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Students should learn Students should be able to a. Introduction to selected homologous
series
homologous series
structural formulae and systematic naming
give systematic names, general formulae, condensed formulae and structural formulae for:
alkanes, alkenes, haloalkanes, alcohols, aldehydes and ketones, carboxylic acids, esters, unsubstituted amides and primary amines
draw the structures of the compounds based on their systematic names
understand the effects of functional groups and the length of carbon chains on physical properties of carbon compounds
identify common trivial names of some carbon compounds (e.g. formaldehyde, chloroform, acetone, isopropyl alcohol, acetic acid)
b. Isomerism
structural isomerism
cis-trans isomerism as exemplified by acyclic carbon compounds containing one C=C bond
enantiomerism as exemplified by compounds containing one chiral carbon
understand that isomerism occurs when two or more compounds have the same molecular formula but different structures
recognise and predict the existence of structural isomerism which includes isomers containing the same functional group and isomers containing different functional groups
recognise the existence of cis-trans isomerism in acyclic carbon compounds resulting from restricted rotation about a C=C bond
show an understanding of structural and cis-trans isomerism by predicting structures of the isomers of some given carbon compounds
recognise the existence of enantiomerism in compounds with only one chiral carbon
use structural formulae and molecular models to demonstrate the arrangement of atoms in isomers of carbon compounds
c. Typical reactions of various functional groups
alkanes
alkenes
haloalkanes
alcohols
aldehydes
ketones
carboxylic acids
esters
amides
describe the following reactions, in terms of reagents, reaction conditions and observations, and write the relevant chemical equations:
i. alkanes: substitution with halogens
ii. alkenes: addition of hydrogen, halogens and hydrogen halides
iii. haloalkanes: substitution with OH－(aq) iv. alcohols: substitution with halides using
hydrogen halides or phosphorus trihalides;
dehydration to alkenes; oxidation of primary alcohols to aldehydes and carboxylic acids; oxidation of secondary alcohols to ketones
v. aldehydes and ketones: oxidation using Cr2O72(aq); reduction using LiAlH4 or NaBH4
vi. carboxylic acids: esterification and amide formation; reduction using LiAlH4
vii. esters: hydrolysis viii. amides: hydrolysis
predict and name the products of the above reactions
d. Inter-conversions of carbon compounds
inter-conversions between the functional groups
laboratory preparations of simple carbon compounds
suggest routes to convert one functional group into another by using the reactions described in (c)
state the reagents and conditions to accomplish conversions of carbon compounds using the reactions described in (c)
predict the major organic products of reactions, with given starting materials, reagents and reaction conditions
describe how to carry out laboratory preparations and purification of simple carbon compounds such as ethanoic acid and ester
calculate the percentage yield of a product obtained from a reaction
I-45 e. Important organic substances
structure and medical applications of acetylsalicylic acid (aspirin)
structures and properties of soaps and soapless detergents
structures, properties and uses of nylon and polyesters
identify the functional groups of the acetylsalicylic acid molecule
recognise that aspirin is used as a drug to relieve pain, reduce inflammation and fever, and the risk of heart attack
describe the structures of soaps and soapless detergents
recognise that detergents can be made from chemicals derived from petroleum
explain the wetting and emulsifying properties of detergents in relation to their structures
relate the cleansing action of soaps and soapless detergents to their structures
recognise that nylon and polyester are condensation polymers
describe the structures and properties of nylon and polyesters
write equations for the formation of nylon and polyesters
state the uses of nylon and polyesters
Suggested Learning and Teaching Activities
Students are expected to develop the learning outcomes using a variety of learning experiences.
Some related examples are:
building molecular models of compounds with different functional groups.
comparing physical properties of the following compounds: propane, butane, pentane, ethanol, propan-1-ol and butan-1-ol.
searching for common trivial names of common carbon compounds.
predicting the structures of the isomers of given carbon compounds.
building molecular models of but-2-ene.
building molecular models of butan-2-ol or 2-hydroxypropanoic acid (lactic acid).
searching for and presenting information on the principles and applications of the alcohol breathalyser.
performing an experiment to study the reduction of vanillin to vanillyl alcohol using sodium borohydride as reducing agent.
inspecting reaction schemes and important synthetic routes in organic chemistry.
inspecting or writing reaction schemes that summarise all the reactions described in this topic.
planning synthetic routes of simple carbon compounds from precursors that are readily available by analysing the structures of the target molecules.
searching for and presenting information about the synthetic routes of some important organic substances commonly found in daily life.
preparing ethanoic acid or ethyl ethanoate.
preparing esters from different alkanoic acids and alcohols using microscale apparatus.
preparing benzoic acid by alkaline hydrolysis of ethyl benzoate.
preparing soap from a fat or an oil, and testing its properties.
searching for and presenting information on cationic surfactants and neutral surfactants.
performing an experiment to prepare 2-chloro-2-methylpropane from 2-methylpropan-2-ol.
searching for and presenting information on the discovery of aspirin and its applications.
performing an experiment to analyse commercial aspirin tablets using back titration.
searching for and presenting information on the historical development of detergents.
performing experiments to investigate the wetting ability and emulsifying action of detergents.
designing and carrying out experiments to compare the cleansing abilities of soaps and soapless detergents.
searching for and presenting information on environmental issues related to the use of detergents.
performing an experiment to prepare nylon.
searching for and presenting information on the structures and uses of important organic substances such as aspirin, paracetamol, ibuprofen, saccharin, aspartame, sucrose, cellulose, starch, triglyceride, cholesterol, insulin and casein.
Values and Attitudes
Students are expected to develop, in particular, the following values and attitudes:
to appreciate that science and technology provide us with useful products.
to appreciate the versatility of synthetic materials and the limitations of their use.
to be aware of the hazards associated with the use and disposal of carbon compounds in the laboratory (e.g. their combustibility and toxicity) and the precautions to be taken.
to show concern for the conservation of our environment and develop a sense of shared responsibility for sustainable development of our society.
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STSE Connections
Students are encouraged to appreciate and comprehend issues which reflect the interconnections of science, technology, society and the environment. Related examples are:
Often more than one synthetic route may be available to prepare a particular carbon compound. However, some synthetic routes may have undesirable effects on our health and our environment. The best synthetic route may not be the one with the fewest steps or the lowest cost. It is, therefore, essential to apply our knowledge of organic chemistry so that useful organic products are developed and manufactured by safe, economic and environmentally acceptable routes.
The search for new carbon compounds often requires the synthesis of hundreds of compounds which are variations of their basic structures. Some compounds which have been synthesised may have certain useful aspects, but also dangerous side-effects which prohibit their general use. It is often necessary to look for other compounds with similar structures but without the side-effects.