Module 1: Basic Concepts and Hydrocarbons



Module 1: Basic Concepts and Hydrocarbons

|Topic - Section from syllabus |Lesson |Objectives – student should be able to: |

|Nomenclature and formulae: Representing formulae of organic compounds |1 |Follow IUPAC rules to name alkanes (straight chain, branched and |

|a) interpret and use the terms: molecular formula, structural formula, | |ring compounds) interpret what is required when asked for: |

|displayed formula, skeletal formula; | |molecular, structural, displayed and skeletal formulae |

|b) state the names of the first ten members of the alkanes homologous series; | | |

|Functional groups and the naming of organic compounds |2 |Be able to recognise the following functional groups: alkene, |

|a) interpret, and use, the terms: | |halogen, alcohol, aldehyde, ketone, carboxylic acid, ester, benzene|

|(i) homologous series (ii) functional group; | |ring; |

|b) use the general formula of a homologous series to predict the formula of any| |Use general formula to represent homologous series |

|member of the series; | | |

|c) interpret and use: empirical formula, general formula; | | |

| |3 |Practice naming organic molecules using molymod models, etc. |

| | |Introduce empirical formula; write empirical formula for different |

| | |organic compounds. |

|Isomerism: |4 |Explain the term structural and stereo- isomerism. Focus on |

|a) Describe and explain the term: | |structural isomerism. Determine the possible structural isomers |

|structural isomers as compounds with the | |(chain, positional and functional group isomerism) of organic |

|same molecular formula but different | |molecules given its molecular formulae. |

|structural formulae, and stereoisomers as compounds with the same structural | | |

|formula but with a different arrangement in space. | | |

|b) determine the possible structural formulae of an organic molecule, given its| | |

|molecular formula; | | |

|Alkanes: Hydrocarbons from crude oil |5 |Explain, in terms of van der Waals’ forces, the variations in the |

|a) explain what a hydrocarbon is; | |boiling points of alkanes with different carbon-chain length and |

|b) state that alkanes and cycloalkanes are | |branching. State that alkanes and cycloalkanes are saturated |

|saturated hydrocarbons; | |hydrocarbons. |

|c) explain, in terms of van der Waals’ forces, the variations in the boiling | |Describe the combustion of alkanes, leading to their use as fuels |

|points of alkanes with different carbon-chain length and branching; | |in industry, in the home and in transport. |

|(d) describe the combustion of alkanes, leading to | |Write out complete and incomplete combustion of alkanes equations- |

|their use as fuels in industry, in the home and in | |explaining incomplete combustion due to lack of O2. Outline the |

|transport; | |potential dangers arising from production of CO in the home and |

|(e) explain, using equations, the incomplete | |from car use. |

|combustion of alkanes in a limited supply of | | |

|oxygen and outline the potential dangers arising | | |

|from production of CO in the home and from car | | |

|use; | | |

|Reaction mechanisms: Substitution reactions of alkanes |6 |Understand what homolytic fission is (forming free radicals). |

|(a) describe the substitution of alkanes using | |Define free radicals. Write out free-radical substitution mechanism|

|ultraviolet radiation, by Cl2 and by Br2, to form | |of Cl2 and Br2 (methane + chlorine). Explain the limitations of |

|halogenoalkanes; | |radical substitution in synthesis, arising from further |

|(b) define the term radical as a species with an | |substitution with formation of a mixture of products. |

|unpaired electron; | | |

|(c) describe how homolytic fission leads to the | |Candidates are not required to use ‘half curly arrows’ in this |

|mechanism of radical substitution in alkanes in | |mechanism. Equations should show which species are radicals using a|

|terms of initiation, propagation and termination | |single ‘dot’ to represent the unpaired electron. |

|reactions (see also 2.1.1.h); | | |

|(d) explain the limitations of radical substitution in synthesis, arising from | | |

|further substitution with formation of a mixture of products. | | |

|(e) describe the different types of covalent bond | | |

|fission: (i) homolytic fission forming two radicals (carries onto heterolytic | | |

|fission in alkenes but not taught just yet) | | |

| |7 |Test on alkanes- past exam questions and go over answers in class. |

|Hydrocarbons from crude oil: (research topics) |8 |Research project topics: (i) Fractional distillation of crude oil |

|a) explain the use of crude oil as a source of | |and uses of its products; (ii) thermal cracking; (iii) catalytic |

|hydrocarbons, separated as fractions with | |cracking (to include isomerism and reforming); (iv) the value of |

|different boiling points by fractional distillation, | |fossil fuels and need to develop renewable fuels; (v) petrol |

|which can be used as fuels or for processing into petrochemicals; | |substitutes- developing plant based fuels like alcohol and |

|(b) describe the use of catalytic cracking to obtain | |biodiesel; (vi) global warming and climate change; (v) outline the |

|more useful alkanes and alkenes; | |processing of waste polymers (vi) development of biodegradable and |

|(c) explain that the petroleum industry processes | |compostable polymers |

|straight-chain hydrocarbons into branched alkanes and cyclic hydrocarbons to | |Produce BIG poster presentation/PowerPoint presentation, (would be |

|promote efficient combustion; | |handy to give them the section from the syllabus they are doing so |

|(d) contrast the value of fossil fuels for providing | |they cover the topic properly. Get the class to include summary |

|energy and raw materials with: (i) the problem of an over-reliance on | |notes (max 1 side of A4) teacher to photocopy when its presented? |

|nonrenewable fossil fuel reserves and the importance of developing renewable | |5-10 (MAX) minutes presentation |

|plant based fuels, i.e. alcohols and biodiesel (see also sustainability | | |

|lesson), | | |

|(ii) increased CO2 levels from combustion of | | |

|fossil fuels leading to global warming and | | |

|climate change (see also lesson 1 resources module); | | |

|(e) outline the processing of waste polymers by: (i) separation into types (ie | | |

|PTFE, etc.) and | | |

|recycling, (ii) combustion for energy production, (iii) use as a feedstock for | | |

|cracking in the production of plastics and | | |

|other chemicals; | | |

|(f) development of biodegradable and compostable polymers, ie from isoprene (2-| | |

|methyl-1,3-butadiene), maize and starch | | |

| |9 |Continue with research project and finish for homework. |

| |10 |Learning about the research topics through the presentations. |

|Properties of alkenes |11 |Explain bonding in alkenes and their bond angles. Recap: |

|(a) state that alkenes and are unsaturated hydrocarbons; | |stereoisomers as compounds with the same structural formula but |

|(b) describe the overlap of adjacent p-orbitals to | |with a different arrangement in space. Explain existence of cis |

|form a π-bond; | |(E)-trans (Z). isomerism. Practice possible E/Z isomers of alkenes.|

|(c) state and explain the trigonal planar shape | | |

|around each carbon in the C=C of alkenes. | | |

|(d) E/Z isomerism as an example of stereoisomerism, in terms of restricted | |Hybridisation not required. Candidates will not be required to use |

|rotation about a double bond and the requirement for two different groups to be| |Cahn–Ingold–Prelog priority rules to identify which stereoisomer is|

|attached to each carbon atom of the C=C group. | |which. |

|(e) determine the possible stereoisomers of an organic molecule, given its | | |

|molecular formula; | | |

|Reaction mechanisms: Addition reactions of alkenes |12 |Practical – carry out simple reactions of alkanes and alkenes ILPAC|

|(a) describe addition reactions of alkenes, i.e. by | |5.1 & 5.2 (or if you wish can do them separately?) |

|ethene and propene, with: halogens to form dihalogenoalkanes, including the use| | |

|of bromine to detect the presence of a double C=C bond as a test for | | |

|unsaturation, | | |

|(b) define an electrophile as an electron pair acceptor; | | |

|I describe how heterolytic fission leads to the mechanism of electrophilic | | |

|addition in alkenes | | |

|(see also 2.1.1.h–j.); | | |

|(d) describe a ‘curly arrow’ as the movement of an electron pair, showing | | |

|either breaking or formation of a covalent bond; | | |

|(e) outline reaction mechanisms, using diagrams, to show clearly the movement | | |

|of an electron pair with ‘curly arrows’; | | |

|(f) describe addition reactions of alkenes with: (i) hydrogen in the presence | | |

|of a suitable catalyst (Ni), to form alkanes, (ii) hydrogen halides to form | | |

|halogenoalkanes, (iii) steam in the presence of an acid catalyst to form | | |

|alcohols; | | |

|(g) outline the use of alkenes in the industrial | | |

|Production of the manufacture of margarine by catalytic hydrogenation of | | |

|unsaturated vegetable oils using hydrogen and a nickel catalyst, | | |

| |13 |Explain why alkenes are referred to as unsaturated hydrocarbon. |

| | |Define electrophiles and heterolytic fission (forms ions). |

| | |Understand why alkenes are susceptible to attack by electrphiles |

| | |and how heterolytic fission leads to production of an electrophile.|

| | |Link to why bromine water turned colourless from practical. Be able|

| | |to write electrophilic addition mechanism for halogens with alkene.|

| |14 |Describe addition reactions of alkenes with: hydrogen with |

| | |catalyst, i.e. Ni, to form alkanes; hydrogen halide; steam and |

| | |catalysts. Industrial application catalytic hydrogenation of |

| | |unsaturated oils to make margarine. |

|Reaction mechanisms: Addition reactions of alkenes |15 |Practical (or demo) Nylon rope trick. describe the addition |

|polymaerisation | |polymerisation of alkenes. Be able to deduce the repeat unit of an |

|(a) describe the addition polymerisation of alkenes; | |addition polymer |

|(b) deduce the repeat unit of an addition polymer | |obtained from a given monomer; and identify the monomer that would |

|obtained from a given monomer; | |produce a given section of an addition polymer; the formation of a |

|(c) identify the monomer that would produce a given | |range of polymers using unsaturated monomer units based on the |

|section of an addition polymer; the formation of a range of polymers using | |ethene molecule, ie H2C=CHCl, F2C=CF2. |

|unsaturated monomer units based on the | | |

|ethene molecule | | |

|Revision on everything so far. |16 | |

|Test |17 |Test on whole unit. |

| |

|Module 2: Resources |

|Topic - Section from syllabus |Lesson |Objectives – student should be able to: |

|Greenhouse effect |1-2 |Watch Al Gore’s An inconvenient truth DVD. After for (big) homework|

|(a) explain that infrared radiation is absorbed by | |find out about carbon capture and storage (CCS). Need to include in|

|C=O, O–H and C–H bonds in H2O, CO2 and | |the essay quick explanation of what greenhouse effect is; how |

|CH4, and that these absorptions contribute to | |global warming is taking place; what measure are taking place |

|global warming; | |nationally, globally; what is CCS. |

|(b) outline the importance of controlling global | | |

|warming resulting from atmospheric increases in greenhouse gases; | | |

|(c) outline the role of chemists in minimizing climate change resulting from | | |

|global warming by: | | |

|(i) providing scientific evidence to governments to verify that global warming | | |

|is taking place, | | |

|(ii) investigating solutions to environmental | | |

|problems, such as carbon capture and storage, CCS, ie the removal of waste | | |

|carbon dioxide as a liquid injected deep in the oceans, storage in deep | | |

|geological formations, by reaction with metal oxides to form stable carbonate | | |

|minerals, | | |

|(iii) monitoring progress against initiatives such as the Kyoto protocol; | | |

|Ozone Layer |3-4 |Challenge misconception- ozone layer is affected/has to do with |

|(a) explain that ozone is continuously being formed and broken down in the | |global warming. Explain the role of the ozone layer. Explain how |

|stratosphere by the action of ultraviolet radiation; | |ozone is formed, explaining the equilibrium that is taking place in|

|(b) using the chemical equilibrium, below: | |the stratosphere. Explain how the concentration of ozone is |

|O2 + O ⇌ O3 | |maintained in the ozone layer. |

|(i) describe and explain how the concentration of ozone is maintained in the | | |

|ozone layer, including the role of ultraviolet radiation, | |Ozone depletion- explaining how radicals from CFCs and NOx |

|(ii) outline the role of ozone in the absorption of harmful ultraviolet | |catalyses the breakdown of ozone. Explain that refrigerant |

|radiation and the essential benefit of this process for life on Earth; | |coolants, etc uses CFCs. Use the steps initiation, propagation, and|

|(c) understand that radicals, eg from CFCs, and NOx from thunderstorms or | |termination steps to show how ozone is broken down by free radicals|

|aircraft, may catalyse the breakdown of ozone by the following simple | |from CFCl3 ·NO. |

|representation: | | |

|R + O3 → RO + O2 | | |

|RO + O → R + O2 | | |

|Where R represents Cl• from a CFC or ·NO from nitrogen oxides. | | |

|Controlling air pollution |5 |Explain how CO, NOx, and unbunt hydrocarbons are made. State the |

|(a) for carbon monoxide, oxides of nitrogen and unburnt hydrocarbons: | |environmental/health concerns. Explain how low level ozone is |

|(i) explain their formation from the internal combustion engine, | |formed and where it is more prevalent. Go onto catalytic |

|(ii) state environmental concerns from their toxicity and contribution to | |convertors, the reactions that are taking place. Define adsorption.|

|low-level ozone and photochemical smog; | |Pupils need to understand that bonding to the catalyst surface must|

|(b) outline how a catalytic converter decreases carbon monoxide and nitrogen | |be weak enough for adsorption and desorption to take place but |

|monoxide emissions from internal combustion engines by: | |strong enough to weaken bonds and allow reaction to take place. |

|(i) adsorption of CO and NO to the catalyst surface, | | |

|(ii) chemical reaction, | | |

|(iii) desorption of CO2 and N2 from the catalyst surface; | | |

|(c) Outline the use of infrared spectroscopy in monitoring air pollution. | | |

|Sustainability |6 probably |Start of with discussion about what sustainability is. Define |

|(a) describe principles of chemical sustainability: |need another|sustainability. Discuss how we can become more sustainable. Recap |

|(i) using industrial processes that reduce or eliminate hazardous chemicals and|lesson to do|from research topics covering: using renewable resources such as |

|which involve the use of fewer chemicals, |more |plant-based substances, seeking alternative energy sources and |

|(ii) designing processes with a high atom economy that minimise the production |calculations|their importance. |

|of waste materials, | |Introduce atom economy and what it is. Carry out question in the |

|(iii) using renewable resources such as plant-based substances, | |textbook. |

|(iv) seeking alternative energy sources such as solar energy, rather than | |Explain the atom economy of a reaction as: |

|consuming finite resources such as fossil fuels that will eventually be | |molecular mass of the desired products |

|exhausted, | |sum of molecular masses of all products |

|(v) ensuring that any waste products produced are non-toxic, and can be | |×100%; |

|recycled or biodegraded by being broken down into harmless substances | |Explain that addition reactions have an atom economy of 100%, |

|in the environment; | |whereas substitution reactions are less efficient. Carry out |

|(b) explain that the apparent benefits may be | |calculations to determine the atom economy of reactions. Describe |

|offset by unexpected and detrimental side effects; | |the benefits of developing chemical processes with a high atom |

|(c) explain the importance of establishing | |economy in terms of fewer waste materials. Carry out calculations |

|international cooperation to promote the | |of percentage yields. Explain that a reaction may have a high |

|reduction of pollution levels; | |percentage yield but a low atom economy. Set for homework – |

|(d) discuss issues of sustainability in contexts | |importance for home and industry to be sustainable. |

|based on the principles in a–c; | | |

|REVISION |7 | |

|Test on topic |8 | |

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