IUPAC Nomenclature Practice Sheet PDF

CLASS XI IUPAC RULES & PRACTICE SHEET Dear Students, IUPAC nomenclature is the most important part of organic chemistry. If you know nomenclature, organic chemistry becomes very easy. So, check out the rules and then try to the examples g...

CLASS XI IUPAC RULES & PRACTICE SHEET Dear Students, IUPAC nomenclature is the most important part of organic chemistry. If you know nomenclature, organic chemistry becomes very easy. So, check out the rules and then try to the examples given in the following practice sheet. There are as many as 149! examples given in the practice sheet. The answers are given at the end of practice sheet. Your journey to IUPAC nomenclature begins here! IUPAC RULES 1. Longest Chain Rule: Select the longest continuous chain of carbon atoms as the parent chain. If some carbon-carbon multiple bond is present, the parent chain must include it. If two equally long chains are possible, the chain with maximum number of side chains is selected as parent chain. 2. Lowest Number Rule: The number which indicates the position of the alkyl group in the parent chain is also called locant. The numbering is done such that, the substituted carbon atoms have lowest possible number. 3. Lowest Set of Locant Rule: If two or more different sets of locants containing same number of terms are possible, then the two sets of locants (each one in order of increasing magnitude) are compared term by term. The set of locants which contains the lowest number on the occasion of first difference, is considered correct for numbering the carbon atoms of parent chain. www.studyhive.in P a g e 1 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET In case of unsaturated hydrocarbons, the carbon atom involved in the multiple bond should get the lowest possible number. 4. Alphabetical arrangement of prefixes: If there are different alkyl substituents, their names are written in alphabetical order. However, the numerical prefixes such as di, tri etc. are not considered for the alphabetical order. 5. Naming of different alkyl substituents at equivalent positions: If two different alkyl groups are located at equivalent positions, then numbering is done in such a way that, the alkyl group alphabetically first gets the lower number. 6. Naming of the complex alkyl substituent: If the alkyl substituent is further branched, it is called substituted alkyl group. The carbon atoms of the alkyl group are separately numbered such that, the carbon atom directly attached to the parent chain is given number 1. The prefix/name of such a substituent is enclosed in brackets. While writing the name of the substituted alkyl group, the first letter of the complete name of the substituted alkyl group is considered. If same complex substituent occurs more than once, the prefixes such as bis (for two), tris (for three), tetrakis (for four) & pentakis (for five) are used and are written before the bracket starts. The name of the substituted alkyl group is enclosed in parenthesis. 7. While naming the compounds containing functional groups, it may be noted that.. The terminal ‘e’ of the primary suffix is removed if the secondary suffix is followed by ‘a’, ‘i’ , ‘o’ , ‘u’ or ‘y’. -NO2, -OR, -X (halo group) are considered as substituents and are indicated as prefixes. Groups like –CHO, -CO-, -COOH, -COCl, -CONH2, -COOR, -CN & -OH are considered as functional groups & are indicated by secondary suffix. The parent chain must include the carbon atom involved in the functional groups like –COOH, -CHO etc. and their carbon atom must get the lowest number. 8. If the compound contains more than one functional similar functional groups, than in addition to various rules, the numerical prefixes such as di (for two), tri (for three) are added before the secondary suffix which indicates the functional group. While adding such words, the vowel ‘e’ of the primary suffix is retained. Eg: Butane-1,2,3-triol. 9. If an unbranched carbon chain is linked directly to more than two carboxyl groups, these groups are named by substitutive use of suffix ‘-tricarboxylic acid’ etc. The principal chain should be linked directly to the maximum possible number of carboxyl groups. The carboxyl groups which are not directly linked to the principal chain are expressed by ‘carboxyalkyl’ prefix. Eg: 3-(carboxymethyl)hexane-1,2,5-tricarboxylic acid. Similarly the substitutive prefixes for aldehydes, cyanides, acylchlorides & amides are respectively carbaldehyde, chlorocarbonyl, carbonitrile & carboxamide. www.studyhive.in P a g e 2 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 10. If the molecule contains more than one dissimilar functional groups, the parent chain must contain maximum possible number of functional groups. The numbering of parent chain should be done such that the functional group having higher priority gets the lowest number. 11. Priority series: Carboxylic acids > acid anhydrides > esters > acid chlorides > amides > nitriles, isocyanides > aldehydes > ketones > alcohols > amines > alkenes, alkynes > halo, nitro, alkoxy, alkyl. 12. The functional group (according to the above priority series) which gets the lowest number (higher priority) is indicated by the secondary suffix and the rest are considered as substituents and are indicated by prefix. Eg: -OH by hydorxy, -CN by cyano, -NC by isocyano, -CHO by formyl or oxo, -COOH by carboxy, -COOR by carbalkoxy, -COCl by chloroformyl, -NH2 by amino, >CO by keto or oxo. 13. If two groups of same preference appear at identical positions from the either end of the chain, then the groups whose prefix comes first in the alphabetical order gets the lower number. Eg: 1-bromo-5-iodopentane. 14. If the compound is cyclic, the prefix ‘cyclo’ is used before the word root. The numbering is done in such a way that the least possible number is assigned to the functional group or substituent in accordance with the rules already discussed. Eg: 3-methylcyclohexanol, eg: 1-methyl-3-nitrocyclohexene, eg: 3-hydroxycyclohexanone. 15. Nomenclature of substituted benzene compounds: The carbon atoms of benzene are numbered from 1-6. The benzene ring is called the nucleus and alkyl groups attached to the ring are called side chains. Benzene can form three di-substituted derivatives namely 1, 2 (ortho ‘o-’), 1, 4 (para ‘p-’), 1, 3 (meta ‘m-’). Tri & poly substituted derivatives are named by numbering the chain in such a way that parent group gets the lowest number and the lowest locant rule is obeyed. C6H6 is benzene while C6H5- is phenyl group. www.studyhive.in P a g e 3 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET IUPAC PRACTICE SHEET Write the IUPAC names of the following: (FIND ANSWERS AT THE END!) 1. C2 H5 H2C CH CH CH CH3 CH2 OHC 2. H3C CH CH2 OH 3. C2 H5 O H3C CH2 CH C O CH3 4. H3C CH CH C OH O 5. OCH3 H3C CH C CH3 6. O H2C C C OC2H5 CH3 7. CH3 H3C CH CH CH2NH2 CH3 8. C2H5 CH3 H3C C CH CH CH3 O www.studyhive.in P a g e 4 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 9. O H3C CH CH2 C Br CH3 10. CH3 CH3 I H3C C CH CH CH3 H3C CH2 11. Cl CH3 CH3 CH2 CH CH C CH3 H3C OH 12. CH CHO CH3 13. CH3 H3C C CH CH3 O 14. Cl CH3 CH3 H3C CH2 CH CH C CH3 OH 15. CH3 H3C C CH CH3 O 16. O H3C C O H3C C O 17. CH2 CHO www.studyhive.in P a g e 5 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 18. H3C CH CH2 Cl CH3 19. O CH3 O C HC CH3 20. CH3 H3C CH CH COOH CH3 21. CH3 H3C C CH3 CHO 22. OH C CH2 CH3 CH3 23. CH3 H3C CH2 CH CONH2 24. CH3 H3C CH CH NH2 CH3 25. CH3 H3C CH2 CH COOC2H5 26. O CH3 H3C CH C CH CH3 CH3 27. CH2CH3 CH2CH3 H3C C CH2 C CH3 CH3 CH3 www.studyhive.in P a g e 6 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 28. CH3 C OH H3C H3C 29. O H3C C C C CH2 CH3 30. H3C CH2 CH CH H3C CH2 CH CH 31. C2H5 H3C CH CH CH CH CH3 CH3 32. H3C CH CHO OCH3 33. H2C C COOCH3 CH3 34. HO CH COOH HO CH COOH 35. O H3C CH C COOH CH3 36. NC CH2 CH2 COOH 37. CH2 COOH HO C COOH CH2 COOH 38. O H3C C CH CH2 C COOC2H5 OH www.studyhive.in P a g e 7 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 39. O O H3C CH C C NH Br CH3 40. Cl CH2 C CH CH2OH CH3 41. O Br CH2 CH C CH2 CH3 CONH2 42. (H3C)3C CH2 CH2 Cl 43. OH OH H3C CH CH CH CHO CH3 44. CH3 H3C C CH CH2 CH2Cl O 45. O H3C CH CH2 C CH3 OH 46. Br OH H3C CH CH CH CH3 Cl 47. Br Cl H3C CH2 C CH CH2 OH Cl 48. C2H5 H3C C CH CH2 CH2 Cl O www.studyhive.in P a g e 8 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 49. HC C CH2 CH2 CH CHO Cl 50. H H3C C C O O 51. O CH3 H3C CH C CH OCH3 CH3 52. H2C C CH2 CH2 OH CH3 53. OH CH CH C O 54. O CH3 H3C CH C CH OCH2CH3 OCH3 55. CH2 CH CH2 HO OH OH 56. O OH OCH3 57. CH3 O C CH3 O www.studyhive.in P a g e 9 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 58. Br Br H3C CH2 CH C CH2Cl CH3 59. NH2 NO 2 NO 2 60. H3C OCH3 CH C CHO H3C CH3 61. H3C CH COOH CH2 OHC 62. O H3C C C OCH2CH3 O 63. O H3C C C CH2 OCH3 O 64. Cl O H3C CH2 N C H 65. O C OH H O 66. www.studyhive.in P a g e 10 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 67. 68. OH 69. OH CH3 70. NO 2 CH3 71. CH3 CH2CH3 72. H3C CH CH CH2 73. O OH 74. CH3 CH3 75. www.studyhive.in P a g e 11 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 76. 77. 78. OH 79. 80. 81. OH O 82. Br O 83. CHO CH3 84. 85. Me Me Me Me 86. Et 87. COOH www.studyhive.in P a g e 12 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 88. OH 89. OH CHO 90. CH3 H3C O 91. Cl Br 92. H3C CHO 93. OH 94. 95. O Cl 96. O H3CO 97. O OCH3 www.studyhive.in P a g e 13 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 98. 99. Me H OH HO H Me 100. 101. Me HO H H 102. Et Me COOH 103. O O 104. N 105. 106. CHO 107. 108. www.studyhive.in P a g e 14 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 109. 110. 111. 112. CH3 113. CH3 CH3 114. CH3 CH3 115. H3C CH3 116. CH2 HC www.studyhive.in P a g e 15 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 117. CH3 H3C CH3 118. CH3 Cl 119. Cl Cl 120. CH2Cl 121. H2C CH2 CH2 Cl 122. HC CH CH2 Cl 123. OH www.studyhive.in P a g e 16 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 124. OH OH 125. OH OH 126. OH OH 127. CH2OH 128. CH2CH2OH 129. CHO 130. CH2CHO www.studyhive.in P a g e 17 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 131. COOH 132. COOH OH 133. CH2COOH 134. CH2COOH OH 135. COOH COOH 136. COOH COOH 137. COOH COOH www.studyhive.in P a g e 18 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 138. COOH OH 139. COOH CH3 140. COCl 141. CONH2 142. CONH2 CONH2 143. O C NH C O 144. O O C O C www.studyhive.in P a g e 19 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 145. O C O C O 146. COOCH3 147. NH2 148. HN CH3 149. H3C N CH3 ANSWERS!!! 1. 5-ethylhept-3-enal 2. 2-phenylpropan-1-ol 3. methyl 2-ethylbutanoate 4. but-2-enoic acid 5. 2-methoxybut-2-ene 6. ethyl 2-methylprop-2-enoate 7. 2,3-dimethylbutan-1-amine 8. 3-ethyl-4-methylpentan-2-one 9. 3-methylbutanoyl bromide 10. 4-iodo-2,2,3-trimethylhexane 11. 4-chloro-2,3-dimethylhexan-2-ol 12. 2-phenylpropanal www.studyhive.in P a g e 20 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 13. 3-methylbutan-2-one 14. 4-chloro-2,3-dimethylhexan-2-ol 15. 3-methylbutan-2-one 16. Ethanoic anhydride 17. Phenylethanal 18. 1-chloro-2-methylprop ane 19. phenyl 2-methylpropanoate 20. 2,3-dimethylbutanoic acid 21. 2,2-dimethylpropanal 22. 2-phenylbutan-2-ol 23. 2-methylbutanamide 24. 3-methylbutan-2-amine 25. ethyl 2-methylbutanoate 26. 2,4-dimethylpentan-3-one 27. 3,3,5,5-tetramethylheptane 28. 3-ethylpentan-3-ol 29. hex-4-yn-3-one 30. octa-3,5-diene 31. 4-ethyl-5-methylhex-2-ene 32. 2-methoxypropanal 33. methyl 2-methylprop-2-enoate 34. 2,3-dihydroxybutanedioic acid 35. 3-methyl-2-oxobutanoic acid 36. 3-cyanopropanoic acid 37. 2-hydroxypropane-1,2,3-tricarboxylic acid 38. 5-ethoxy-4-methyl-5-oxopent-3-enoic acid 39. N-bromo-3-methyl-2-oxobutanamide 40. 4-chloro-3-methylbut-2-en-1-ol 41. 2-(bromomethyl)-3-oxopentanamide 42. 1-chloro-3,3-dimethylbutane 43. 2,3-dihydroxy-4-methylpentanal 44. 5-chloro-3-methylpentan-2-one 45. 4-hydroxypentan-2-one 46. 3-bromo-4-chloropentan-2-ol 47. 3-bromo-1,2-dichloropentan-3-ol 48. 5-chloro-3-ethylpentan-2-one 49. 2-chlorohex-5-ynal 50. 2-oxopropanal 51. 2-methoxy-4-methylpentan-3-one 52. 3-methylbut-3-en-1-ol 53. 3-phenylprop-2-enoic acid 54. 2-ethoxy-4-methoxypentan-3-one 55. propane-1,2,3-triol 56. 2-methoxybenzoic acid 57. phenyl 2-methylpropanoate www.studyhive.in P a g e 21 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 58. 2,3-dibromo-1-chloro-2-methylpentane 59. 2,4-dinitroaniline 60. 2-methoxy-2,3-dimethylbutanal 61. 2-methyl-4-oxobutanoic acid 62. ethyl 2-oxopropanoate 63. 1-methoxybutane-2,3-dione 64. N-chloro-N-ethylmethanamide 65. oxoethanoic acid 66. Cyclohexane 67. Cyclopentane 68. Cyclohexanol 69. 3-methylcyclohexanol 70. 1-methyl-3-nitrocyclohexene 71. 1-ethyl-2-methylcyclobutene 72. but-3-en-2-ylcyclopentane 73. 3-hydroxycyclohexanone 74. 1,5-dimethylcyclopentene 75. buta-1,3-diene 76. 4-methylpenta-1,3-diene 77. hexa-1,3,5-triene 78. pent-1-en-3-ol 79. 3-ethyl-4-methylpenta-1,3-diene 80. 6-ethyl-1-methylcyclohexa-1,3-diene 81. 2,6-dimethylhepta-2,5-dienoic acid 82. 2-bromopentan-3-one 83. 3-methylpent-4-enal 84. 2-ethenyl-3-methylcyclohexa-1,3-diene 85. 5,6-diethyldec-4-ene 86. 1-ethylcyclohexene 87. 5-methylcyclohex-2-ene-1-carboxylic acid 88. cyclohex-3-en-1-ol 89. 2-hydroxycyclopentanecarbaldehyde 90. 2,3-dimethylcyclohexanone 91. 1-bromo-2-chlorocyclobutene 92. 2-cyclobutylpropanal 93. 4-cyclopropylpentan-2-ol 94. 4-ethenyl-5-ethyloctane 95. 2-methylpropanoyl chloride 96. methyl propanoate 97. methyl 2-ethylbutanoate 98. 5-ethyl-4,6-dimethyloct-1-ene 99. butane-2,3-diol 100. 5,6-diethyl-8-methyldec-4-ene 101. 3-methylcyclopentanol 102. 7-ethyl-6-methylundec-6-enoic acid www.studyhive.in P a g e 22 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 103. ethyl propanoate 104. N-ethyl-N-methylpropan-1-amine 105. hex-3-yne 106. 3-ethyl-4-methylpentanal 107. benzene 108. naphthalene 109. anthracene 110. Phenanthrene 111. Diphenyl 112. Methylbenzene (Toluene) 113. 1,2-dimethylbenzene (o-Xylene) 114. 1,3-dimethylbenzene (m-Xylene) 115. 1,4-dimethylbenzene (p-Xylene) 116. Ethenylbenzene (vinyl benzene or styrene) 117. 1,3,5-trimethylbenzene 118. 1-chloro-3-methylbenzene 119. 1,4-dichlorobenzene 120. Phenyl chloromethane 121. 1-chloro-3-phenylpropane 122. 3-chloro-1-phenylprop-1-ene 123. phenol 124. benzene-1,2-diol (Catechol) 125. benzene-1,3-diol (Resorcinol) 126. benzene-1,4-diol (p-quinol or hydroquinone) 127. Phenylmethanol 128. 2-phenylethanol 129. Benzaldehyde 130. Phenylacetaldehyde 131. benzoic acid 132. 2-hydroxybenzoic acid 133. phenylethanoic acid 134. (2-hydroxyphenyl)acetic acid 135. benzene-1,2-dicarboxylic acid (phthalic acid) 136. benzene-1,3-dicarboxylic acid (isophthalic acid) 137. benzene-1,4-dicarboxylic acid (terephthalic acid) 138. 2-hydroxybenzoic acid (o-salicylic acid) 139. 2-methylbenzoic acid (o-toluic acid) 140. benzoyl chloride 141. Benzamide 142. benzene-1,2-dicarboxamide (phthalamide) 143. Phthalimide 144. benzoic anhydride 145. Phthalic anhydride 146. methyl benzoate 147. Aniline www.studyhive.in P a g e 23 | 24  CLASS XI IUPAC RULES & PRACTICE SHEET 148. N-methylaniline 149. N,N-dimethylaniline -----END------ www.studyhive.in P a g e 24 | 24