1 ORGANIC CHEMISTRY GRADE:X 2 SLO: 11.1.1: Discuss general characteristics of organic compounds. 1. Origin: Most of them come from living things (plants and animals) or from the things that were once living (fossils). 2. Composition: Carbon is the main constituent of organic compounds. Hydrogen is also frequently present in organic compounds. Other elements like oxygen, nitrogen, sulphur, phosphorous and halogens are present in many organic compounds. 3. Covalent linkage: Organic compounds contain covalent bond(polar or non-polar) due to presence of carbon atom. 4. Solubility: Organic compounds are non-polar in nature therefore mostly are soluble in organic solvent such as ether, benzene, carbon disulphide etc. Polar organic compounds are soluble in alcohols such as methyl alcohol and ethyl alcohol. 5. Electrical conductivity: Organic compounds are poor conductor of electricity due to presence of covalent bond. 6. Melting and boiling point: Generally organic compounds are volatile. So they have low melting and boiling points. 7. Stability: They are less stable as they have low melting and boiling points. 8. Combustibility: Since organic compound possesses high percentage of carbon, they are combustible. 9. Isomerism: Organic compounds have tendency to exhibits isomerism (Isomerism is the phenomenon in which more than one compounds have the same molecular formula but different molecular structures). 10. Rate of reaction: Organic compounds are generally less stable than inorganic compounds. Due to covalent bonding in them, their reaction rates are often slow. SLO: 11.1.2: Explain the diversity and magnitude of organic compounds. 1. Catenation: The ability of carbon atoms to link with other carbon atoms is called catenation. The main reason for the existence of large number of organic compounds is that carbon atoms can link with one another by means of covalent bonds to form long chain or rings of carbon atoms. The chain can be straight or branched. 2. Isomerism: Another reason for the abundance of organic compounds is the phenomenon of isomerism. Number of isomers increases with the increase in number of carbon atoms in the given molecular formula. 3. Strength of covalent bonds of carbon: Due to its very small size, carbon can form very strong covalent bonds with other carbon atoms, hydrogen, oxygen, nitrogen and halogens. This enables it to form a large number of compounds. 4. Multiple bonding: In order to satisfy its tetravalency, carbon can make multiple bonds (i.e double and triple bonds). 3 SLO: 11.1.3: List some sources of organic compounds. • Coal Dead plants • Natural gas • Petroleum • Carbohydrates • Proteins • Fats/oils • Vitamins Living organisms • Medicine • Cosmetics Synthesis in laboratory • Paints • Plastics, • Fertilizer • Detergents • Synthetic fibres • Rubber • Insecticides and pesticides SLO: 11.1.4: Recognizes the uses of organic compounds in daily life. • Uses as food: The food we eat daily contain carbohydrates, fats, protein (energy sources), vitamins and minerals which are required for healthy functioning of our body. • Uses as clothing: Natural fibres (cotton, silk and wool etc.) and synthetic fibres (nylon, Dacron and acrylic etc.) are used for clothing. • Uses as houses: wood is cellulose. It is used for making houses and furniture. • Uses as fuel: Coal, natural gas, petroleum etc are common fuels which we use for automobiles and domestic purpose. Propane and butane which are gases obtained from natural gas are widely available as LPG. • Uses as medicines: A large number of organic compounds are used as medicine by us. Most of the lifesaving medicines and drugs such as antibiotics are synthesized in laboratories. Compound of phenol help to ensure antiseptic conditions in hospital operating rooms. • Uses as raw material: To prepare a variety of material such as rubber, paper, ink, drugs, dyes, paints, varnishes, pesticides. It is used in manufacturing of organic chemicals and products such as plastic, acetic acid, antifreeze etc. • Uses for welding and cutting metals: Acetylene is widely used in the oxy-acetylene form for welding and cutting metals. • Uses as solvent: Methanol is used as a solvent for fats, oils, paints and varnishes. 4 SLO: 11.2.1: Classify organic compounds into Acyclic and cyclic compounds with examples. A. Acyclic / Open Chain Compounds / Aliphatic Compounds: The carbon atoms are present in the form of an open chain. This chain may either be a straight chain or a branched chain. Open chain compounds are those in which end carbon atoms are not joined with each other. • Straight Chain Compounds: The carbon skeleton is in the form of a straight chain. Examples: Propane CH3-CH2-CH3 Propene CH2=CH-CH3 • Branched Chain Compounds: The carbon skeleton is in the form of a branched chain. Examples: Isobutylene 5 B. Cyclic or Closed Chain Compounds They are marked by the presence of one or more closed chains or ring of atoms in their structure. Depending on whether there is a presence of any other atom apart from carbon in the constitution of the ring, they are further classified as: a. Homocyclic or Carbocyclic Compounds b. Heterocyclic Compounds a. Homocyclic or Carbocyclic Compounds: The rings in these compounds are entirely made up of carbon atoms. No other atom is present in the ring skeleton. These can be further divided into two sub-classes: I. Alicyclic Compounds II. Aromatic Compounds I. Alicyclic / Non-Benzenoid Compounds: Carbocyclic compounds which do not have benzene ring in their molecules are called alicyclic or non-benzenoid compounds. Their name is attributed to their resemblance to Aliphatic compounds in their properties. The examples of this category include cyclopropane, cyclobutane, cyclopentane, cyclohexane, etc. II. Aromatic / Benzenoid Compounds: These organic compounds contain at least one benzene ring in their molecule. A benzene ring is made up of six carbon atoms with three alternating double bonds. They are called aromatic because of aroma or smell they have. These are cyclic unsaturated compounds. They derive their name from the Greek word Aroma which means “fragrant smell” since most of these compounds bear a pleasant smell. These are further classified into two types: They are characterized by the presence of one or more fused or isolated benzene rings as well as their derivatives in their structure. Depending upon the number of benzene rings that are fused together in their structure, they can be further classified as Monocyclic, Bicyclic, Tricyclic. 6 b. Heterocyclic Compounds When one or more heteroatoms such as oxygen, nitrogen, sulphur, boron, silicon etc. are present in the ring such compounds are known as heterocyclic compounds. • Alicyclic heterocyclic compounds: Aliphatic heterocyclic compounds that contain one or more heteroatoms in their rings are called alicyclic heterocyclic compounds. • Aromatic heterocyclic compounds Aromatic heterocyclic compounds that contain one or more heteroatoms in their ring skeleton are called aromatic heterocyclic compounds. 7 SLO: 11.2.2: Identify straight chain hydrocarbons up to ten carbon atoms on the basis of their structural, condensed and molecular formulae. General Formula of Alkanes: CnH2n+2 General Formula of Alkenes: CnH2n General Formula of Alkynes: CnH2n-2 ALKANES (CnH2n+2) Alkanes Molecular Formula Methane CH4 Ethane C2H6 Condensed formula Structural formula 8 ALKENES (CnH2n) Alkenes Molecular Formula Condensed formula Structural formula 9 ALKYNES (CnH2n-2) Alkynes Molecular Formula Condensed formula Structural formula 10 11 SLO: 11.3.1: List the name of straight chain alkanes up to decane. SLO 11.3.2: Illustrate the formation of alkyl groups by the removal of hydrogen atom from their corresponding alkanes (up to five carbon atoms). Alkanes Methane CH4 Structural formula Alkyl radical Name Methyl Ethane C2H6 Propane Butane 12 Pentane SLO 11.4.1: Define the homologous series and its characteristics. A homologous series is a family of organic compounds with the same functional group and similar chemical properties. Characteristics: • All members of a series can be represented by a general formula for example CnH2n+2 for alkanes, CnH2n for alkenes and CnH2n-2 for alkynes. • Successive members of the series differ by one unit CH2and 14 units in their relative molecular mass. • They have the same functional group. • They have similar chemical properties. • There is a gradual change in their physical properties as we go down the series from one member to the next due to increase in their molecular masses. • They can be prepared by similar general method. SLO 11.4.2: Define the term isomerism and its types i.e. structural isomerism and stereoisomerism. Isomerism Two or more compounds having the same molecular formula but different structural formulas and properties are said to be isomers and the phenomenon is called isomerism. Structural isomerism Structural isomerism, or constitutional isomerism, is a type of isomerism where isomers have same molecular formula but have different arrangements of atoms within the molecule. e.g. n pentane, isopentane and neopentane are structural isomers. 13 Stereoisomerism When isomers have the same structural formula but differ in relative arrangement of atoms or groups in space within the molecule, these are known as stereoisomers and the phenomenon as stereoisomerism. The spatial arrangement of atoms or groups is also referred to as configuration of the molecule and thus we can say that the stereoisomers have the same structural formula but different configuration SLO 11.4.3: Describe chain isomerism as a type of structural isomerism Chain isomerism is a type of structural isomerism where the isomers have same molecular formula but they differ in the order in which the carbon atoms are bonded to each other. Thus the isomers arise with different types of branching in carbon chains. For example, Pentane, C5H12, has three chain isomers. These are n-pentane, isopentane and neopentane. 14 SLO 11.4.4: Draw possible structures of the chain isomers of given alkanes up to five carbon atoms. Isomers of pentane SLO 11.5.1: Define the term functional group. An atom or group of atoms or presence of double or triple bond which determine the characteristic properties of an organic compound is known as the functional group. 15 SLO 11.5.2: Classify various organic compounds i.e alkane, alkene, alkyne, alkylhalide, alcohol, amine, ether, aldehyde, ketone, carboxylic acid, acid amide, ester and nitro compounds on the basis of their functional groups. c-x, where X=F, Cl, Br, I Alkyl halides /Haloalkanes H3C-CH2-Cl Chloroethane Ethyl 16 Draw and name simple molecules that contain the following functional group. chloride 2,2-dimethyl propane 2-butyne 2-propanol Methoxy ethane Propanal Butanone Ethanoic acid Ethyl Ethanoate Bromoethane Ethanamine 17 SLO 11.5.3: Identify a molecule’s functional group using structural formula and systematic names of compounds up to five carbon atoms. SLO 11.5.4: Determine carboxylic acid, phenols, amines, aldehydes and ketones using different tests. Function al Group Carboxy lic acids Phenols Amines Test Observation Inference / Result Litmus Paper turns into Red Carboxylic acid group is present ii. NaHCO3 solution test: Solution of Organic compound in a test tube + add Sodium bicarbonate CO2 gas with effervescence evolves Carboxylic acid group is present iii. Ester formation test: Take organic compound solution in a test tube + add small amount of alcohol + 1-2 drops of H2SO4 Fruity smell will be given out Carboxylic acid group is present Purple / Violet coloration will appear Phenol group is present Extremely unpleasant odour will be given out. Amine group is present i. Litmus test: Dip Litmus Paper into organic compound solution i. Ferric Chloride Test: Take organic compound solution in a test tube + few drops of freshly prepared FeCl3 Solution. i. Carbyl amine test: Heat organic compound in a test tube + few mL of Chloroform (CHCl3) + few mL of alcoholic KOH 18 Aldehydes Ketones i. Fehling’s solution test: Take organic compound in a test tube + Fehling’s solution A and B + boil it for 5 minutes. Red precipitate will be formed. Aldehyde group is present ii. Tollens’ Test / Silver Mirror Test: Organic compound solution + Tollen’s reagent (Alkaline ammoniacal silver nitrate) + reflex/ boil for few minutes Silver Mirror formed at the walls of the test tube Aldehyde group is present i. Phenyl hydrazine test: Take organic compound + phenyl hydrazine solution Orange red precipitate will be formed Ketone group is present ii. Sodium nitroprusside test: sodium nitroprusside solution + 2-3 drops of NaOH solution + pinch of organic compound Red colour will be formed Ketone group is present i. Carboxylic Acid Litmus paper: • Shake a pinch of the given compound with water and add a drop of blue litmus solution. • Solution will turn red. NaHCO3 about 2.0cm3of 5% NaHCO3 solution and add a pinch of given compound. • CO2 gas with effervescence evolves. ii. Phenol: • Take Ferric chloride test: • Add few crystals of organic compound to ethanol and water mixture then add few drops of freshly prepared FeCl3 solution OR Add small amount of organic compound in a test tube and add freshly prepared FeCl3solution. • Purple or blue black colour appears. iii. Amine Sodium Hydroxide test: • A little of the substance is boiled with dil NaOH. • Ammonia gas is evolved. 19 Carbyl amine test. • Heat about 0.2g of the given compound and add 0.5 cm3of chloroform and 2-3 cm3of alcoholic KOH. • Extremely unpleasant odor will be given out. iv. Aldehyde Fehling’s solution • Mix 3cm3of Fehling’s solution A with 3 cm3of Fehling’s solution B in a test tube. Dissolve a few crystals of glucose in 3 cm3 water. Mix the two solutions. Heat the test tube containing the above mixture for about five minutes. • Red precipitate will be formed. Sodium Bisulphite test • Shake 0.2 gm or 0.5cm3of the given compound with 1-2 cm3of saturated solution of sodium bisulphite. • A crystalline white precipitate will be formed. v. Ketone Phenyl hydrazine test • Shake a pinch of the given organic compound with about 2.0cm3of phenyl hydrazine solution • Orange red precipitate will be formed. Sodium nitroprusside test • Take about 2.0cm3of sodium nitroprusside solution in a test tube and add 2-3 drops of NaOH solution. Now add a pinch of the given compound and shake. • Red colour will be formed. Tollen https://www.youtube.com/watch?v=7I-y3I3VzM8 Fehling https://www.youtube.com/watch?v=_C1llXoimns Pheny hydrazine https://www.youtube.com/watch?v=JAQ060bSZG8 Phenol test https://www.youtube.com/watch?v=HSGlfbV7W84