Cape Chemistry Module 1

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 UNIT 2: CHEMICAL PRINCIPLES AND APPLICATIONS II

MODULE 1: THE CHEMISTRY OF CARBON COMPOUNDS

GENERAL OBJECTIVES

On completion of this Module, students should:

1. appreciate the scope and nature of carbon-based compounds;

2. understand the processes involved in the formation of carbon compounds;

3. understand the reactions of various functional groups of carbon compounds; and,

4. critically assess the impact of carbon-based compounds on our daily lives.

SPECIFIC OBJECTIVES EXPLANATORY NOTES SUGGESTED PRACTICAL


ACTIVITIES

1. Structure and Formulae

Students should be able to:

1.1. explain the occurrence of Catenation, tetravalency,


carbon compounds with hybridisation, and
straight chains, branched resonance of carbon atoms
chains and rings; to be used as basis.

1.2. explain the meaning of Chemical and physical


the term ‘homologous characteristics.
series’;

1.3. distinguish among


empirical, molecular, and
structural formulae;

1.4. determine formulae from


experimental data;

1.5. write structural formulae; Structural formulae may be


written in the following
formats:

Displayed
H H
H C C O H

H H

CXC A11/U2/17 36
UNIT 2
MODULE 1: THE CHEMISTRY OF CARBON COMPOUNDS (cont’d)

SPECIFIC OBJECTIVES EXPLANATORY NOTES SUGGESTED PRACTICAL


ACTIVITIES

Structure and Formulae cont’d

Students should be able to:

Condensed
CH3(CH2)4CH3; CH3CH2OH

Benzene can be
represented by

and cyclohexane by

1.6. apply the IUPAC rules to


named organic compounds;

1.7. define, structural Examples should be


isomerism; given. Include chain,
functional group, and
positional isomers.

1.8. explain stereoisomerism; Geometrical (cis/trans)


and, isomers resulting from
restricted rotation about

C C

double bond; optical


isomerism due to
asymmetry in molecules
(confined to compounds
with one identified chiral
centre and drawing the
two optical isomers).
Optical isomers have an
effect on plane polarised
light. (No further
treatment required).

1.9. determine the possible


isomers from given
molecular formulae.

CXC A11/U2/17 37
UNIT 2
MODULE 1: THE CHEMISTRY OF CARBON COMPOUNDS (cont’d)

SPECIFIC OBJECTIVES EXPLANATORY NOTES SUGGESTED PRACTICAL


ACTIVITIES

2. Functional Group Analysis, Reactions and Mechanisms

Students should be able to:

2.1. identify homologous series Include general formulae.


of organic/carbon
compounds;

2.2. describe selected chemical Halogenation, cracking, and


reactions of alkanes; combustion.
Equations required.

2.3. explain the steps involved Steps should include


in the mechanism of free initiation, propagation, and
radical substitution; termination. For example,
methane and chlorine,
homolytic fission.
Include movement of
electrons to be indicated
by curved arrows and fish
hook notations.

2.4. describe selected chemical


C C
reactions of alkenes;
Alkenes with Br2 (l),

Br2(aq), (addition reaction)


Cold - KMnO4(aq)/H+(aq)
(oxidation and diol
formation),
Hot - KMnO4(aq)/H+(aq)
(cleavage).
Hydrogen halides.
(Markovnikov rule for
addition to asymmetric
alkenes).
Include catalytic
hydrogenation of fats to
produce trans–fats which
are harmful, for example,
margarine.
Equations for reactions of
alkenes with KMnO4(aq)
/H+(aq) are not required.

CXC A11/U2/17 38
UNIT 2
MODULE 1: THE CHEMISTRY OF CARBON COMPOUNDS (cont’d)

SPECIFIC OBJECTIVES EXPLANATORY NOTES SUGGESTED PRACTICAL


ACTIVITIES

Functional Group Analysis, Reactions and Mechanisms cont’d

Students should be able to:

2.5. explain the steps involved Electrophilic addition of


in the mechanism of bromine and hydrogen
selected chemical reactions bromide to alkenes.
of alkene functional group;
Include movement of
electrons. To be indicated
by curved arrows and fish
hook notation.

2.6. describe selected chemical Reactions of alcohols to Perform experiments


reactions of alcohols; include primary, secondary examining the fragrances
and tertiary (10, 20, and 30 produced when different
respectively) with esters are formed.
KMnO4(aq)/H+(aq) purple to
colourless with primary and
secondary; no reaction with
tertiary;
K2Cr2O7(aq)/H+(aq) orange to
green with primary and
secondary; no reaction with
tertiary;
Carboxylic acid (R-COOH);
conc. sulfuric acid. A
solution of I2 and NaOH
(iodoform test).
Equations for reactions of
alcohols with carboxylic acid
and conc. sulfuric acid only
are required.

2.7. describe selected reactions Limited to hydrolysis of


of halogenoalkanes; primary and tertiary
halogenoalkanes using
NaOH(aq). (No elimination
reaction required).

CXC A11/U2/17 39
UNIT 2
MODULE 1: THE CHEMISTRY OF CARBON COMPOUNDS (cont’d)

SPECIFIC OBJECTIVES EXPLANATORY NOTES SUGGESTED PRACTICAL


ACTIVITIES
Functional Group Analysis, Reactions and Mechanisms cont’d

Students should be able to:

2.8. explain the steps involved Nucleophilic substitution of


in the mechanism of halogenoalkanes with
selected reactions of hydroxyl ions.
halogenoalkanes;
Include movement of
electrons to be indicated by
curved arrows and fish hook
notation. Illustrate bond
breaking or bond making as
occurring in either a stepwise
or concerted manner.

2.9. describe selected chemical NaCN/HCl(aq); 2, 4 – DNP


reactions of carbonyl (Brady’s Reagent), Tollens’
compounds reagent/Fehling’s solution;
KMnO4(aq))/H+(aq); LiAlH4;
O
H2/Pt.
C
No equations required

2.10. explain the steps involved Nucleophilic addition.


in mechanisms of selected Include reaction of carbonyl
chemical reactions of compounds with hydrogen
carbonyl compounds; cyanide as an example.
Include movement of
electrons to be indicated by
curved arrows and fish hook
notation.

2.11. describe selected chemical NaOH, NaHCO3, metals,


reaction of carboxylic acids alcohols PCl5/PCl3 or SOCl2.
(R-COOH); Equations are not required
for reaction with PCl5, PCl3
or SOCl2.

2.12. describe selected chemical Acid and base hydrolysis. Simple soap production
reactions of esters; Include saponification, using vegetable oil and
transesterification biodiesel NaOH.
production.

CXC A11/U2/17 40
UNIT 2
MODULE 1: THE CHEMISTRY OF CARBON COMPOUNDS (cont’d)

SPECIFIC OBJECTIVES EXPLANATORY NOTES SUGGESTED PRACTICAL


ACTIVITIES

Functional Group Analysis, Reactions and Mechanisms cont’d

Students should be able to:

2.13. perform suitable laboratory PCl3 should be used in a


tests for functional groups fume cupboard.
in carbon compounds Theoretical considerations
referred to above; are satisfactory for SOCl2.

2.14. describe the chemical


reaction of primary amines
(RNH2) with dilute acid;

2.15. describe selected chemical Benzene and


reactions of benzene methylbenzene with
methylbenzene and Br2/FeBr3; conc.
nitrobenzene; HNO3/conc. H2SO4.
Equations are required.

The reaction of
nitrobenzene with Sn/HCl
(conc). Equations are not
required.

2.16. explain the steps involved Electrophilic substitutions.


in the mechanism of Nitration of benzene.
selected chemical reactions
of benzene; Include the movement of
electrons to be indicated
by curved arrows and fish
hook notation.

2.17. describe selected chemical Phenol with acyl halides,


reactions of phenol; aqueous bromine, sodium
hydroxide. Equations are
required.

2.18. describe the formation of Phenylamine with HNO2


an azo compound; and, and HCI coupling with
phenol to give azo
compounds.

2.19. state uses of azo Dyes, intermediates in


compounds. organic synthesis.

CXC A11/U2/17 41
UNIT 2
MODULE 1: THE CHEMISTRY OF CARBON COMPOUNDS (cont’d)

SPECIFIC OBJECTIVES EXPLANATORY NOTES SUGGESTED PRACTICAL


ACTIVITIES

3. Acidic and Basic Character of Organic Compounds

Students should be able to:

3.1. explain the difference in Include chlorosubstituted


acidity of alcohols, phenols acids. Reference should be
and carboxylic acids; made to the relationship
between acid strength, pH
and pKa.

Inductive and conjugative


effects.

3.2. explain differences in basic pH and pKb.


character of aliphatic
amines, amides, and Inductive and conjugative
aromatic amines; and, effects.

3.3. explain the acid-base Formation of zwitterions.


properties of amino acids.

4. Macromolecules

Students should be able to:

4.1. describe the characteristics Examples to include


of addition polymerisation; polyethene;
polyvinyl chloride; and,
polytetrafluoroethene.

Include monomers for each


polymer respectively.

4.2. describe the characteristics Terylene; nylon 6.6,


of condensation (specific monomers are
polymerisation; required); proteins, starch,
(representative structure
required).

CXC A11/U2/17 42
UNIT 2
MODULE 1: THE CHEMISTRY OF CARBON COMPOUNDS (cont’d)

SPECIFIC OBJECTIVES EXPLANATORY NOTES SUGGESTED PRACTICAL


ACTIVITIES

Macromolecules cont’d

Students should be able to:

4.3. predict types of polymer


formed from given
monomers;

4.4. deduce the repeat unit of a


polymer;

4.5. identify proteins as Treat amino acids as


naturally occurring monomeric molecules.
macromolecules;
Generalised monomer and
linkage required.

4.6. identify carbohydrates as Include the following:


naturally occurring cellulose, starch, and
macromolecules; and, pectin. Treat simple
sugars as monomeric
materials.

Generalised monomer and


linkage required.

4.7. illustrate the connection


between carbohydrates and
their monomers.

Suggested Teaching and Learning Activities

To facilitate students’ attainment of the objectives of this Module, teachers are advised to engage
students in the teaching and learning activities listed below.

1. Arrange for students to view videos and interactive materials on industrial carbon chemistry.
This should be followed by class or group discussion.

2. Arrange site visits, wherever possible, to industrial institutions, for example, (refineries,
breweries, forensic laboratories, petrochemical plants).

3. Ask students to create a product which is marketable using simple organic reactions.

4. Ask students to construct and use models in sections dealing with structures.

5. Discuss articles in relevant reference journals and periodicals, for example, Chemistry in
Education.

CXC A11/U2/17 43

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