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Tamilnadu Board Class 11 Chemistry Chapter 11

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Tamilnadu Board Class 11 Chemistry Chapter 11 Unit 11 Fundamentals of Organic Chemistry Learning Objectives After studying this unit students will be able to • understand the reason for the tetra valency of carbon and shapes of organic molecules • classify the organic compounds • name the organic compounds according to IUPAC nomenclature and derive the structure from the IUPAC name • describe various types of isomerism Friedrich Wöhler, was a German pioneer in organic • explain the principles of detection and estimation chemistry. He is best known of elements in organic compounds for his synthesis of urea an the organic compound from • describe various techniques used in the the inorganic compound, purification of organic compounds ammonium cyanate. This finding went against the Introduction mainstream theory of that time called vitalism which Organic chemistry is the study of compounds stated that organic matter of carbon. Carbon has a tendency to form more possessed a special force compounds with itself and other atoms (H, O, N, S or vital force inherent to and halogens) than any other elements. The tendency all living things. He is also of an atom to form a chain of bonds with the atoms the first to isolate several of the same element is called catenation. The high chemical elements. He is the strength of C-C bond is responsible for its catenation discoverer of the element property. aluminum and also the co-discoverer of yttrium, The word 'organic' means 'derived from living beryllium, and titanium. organisms'. Organic compounds were thought to be found only in living things. Cell the basic unit of living things, consumes, creates and consists of mainly organic compounds. DNA, the genetic material, the 110 Unit 11 revised.indd 110 27-08-2018 17:53:46 lipids, that forms our cell membrane and The formation of four covalent the glycogen the energy reserve stored bonds can be explained as below. During in our liver are all organic compounds. bond formation, one of the electrons Except few inorganic compounds like from 2s orbital is promoted to 2pz orbital. salt, water etc... all others such as food, The formation of four sigma bonds by medicine, clothing, cosmetics, fuel etc... carbon can be explained on the basis are compounds of carbon. All the essential of sp3 hybridisation of carbon. Carbon biochemical reactions are also organic in forms multiple (double and triple) bonds nature leading to the fomation various in certain compounds. These can be essential bioorganic molecules such as explained by sp2 and sp hybridisation of lipoproteins, phospolipids, glycolipids carbon. The carbon forms relatively short etc... bonds which enable the lateral overlap of unhybridised 2p orbitals of sp2 and sp Synthesis of acetic acid by kolbe hybridised carbon to form one and two pi and methane by Berthlot, confirmed that bonds respectively. organic compounds can be synthesized in laboratory. Since then, millions of Molecular stucture can be derived organic compounds were synthesised from the type of hybridisation. An sp3 and characterised. The field of organic hybridised carbon will have a tetrahedral chemistry is very vast and its principles geometry, a sp2 hybridised carbon will find applications in many industries have trigonal planar geometry. and sp including food, textile, pertrochemical, hybridised carbon will have a linear pharmaceutical, dye, polymers, fetiliser, geometry. cosmetics etc... Discussing the importance of organic chemistry is just like describing Characteristics of organic compounds: a drop of water in a mighty ocean. All organic compounds have the following characteristic properties. The knowledge of chemical bonding and molecular structure will help 1. They are covalent compounds of in understanding the properties of organic carbon and generally insoluble in compounds. We know that, the carbon has water and readily soluble in organic four valance electrons and its ground state solvent such as benzene, toluene, electronic configuration is 1s2 2s2 2p2. ether, chloroform etc... An atom can attain noble gas electronic 2. Many of the organic compounds are configuration either by transferring or inflammable (except CCl ).They sharing of electrons. It is not possible for 4 possess low boiling and melting the carbon to form either C4+ or C4- ions to points due to their covalent nature attain the nearest noble gas configuration, as it requires large amount of energy. This 3. Organic compounds are characterised implies that carbon cannot form ionic by functional groups. A functional bond. Almost in all compounds of carbon, group is an atom or a specific it forms four covalent bonds. combination of bonded atoms that 111 Unit 11 revised.indd 111 27-08-2018 17:53:46 react in a characteristic way, irrespective of the organic molecule in which it is present. In almost all the cases, the reaction of an organic compound takes place at the functional group. They exhibit isomerism which is a unique phenomenon. 4. Homologous series: A series of organic compounds each containing a characteric functional group and the successive members differ from each other in molecular formula by a CH2 group is called homologous series. Eg. Alkanes: Methane (CH4), Ethane (C2H6), Propane (C3H8) etc.. Alcohols: Methanol (CH3OH), Ethanol (C2H5OH) Propanol (C3H7OH) etc..) Compounds of the homologous series are represented by a general formula Alkanes CnH2n+2, Alkenes CnH2n, Alkynes CnH2n-2 and can be prepared by general methods. They show regular gradation in physical properties but have almost similar chemical property. 11.2 Classification of organic compounds The existing large number of organic compounds and ever-increasing number have made it necessary to classify them. They may be classified based on their structure or the functional group. 11.2.1 Classification based on the structure: Organic Compunds Acyclic or open chain or aliphatic Cyclic compounds compounds Example : CH3–CH2–CH3 (propane) Homocyclic compounds Heterocyclic compounds Alicyclic Compounds or Aromatic Alicyclic compounds Aromatic compounds carbocyclic compounds N CH2 Pyridine THF O H2C CH2 Cyclopropane Non-Benzenoid compounds also Benzenoid compounds or aromatic aromatic homocyclic homocyclic OH Phenol azulene 112 Unit 11 revised.indd 112 27-08-2018 17:53:46 Based on the above classification let us 11.2.2 Classification based on functional classify the following compounds. groups: 1. Classify the following compounds Table 11.1 Class of compounds and their based on the structure functional group i) CH ≡ C– CH2–C ≡ CH ii) CH3 – CH2 – CH2 - CH2– CH3 S. No. Class of CH compounds General formula (R - Alkyl group) 3 group Functional iii) 1 Alkene – CnH2n 2 Alkyne – CnH2n-2 F, Br, 3 Alkyl halide Cl, I R- X CH –CH –CH –CH iv) 2 2 2 3 4 Alcohol OH R-OH S 5 Ether O R-O-R' Solutions: O 6 Aldehyde R-CHO (i) Unsaturated open chain compound C H (ii) saturated open chain compound 7 Ketone CO R-CO-R' (iii) aromatic benzenoid compound Carboxylic O 8 R-COOH acid C OH (iv) alicyclic compound O 9 Ester RCOOR' C OR Evaluate Yourself ? Acid O O 10 R-CO-O-CO-R' C O C 1) Give two examples for each anhydride of the following type of organic O 11 Acyl chloride R-COX compounds. C X SO3H (i) non-benzonoid aromatic, 12 Sulphonic acid R-SO3H NO2 (ii) aromatic heterocyclic, 13 Nitro alkane R-NO2 (iii) alicyclic and NH2 14 Amine R-NH2 (iv) aliphatic open chain. O 15 Amide R-CO-NH CNH2 2 113 Unit 11 revised.indd 113 27-08-2018 17:53:47 for measurement; atomic weights, and many other critically-evaluated data. According to IUPAC recommendations S. No. Class of to name any organic compound, it is compounds General formula considered as a derivative of its parent (R - Alkyl group) Functional group Functional saturated hydrocarbon. The IUPAC name Cyanide 16 C N R-CN of an organic compound consists of three (Nitrile) parts. 17 Isocyanide NC R-NC prefix + root word + suffix 18 Cyanate OCN R-OCN Root word denotes the number of carbon 19 Isocyanate NCO R-NCO atoms in the longest continiuous chain 20 Thiocyanate SCN R-SCN in molecules. Prefix denotes the group(s) attached to the main chain which is 21 Isothiocyanate NCS R-NCS placed before the root. Suffix denotes the Thioalcohols 23 SH R-SH funtional group and is paced after the root or thiols word. 24 Thioethers S R R-S-R' Table 11.2 Number of carbons in 25 Imines NH R-CH=NH parent chain and the corresponding Nitroso root words 26 NO R-NO compounds NH NH2 27 Hydrazines R-NH-NH2 Hydrazo 28 NH NH R-NH-NH-R compounds Root word Root word OH Chain length(or) Chain length(or) 29 Phenols C H OH carbon of atom no. 6 5 carbon atoms of no. C1 Meth- C17 Heptadec- O R O RCON(R') 30 Imide C2 Eth- C18 Octadec- C N C COR'' C3 Prop- C19 Nonadec- C4 But- C20 Eicos- 11.3 Nomenclature of organic C5 Pent- C21 Henecos compounds: C6 Hex- C22 Docos C Hept- C Triacont- The International Union of Pure and 7 30 Applied Chemistry (IUPAC) is the world C8 Oct- C31 Hentriacont authority on chemical nomenclature and C9 Non- C32 Ditriacont terminology, naming of new elements in C10 Dec- C40 Tetracont- the periodic table standardized methods C11 Undec- C50 Pentacont- 114 Unit 11 revised.indd 114 27-08-2018 17:53:49 Secondary suffix: It is used to denote the nature of functional group present in the organic compound. It is added to the primary suffix by removig its terminal ‘e’. Root word Root word Secondary suffix names for some functional Chain length(or) Chain length(or) Chain length(or) groups is listed below in table 11.4 no. of carbon of atom no. no. of carbon of atoms no.
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