon and poly(ethylene terephthalate) are thermoplastics as well as
condensation polymers. NOT all thermoplastics are addition polymers.
Questions often give the repeating unit of a polymer and ask about
information concerning the polymer.
e.g.

2 a) Polyesters contain the ester linkage

b) Polyesters are formed by condensation polymerization.

whether it is an addition polymer or a condensation polymer;

whether it is formed from one monomer or two different
monomers.

37

Topic 8

38

Unit 33 Important organic substances

Chemistry of Carbon Compounds

Remarks*
Remarks

Example
Twaron is a heat resistant, high strength fibre used in protective clothing. A short
section of the structure of Twaron is shown below.
O

N
C

O
N

N
C

a) Draw the repeating unit of Twaron.

Look at the polymer structure.

O
N
H

Given the structure of a polymer, students should be able to deduce the

structure(s) of monomer(s) used to produce the polymer.

C
O

If the polymer backbone contains only carbon atoms, then the polymer
is an addition polymer produced from one monomer.
e.g.

(1 mark)

b) Draw the structures of the two monomers that could be used to prepare Twaron.
(2 marks)
c) Explain why Twaron has a great strength.

(1 mark)

C6H5 H

C6H5 H

C6H5

from the following monomer:

Answer
a)

N
N

O
N

H
b) H2N
HOOC

C
O

NH2
COOH

c) There are strong hydrogen bonds between chains of Twaron.

(1)
(1)
(1)
(1)

is an addition polymer formed

C6H5

If the polymer backbone contains other atoms, then the polymer is a

condensation polymer, probably produced from two monomers (see Twaron
shown above).
Some condensation polymers are produced from one monomer.
e.g.
the repeating unit of polylactide is shown below:
CH3 O
O

H
It is a condensation polymer formed from one monomer, lactic acid.
CH3 O
HO

H
lactic acid

OH

39