M Prakash Institute X-2Yrs Chemistry L: 28 Carbon and IUPAC Nomenclature Organic chemistry is by itself a major branch of Chemistry. It deals with the chemistry of all such compounds that have hydrogen and carbon in them bonded by specific covalent bonds. The word “organic was assigned to it as it was earlier thought that these are the compounds of natural origin and can’t be manufactured artificially. It was Jons Jacob Berzelius (Sweden) who put up the ‘Vital force theory’. It said that organic compounds cannot be prepared without ‘vital force’; that is support of a living cell of plant or animal. But in 1828, Friedrich Wohler (Germany) for the first time synthesised Urea in lab using an inorganic compound, Ammonium cyanate. In 1845, Hermann Kolbe (Germany) synthesised Acetic acid from carbon disulphide. Today we are able to manufacture these compounds in the lab but the name ‘organic’ still remains. Carbon is one of the most unique elements found in the nature. Carbon is an essential component of all living organisms. Apart from this there are so many special properties of Carbon that are responsible for the extremely large number of organic compounds available. Following is a brief of all such properties of Carbon. Unique character of Carbon Carbon is the only element that heads a complete branch in Chemistry. We find quite a few reasons for the unique character of Carbon in its periodic placing. a) Carbon has the smallest atomic radius and lowest atomic volume of all the elements of the group. b) It has the highest melting and boiling points of the group. c) It has the highest ionization energy, much higher than the other elements of the group and is the most electronegative element in this group. d) There is no ‘d’ orbital . So it has the least tendency to form complex compounds. e) Its maximum covalency remains 4. Carbon can form multiple bonds, i.e. double and triple bonds. f) Carbon, due to its small size is capable of forming ‘pi’ bonds with oxygen involving p- orbitals. g) Carbon exhibits the remarkable property of catenation, i.e. to form chains of identical atoms. The tendency of an element to form chains depends upon the strength of the element- element bond which is maximum in the case of Carbon. As a result, carbon atoms can link together to form linear chains, branched chains and even rings of different sizes. General characteristics of organic compounds Composition: Besides carbons and hydrogen, organic compounds may contain other elements like oxygen, fluorine, chlorine, bromine, iodine, nitrogen, sulphur, phosphorus and a few metals. Catenation: Organic compounds are generally covalent compounds. The carbon atoms can attach themselves to one another to form long chains and rings by covalent bonds. This property of bonding between the atoms of same element to form long chains and rings is known as catenation. Structure: Organic compounds are usually more complex and possess high molecular weights e.g. DNA, chlorophyll etc. They also show the presence of double and triple bonds in the atoms. Solubility A large number of organic compounds is insoluble in water but they are soluble in organic solvents like ether, alcohol, benzene etc. Melting point and boiling point: Organic compounds have generally low melting point and boiling points. Therefore, a number of them are volatile compounds e.g. acetone (b.p. 329 K) etc. Odour: Majority of organic compounds have characteristic odour e.g. amines have fishy smell, esters have fruity smell etc. Rate of reactions: Organic compounds react rather slowly. Functional group: Organic compounds contain an atom or a group of atoms called functional group, which determines their chemical behavior e.g. ketones (-C=O), aldehydes (-CHO) etc. The other functional groups will be discussed as a separate topic later. Isomerism/ Isomerisation: Organic compounds show phenomena of isomerism i.e. these compounds have same molecular formula but have different structural formula. Polymerism/ Polymerisation: Organic compounds show phenomenon of polymerization. It is the phenomenon by virtue of which small organic molecules of low molecular weight(monomer) link together to form big and complex molecules of high molecular weight (polymer) e.g. polythenes , nylons etc. Classification of organic compounds: For systematic study of organic chemistry , it is necessary to classify organic compounds into different groups. Compounds are generally classified on the basis of either their structural feature or the types of functional groups present in the molecules. Classification on the basis of structure : Organic compounds are classified into two groups. 1) Open chain or Aliphatic or Acyclic compounds: In these compounds, carbon atoms are linked together in open chains . CH3 CH2 CH2 CH3 CH2 CH CH2 . n-butane 1-Propene CH3 CH3 . CH CH3 Isobutane 2) Closed chain or Cyclic compounds : These compounds contain one or more closed chains of atoms. These are further divided into two types: a) Homocyclic or carbocyclic compounds: These are the compounds which contain one or more closed chains of carbon atoms only. They are further subdivided into two types: i) Alicyclic compounds: These are cyclic compounds and resemble aliphatic compounds in their properties e.g. cyclopropane, cyclohexane etc. CH2 CH2 CH2 CH2 . CH2 CH2 CH2 . Cyclopropane Cyclobutane Alicyclic compounds are important compounds as alicyclic rings are present in a number of natural product e.g. steroids, alkaloids etc.. ii) Aromatic compounds: These are cyclic compounds which generally contain at least one benzene ring. (benzene ring ring of six carbon atoms having alternate single and double bonds) e.g. benzene, naphthalene, phenol etc. . . Benzene Naphthalene b) Heterocyclic compounds: These are cyclic compounds which contains at least one atom other than carbpon in the ring e.g. furan, pyridine, thiazole etc. CH CH CH CH CH CH O CH CH CH N . Furan Pyridine ————————————————————————————– Hydrocarbons: Organic compounds containing carbons and hydrogen only are known as hydrocarbons. Hydrocarbons are further divided into two classes: saturated and unsaturated. Saturated hydrocarbons: The hydrocarbons in which all the available valencies of carbon are satisfied by hydrogen are known as saturated hydrocarbons. In saturated hydrocarbons, the carbons atoms are joined to each other by a single covalent bond e.g. alkanes. Unsaturated hydrocarbons: The hydrocarbons in which the proportion of hydrogen is less as compared to the available valencies of carbon are known as unsaturated hydrocarbons. Hydrocarbons, two carbons atoms are joined to each other by double bond (alkenes) or a triple bonds(alkynes). Nomenclature of Organic Compounds With the development of Organic chemistry a large number of organic compounds have been prepared. In order to systematise the study of organic compounds, attempts have been made to frame certain rules to classify them and give their names. Quite for a long time, these compounds were named by common names,generally named after the name of the source from which they were obtained. Now, International Union of Pure and Applied Chemistry (IUPAC) has developed a new system of naming compounds and is known as IUPAC nomenclature. This system of nomenclature was first introduced in 1947 and was modified from time to time.The most exhaustive rules for nomenclature were first published in 1979 and later revised and updated in 1993. IUPAC scheme: General Rules For IUPAC Nomenclature: According to IUPAC system, the name of an organic compound consists of three parts: 1. Word root 2. Suffix (Primary and secondary) 3. Prefix(Primary and secondary) 1. Word root: The word root represents the number of carbon atoms present in the parent chain. For chains containing upto four carbon atoms (C1 to C4) , special word roots are used and for chains containing more than four carbon atoms (C5 onwards), Greek numerals are used as given below: Chain length C −1 C −2 C −3 C −4 C −5 C −6 C −7 C −8 C −9 C − 10 Word Root Chain length MethC11 EthC12 PropC13 ButC14 PentC15 HexC16 HeptC17 OctC18 NonC19 DecC20 Word Root UndecDodecTridecTetradecPentadecHexadecHeptadecOctadecNonadecIcos- 2. Suffix. The word root is linked to the suffix which maybe (i) primary (1o ) (ii) secondary (2o ) (i) Primary (1o ) suffix: It indicates the linkages in the carbon atoms, For single bonded carbon atoms (C-C),the primary suffix is ane, for double bonded carbon atoms (C = C), it is ene and for the triple bonded carbon atoms (C ≡ C), suffix is yne. If the parent chain contains two, three or more double or triple bonds, then the prefixes such as di (for two), tri (for three), tetra (for four), etc. are added to the primary suffix. e.g.: 2 ‘=’ diene 3 ‘=’ triene 2 ‘≡’ bonds diyne 3‘≡’ bonds triyne An extra ‘a’ is added to the word root if the primary suffix to be added begins with a consonant (other than a, e, i, o, u). e.g. : for two double bonds, suffix is diene and if it is to be added to word root but (for 4 carbon atoms), it becomes ‘butadiene’. Wordroot and primary suffix are mandatory for every IUPAC name. e.g. : the 1st Hydrocarbon Methane is ‘Meth’ for 1 C atom + ‘ane’for no double or triple bond. (ii) Secondary (2o ) suffix: It represents the functional group present in the molecule.Functional group is an atom, radical or bond which defines the structure of organic compounds and confers characteristic properties to it. For eg: Alcohol: -OH; Aldehyde: -CHO; carboxylic acids: -COOH; etc. It is added after the primary suffix. Prefix: The word root is linked to the prefix which maybe (i) primary (ii) secondary. (i) Primary (1o ) prefix: For linear acyclic compounds, there is no primary prefix. For cyclic compounds prefixes like ‘cyclo’, ‘bicyclo’, etc. are used. (The details are beyond scope here) (ii) Secondary (2o ) prefix: When an organic compound has more than one functional groups attached to it, secondary prefixes come into play. A list of functional groups in order of predence is released by the IUPAC. As per the list, the functional group in the compound that is top most in the list determines the class of the compound and is named as secondary suffix. All the other functional groups are considered as attachments and written as secondary prefixes.Prefixed substituents are ordered alphabetically,excluding any modifiers such as di-,tri-, etc. Also, there are ALWAYS JUNIOR functional groups that appear in 2o prefix. Refer the scheme for more details. The words used to denote a functional group as secondary suffix and secondary prefix are different. Following is a list of 13 functional groups in their order of predence with their denotations as secondary suffixes and secondary prefixes. 5. 6. 7. 8. Acid halide Amide Nitrle Isonitrile -COX −CON H2 −C ≡ N −N ≡ C 20 prefix carboxy Sulpho – Alkoxy carbonyl Halocarbonyl Carbamoyl Cyano Isocyano 9. Aldehyde -CHO Formyl 10. 11. 12. 13. 14. 15. Ketone Alcohol Amine Halo double bond triple bond -C=O -OH −N H2 -X = ≡ Keto/oxo Hydroxy Amino Halo No. 1. 2. 3. 4. Class FG Carboxylic acid -COOH Sulphonic acid -SO3 H Acid Anhydride -OC-O-COester -COOR 20 suffix -oic acid -sulphonic acid -oic anhydride Alkyl ... oate -oyl halide -amide -nitrile -isonitrile (or) carbylamine -al (or) carbaldehyde -one -ol -amine – -ene -yne I. Rules for nomenclature of Saturated Hydrocarbons: 1. Longest chain rule: Select the longest continuous chain of carbon atoms in the molecule. The longest continuous chain, containing the maximum number of carbon atoms, is taken as the parent chain and it gives the name of the parent hydrocarbon. The other parts which are not included in the parent chain are identified substituents or branched chains. Cs H3 Cp H 3 Cp H Cp H2 Cp H2 Cp Cp H 2 Cp H3 Cs H3 Cs H3 The ‘Cp ’s make the parent chain and the ‘Cs ’ make the substituents. It may be noted that the longest chain may or may not be straight but it must be continuous. For example, . C1 H3 C2 H2 C3 H CH2 CH3 C4 H2 C5 H2 C6 H3 Correct parent chain indicated by C 1 to C 6 C1 H3 C2 H2 C3 H C4 H2 C5 H3 . . CH2 CH2 CH3 . Wrong parent chain indicated by C 1 to C 5 So the parent hydrocarbon here is Hexane and not Pentane. If two different chains of equal lengths are possible, the chain with maximum number of side chains or alkyl groups is selected. For example, CH3 (a) C1 H3 C2 H2 C3 H C4 H CH CH3 C5 H3 CH3 CH3 (b)CH3 CH2 C3 H C2 H C4 H CH3 C1 H3 C5 H3 In (a),C 1 to C 5 is the longest chain but only 2 substituents. In (b), C 1 to C 5 is the longest chain with 3 substituents; so (b) is the correct parent chain 2. Lowest set of locants: Number the carbon atoms in the parent chain as 1,2, 3.... etc., starting from the end which gives smaller number to the carbon atoms carrying the substituent. For example, if S represents a substituent; S S C5 . . C4 C3 C2 Structure ‘A’ Correct numbering C1 C1 C2 C3 C4 Structure ‘B’ Wrong numbering. C5 The numbering of the carbon chain as given in the structure B is wrong because it gives higher number to the carbon atom carrying the substituent. The number that indicates the position of the substituent or side chain is called locant. The position of the locant in the above structure is 2. When there are two or more different substituents attached to the parent chain, then the end of the parent chain which gives lowest set of the locants is preferred for numbering. This rule is called lowest set of locants. This means that when two or more different sets of locants are possible, that set of locants which when compared term by term with other sets, each in order of increasing magnitude, has the lowest term at the first point of difference. This rule is used irrespective of the nature of the substituents. This rule is very simple to apply. We are to compare the position of substituents term by term. This means that compare the first term, whichever is lower will get the preference. If both ends have same position for preference, the first substituent, compare the second, then third that gives the lower number to carbon will get preference. Similarly, compare, third term if needed and so on.For example, CH3 CH3 C6 H3 . C5 H2 C4 H2 C3 H C2 H Set of locants = 2,3 (Correct) CH3 C1 H3 . C1 H3 . C8 H3 . CH3 C2 H2 C3 H2 C4 H C5 H Set of locants = 4,5 (Wrong) CH3 C1 H3 C6 H3 CH2 CH3 CH3 C2 H C3 H2 C4 H C5 H2 C6 H2 Set of locants = 2,4,7 (Correct) C7 H CH3 CH3 CH2 CH3 C7 H C6 H2 C5 H C4 H2 Set of locants = 2,5,7 (Wrong) C3 H2 C2 H C8 H3 C1 H3 While writing the name of the compound, the position of each substituent or side chain is indicated by the number of the carbon atom to which it is attached. The names of the substituents are separated from the number indicating their positions by using hyphens. For example, CH3 . . C5 H3 C4 H2 C3 H2 C2 H 2-Methylpentane C1 H3 3. Presence of more than one same substituent: If the same substituent occurs more than once in the parent chain, it is indicated by the prefixes such as di, tri, tetra, etc. to indicate 2, 3, 4, etc. same substituents.The positions of each substituent whether same or different are indicated separately and the numerals different representing their positions are separated by commas. For example, CH3 . C1 H3 C2 H C3 C4 H2 C5 h C6 H3 CH3 CH3 CH3 2,3,3,5- Tetramethylhexane . 4. Naming different substituents: If two or more substituents are present on the parent chain, they are named in the alphabetical order along with their appropriate positions. It may be noted that di, tri, etc. are not considered while comparing the substituents for alphabetizing purposes. For example: CH2 CH3 . . C5 H3 C4 H3 C3 C2 H C1 H3 CH3 CH3 3-Ethyl-2,3-dimethylpentane. 5. Naming different substituents at equivalent positions: If two different substituents are present at equivalent positions from the two ends of the chain (two sets of locants are equally possible), then the numbering of the chain is done in such a way that the substituent which comes first in the alphabetical order (written first in the name) gets lower number. For example, in the compound given below the methyl is at 3rd position if numbering is done from left to right and ethyl groups is at 3rd position if numbering is done from right to left.In such a case, the carbon bearing the ethyl group gets lower position because it is cited first in the name according to alphabetical order of substituents.Thus, C7 H3 C6 H2 C5 H C4 H2 C3 H C2 H2 C1 H3 . CH3 CH2 CH3 3-Ethyl-5-methylheptane (Not 5-Ethyl-3-methylheptane) II. Rules for nomenclature of unsaturated hydrocarbons :(containing Double and Triple bonds): 1. Longest chain rule: Select the longest continuous chain containing the carbon atoms involved in the multiple bonds (double or triple). This gives the parent name of the ailkene or alkyne. For eg.,in the structures given below, the longest chain has five carbon atoms and not six C1 H3 C1 H3 C2 H2 C2 H2 C3 H2 . C4 C5 H2 CH2 CH3 Correct chain C3 H2 C4 CH2 C5 H2 C6 H3 Wrong chain. It maybe noted that the selected chain may or may not be the longest chain. But it must contain double or triple bonded atoms. For example, in the above example, the largest chain containing double bonded carbon atoms is of five carbon atoms and not of six. 2. While writing the name of the alkene or alkyne, the suffix ‘ane’of the corresponding alkane is replaced by ‘ene’ or ‘yne’ respectively. 3. If the multiple bond occurs twice in the parent chain, the alkene and alkyne are called ‘diene’ and ‘diyne’ respectively. 4. The numbering of atoms in parent chain is done in such a way that the carbon atom containing the double or triple bond gets the lowest number. For example, . C1 H3 C2 H C3 H C4 H2 C5 H3 . Pent-2-ene (Not Pent-3-ene) The position of the double bond may be indicated by any of the three ways: 2-Pentene or Pent-2-ene or Pentene-2. 5. All the rules for naming the side chains or substituents are then followed (as in alkanes). For example: CH3 . C6 H3 C5 C4 H C3 H C2 H C1 H3 CH3 CH3 . 4,5,5-Trimethylhex-2-ene. Important notes:If the parent chain contains both double and triple bonds, the following rules should be remembered: i) The terminal ‘e’ in the name is dropped when it is followed by the suffix beginning with any vowel or ‘y’. Therefore, the terminal ‘e’ of ene in ‘en-yne’ and a ‘dien-yne’ is dropped because it comes before ‘y’(of - yne) However, e is not dropped in case of ‘enediyne’ because it comes before d of - diyne. ii) Numbers as low as possible are given to double bond and triple bond as a set, even though this may at times give -yne a lower number than -ene. However, if a choice is there, preference for lower locants is given to double bond. iii) These compounds are named as derivatives of alkynes rather than alkenes. For example, i). C5 H C4 C3 H2 C2 H C1 H2 . Pent-1-en-4-yne In this compound numbering is 1-4 from both sides, then preference of lower locant for ‘ene’ ii) . C1 H C2 C3 H C4 H C5 H2 . Pent -3-en-1-yne. The name of this compound cannot be Pent-2-en-4-yne as the lowest set of locants is is 1, 3 rather than 2, 4. In the case of cyclic alkenes, the position of double bond is always given the number 1. . CH3 CH3 (2,3-dimethylcyclohex-1-ene; Not 1,6-Dimethylhex-1-ene; ) III Nomenclature of Compounds containing One Functional Group or Secondary Suffix:In naming the organic compounds containing one functional group, the numbering of the atoms in the parent chain is done in such a manner that the carbon atom bearing the functional group gets the smallest possible number. All other rules for naming the side chains or substituents are then followed. 1. Select the longest continuous chain containing the carbon atom having the functional group. 2. The numbering of atoms in the parent chain is done in such a way that carbon atom bearing the functional group gets the lowest number. 3. All the rules for naming side chains or substituents are then followed as discussed in case of alkanes. The different classes of functional groups including multiple bonded compounds and the suffix required to name these compounds are given in the table above.For example, O C6 H3 C5 H C4 H2 C3 C2 H2 C1 H3 CH3 . 5-Methylhexa-3-one It may be noted that the functional group should get the lowest number even if it violates the lowest set rule. Preference should be given only to the functional group. If functional groups such as CHO,COOH,CONH2 ,COOR,COCl,CN are present in the molecule, the number of parent chain must start from the carbon atom of the functional group (secondary suffix). The position of the functional group will always be number 1. The position is normally not indi- cated in the IUPAC name of the compound. Example: CH3 i) CH3 CH2 C2 C3 H2 C4 H3 C1 HO . 2-Ethyl-2-methylbutanal 5 ii) C H3 C4 C3 C2 H2 C1 HO . Pent-3-ynal If a compound contains two same functional groups, the numerical prefix di, is used before the name of the secondary suffix. In this case, the terminal e of the primary suffix is retained while writing the IUPAC name. OHC CH2 CH2 CHO HOOC CH2 CH2 CO . Butanedial Butanedioic acid. In these structures, the positions of CHO or COOH group are not indicated because these groups will always be at the terminal position, having number 1 and last i.e., Butane-1,4-dial or Butane-1, 4-dioic acid. O O NC CH2 CH2 . Butanedinitrile CN C5 H3 C4 C3 H2 C2 Pentane-2,4-dione C1 IV. Nomenclature of Compounds having Functional Groups, Multiple Bonds, Side Chains, Substituents: If the organic compound contains a functional group, multiple bond, side chain or substituent, the order of preference is : Functional > Double bond> Triplebond > Substituent/ Side chain Examples: O i)C5 H2 . C4 H C3 H2 Pent-4-en-2-one C2 C1 H3 CH3 ii)C9 H3 . C8 H2 C7 H2 C6 H2 2-Methylnon-3-enal O C5 H2 iii) C6 H5 . C3 H C2 H C1 OH 3-Phenyl prop-2-enoic acid iv)C4 H3 C3 H . C2 H C4 H C3 H CH3 C1 OOH Cl 3-Chloro-2-methylbutanoic acid. Exercise: Q 1. The ‘Vital force theory’ was proposed by —. Q 2. How and when was the ‘Vital force theory’ proven wrong? Q 3. The highest level of catenation is observed in —- elemnt. Q 4. Which of the folowing statements is wrong? (i) Organic compounds possess low melting and boiling points. (ii) Organic compounds exhibit isomerism. (iii) Organic compounds are obtained only from netural resources. (iv) Organic compounds can be synthesised in the laboratory. Q 5. Which of the following is called an unsaturated compound by definition? (i) CH3 CH = CH2 (ii) CH3 C ≡ N O C (iv) All the above (iii) CH3 CH3 Q 6. Which of the following is classified as an alicyclic compound? CH CH CH CH CH CH (i) O (ii) CH CH CH N C2 H C (iii) (iv) Q 7. Regarding straight chained and branched alkanes, which of the following statement is true? (i) Branched alkanes have the same molecular formula as straight chained with the same number of carbon atoms. (ii) Straight shained alknaes have a higher boiling point compared with branched alkane with the same number of carbon atoms (iii) Side groups only consist of alkyl groups with a variable number of carbon atoms. (iv) All the above. Q 8. The purity of an organicsolid is checked by its (i) Sharp MP (ii) Mixed MP (iii) Ability to sublime (iv) Tendancy to dissolve in organic solvent. ————————————————————————————— Give the IUPAC names for given Alkanes: 1. CH3 CH2 CH CH3 2. CH3 CH CH3 CH2 CH CH3 3. CH3 CH CH3 CH2 CH3 CH CH2 CH3 CH3 4. CH3 C CH2 CH3 CH3 5. CH3 CH3 CH3 CH3 CH CH CH3 CH2 CH3 CH3 6. CH3 CH CH2 CH CH3 CH CH CH CH3 CH3 CH3 CH2 CH3 7. CH3 CH2 CH3 CH3 8. CH3 CH2 C CH2 CH3 9. CH3 CH2 CH3 CH3 CH CH CH2 CH3 CH2 CH3 CH3 CH2 10. CH3 CH2 CH2 CH2 CH CH2 CH3 CH3 Give the IUPAC names for given Alkenes: 1. CH3 − CH = CH2 2. CH3 − CH = CH − CH = CH2 3. CH2 CH CH CH3 4. CH3 CH2 5. CH2 C 6. CH3 CH3 CH CH3 C CH3 C CH3 C3 H7 CH3 CH2 CH CH2 CH3 CH3 CH CH CH CH CH3 7. C CH2 CH CH3 8. CH3 C CH CH 9. CH2 CH3 C CH2 CH3 CH2 10. CH2 CH3 C CH CH3 CH2 CH3 CH2 CH3 11. CH3 C2 H5 CH2 CH2 CH2 CH CH2 Give the IUPAC names for given Alkynes and unsaturated hydrocarbons: 1. CH3 − C ≡ CH2 − CH3 2. CH3 C C CH ≡C C ≡ CH 3. 4. HC ≡C CH ≡C CH3 CH CH CH2 CH3 CH3 CH3 CH3 CH3 CH CH CH CH3 CH2 CH3 CH3 5. CH ≡C 6. CH3 C CH2 CH3 CH3 C≡C CH ≡C C≡C CH3 7. 8. CH3 CH ≡C CH2 C C≡C C C3 H7 C3 H7 9. CH3 10. CH3 C≡C C≡C CH CH C≡C CH CH2 CH3 CH C CH3 CH3 CH3 CH CH3 CH3 CH2 CH3 CH2 Give the structure of the following compounds: 1) 2,3 dimethyl-1-butane 2) 2- methyl- 1- propene 3) 1- propyne 4) 2,3,4-trimethy-l- hexane 5) 3-methyl-2- pentene 6) 3-methyl-1- butyne 7) 4,4,5-trimethy-l,2-hexyne 8) 2,2,3,4-tetramethy-1-pentane 9) 1,4-hexadiene 10) 3-heptyne ———————————————————————————— Alkyl halides: Give the Trivial or common names of following compounds: 1) CH3 Cl 2) C2 H5 Br 3) CH3 CHICH3 4) (CH3 )3 CBr Give the IUPAC name of following compounds 1) CH3 Cl 2) C2 H5 Br 4) CH3 − CH2 − CH2 − CH2 − Cl 3) CH3 CHCH3 CH3 5) 7) CH3 H CH2 CH H H C C Cl Cl 6) CH3 Cl 8) H CH3 H H C C H Cl C CH3 Cl 9) CH3 CHCl2 ————————————————————————————Alcohols/Acids: Give the common names of the following compounds 1) CH3 OH 2) C2 H5 OH 3) CH3 CH2 CH2 CH2 OH 4) CH3 CH2 CH2 OH CH3 5) CH3 C CH3 6) H CH3 OH C CH3 CH2 OH 7) CH3 H7 OH C CH3 OH 8) C4 H9 OH H 9) CH3 C OH H 11) CH3 10) CH3 C CH3 OH C CH2 CH3 OH H CH CH3 CH3 12) CH3 CH2 CH CH3 CH2 OH 13) CH3 CH C 15) CH3 CH2 CH3 CH2 COOH CH3 CH2 14) CH3 CH3 16) CH3 CH3 OH 17) CH3 C CH CH2 18) CH3 CH3 CH2 CH2 CH3 CH CH3 CH3 CH3 19) HCOOH CH C OH COOH CH3 CH2 OH CH3 20) CH3 COOH Give IUPAC names of the following acids/ esters Molecular formula: 1) CH3 COOH 2) HCOOCH3 3) CH3 CH2 CH2 COOH 4) (CH3 )2 CHCOOH 5) C2 H5 COOCH3 6) HCOOCH(CH3 )2