8.6 ISOMERISM isomers and this phenomenon is termed as position isomerism. For example, the The phenomenon of existence of two or more molecular formula C3H8O represents twocompounds possessing the same molecular alcohols: formula but different properties is known as isomerism. Such compounds are called OH as isomers. The following flow chart shows different types of isomerism. CH3CH2CH2OH CH3−CH-CH3 Propan-1-ol Propan-2-ol 8.6.1 Structural Isomerism Compounds having the same molecular (iii) Functional group isomerism: Two or formula but different structures (manners more compounds having the same molecular in which atoms are linked) are classified as formula but different functional groups structural isomers. Some typical examples are called functional isomers and this of different types of structural isomerism are phenomenon is termed as functional group given below: isomerism. For example, the molecular (i) Chain isomerism: When two or more formula C3H6O represents an aldehyde and compounds have similar molecular formula but a ketone: Isomerism Structural isomerism Stereoisomerism Chain Position Functional Metamerism Geometrical Optical isomerism isomerism group isomerism isomerism isomerism Reprint 2025-26 organic chemistry – some basic principles and techniques 271 in understanding the reactivity of organic O H compounds and in planning strategy for their   synthesis. CH3−C-CH3 CH3−CH2—C= O In the following sections, we shall learn Propanone Propanal some of the principles that explain how these (iv) Metamerism: It arises due to different reactions take place. alkyl chains on either side of the functional 8.7.1 Fission of a Covalent Bond group in the molecule. For example, C4H10O represents methoxypropane (CH3OC3H7) and A covalent bond can get cleaved either by : (i) ethoxyethane (C2H5OC2H5). heterolytic cleavage, or by (ii) homolytic cleavage.8.6.2 Stereoisomerism In heterolytic cleavage, the bond breaks The compounds that have the same in such a fashion that the shared pair of constitution and sequence of covalent bonds electrons remains with one of the fragments. but differ in relative positions of their atoms After heterolysis, one atom has a sextet or groups in space are called stereoisomers. electronic structure and a positive charge and This special type of isomerism is called as the other, a valence octet with at least one lone stereoisomerism and can be classified as pair and a negative charge. Thus, heterolytic geometrical and optical isomerism. + cleavage of bromomethane will give C H3 and

8.2 Name the following compounds according to IUPAC system of nomenclature: (i) CH3CH(CH3)CH2CH2CHO (ii) CH3CH2COCH(C2H5)CH2CH2Cl (iii) CH3CH=CHCHO (iv) CH3COCH2COCH3 (v) CH3CH(CH3)CH2C(CH3)2COCH3 (vi) (CH3)3CCH2COOH (vii) OHCC6H4CHO-p

8.4 Classification of Organic (homocyclic). Compounds The existing large number of organic compounds and their ever -increasing numbers has made it necessary to classify them on the basis of their structures. Organic Cyclopropane Cyclohexane Cyclohexene compounds are broadly classified as follows: Sometimes atoms other than carbon are also present in the ring (heterocylic). Tetrahydrofuran given below is an example of this type of compound: Tetrahydrofuran These exhibit some of the properties similar to those of aliphatic compounds. (b) Aromatic compounds Aromatic compounds are special types of compounds. You will learn about these compounds in detail in Unit 9. These include benzene and other related ring compounds (benzenoid). Like alicyclic compounds, aromatic comounds may also have hetero atom in the ring. Such compounds are called I. Acyclic or open chain compounds hetrocyclic aromatic compounds. Some of the examples of various types of aromatic These compounds are also called as aliphatic compounds are: compounds and consist of straight or branched chain compounds, for example: Benzenoid aromatic compounds CH3CH3 Ethane Isobutane Benzene Aniline Naphthalene Non-benzenoid compound Acetaldehyde Acetic acid II Cyclic or closed chain or ring compounds (a) Alicyclic compounds Tropone Alicyclic (aliphatic cyclic) compounds contain carbon atoms joined in the form of a ring Reprint 2025-26 262 chemistry Heterocyclic aromatic compounds so because it is found in citrus fruits and the acid found in red ant is named formic acid since the Latin word for ant is formica. These names are traditional and are considered as trivial or common names. Some common Furan Thiophene Pyridine names are followed even today. For example, Organic compounds can also be classified Buckminsterfullerene is a common name on the basis of functional groups, into families given to the newly discovered C60 cluster (a or homologous series. form of carbon) noting its structural similarity to the geodesic domes popularised by the8.4.1 Functional Group famous architect R. Buckminster Fuller. The functional group is an atom or a group Common names are useful and in many of atoms joined to the carbon chain which is cases indispensable, particularly when the responsible for the characteristic chemical alternative systematic names are lengthy and properties of the organic compounds. The complicated. Common names of some organic examples are hydroxyl group (–OH), aldehyde compounds are given in Table 8.1. group (–CHO) and carboxylic acid group (– COOH) etc. Table 8.1 Common or Trivial Names of Some Organic Compounds 8.4.2 Homologous Series A group or a series of organic compounds each containing a characteristic functional group forms a homologous series and the members of the series are called homologues. The members of a homologous series can be represented by general molecular formula and the successive members differ from each other in molecular formula by a –Ch2 unit. There are a number of homologous series of organic compounds. Some of these are alkanes, alkenes, alkynes, haloalkanes, alkanols, alkanals, alkanones, alkanoic acids, amines etc. It is also possible that a compound contains two or more identical or different functional groups. This gives rise to polyfunctional compounds.