ORGANIC CHEMISTRY RESOURCES GWR updated 2020

12CHM20 INSTRUCTIONAL WORKSHEET #

Unit 4: organic chemistry TOPIC: FUNCTIONAL GROUPS & IUPAC nomenclature

Name the following compounds following IUPAC rules and order of priorities

IUPAC rules See: http://chemwiki.ucdavis.edu/Organic_Chemistry for more details

1. Identify the longest carbon chain. This chain is called the parent chain. 

2. Identify all of the substituents (groups appending from the parent chain). 

3. Number the carbons of the parent chain from the end that gives the substituents the lowest numbers. When
comparing a series of numbers, the series that is the "lowest" is the one which contains the lowest number at the
occasion of the first difference. If two or more side chains are in equivalent positions, assign the lowest number to the
one which will come first in the name. 

4. If the same substituent occurs more than once, the location of each point on which the substituent occurs is
given. In addition, the number of times the substituent group occurs is indicated by a prefix (di, tri, tetra, etc.). 

5. If there are two or more different substituents they are listed in alphabetical order using the base name (ignore
the prefixes). The only prefix which is used when putting the substituents in alphabetical order is iso as in isopropyl or
isobutyl. The prefixes sec- and tert- are not used in determining alphabetical order except when compared with
each other. 

6. If chains of equal length are competing for selection as the parent chain, then the choice goes in series to:
a)
the chain which has the greatest number of side chains.
b) the chain whose substituents have the lowest- numbers.

c) the chain having the greatest number of carbon atoms in the smaller side chain.
d)the chain having the least
branched side chains. 

7. A cyclic (ring) hydrocarbon is designated by the prefix cyclo- which appears directly in front of the base name.

In summary, the name of the compound is written out with the substituents in alphabetical order followed by the
base name (derived from the number of carbons in the parent chain). Commas are used between numbers and
dashes are used between letters and numbers. There are no spaces in the name.

order of priorities

name functional compound name substituent MOST OF

group suffix prefix substituent prefix
text (if highest (if lower precedence) information IS FOR
abbreviation precedence) REFERENCE ONLY
alkanoic acid RCOOH -oic acid x-carboxy- ONLY ALKYL AND
alkyl alkanoate RCOOR’ -oate x-alkyloxycarbonyl HALO
amide RC(O)NR2 -amide x-carbamoyl SUBSTITUENTS are
reference FYI only

needed to be known
nitrile RCN -nitrile x-cyano
for naming in
alkanal RCHO -al x-formyl- 12CHM
alkanone R(O)R -one x-oxy-
How to use:
alkanol ROH -ol x-hydroxy-
Start from the top
amine RNR2 -amine x-amino- down until you see the
alkene RRC=CRR -ene x-en- functional group – this
alkyne RC≡CR -yne x-yn- is the ‘parent”
compound name
alkane RH -ane x-alkyl
(suffix)
methyl, ethyl, propyl etc
Other functional
ether ROR -ether x-alkoxy- groups are named as
haloalkane RX - x-halo substituents (prefix)
fluoro, chloro, bromo, iodo

Practice problems next page… name the un-named compounds using IUPAC rules

There are many more examples (to guide you) than problems … the ones you are
expected to named haven’t been named.
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Many examples are given (especially of nomenclature outside the scope of this course unit)
for both these examples note the systematic way the name fits the structure by numbering the
carbons and fitting the name to the structure.

1. butane

2. hexane
3.
butane

4. pentane

5. nonane

8. 3-ethyl-2,2-dimethylpentane
6. 2-methylbutane

7.

2,2,3-trimethylpentane

You are not expected to name cyclo compounds

10. methylcyclopentane

9. cyclopentane 11. cyclohexane

The alkenes following have stereochemistry denoted around the double bond: cis(Z) trans (E)

13. but-2E-ene
14. hex-3E-ene

12.

1,2-dimethylcyclopentane
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15. hexene
17. pent-2Z-ene
16.
pent-2E-ene

You are not expected to name dienes (or multi-enes) examples given for reference and to see IUPAC naming logic

20. oct-3Z,5E-diene

18. 19. hept-2Z,4Z-diene

hept-2E,4E-diene

23. 3-ethyl-4,4-
dimethylpentene
22. 2,3-dimethylpentene

21.
3-methylbut-2Z-ene

You are not expected to name cycloalkanes/enes -examples given for reference and to see IUPAC naming logic

25. 3-methylcyclopentene
24. cyclopentene

26. cyclohexene

You are not expected to name alkynes (triple bonded carbons) examples given for reference and to see IUPAC naming
logic

27. 4,5-
28. Cyclohept-1,3-diene
dimethylcyclohexene 29. propyne

31. hex-2-yne 32. hex-3-yne

30. but-2-yne

33. pent-4-yn-2E-ene 34.

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note that order of priorities is ene before
bromononane
yne

37. 2,3,4,5 tetrachlorohexane

35. chlorobutane 36. bromomethane

38. 40. bromocyclopentane

39.

41. 1,2-
difuorocyclobutane 43. 2-chlorohex-3-yne
42. chloropropene

You are not expected to name ethers - examples given for reference and to see IUPAC naming logic

44. bromopent-4-yn-2E- 46. ethylmethylether

45. diethylether
ene

48. pentylpropylether

47.
dimethylether
51. (1-methyl)ethyl methyl ether
(or isopropylmethyl ether)
49. diethylether 50. butylmethylether

52. Example of a multifunctional compound named using order of

53. methanol

priorities: 4,6-dibromo-8-methoxydec-2E-ene
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56. 1-methylethanol
54. butanol 55. ethanol

58. pentanol 59. propan-2-ol

57. 2-methylbutanol

60. pemtan-3-ol 62. 2-methylpentan-2-ol

61. hexan-3-ol

64. Now the alcohol is higher

priority than the alkene:
4-methylpent-4-en--3-ol
63. 2,3-dimethylhexan-2-ol
65. 2,2-dichloropent-3-en-1-ol

67. cyclohexanol 68. cyclohexan-1,2-ol

66. butan-2-ol

CH3CH2CH(OH)CH3

You are not expected to name diols - examples given for reference and to see IUPAC naming logic

70. hexan-2,3,4-triol
69. butan-2,4-diol
71. ethanal
(acetaldehyde)

73. butanal 74. ethanal

72. methanal
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75. 2-methylbutanal 76. 3-flouropentanal
77. 3-hydroxymethanal

79. 2,3-dibromo-3-
methylpentanal
78. hex-2-ene-anal 80. 3-methylpentanal

81. 2-hydroxybutanal
82. 2,2-dichloropent-3E-eneal
83. hex-2-yn-anal

85. propan-2-one
86. pentan-2-one
84. propan-2-one

88. 3-methylpentan-2-one
87. hexan-3-one 89. 4-fluorohexan-2-one

91. 3,3-dibromobutan-2-one 92. 4-methoxypentan-2-one

90. hept-3E-en-2-one

94. 3-hydroxypentan-2-one
93. hept-3E-en--2-one (as #90)
95. but-3-yn--2-one
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96. cyclohexanone 97. 3-methylcyclohexanone 98. 3,3-dichlorohex-4E-en-2-one

101. Cycopentan-1,3,4-trione
99. Aldehydes have higher priority than 100. 3-hydroxy-4-oxy-
ketones – the keto group is now a
substituent; 3-oxopentanal

pentanal

102. Have a go… 3,5,7-trimethyldec-3E,5E,7E-en-1-ol

103. Ethanoic acid (acetic acid) 104. methanoic acid 105. same as 105

(formic acid)

106. propanoic acid 108. 3,3-dibromopropanoic acid

107. propanone

110. 3-methoxybutanoic
111. 3-oxo-pentanoic acid
acid
109. pentanoic acid

112. 2-hydroxybutanoic acid

113. prop-2-ynanoic acid 114. pent-2E-enoic acid

115. 2-hydroxy-3-formylpropanoic
acid
116. Have a go… 6,8-dihydroxyhexadec-3-en-2,1,15-trione
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118. methylethanoate
119. methylpropanate
117. Ethyl propanate

120. ethylmethanoate 121. methylbutanoate 122. ethylpropanoate

123. methylbutanoate 124. ethylpropanoate 125. ethylbutanoate

126. ethyl decanoate 127. butylmethanoate

129. methylamine 130. ethylamine (same as 129)

128. ethylamine

132. methylpropylamine
131. diethylamine 133. trimethylamine

135. triethylamine
134. nonylamine

137. ethylmethylpropylamine
136. pentylpropylamine

138. butanamide 140. methanamide

139. ethanamide

(formamide)
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142. N-hexylbutanamide
141. N-methylethamide

144. N,N’-dimethylethamide 145. N,N’-diethylproanamide

143. N-methylmethanamide

146. N-methyl,N’-pentyl ethanamide 147. N.N’-dimethylmethanamide

assign the following names to the below compounds. (some names can be used more than once):

phenyl ring, phenol, aspirin, 2-hydroxy benzoic acid, acetyl salicylic acid, benzoic acid, hydroxy
benzene, salicylic acid, 2-acetoxy benzoic acid, benzene

149. Phenol,
hydroxybenzene

150. benzoic acid

148. Benzene
Phenyl ring

151. 2-hydroxybenzoic acid,

salicylic acid

152.
Aspirin ; acetylsalicylic acid; 2-acetoxybenzoic acid