Chemistry Module 7

CHEMISTRY MODULE 7 Organic Chemistry CHEMISTRY MODULE 7 – ORGANIC CHEMISTRY NOMENCLATURE Inquiry question: How do we systematically name organic chemical compounds? ● investigate the nomenclature of organic chemicals, up to C8, using IUPAC conventions, including simple methyl and ethyl branched chains, including: (ACSCH127) – alkanes – alkenes – alkynes – alcohols (primary, secondary and tertiary) – aldehydes and ketones – carboxylic acids – amines and amides – halogenated organic compounds ● explore and distinguish the different types of structural isomers, including saturated and unsaturated hydrocarbons, including: (ACSCH035) – chain isomers – position isomers – functional group isomers HYDROCARBONS Inquiry question: How can hydrocarbons be classified based on their structure and reactivity? ● construct models, identify the functional group, and write structural and molecular formulae for homologous series of organic chemical compounds, up to C8 (ACSCH035) : – alkanes – alkenes – alkynes ● conduct an investigation to compare the properties of organic chemical compounds within a homologous series, and explain these differences in terms of bonding (ACSCH035) ● analyse the shape of molecules formed between carbon atoms when a single, double or triple bond is formed between them ● explain the properties within and between the homologous series of alkanes with reference to the intermolecular and intramolecular bonding present ● describe the procedures required to safely handle and dispose of organic substances (ACSCH075) ● examine the environmental, economic and sociocultural implications of obtaining and using hydrocarbons from the Earth PRODUCTS OF REACTIONS INVOLVING HYDROCARBONS Inquiry question: What are the products of reactions of hydrocarbons and how do they react? ● investigate, write equations and construct models to represent the reactions of unsaturated hydrocarbons when added to a range of chemicals, including but not limited to: CHEMISTRY MODULE 7: ORGANIC CHEMISTRY PAGE 1 OF 65 – hydrogen (H2) – halogens (X2) – hydrogen halides (HX) – water (H2O) (ACSCH136) ● investigate, write equations and construct models to represent the reactions of saturated hydrocarbons when substituted with halogens ALCOHOLS Inquiry question: How can alcohols be produced and what are their properties? ● investigate the structural formulae, properties and functional group including: – primary – secondary – tertiary alcohols ● explain the properties within and between the homologous series of alcohols with reference to the intermolecular and intramolecular bonding present ● conduct a practical investigation to measure and reliably compare the enthalpy of combustion for a range of alcohols ● write equations, state conditions and predict products to represent the reactions of alcohols, including but not limited to (ACSCH128, ACSCH136): – combustion – dehydration – substitution with HX – oxidation ● investigate the production of alcohols, including: – substitution reactions of halogenated organic compounds – fermentation ● investigate the products of the oxidation of primary and secondary alcohols ● compare and contrast fuels from organic sources to biofuels, including ethanol REACTIONS OF ORGANIC ACIDS AND BASES Inquiry question: What are the properties of organic acids and bases? ● investigate the structural formulae, properties and functional group including: – primary, secondary and tertiary alcohols – aldehydes and ketones (ACSCH127) – amines and amides – carboxylic acids ● explain the properties within and between the homologous series of carboxylic acids amines and amides with reference to the intermolecular and intramolecular bonding present ● investigate the production, in a school laboratory, of simple esters ● investigate the differences between an organic acid and organic base ● investigate the structure and action of soaps and detergents ● draft and construct flow charts to show reaction pathways for chemical synthesis, including those that involve more than one step CHEMISTRY MODULE 7: ORGANIC CHEMISTRY PAGE 2 OF 65 POLYMERS Inquiry question: What are the properties and uses of polymers? ● model and compare the structure, properties and uses of addition polymers of ethylene and related monomers, for example: – polyethylene (PE) – polyvinyl chloride (PVC) – polystyrene (PS) – polytetrafluoroethylene (PTFE) (ACSCH136) ● model and compare the structure, properties and uses of condensation polymers, for example: – nylon – polyesters CHEMISTRY MODULE 7: ORGANIC CHEMISTRY PAGE 3 OF 65 IUPAC NOMENCLATURE OUTCOMES ● investigate the nomenclature of organic chemicals, up to C8, using IUPAC conventions, including simple methyl and ethyl branched chains, including: (ACSCH127) – alkanes – alkenes – alkynes – alcohols (primary, secondary and tertiary) – aldehydes and ketones – carboxylic acids – amines and amides – halogenated organic compounds ● analyse the shape of molecules formed between carbon atoms when a single, double or triple bond is formed between them HYDROCARBONS Hydrocarbons are compounds that contain only carbon and hydrogen. They are the main constituents of natural gas and crude oil. Hydrocarbons can be saturated (in hydrogen) or unsaturated, depending on whether they contain just single bonds or double/triple bonds, respectively. ALKANES - Contain only C-C single bonds in backbone - Saturated hydrocarbon - General formula for straight chained and branched alkanes = 퐶푛퐻2푛+2 Alkanes are called saturated hydrocarbons because no more hydrogen atoms can be added to the carbon atoms. Alkanes are a homologous series: family of compounds that can be represented by one general molecular formula. Name Molecular Formula MP BP methane -182 -164 ethane -183 -89 propane -190 -42 butane -138 0 pentane -130 36 hexane -95 69 heptane -91 98 octane -57 126 CHEMISTRY MODULE 7: ORGANIC CHEMISTRY PAGE 4 OF 65 MOLECULAR STRUCTURE OF ALKANES BRANCHED ALKANES Branched alkanes are alkane compounds containing alkyl side groups. Alkyl Groups Molecular Formula Methyl Ethyl Propyl Butyl Pentyl CHEMISTRY MODULE 7: ORGANIC CHEMISTRY PAGE 5 OF 65 STEM NOMENCLATURE Longest Carbon Chain Prefix Number of identical groups Prefix 1 Meth- 5 Pent- 2 Eth- 6 Hex- 3 Prop- 7 Hept- 4 But- 8 Oct- NAMING BRANCHED CHAIN ALKANES 1) Find the longest continuous chain of carbon atoms. Assign a parent name based on this number. 2) Find whatever groups that are not part of the longest continuous chain. Name these as prefixes and put them in alphabetical order. 3) Assign numbers to groups by counting from one end of the chain. A chain has two ends, and the end we start from is the one that gives the lowest set of numbers to the groups. eg: 3-methylhexane NAMING ALKANES WITH MULTIPLE ALKYL GROUPS Number of identical groups Prefix Number of identical groups Prefix 2 Di 5 Penta 3 Tri 6 Hexa 4 Tetra 7 Hepta LOWEST SET OF NUMBERS To determine the lowest set of numbers: 1) Work out the numbers for the two possible names (going along the longest carbon chain in both directions) 2) List the numbers in each name in increasing order 3) Compare the first number of each name a. If there is a difference, the name with the lower number is correct b. If the numbers are the same, move onto the second number and so on until there’s a difference CHEMISTRY MODULE 7: ORGANIC CHEMISTRY PAGE 6 OF 65 ALKENES - Contains at least one C=C double bond in backbone - Unsaturated hydrocarbons - General formula = 퐶푛퐻2푛 Carbon atoms with double and triple bonds can accept more hydrogen therefore alkenes and alkynes are unsaturated hydrocarbons. The double bond carbon atoms are called functional groups because they are sites of chemical activity. - A functional group is an atom, or group of atoms, which give a compound some characteristic physical and chemical properties. It is necessary to assign a number to describe the location of the double bond. The bonds are numbered much like carbons. The lowest number is assigned to the bond. ALKYNES - Contain at least one C≡C triple bond in backbone - Unsaturated hydrocarbons - General formula = 퐶푛퐻2푛−2 SHAPE Bonds around Carbon Angle between Bonds Number of VSEPR groups Shape around carbon Four Single Bonds 109.5 4 Tetrahedral Two single bonds and one 120 3 Trigonal planar double bond Two Double bonds or one 180 2 Linear triple bond and one single CHEMISTRY MODULE 7: ORGANIC CHEMISTRY PAGE 7 OF 65 EXTENSION: CYCLIC HYDROCARBONS Hydrocarbon compounds in which the carbon atoms have joined to form closed ring structures are called cyclic (or alicyclic) hydrocarbons. They may also be saturated or unsaturated: - Those that contain only C-C bonds are called cycloalkanes. - Those that contain C=C bonds or C≡C bonds are called cycloalkenes and cycloalkynes respectively. Due to the extra C-C bond that closes the ring structure, there are always two less hydrogen atoms than the respective straight chain. Cyclohexane 3-methylcycloheptene EXTENSION: AROMATIC HYDROCARBONS A unique type of cyclic structure is the aromatic hydrocarbons. These structures contain a ring of carbon atoms linked together such that they have delocalised electrons. Delocalised electrons are not held within bonds but are free to move around a structure. Benzene - The electrons of the double bond are free to move around the entire ring, forming a “cloud” of delocalised electrons above and below the plane of the ring. - The delocalisation is shown by drawing a circle around the inside of the ring. This depiction represents the equivalent nature of the six carbon-carbon bonds. The delocalisation of the

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