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Organic Chemistry Saturated & Unsaturated Hydrocarbons Organic Chemistry Saturated & Unsaturated Hydrocarbons BIOB111 CHEMISTRY & BIOCHEMISTRY | Courtesy of SAMPORHELP | Downloaded fromSession https://www.thebigvault.net 8 Key concepts: session 8 From this session you are expected to develop an understanding of the following concepts: Concept 1: Solubility of hydrocarbons in H2O Concept 2: Creation of CFC compounds Concept 3: Alkyl groups Concept 4: Reactivity of saturated vs unsaturated hydrocarbons Concept 5: Alkanes vs alkenes vs alkynes Concept 6: Conversion between the hydrocarbon functional groups (alkane, alkene and alkyne) Concept 7: Bromination reactions Concept 8: Properties of benzene Concept 9: Hydration reactions Concept 10: Identifying primary, secondary and tertiary alcohols These concepts are covered in the Conceptual multiple choice questions of tutorial 8 | Courtesy of SAMPORHELP | Downloaded from https://www.thebigvault.net Session Overview Part 1: Exploring saturated hydrocarbon compounds • Saturated vs unsaturated hydrocarbon compounds • Chemical properties of alkanes • Alkyl groups are derived from alkanes Part 2: Exploring unsaturated hydrocarbon compounds • Chemical properties of alkenes • Bromination reactions • Chemical properties of alkynes • Chemical properties of benzene Part 3: The alcohol function group • Hydrocarbon derivatives • Chemical properties of alcohols | Courtesy of SAMPORHELP | Downloaded from https://www.thebigvault.net Part 1: Exploring saturated hydrocarbon compounds • Saturated vs unsaturated hydrocarbon compounds • Chemical properties of alkanes • Alkyl groups are derived from alkanes | Courtesy of SAMPORHELP | Downloaded from https://www.thebigvault.net Hydrocarbon derivatives Life on earth would not exist without organic compounds that contain carbon atoms • Our genetic material (DNA) contains many carbon atoms • Our bodies rely on the organic compounds below to function: – Proteins are made up of amino acids – Lipids are often made up of fatty acids (long hydrocarbons) and glycerol – Carbohydrates are made up of one or more monosaccharide (sugar) units | Courtesy of SAMPORHELP | Downloaded from https://www.thebigvault.net Saturated vs unsaturated hydrocarbon compounds Hydrocarbon compounds: The most basic organic compounds are hydrocarbons – Hydrocarbons contain only carbon and hydrogen atoms – Hydrocarbons compounds are created in nature and can be synthesised in the laboratory Structures of Hydrocarbon compounds Each line connecting the atoms below represents a covalent bond (2 electrons shared between the two | Courtesy of SAMPORHELP | connected atoms) Downloaded from https://www.thebigvault.net Saturated vs unsaturated hydrocarbon compounds HYDROCARBONS BELONG TO ONE OF THREE FUNCTIONAL GROUPS Type Type Type ALKANE ALKENE Example Definition Definition ALKYNE CONTAIN ONLY CONTAIN ONE CONTAIN ONE OR Example Definition Example SINGLE CARBON MORE DOUBLE OR MORE TO CARBON CARBON TO TRIPLE CARBON BONDS CARBON BONDS TO CARBON BONDS | Courtesy of SAMPORHELP | Downloaded from https://www.thebigvault.net Saturated vs unsaturated hydrocarbon compounds ORGANIC COMPOUNDS THAT CONTAIN CARBON Definition AND HYDROGEN ATOMS HYDROCARBONS Type REACTIVE SATURATED Due to HYDROCARBON Type Are Are DOUBLE AND TRIPLE CARBON TO CARBON UNREACTIVE UNSATURATED BONDS CAN EASILY BE Definition Due to HYDROCARBON BROKEN IN A CHEMICAL REACTION Definition LARGE AMOUNT OF ENERGY NEEDED TO CONTAIN ONE OR MORE DOUBLE OR CONTAIN ONLY BREAK THE SINGLE TRIPLE CARBON TO CARBON BOND, SINGLE CARBON TO BONDS PRESENT ALSO CONTAIN ONE OR MORE | Courtesy ofCARBON SAMPORHELP | BONDS SINGLE CARBON TO CARBON BONDS Downloaded from https://www.thebigvault.net Saturated vs unsaturated hydrocarbon compounds Saturated hydrocarbons Unsaturated hydrocarbons • Contain only single carbon to • Contain one or more double or carbon bonds triple carbon to carbon bond – Are also likely to contain one or • Functional groups: Alkane more single carbon to carbon bonds • Unreactive and stable • Functional groups: Alkene, alkyne – Due to the large amount of energy • Reactive and unstable (compared needed to break the existing chemical to saturated hydrocarbons) bonds – Due to the small amount of energy required to break the double or triple carbon to carbon bonds present | Courtesy of SAMPORHELP | Downloaded from https://www.thebigvault.net Saturated vs unsaturated hydrocarbon compounds Saturated Hydrocarbons – Saturated hydrocarbons have only single carbon to carbon bonds – The carbon atoms in saturated hydrocarbons form bonds to the maximum amount of hydrogen atoms possible • These compounds are saturated with hydrogen atoms – Include alkanes (straight chains) & cycloalkanes (carbon rings) | Courtesy of SAMPORHELP | Downloaded from https://www.thebigvault.net Saturated vs unsaturated hydrocarbon compounds Unsaturated Hydrocarbons – Unsaturated hydrocarbons have one or more double or triple carbon to carbon bond(s) • Will also contain single carbon to carbon bonds – The carbon atoms in unsaturated hydrocarbons form bonds to less than the maximum amount of hydrogen atoms possible • These compounds are not saturated with hydrogen atoms (unsaturated) – Due to the presence of double or triple carbon to carbon bonds – Include Alkenes (straight chains) & Cycloalkenes (carbon rings) | Courtesy of SAMPORHELP | Downloaded from https://www.thebigvault.net Saturated vs unsaturated hydrocarbon compounds Number of Carbon Atoms Prefix Alkane Alkene Alkyne 1 Meth- Methane - - 2 Eth- Ethane Ethene Ethyne 3 Prop- Propane Propene Propyne 4 But- Butane Butene Butyne 5 Pent- Pentane Pentene Pentyne 6 Hex- Hexane Hexene Hexyne 7 Hept- Heptane Heptene Heptyne 8 Oct- Octane Octene Octyne 9 Non- Nonane Nonene Nonyne 10 Dec- Decane Decene Decyne | Courtesy of SAMPORHELP | Downloaded from https://www.thebigvault.net Propane is an alkane: Chemical properties of alkanes Used as a fuel for cars (LPG gas) Functional Group: Alkane Distinguishing characteristic: Alkane compounds contain only single carbon to carbon bonds Naming convention: Alkane compounds have –ane at the end of their name e.g. propane Example compound: | Courtesy of SAMPORHELP | Propane Downloaded from https://www.thebigvault.net Chemical properties of alkanes HYDROCARBONS BELONG TO ONE OF THREE FUNCTIONAL GROUPS Type Type Type ALKANE ALKENE Example Definition Definition ALKYNE CONTAIN ONLY CONTAIN ONE CONTAIN ONE OR Example Definition Example SINGLE CARBON MORE DOUBLE OR MORE TO CARBON CARBON TO TRIPLE CARBON BONDS CARBON BONDS TO CARBON BONDS | Courtesy of SAMPORHELP | Downloaded from https://www.thebigvault.net Chemical properties of alkanes Alkanes are non-polar compounds – Alkanes contain only carbon and hydrogen atoms which are connected via non-polar covalent bonds (equal electron sharing) H2O is a polar compound – H2O contains polar covalent bonds where the shared electrons are more attracted to the oxygen atom than the hydrogen atoms • Compounds must be polar to dissolve in H2O | Courtesy of SAMPORHELP | Downloaded from https://www.thebigvault.net Chemical properties of alkanes Will an alkane compound (such as propane) dissolve in H2O? – Non-polar alkanes do not dissolve in polar H2O – Alkanes are insoluble in H2O – The non-polar alkane will only dissolve in Propane non-polar solvents such as chloroform | Courtesy of SAMPORHELP | Downloaded from https://www.thebigvault.net Chemical properties of alkanes Combustion – Combustion reactions are exothermic reactions that release heat – Alkanes burn in the presence of oxygen producing CO2, H2O and heat via combustion reactions – Example: combustion of methane CH4 + 2O2 → CO2 + 2H2O + Energy – All combustion reactions are redox reactions where one reactant is oxidised and one is reduced • Oxygen is always reduced | Courtesy of SAMPORHELP | in redox reactions https://www.freeimages.com/photo/fire-camp-1174281 Downloaded from https://www.thebigvault.net Chemical properties of alkanes Halogenation – Halogenation reactions involve an alkane reacting with a halogen molecule such as Cl2 or F2 – The end result of a halogenation reaction: • Substitution of one of the alkane’s hydrogen atoms with a halogen atom, producing a halogenated alkane Methane Halogen Halogenated molecule alkane | Courtesy of SAMPORHELP | Stoker 2014, p368-70 Downloaded from https://www.thebigvault.net Halogenation • During a halogenation reaction the alkane’s hydrogen atom is replaced by a single halogen atom, producing a halogenated alkane • The lost hydrogen atom forms a compound with the other halogen atom (from the halogen molecule), in this case creating the strong acid HCl H Large energy H input H C H + Cl Cl H C Cl + H Cl Halogen H molecule H Methane Halogenated alkane • Additional hydrogen atoms can be substituted in the halogenated alkane by performing | Courtesy of additionalSAMPORHELP | halogenation reactions Downloaded from https://www.thebigvault.net Chemical properties of alkanes Halogenated alkane H Energy HCl product input Energy input H C H + Cl Cl Halogen H molecule Methane Reactant Reactant Animation of a halogenation reaction | Courtesy of SAMPORHELP | Downloaded from https://www.thebigvault.net Chemical properties of alkanes Chlorofluorocarbons (CFCs) – Synthetic organic compounds that were developed to be used as refrigerants • Refrigerants can be used to heat a pump that powers refrigeration – The 2 most commonly used CFCs were Freon-11 and Freon-12 • CFCs destroyed a significant amount of the ozone layer in the stratosphere until banned | Courtesy of SAMPORHELP | Stoker 2014, p373 Downloaded from https://www.thebigvault.net
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