Organic chemistry IGCSE Chemistry 0620 What are organic compounds? Organic compounds are hydrocarbons and related compounds Hydrocarbons are compounds made up of carbon and hydrogen only. Carbon atoms can join to another Carbon atom to form long Carbon chains. Because of this there are huge number of organic compounds. Saturated and unsaturated compounds If all bonds between carbon atoms are single, the compounds are saturated compounds. If a double bond is present between carbon atoms, the compounds are called unsaturated. In saturated compounds, all four valencies of carbon atoms are used up. So saturated compounds are not reactive. Naming hydrocarbons Each organic compound has two parts in their names: Prefix depends on how many carbon atoms present. 1 carbon compound Meth 2 carbon compound Eth 3 carbon compound Prop 4 carbon compound But 5 carbon compound pent 6 carbon compound hex Naming hydrocarbons Suffix (second part) depends on the bond between carbon atoms. Single bond –ane Double bond –ene Single bond hydrocarbons are called ALKANES Alkanes have a general formula: CnH(2n+2) where n is the number of carbon atoms. Methane CH4 Butane C4H10 Ethane C2H6 Pentane C5H12 Propane C3H8 Hexane C6H14 Double bond hydrocarbons are called ALKENES Alkenes have a general formula: CnH2n where n is the number of carbon atoms. Ethene C2H4 Pentene C5H10 Propene C3H6 Hexene C6H12 Butene C4H8 https://www.youtube.com/watch?v=Sfm3e He57PU Formula of Saturated Hydrocarbons (Alkanes) Unsaturated compounds (Alkenes) have free valencies with carbon atoms. Second bond in the double bond is weak and temporary. So if other atoms available, unsaturated compounds are very reactive. Formula of unsaturated compounds (Alkenes) Test to find if a compound is saturated or unsaturated Mix the compound with bromine water. (Bromine water is red brown in colour) If the hydrocarbon is unsaturated (alkene), it will react with bromine in bromine water and becomes colourless. If the hydrocarbon is saturated (alkane), no reaction will take place with bromine and colour remains the same Video https://www.youtube.com/watch?v=1r9aY S4Ndac Crude oil Crude oil is a source of many hydrocarbons Crude oil is formed from the dead bodies of animals (mainly aquatic) which were living millions of years ago. These bodies are covered with sand and mud. Due to changes in temperature and pressure, the bodies are changed in to a dark viscous liquid called crude oil(petroleum). Soil changed into sedimentary rock. Crude oil Crude oil is pumped out from the oil wells. Important substances from crude oil are separated in an oil refinery. Fractional distillation of crude oil Various useful substances are separated from crude oil by fractional distillation. Fractions with low boiling points with low density are collected at the top. Following increase when coming down in the fractionating column: Density Molecular mass (No of C atoms) Viscosity Colour darker Boiling point Fuels Fuels give out energy. Coal, natural gas, petrol etc are fuels Natural gas (petroleum gas) is mainly methane. Hydrocarbons burn in air to produce carbon dioxide and water together with energy(heat) Methane + oxygen Carbon dioxide + water CH4 + 2O2 CO2 + 2H2O Ethane + oxygen carbon dioxide + water 2C2H6 + 7O2 4CO2 + 6H2O Functional group Double bond = Alcohol -OH Carboxylic acid –COOH Halide -Cl -Br -I Group of compounds with similar properties is called HOMOLOGOUS SERIES Examples: Alkanes, Alkenes, Alcohols, Carboxylic acids etc Alcohols Methanol (1Carbon alcohol) CH3OH Ethanol (2 Carbon alcohol) C2H5OH or CH3-CH2-OH Propanol (3 Carbon alcohol) C3H7OH or CH3-CH2-CH2-OH Carboxylic acids Methanoic acid (1Carbon acid) HCOOH Ethanoic acid (2 Carbon acid) CH3COOH Propanoic acid (3 Carbon acid) CH3CH2COOH Alkanes Alkanes are saturated hydrocarbons. So they are not reactive. Alkanes burn in oxygen to form carbon dioxide and water. CH4 + 2O2 CO2 + 2H2O Energy is given out when alkanes burn. So alkanes are present in fuels. Petrol and diesel are mixtures of alkanes. Substitution reaction If atoms are replaced by other atoms, the reaction is called substitution reactions. Alkanes show substitution reaction. Hydrogen atoms are replaced by more reactive halogen atoms in presence of light. Here light works as a catalyst. CH4 + Cl2 CH3Cl + HCl UV Alkenes Alkenes are unsaturated compounds having a double bond between carbon atoms. Alkenes are highly reactive. They also burn in oxygen to produce carbon dioxide gas and water. Ethene + Oxygen Carbon dioxide + Water C2H4 + 3O2 2CO2 + 2H2O Addition reaction Unsaturated compounds undergo addition reaction. Atoms are added to the double bond to form a single product (No replacement). This kind of reaction is called addition reaction. During addition reaction, double bond compounds(less stable) change into single bond compounds (stable) Alkenes Alkanes Addition of halogen (bromine) Ethene + Bromine dibromo ethane CH2=CH2 + Br2 CH2Br-CH2Br Addition of hydrogen Heat and a catalyst (Nickel) are needed for the addition of hydrogen to alkene. Ethene + Hydrogen Ethane (Heat & Ni needed) CH2=CH2 + H2 CH3-CH3 Addition of water Heat and high pressure are needed for this. Ethene + steam Ethanol CH2=CH2 + H2O CH3-CH2-OH Test for unsaturated compounds Saturated compounds have single bonds between carbon atoms Unsaturated compounds have a double/triple bond between carbon atoms. When an unsaturated compound is passed through bromine water, the colour will change from orange brown to colourless. This is because of the addition reaction with unsaturated compound and bromine. CH2=CH2 + Br2 CH2Br-CH2Br (orange brown) (colourless) Alcohols Common alcohols are methanol, ethanol and propanol CH3OH, C2H5OH, C3H7OH Ethanol is present in alcoholic drinks. Also used in hospitals, industries (as a solvent) and different types of medicines. Widely used as fuel for car engines. Methanol is poisonous Propanol is a good solvent used to clean audio and video heads. Ethanol Two methods of making ethanol are: Batch process In this method glucose is fermented using yeast. Enzymes in yeast change glucose into ethanol and carbon dioxide (anaerobic respiration by yeast) Glucose ethanol + carbon dioxide C6H12O6 2C2H5OH + 2CO2 Ethanol formed is separated by distillation Continuous process In this process, ethene is treated with super heated steam at high temperature and pressure in presence of concentrated acid as a catlyst (addition) CH2=CH2 + H-OH CH3-CH2OH Ethene is a by-product during the petroleum industry. The production of ethanol takes place continuously. Advantages and disadvantages Batch process Advantage: environmental friendly Disadvantage: Takes long period of time for yeast to ferment Continuous process Advantage: quick and continuous production Disadvantage: can cause pollution and expensive (need of fuel) Cracking It is opposite of polymerisation Large molecules are broken down into small molecules using catalyst or heat. Most petroleum products are large hydrocarbon molecules. These large molecules are cracked into small molecules which are present in petrol (5-10 carbon atoms). Alkenes will be formed when alkanes are cracked Fermentation:Yeast changes glucose into alcohol and carbon dioxide gas is called fermentation. Fermentation is anaerobic respiration. Ethene formed as by-product during cracking is useful in the manufacture of ethanol. C12H26 C8H18 + 2C2H4 (large alkane) (useful alkane) Ethene Ethanol when burns in oxygen (air), it gives out carbon dioxide, water and energy. Ethanol + Oxygen Carbon dioxide + water C2H5OH + 3O2 2CO2 + 3H2O + Energy Acids Important carboxylic acids are: Methanoic acid, Ethanoic acid and Propanoic acid H-COOH CH3-COOH C2H5-COOH Ethanoic acid is prepared by the oxidation of ethanol using potassium manganate(VII). C2H5OH + 2(O) CH3COOH + H2O Acid present in vinegar is Ethanoic acid. Alcohol (wine) turns sour if left open in air (acid formation) Ethanoic acid is a weak acid(Hydrogen ions are given out partially) Esterification When an organic acid reacts with an alcohol, ester and water are formed. This is done in presence of conc sulphuric acid.(dehydrating agent) Example: Ethanol reacts with ethanoic acid will produce ethyl ethanoate ester and water. C2H5OH + CH3COOHC2H5OOCCH3 + H2O Ethanol Ethanoic acid Ethyl ethanoate water Propanol + Ethonoic acid Propyl ethanoate + water C3H7OH + CH3COOH C3H7OOCCH3 + H2O Propanol Ethanoic acid Ethyl ethanoate water Methyl propanoate is formed from which alcohol and acid? Methanol and Propanoic acid Write formula of Methanol, Propanoic acid and methyl propanoate CH3OH, C2H5COOH, CH3OOCC2H5 Write names of any two esters, alcohol and acid from which they are formed and write their formulas. Esters are sweet smelling substances (found in fruits). So they are used to make perfumes. Macromolecules Macromolecules are large molecules (polymers) formed from small molecules (monomers). Macromolecules are synthetic(man made) or natural. Synthetic polymers. Poly ethene, poly propene and chloro ethene are polymers formed by the addition polymerisation (of double bond monomers). Non biodegradable plastics stay in soil and cause soil pollution. Bio-degradable plastics can be removed by micro organisms. Polymerisation Small molecules(monomers) join one another to form a large molecule (polymer). This kind of reaction is called polymerisation. 1. Addition polymerisation. At high temperature and pressure, alkenes undergo polymerisation to form different polymers (Plastics) During polymerisation, double bond becomes single. Ethene Poly ethene (Polythene) …CH2=CH2 + CH2=CH2 + CH2=CH2 + CH2=CH2…. -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2 The above reaction can be summarised as nCH2=CH2 -(CH2-CH2)-n Another example is chloroethene when polymerised, we get polychloroethene (PVC) nCH2=CHCl -(CH2-CHCl)-n Propene when polymerised we get polypropene (another plastic) 2. Condensation polymers Some polymers are made from non-double bond compounds. Example: Nylon is a polymer from an amine and acid. Water molecules removed. The bond formed is called amide OR Another example is Terylene Water molecules removed Natural polymers Mainly carbohydrates, proteins and fats These are food constituents Carbohydrates macromolecules such as starch is made up of simple sugars like glucose or fructose. -OH + HO- groups joined here. Water molecules removed. Complex carbohydrates when hydrolyse turn into simple sugars back Starch + water glucose Hydrolysis is breaking large molecules into smaller ones by adding water. In our body, digestive enzymes help in hydrolysis. Proteins and fats Proteins are made up of amino acids. Many amino acid molecules join to form proteins. Amino group (-NH2) is basic and acid group (COOH) is acidic. So amino group and acid group react to form amide link (peptide bond). Water is removed during the process. • Proteins on hydrolysis give the amino acids. • Fats and oils(lipids) are macromolecules of fatty acids and glycerol. • Glycerol and fatty acids are joined like that in terylene • Fats on digestion (hydrolysis) gives fatty acids and glycerol. • Fats when hydrolyse with alkali we get soaps. • Amino acids from protein molecules are separated and identified by chromatography. THE END