1. Nomenclature & Introduction of Major Families of Organic Compounds

2. Classification of Hydrocarbons
alkadienes, etc.
cycloalkadienes, etc.
Huckel rule

3. 1. Hydrocarbons
Organic compounds containing carbon and hydrogen only.

4. (a) Alkanes (CnH2n+2)
Alkanes are hydrocarbons that contain only C – C and C – H single bonds(except CH4)
Relatively inert as the  bonds are strong
 saturated hydrocarbons
contain the maximum possible number of hydrogen atoms per molecule

5. CH4 Methane C6H14 Hexane C2H6 Ethane C7H16 Heptane
The first 10 members of the unbranched (acyclic) alkane series are :
CH4 Methane C6H14 Hexane
C2H6 Ethane C7H16 Heptane
C3H8 Propane C8H18 Octane
C4H10 Butane C9H20 Nonane
C5H12 Pentane C10H22 Decane

6. Cycloalkanes are alkanes in which all or some of the carbon atoms are arranged in a ring

7. Cycloalkanes in skeletal forms
Angle strain arises from repulsions between adjacent bond pairs
Most stable due to less angle strain

8. Cycloalkanes in skeletal forms

9. Alkanes and Cycloalkanes
General formula of acyclic alkanes: CnH2n+2
General formula of cycloalkanes: Q.1
CnH2n

10. The First Three Members of Alkanes
Methane (CH4)
Ethane (CH3CH3)
Propane (CH3CH2CH3)

11. Starting from C4H10, two or more structures are possible for the same molecular formula.
This phenomenon is called isomerism.
The different structures with the same molecular formula are called isomers.

12. Q.2 C4H10
All carbon atoms are sp3 hybridized - zigzag

13. Q.2 C5H12

14. Q.2 C6H14

15. Nomenclature of Alkanes
IUPAC Conventions

16. Condensed structural formula
Straight-Chain Alkanes
Name
Number of carbon atoms
Condensed structural formula
Methane
Ethane
Propane
Butane
Pentane
Hexane
Heptane
Octane
Nonane
Decane 1 2 3 4 5 6 7 8 9 10
CH4
CH3CH3
CH3CH2CH3
CH3(CH2)2CH3
CH3(CH2)3CH3
CH3(CH2)4CH3
CH3(CH2)5CH3
CH3(CH2)6CH3
CH3(CH2)7CH3
CH3(CH2)8CH3

17. Branched-Chain Alkanes
Name the longest possible straight chain
 give the parent name for the alkane

18. Branched-Chain Alkanes
Name the substituent groups – the branches
CnH2n+1– Alkyl groups (derived from alkanes)
CH3 – methyl
C2H5 – ethyl

19. C3H7 –
propyl
isopropyl

20. C4H9 –
sec-butyl
butyl
secondary, 2 carbon
isobutyl
tert-butyl
tertiary, 3 carbon

21. 3. Number the positions of the substituent
3. Number the positions of the substituent groups with the smallest possible numbers 2
2-methyl
2-methylbutane

22. If more than one substituent group of the same kind exist, the numbers are denoted by prefixes.
2  di
3  tri
4  tetra
5  penta
6  hexa

23. tetramethyl
tetramethylmethane

24. 2
propane
2,2-dimethylpropane

25. 1 5
1,5,5-trichloro
1,5,5-trichlorohexane

26.   6 2 1 5 1,5,5-trichloro 2,2,6-trichloro
‘Lowest numbers’ does NOT refer to the smallest sum

27. prefix is not considered
If two or more different substituent groups exist, they are named in alphabetical order but NOT in numerical order of their positions. 3
2,2-dimethyl 2
3-ethyl
3-ethyl-2,2-dimethylpentane
prefix is not considered

28. 3
tert-butyl
3-ethyl-2,2-dimethylpentane
 
3-tert-butylpentane

29. (b) Alkenes (CnH2n) One C=C double bond
More reactive than alkanes due to weaker  bond
 unsaturated hydrocarbons
NOT contain the maximum possible number of hydrogen atoms per molecule

30. (b) Alkenes (CnH2n) First member is ethene (ethylene)
Cyclic structures are possible
cyclopropene
cyclobutene

31. (b) Alkenes (CnH2n) First member is ethene (ethylene)
Cyclic structures are possible
cyclopentene
cyclohexene
Q.3
CnH2n-2

32. Starting from C4H8, isomerism occurs
Structural isomerism :
same molecular formula
different linking orders of atoms

33. Functional group isomerism
Chain isomerism
Different carbon skeletons
Functional groups in different positions
Structural isomerism
Position isomerism
Functional group isomerism
Different functional groups

34. Geometrical isomerism Same linking order of atoms
Stereoisomerism
Optical isomerism
Different spatial arrangements of atoms

35. Geometrical Isomerism
e.g. cis-but-2-ene and trans-but-2-ene

36. Both substituent groups are on the same side w. r. t
Both substituent groups are on the same side w.r.t. the axis of the C=C double bond
Both substituent groups are on the opposite sides w.r.t. the axis of the C=C double bond

37. cannot be inter-converted at lower temperatures

38. maximum overlap of pz orbitals minimum overlap of pz orbitals
Rotation about the axis of a double bond through an angle of 90o results in the breaking of the π bond

39. Geometrical Isomerism
Arises from restricted rotation about the axis of the C=C double bond.

40. Position isomers Q.4 Chain isomerism position isomers
trans
cis
Geometrical isomers

41. Q.4
Position isomers
Chain isomerism

42. Functional group isomerism
Q.4
Functional group isomerism

43. Q.4
Chain isomerism
A total of 11 isomers

44. Q.4
C5H8
C5H6

45. 1
pent-1-ene 2
pent-2-ene

46. Geometrical Isomerism cis2
pent-2-ene
(2E)-pent-2-ene
trans
Geometrical Isomerism
cis
(2Z)-pent-2-ene

47. E : in opposition to  trans
E/Z notation
If there are three or four different groups attached to the C atoms of C=C double bond
E/Z notation rather than the cis/trans notation is used to name the stereoisomers of a molecule.
E : in opposition to  trans
Z : together  cis

48. (2Z)-3-methylpent-2-ene1 2 3
(2Z)-3-methylpent-2-ene
(2E)-3-methylpent-2-ene

49. Q.4
2-methylbut-1-ene 2 1
2-methylbut-2-ene 2
3-methylbut-1-ene 3 1
Functional group has a higher priority than branches

50. Q.4
cyclopentane
methylcyclobutane

51. Q.4
1,2-dimethylcyclopropane
ethylcyclopropane
1,1-dimethylcyclopropane

52. bicyclo[1.1.1]pentane
spiro[2.2]pentane
bicyclo[2.1.0]pentane
Polycyclic hydrocarbons contain two or more rings that share two or more carbon atoms
A spiro compound is a bicyclic compound with rings connected through just one atom

53. tricyclo[ ,3]hexane
tricyclo[ ,3]pentane

54. Cycloalkenes and alkadienes have the same general formula as alkynes
(c) Alkynes (CnH2n-2)
One CC triple bond
Reactive (unsaturated) due to weak  bonds
First member is ethyne (acetylene), C2H2
Cycloalkenes and alkadienes have the same general formula as alkynes

55. (c) Alkynes (CnH2n-2) C atoms in triple bond are sp hybridized Linear
Cyclic structures are highly unstable
due to great angle strain
90 << 180

56.  In naming alkenes and alkynes,
the ‘longest’ carbon chain need NOT be the one that contains the multiple bond. 1 2 
2-ethylpent-1-ene

57.  In naming alkenes and alkynes,
the ‘longest’ carbon chain need NOT be the one that contains the multiple bond. 1 3 
3-methylenehexane

58. Q.5(a) 2 5
(2E)-5-methylhex-2-ene
Functional group has the higher priority than branch.

59. Q.5(b) 1 3
(3E)-penta-1,3-diene

60. Q.5(c) 1 2 4 5 3 3 1 4 5 2
1,3 > 2,4

61. Q.5(c) 1 3
(3E)-pent-3-en-1-yne
NOT ene

62. although -yne has the smaller number
Q.5(d) 1 2 4 5 3 3 1 4 5 2
1,3 > 2,4
although -yne has the smaller number

63. Q.5(d) 3 1 4 5 2
pent-1-en-3-yne
NOT ene

64.   Q.5(e) 1 4 1 4 pent-4-en-1-yne pent-1-en-4-yne
If the same set of numbers is obtained by counting in either direction, the number is assigned in alphabetical order. Refer to 5(i)

65. If the enyne chain is longer, enyne > diene 8
Q.5(f) 1  8
diene has a higher priority than enyne
If the enyne chain is longer, enyne > diene
The length of C chain is more important !

66. 8 Q.5(f) 3 4 5 6 7 5-ethyl 1 6-ethynyl 3,7-dimethyl octa-1,6-diene
4-methylidene
5-ethyl-6-ethynyl-3,7-dimethyl-4-methylideneocta-1,6-diene

67. 1 8 6
Q.5(g) 7 8
octa-1,7-diene
octa-1,6-diene  

68. 1 8 6 Q.5(g) 3 4 5 7 5-ethyl 3,7-dimethyl octa-1,6-diene 4-methylidene
6-vinyl
5-ethyl-3,7-dimethyl-4-methylidene-6-vinylocta-1,6-diene

69. Q.5(h) 1 8 6 3 4 5 7
octa-1,7-diene substituents at 3,4,5,6

70. Q.5(h) 1 8 6 3 4 5 7
octa-1,7-diene substituents at 3,4,5,6

71. 1 8 6 3 4 5 7
Q.5(h)
octa-1,7-diene substituents at 3,4,5,6,7

72. 1 8 6 3 4 5 7 2
Q.5(h)
octa-1,7-diene substituents at 2,3,4,5,6 

73. 1 8 6 3 4 5 7 2 Q.5(h) 4-ethyl 2,6-dimethyl octa-1,7-diene
5-methylidene
3-ethenyl
3-ethenyl-4-ethyl-2,6-dimethyl-5-methylideneocta-1,7-diene
vinyl
methylene

74. Q.5(i) 1 2 3 4 5 6 7 8
octa-1,7-diene substituents at 3,4,5,6

75. Q.5(i) 8 7 6 5 4 3 2 1
octa-1,7-diene substituents at 3,4,5,6

76. Q.5(i) 1 2 3 4 5 6 7 8
octa-1,7-diene substituents at 3,4,5,6
5-ethyl
3,6-dimethyl
4-methylidene

77. Q.5(i) 8 7 6 5 4 3 2 1
octa-1,7-diene substituents at 3,4,5,6
4-ethyl
4,3,6,5 > 5,3,6,4
3,6-dimethyl
5-methylidene
4-ethyl-3,6-dimethyl-5-methylideneocta-1,7-diene

78. ethenylcyclohexane ethynylcyclohexane
In naming hydrocarbons, cyclic structures always have higher priority than C=C, CC.
ethenylcyclohexane
ethynylcyclohexane

79. Also, cyclic structure rather than the length of the carbon chain is first considered.
heptylcyclohexane

80. 1 3
but-3-en-1-ylcyclohexane
The C directly bonded to the ring is assigned the lowest possible number

81. but-1-en-2-ylcyclohexane3
but-3-en-2-ylcyclohexane

82. 1-ethyl-2-methylcyclohexane
In naming cyclic hydrocarbons, the side branches are numbered in alphabetical order. 1
1-ethyl 2
2-methyl
1-ethyl-2-methylcyclohexane

83. 1-methyl-2-(propan-2-yl)cyclohexane
In naming cyclic hydrocarbons, the side branches are numbered in alphabetical order.
1-methyl 1 2 2
2-(propan-2-yl)
1-methyl-2-(propan-2-yl)cyclohexane

84. 1-(butan-2-yl)-2-methylcyclohexane
In naming cyclic hydrocarbons, the side branches are numbered in alphabetical order. 1
1-butan-2-yl 2
2-methyl
1-(butan-2-yl)-2-methylcyclohexane

85. Q.6
propan-2-ylcyclopropane
1,2-dimethyl-3-(propan-2-yl)cyclopropane

86. (2-methylprop-1-en-1-yl)
Q.6 1 2 3
prop-1-en-1-yl
(2-methylprop-1-en-1-yl)
(2-methylprop-1-en-1-yl)cyclobutane

87. Q.6 1 2
1-methylcyclobutene 2 1
2-methylcyclobutene

88. Q.6 1 2 3
3-methylcyclobutene 2 1 4
4-methylcyclobutene

89. Q.6 1 2 3
3-methylcyclobutene 4 1 2 3

90. (d) Aromatic hydrocarbons
With a total of (4n + 2)  electrons in the conjugated system
(alternating single and double bonds)

91. (d) Aromatic hydrocarbons
Extra stability (aromaticity) due to delocalization of  electrons
Also called arenes

92. (d) Aromatic hydrocarbons
C6H5 –  phenyl group
C10H7 –  naphthyl group
Both are aryl groups

93. Q.7
6 = 41+2
aromatic
methylbenzene

94. Q.7
10 = 42+2
aromatic
naphthalene

95. Q.7
14 = 43+2
aromatic
anthracene

96. Q.7
8  4n+2
NOT aromatic
cyclooctatetraene

97. Q.7
8  4n+2
NOT aromatic
cyclooctatetraene, 環辛四烯
The molecular is not planar
2pz orbitals are not parallel to one another
poor delocalization of  electrons

98. 2. Hydroxy compounds
Organic compounds with one or more hydroxyl groups, –OH.

99. R – OH (a) Alkanols (alcohols) Derived from alkanes
Contain one or more –OH groups attached to an alkyl group.
R – OH
Alkyl group
Hydroxyl group

100. (a) Alkanols (alcohols) (a) Alkanols (alcohols)
Hydroxy derivative of alkane
Alkyl derivative of water RH
ROH
H replaced by OH
HOH
H replaced by R

101. (a) Alkanols (alcohols)
General formula : CnH2n+1OH (acyclic)
Three classes :
Primary, 1
Tertiary, 3
Secondary, 2

102. Naming of alkanols : -
The longest C chain containing the –OH group is chosen.
–ane  –anol
The position of –OH group is indicated by the smallest possible number.

103. 1 2 3 4 5
pentane
pentan-2-ol

104. 1 2 3 4 5
pentane
pentan-3-ol

105. 1 2 3 4 5
pentane
pentane-2,4-diol
‘e’ is retained in diol

106. Ar – OH (b) Phenols Derived from aromatic hydrocarbons
Contain one or more –OH groups attached to an aryl group
Ar – OH
Aryl group
Hydroxyl group

107. 1 2 
phenol
2-hydroxyphenol
Benzene-1,2-diol 

108. o  ortho m  meta p  para 2-chlorophenol 3-chlorophenol1 2 3 4
o-chlorophenol
o  ortho
m-chlorophenol
m  meta
p-chlorophenol
p  para

109. Q.8 1 6 4 2
4-methylhexan-2-ol 1 5 4 2
4-methylpentan-2-ol

110. - OH has a higher priority than C=C
Q.8
trans- 1 2 3 4 5
- OH has a higher priority than C=C
pent-3-en-2-ol
(3E)-pent-3-en-2-ol

111. Propan-2-yl
Q.8 2
Menthol (薄荷醇)
cyclohexanol
with
TWO branches
methyl

112. 2,5 > 3,6 5-methyl-2-(propan-2-yl)cyclohexanol Q.8 menthol 2 6 3 51 1 4 6 4 2 5 3
2,5 > 3,6
5-methyl-2-(propan-2-yl)cyclohexanol

113. 3. Ethers
Contain the oxy, –O-, group or
alkoxy, R-O- group
oxy group

114. 3. Ethers Alkoxy group Contain the oxy, –O-, group or
alkoxy, R-O- group
Alkoxy group

115. 3. Ethers
Alkyl derivatives of water
2H replaced by 2R

116. 3. Ethers Three classes of ethers : -
a,b,c,are all greater than 105 due to
stronger van der Waals’ repulsive forces between bulky alkyl/aryl groups than between H atoms

117. 3. Ethers
Naming : -
The alkoxy groups are always treated as substituents and expressed as prefixes.

118. Q.9
ethane
methoxy
methoxyethane 

119. Q.9
methane
ethoxy 
ethoxymethane

120. Q.9
methoxy
benzene 
methoxybenzene

121. Q.9
phenoxy
methane
phenoxymethane 

122. Q.9 2 1 3
propane
methoxy
2-methoxypropane 

123. 4. Carbonyl compounds
Organic compounds with the carbonyl group,

124. 4. Carbonyl compounds Aldehydes
Products of dehydrogenation of alcohols
At least ONE H attached to C
R : alkyl, aryl or H

125. Aldehydes Examples : - –ane replaced by –anal methanal ethanal
propanal
benzaldehyde
–ane replaced by –anal

126. The aldehye group, –CHO, always occupies the terminal position
Aldehydes
Examples : -
propan-1-al
methanal
ethanal
propanal
benzaldehyde
The aldehye group, –CHO, always occupies the terminal position
 No need to specify its position

127. 4. Carbonyl compounds (b) Ketones
No H atom is directly attached to the carbonyl group
R, R’ : alkyl or aryl group

128. –ane replaced by –anone
(b) Ketones
Examples : -
propanone
butanone
–ane replaced by –anone

129. (b) Ketones
Examples : - 2 3
pentan-2-one
pentan-3-one

130. (b) Ketones Examples : - 2 3 2 4 4-methylpentan-2-one

131. (b) Ketones
Examples : - 2 3 2 4
pentane-2,4-dione
pentane-2,3-dione

132. 5. Carboxylic acids
Organic compounds with the carboxyl group,

133. 5. Carboxylic acids Organic compounds with the carboxyl group,
carbonyl
carboxyl
hydroxyl

134. 5. Carboxylic acids Organic compounds with the carboxyl group,
R : alkyl, aryl or H
If R is an alkyl group, the compound is an alkanoic acid, CnH2n+1COOH.

135. –ane replaced by –anoic acid
Carboxylic acids
Examples : -
methanoic acid
ethanoic acid
propanoic acid
–ane replaced by –anoic acid

136. The carboxyl group, –COOH, always occupies the terminal position
Carboxylic acids
Examples : -
methanoic acid
ethanoic acid
propanoic acid
The carboxyl group, –COOH, always occupies the terminal position
 No need to specify its position

137. Carboxylic acids Examples : - benzoic acid 2-hydroxybenzoic acid1 3 1 2
benzoic acid
2-hydroxybenzoic acid
3-methylbenzoic acid

138. Carboxylic acids Examples : - cyclohexanecarboxylic acid benzoic acid
cyclohexylethanoic acid
cyclohexylacetic acid

139. Carboxylic acids
Examples : -
hexanedioic acid

140.   Carboxylic acids Examples : - hexanedioic acid1 6  
hexanedioic acid
hexane-1,6-dioic acid

141.    Carboxylic acids Examples : - hexanedioic acid1 4  
hexanedioic acid
hexane-1,6-dioic acid
hexane-1,4-dioic acid 

142. 6. Acids derivatives acyl group FOUR types : - carboxylic acid
OH replaced by Cl
carboxylic acid
acyl(acid) chloride

143. R  R’ for mixed acid anhydride
6. Acids derivatives
FOUR types : -
acid anhydride
H2O
R  R’ for mixed acid anhydride

144. 6. Acids derivatives FOUR types : - H2O ester R : alkyl, aryl or H
R’ : alkyl or aryl

145. 6. Acids derivatives FOUR types : - H2O 1° amide
N links to only ONE C
1° amide

146. 6. Acids derivatives FOUR types : - H2O 1o amine 2° amide
N links to TWO C atoms

147. 6. Acids derivatives FOUR types : - H2O 2o amine 3° amide
N links to THREE C atoms

148. Naming of acids derivatives
Acyl chloride : oic acid to oyl chloride
ethanoyl chloride Or
acetyl chloride

149. Naming of acids derivatives
Acyl chloride : oic acid to oyl chloride
ethanoyl chloride
spacing

150. Naming of acids derivatives
Acid anhydride : oic acid to oic anhydride
ethanoic anhydride
spacing

151. Naming of acids derivatives
Acid anhydride : oic acid to oic anhydride
ethanoic propanoic anhydride
For mixed anhydride, the parent acids are named in alphabetical order

152. Naming of acids derivatives
Ester : oic acid to oate preceded by R group of ROH
ethanoate
methyl
spacing

153. Naming of acids derivatives
Ester : oic acid to oate preceded by R group of ROH
propanoate
ethyl

154. Naming of acids derivatives
Ester : oic acid to oate preceded by R group of ROH
propenoate
ethyl
Or, ethyl acrylate

155. Naming of acids derivatives
Ester : oic acid to oate preceded by R group of ROH
ethyl
2-methylpropenoate 2 1 Or
ethyl 2-methylacrylate

156. Naming of acids derivatives
Amides : oic acid to amide
ethanamide

157. Naming of acids derivatives
Amides : oic acid to amide
Or, N-methylacetamide
N-methyl
ethanamide
NO spacing

158. Naming of acids derivatives
Amides : oic acid to amide
N,N-dimethyl
ethanamide

159. N-ethyl-N-methylacetamide
Naming of acids derivatives
Amides : oic acid to amide
-N-methyl
N-ethyl
ethanamide Or
N-ethyl-N-methylacetamide

160. R – X X : halogens 7. Halogeno hydrocarbons
Hydrocarbons containing at least one halogen atom
R – X
X : halogens

161. Always treated as substituents (shown by prefixes)
7. Halogeno hydrocarbons
Hydrocarbons containing at least one halogen atom
-F fluoro
-Cl chloro
-Br bromo
-I iodo
Always treated as substituents (shown by prefixes)

162. 7. Halogeno hydrocarbons
Examples : -
bromomethane
dibromomethane

163. 7. Halogeno hydrocarbons
Examples : -
BTM
bromotrifluoromethane
Both are used in fire extinguishers
bromochlorodifluoromethane
BCF

164. 7. Halogeno hydrocarbons
Examples : -
bromobenzene
1,2-dibromobenzene

165.   7. Halogeno hydrocarbons Examples : - 1-bromo-4-chlorobenzene

166.   7. Halogeno hydrocarbons Examples : - 1-bromo-2,4-dichlorobenzene5 1 2 4  
1-bromo-2,4-dichlorobenzene
2-bromo-1,5-dichlorobenzene

167.  7. Halogeno hydrocarbons Examples : - 4-bromo-1,2-dichlorobenzene 13 4 4 2 1 
4-bromo-1,2-dichlorobenzene

168. 7. Halogeno hydrocarbons
Examples : -
hexabromobenzene

169. All acyclic structures of C4H8Cl2
Q.10
All acyclic structures of C4H8Cl2
1,1-dichlorobutane
2,2-dichlorobutane

170. * chiral centre, optical isomers exist
Q.10
1,2-dichlorobutane
1,3-dichlorobutane
1,4-dichlorobutane
2,3-dichlorobutane *
* chiral centre, optical isomers exist

171. 2-(dichloromethyl)propane
Q.10 1 2 3
1,1-dichloro-2-methylpropane   1 2 3
2-(dichloromethyl)propane
171

172. 1,1-dichloro-2-methylpropane
Q.10 1 2 3
1,1-dichloro-2-methylpropane
1,2-dichloro-2-methylpropane
1,3-dichloro-2-methylpropane

173. 8. Amines Derivatives of ammonia NH3 Primary(1°) amine
Secondary(2°) amine
Tertiary (3°) amine

174. 8. Amines Naming amines derived from hydrocarbons
The amino group, is always treated as the principal functional group and expressed as suffix. e replaced by amine
methanamine
ethenamine
(ethylenamine)
ethynamine (acetylenamine)

175. 8. Amines
Naming amines with functional groups other than CC, C=C, X- and RO-
The amino group, is always treated as the substituent and expressed as prefix, amino- 1 2
2-aminoethanol

176. 2° amine 8. Amines Examples : - methanamine N-methyl N-methyl

177. 8. Amines
3° amine
N,N-dimethyl
ethanamine
N,N-dimethyl
methanamine

178. 8. Amines
NOT benzenamine
phenylamine or aniline

179. 8. Amines 2-methylaniline 3-methylaniline 4-methylaniline1 3 4
2-methylaniline
3-methylaniline
4-methylaniline
or o-toluidine
or m-toluidine
or p-toluidine

180. 8. Amines
2-methylaniline 
N-methylaniline 
N-phenylmethanamine

181. 8. Amines
1-phenylmethanamine

182. 8. Amines 1 2 3
Prop-2-en-1-amine
Prop-1-en-2-amine

183. 8. Amines
linear 1 2 3 4
but-3-yne-1,2-diamine

184. 8. Amines
N2-ethyl 1 2 3
propane-1,2-diamine

185. Q.11
2-aminophenol
benzene-1,2-diamine
2-aminobenzoic acid

186. N-methylbutan-1-amine
Q.11 1 2 3 4
N-methylbutan-1-amine 1 2 3 4 5
pentan-2-amine

187. Q.11 1
butan-1-amine 2
butan-2-amine

188. N1-ethylpropane-1,2-diamine
Q.11
propane-1,2-diamine
N1-ethylpropane-1,2-diamine 1 2 3 1 2 3 4
N-methylbutan-2-amine

189. N-ethyl-2-methoxy-N-methylethanamine
Q.11
N-ethyl 2
2-methoxy
ethanamine
N-methyl 1
N-ethyl-2-methoxy-N-methylethanamine

190.  3 substituents > 2 substituents Q.11 ethanamine N-methyl
N-(2-methoxyethyl) 1 
N-(2-methoxyethyl)-N-methylethanamine
3 substituents > 2 substituents

191. N-(2-methoxyethyl)-N-methylpropan-1-amine
Q.11 1 2 3
propan-1-amine
N-methyl
N-(2-methoxyethyl) 2 1
N-(2-methoxyethyl)-N-methylpropan-1-amine

192. N-(2-methoxyethyl)-N-methylpropan-2-amine
Q.11 1 2 3
propan-2-amine
N-methyl 1 2
N-(2-methoxyethyl)
N-(2-methoxyethyl)-N-methylpropan-2-amine

193. 9. Nitriles
Containing the cyano group, -CN

194. 9. Nitriles Naming : - If acting as the principal functional group,
it is expressed as the suffix, nitrile
If acting as the substituent,
it is expressed as the prefix, cyano.

195. 9. Nitriles Examples : - ethanenitrile 2-methylpropanenitrile1 2 3
2-methylpropanenitrile
The carbon of the -CN group is counted as part of the longest carbon chain.

196. 9. Nitriles Examples : - ethanenitrile 2-methylpropanenitrile1 2 3
2-methylpropanenitrile
The -CN group always occupies the terminal position.
No need to specify its position.

197. 9. Nitriles 1 2 3 4 5
4-hydroxypentanenitrile

198. 9. Nitriles propanoic acid 3-cyano-2-methyl1 3
3-cyano-2-methyl
propanoic acid
If used as prefix, its carbon is not counted as part of the main carbon chain

199.  9. Nitriles propanoic acid 2-(cyanomethyl) Only one substituent  31 3
2-(cyanomethyl)
propanoic acid
Only one substituent  

200. 10. Poly-functional compounds
With two or more functional groups

201. 10. Poly-functional compounds
With identical functional groups 1 2 3 4
buta-1,3-diene
buta-1,3-diyne

202. ＝ 2Z > 2E (2E,4E)-hexa-2,4-diene (2Z,4Z)-hexa-2,4-diene
(2Z,4E)-hexa-2,4-diene
(2E,4Z)-hexa-2,4-diene
2Z > 2E

203. 10. Poly-functional compounds
With identical functional groups
ethanedioic acid
pentanedial
-COOH and –CHO groups always occupy the terminial positions.
No need to specify its position

204. 10. Poly-functional compounds
With identical functional groups
hexane-1,6-diamine
heptane-2,4,6-trione

205. 10. Poly-functional compounds
With identical functional groups 1 3 2
propane-1,2,3-triol

206. xylitol 1 2 3 4 5
pentane-1,2,3,4,5-pentol
206

207. 10. Poly-functional compounds
With different functional groups 1 2 3
2-aminoethanoic acid
or glycine
2-hydroxypropanoic acid

208. 10. Poly-functional compounds
With different functional groups 1 6 2 3 4 5 7
(2E)-hept-2-en-6-yn-1-ol

209. 10. Poly-functional compounds
Naming : -
The functional group with the highest priority (the principal functional group) is expressed as the suffix.

210. >
>
-CN
>
-OH > -NH2 > CC > C=C > -OR = X

211. 10. Poly-functional compounds
Naming : -
2. The main carbon skeleton should be the one that contains the greatest number of principal functional groups.
The main carbon chain needs NOT be the longest one except
3-methylidenehexane
p.5

212. 10. Poly-functional compounds
Naming : -
The position(s) of the principal functional group(s) is/are given the lowest possible number(s)
Exception : p.5 Q.5(e)

213.   Q.5(e) 1 4 1 4 pent-4-en-1-yne pent-1-en-4-yne
If the same set of numbers is obtained by counting in either direction, the number is assigned in alphabetical order.

214. (2Z)-3-hydroxypent-2-enoic acid Z
Worked examples : -
(a) 1 2 3 4 5
(2Z)-3-hydroxypent-2-enoic acid Z
C2 : COOH > H
atomic masses are compared
C3 : OH > CH2C

215. (2Z)-3-hydroxypent-2-en-4-ynoic acid Z
Worked examples : -
(b)
linear 1 2 3 4 5
(2Z)-3-hydroxypent-2-en-4-ynoic acid Z
C2 : COOH > H
C3 : OH > CC

216. (2Z)-3-hydroxypent-2-enedioic acid Z
Worked examples : -
(c) 1 2 3 4 5
(2Z)-3-hydroxypent-2-enedioic acid Z
C2 : COOH > H
C3 : OH > CH2C

217.   Worked examples : - (d) (3Z)-3-hydroxy-2-oxopent-3-enedioic acid1 2 3 4 5 1 2 4 3 5  
(3Z)-3-hydroxy-2-oxopent-3-enedioic acid
(2Z)-3-hydroxy-4-oxopent-2-enedioic acid

218. (2Z)-4-cyano-3-hydroxypent-2-enedioic acid
Worked examples : -
(e) 1 2 3 4 5
(2Z)-4-cyano-3-hydroxypent-2-enedioic acid

219. Worked examples : -
(f) 1 2 3 4 5 
4-formylpentanenitrile

220. Worked examples : -
(f) 1 2 3 4 5 
4-methyl-5-oxopentanenitrile

221. Carbonyl C is counted as part of the main carbon chain
Worked examples : -
(g) 1 2 3 4 5
Carbonyl C is counted as part of the main carbon chain  
3-hydroxy-5-oxopentanoic acid
3-hydroxy-4-formylbutanoic acid
The one with the longer C chain is preferred

222. Worked examples : -
(h) 5 1 2 3 4
(2Z)-2-formyl-3-hydroxy-4-oxopent-2-enedioic acid

223. Worked examples : - (h) Z C3 : OH > COC; C2 : COOH = CHO;5 1 2 3 4
(2Z)-2-formyl-3-hydroxy-4-oxopent-2-enedioic acid Z
C3 : OH > COC;
C2 : COOH = CHO;
COOH = CHO;
COOH > CHO

224.   Worked examples : - (i) 5-amino-5-oxopentanoic acid1 2 3 4 5
(i)  
5-amino-5-oxopentanoic acid
4-(aminocarbonyl)butanoic acid

225. 2A4O > 4A2O Worked examples : - (j) 2-(aminocarbonyl) 3-hydroxy
4-oxo 1 2 3 4 5
3-hydroxy
2A4O > 4A2O
2-(aminocarbonyl)-3-hydroxy-4-oxopentanedioic acid

226. 2A4O > 4A2O Worked examples : - (j) 2-(aminocarbonyl) 3-hydroxy
4-oxo 1 2 3 4 5
3-hydroxy
2A4O > 4A2O
If the same set of numbers is obtained from either direction, substituents are numbered in alphabetical order

227. 5-chloro-5-oxopentanoic acid
Worked examples : - 2 1 3 4 5
(k)
5-chloro-5-oxopentanoic acid

228. 2C4O > 4C2O Worked examples : - (l) 2-(chlorocarbonyl) 3-hydroxy
4-oxo
(l) 1 2 3 4 5
3-hydroxy
2C4O > 4C2O
2-(chlorocarbonyl)-3-hydroxy-4-oxopentanedioic acid

229. 5-methoxy-5-oxopentanoic acid
Worked examples : - 1 2 3 4 5
(m)
5-methoxy-5-oxopentanoic acid

230.  Worked examples : - (n) 2-(methoxycarbonyl) 3-hydroxy 4-oxo5 1 2 3 4
3-hydroxy 
3-hydroxy-2-(methoxycarbonyl)-4-oxopentanedioic acid

231. 5-(ethanoyloxy)-5-oxopentanoic acid
Worked examples : -
(o) 1 2 3 4 5
5-(ethanoyloxy)-5-oxopentanoic acid

232. 3-[(ethanoyloxy)carbonyl] 3-(oxycarbonyl) 3-carbonyl
Worked examples : -
pentanedioic acid 1 2 3 4 5
(p)
3-[(ethanoyloxy)carbonyl]
3-(oxycarbonyl)
3-carbonyl
3-[(ethanoyloxy)carbonyl]pentanedioic acid

233. 3-[(carbonyloxy)carbonyl]
Worked examples : -
pentanedioic acid 1 2 3 4 5
(p)
3-[(carbonyloxy)carbonyl]
3-{[(methoxycarbonyl)oxy]carbonyl}
3-(oxycarbonyl)
3-carbonyl
3-{[(methoxycarbonyl)oxy]carbonyl}pentanedioic acid

234. Worked examples : -
(q)
N,N-dimethyl
N-carboxy-
ethanaminium ion 6B

235. Worked examples : -
N,N-dicarboxy-
(r)
N-methyl
ethanaminium ion

236.   Worked examples : - Citric acid (s) 3-carboxypentanedioic acid1 2 3 4 5
(s) 1 2 3 
3-carboxypentanedioic acid
Propane-1,2,3-tricarboxylic acid Or
Propane-1,2,3-trioic acid 

237. propane-1,1,2,3-tetracarboxylic acid
Worked examples : -
(t) 3 2 1
propane-1,1,2,3-tetracarboxylic acid

238. 5-hydroxypenta-1,4-diene- 1,1,5-tricarboxylic acid2 3 4 5
(4Z)-
5-hydroxypenta-1,4-diene-
1,1,5-tricarboxylic acid
238

239. 3-amino-3-oxopropanoic acid
Q.12(a)
3-amino-3-oxopropanoic acid

240. 3-(aminocarbonyl)pentanedioic acid
Q.12(a)
3-(aminocarbonyl)pentanedioic acid

241. Q.12(b)
4-oxobutanoic acid

242. 3-formylpentanedioic acid
Q.12(b)
3-formylpentanedioic acid

243. Q.12(c)
3-oxopropanenitrile

244. Q.12(c)
4-cyanobutanoic acid

245. Q.12(c)
4-cyanopentanoic acid

246. 3-(methoxycarbonyl)pentanedioic acid
Q.12(d)
3-(methoxycarbonyl)pentanedioic acid

247. 4-methoxy-4-oxobutanoic acid
Q.12(d)
4-methoxy-4-oxobutanoic acid

248. 3-(acetyloxy)propanoic acid
Q.12(d)
3-(acetyloxy)propanoic acid

249. Q.12(e)
5-chloro-4-methyl-5-oxopentanoic acid

250. Q.12(e)
2-methylpentanedioic acid
5-chloro-4-methyl-5-oxopentanoic acid
4-(chlorocarbonyl)pentanoic acid is wrong since the structure should be viewed as the derivative of 2-methylpentanedioic acid.

251. 3-(chlorocarbonyl)pentanedioic acid
Q.12(e)
3-(chlorocarbonyl)pentanedioic acid

252. 3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid
Q.12(e)
3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid

253. hexanedioyl dichloride
Q.12(f)
hexanedioyl dichloride

254. 6-bromo-6-oxohexanoyl chloride 6-chloro-6-oxohexanoyl bromide
Q.12(e) 1 2 3 4 5 6 6 5 4 3 2 1  
6-bromo-6-oxohexanoyl chloride
6-chloro-6-oxohexanoyl bromide

255. 3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid
Q.12(e)
3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid

256. 3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid
Q.12(e)
3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid

257. Q.13(a)
Cyclohexylamine

258. Q.13(b)
Benzene-1,3-dioic acid 1 3

259. Q.13(c)
(3E)-hept-3-ene-2,5-diol 5 3 2 1

260. Q.13(d)
Propane-1,2,3-triol 2 1 3

261. 1,2-dichloro-1,1,2,2-tetrafluoroethane
Q.13(e)
1,2-dichloro-1,1,2,2-tetrafluoroethane 1 2

262. Methyl 2-methylpropenoate
Q.13(f)
Methyl 2-methylpropenoate 2 1

263. 3-hydroxy-2,4-dioxohex-5-enal
Q.13(g)
3-hydroxy-2,4-dioxohex-5-enal 2 4 3 1 5

264. 3-ethoxypentanedioic acid
Q.13(h)
3-ethoxypentanedioic acid 3

265. Q.13(i)
(5E)-5,6-dibromo-4-hydroxyhex-5-en-2-ynoic acid 2 1 4 6 5

266. Q.13(j)
Cyclohexa-2,5-dien-1-ol 1 2 5

267. Q.13(k)
4-bromo-5,5-dichlorocyclohex-2-en-1-ol 1 5 4

268. 1-butyl-2,4,5-trimethylbenzene
Q.13(l)
1-butyl-2,4,5-trimethylbenzene 1 2 5 4

269. Q.13(m)
Pentan-2-ylbenzene

270. (2Z)-pent-2-en-2-ylbenzene

271. All C atoms are sp2 hybridized
Q.14
aspirin
All C atoms are sp2 hybridized
271

272. Q.14
Analgesic
C9H8O4
carboxyl
Ester

273. Q.14
Caffeine
sp3 hybridized
sp2 hybridized
273

274. C8H10N4O2 Q.14 Tertiary amide C=C bond carbonyl C=N bond
Tertiary amino
carbonyl
C=N bond

275. Q.14
Acetaminophen
sp2 hybridized
sp3 hybridized
275

276. Q.14
Acetaminophen
Secondary amide
hydroxyl
C8H9NO2

277. Q.14
Adrenalin
sp2 hybridized
sp3 hybridized
277

278. Q.14
Adrenalin
C9H13NO3
hydroxyl
Secondary amino

279. Q.14 Dopamine sp2 hybridized sp3 hybridized
A neurotransmitter – A deficiency is associated with Parkinson’s disease
sp2 hybridized
Dopamine
sp3 hybridized
279

280. Q.14
A neurotransmitter – A deficiency is associated with Parkinson’s disease
Dopamine
hydroxyl
Primary amino
C8H11NO2

281. Menthol – from peppermint oil
Q.14
Menthol – from peppermint oil
sp3 hybridized
281

282. Q.14
Menthol – from peppermint oil
C10H20O
hydroxyl

283. Q.14
sp2 hybridized
Insecticide
sp3 hybridized
283

284. Q.14
Insecticide
Chloro
C14H9Cl5

285. Q.14
sp2 hybridized
sp3 hybridized
285

286. Q.14
hydroxyl
C20H14O4
Ester

287. Q.14
Insecticide
sp2 hybridized
sp3 hybridized
287

288. Q.14
Insecticide
Tertiary amino
C=N
C10H14N2

289. 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)
Q.14
2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)
sp2 hybridized

290. Q.14
One of the most toxic chemical known – A class 1 carcinogen
Ether
Chloro
C12H4O2Cl4

291. Q.14
Anti-hypertensive
sp2 hybridized
sp3 hybridized
291

292. Q.14
Anti-hypertensive
C20H28N2O5

293. C20H28N2O5 Q.14 Anti-hypertensive Tertiary amide Ester Secondary amino
Carboxyl
293

294. Q.14
A local anesthetic
sp2 hybridized
sp3 hybridized
294

295. Q.14
A local anesthetic
C17H21NO4
Ester
Tertiary amino

296. Addictive cough medicine
Q.14
Addictive cough medicine
sp2 hybridized
sp3 hybridized

297. Addictive cough medicine
Q.14
Addictive cough medicine
Tertiary amino
C18H21NO3
C=C bond
Hydroxyl
Ether
297

298. Q.14 sp2 hybridized sp3 hybridized
A potent addictive analgesic from opium
sp2 hybridized
sp3 hybridized
298

299. C17H19NO3 Q.14 A potent addictive analgesic from opium Tertiary amino
C=C bond
Hydroxyl
Ether

300. Q.14
Acetylated morphine
sp2 hybridized
sp3 hybridized
300

301. Q.14
Acetylated morphine
Tertiary amino
C21H23NO5
C=C bond
Ester
Ether

302. Q.14 sp2 hybridized sp3 hybridized
Tranquilizer for elephants – 2000 times more potent than morphine
sp2 hybridized
sp3 hybridized
Q.14
302

303. Tranquilizer for elephants – 2000 times more potent than morphine
Tertiary amino
Hydroxyl
C25H33NO4
Ether
C=C
Q.14

304. Q.14
Narcotic analgesic
sp2 hybridized
sp3 hybridized
304

305. Q.14
Narcotic analgesic
C21H27NO
Carbonyl
Tertiary amino

306. Q.14
You don’t need it !
sp2 hybridized
sp3 hybridized
306

307. Q.14
C=C
C=N
Tertiary amino
Secondary amide
Ether
C22H30N6O4S

308. Analgesics and antipyretics
Aspirin
Analgesics and antipyretics 1 2

309. Analgesics and antipyretics1 4
Acetaminophen
Analgesics and antipyretics

310. Vitamin C
Helps maintain elasticity of the skin, aids the absorption of iron and improves resistance to infection. 1 2 3 4 5 1 2

311. Treating asthma, emphysema and chronic bronchitis
Albuterol
Treating asthma, emphysema and chronic bronchitis 1 2 1 2 4

312. 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
Camphor(樟腦) 7 4 5 6 3 2 1
1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

313. Ketamine(氯胺酮) C13H16ClNO 2-(2-chlorophenyl) 2-(methylamino)
cyclohexanone
313

314. 3-(2-chlorophenyl)-3-(methylamino)cyclohexane-1,2-dione
314

315. 6-(2-chlorophenyl)-6-(methylamino)cyclohex-3-ene-1,2-dione
315

316. Name it !
C24H15Cl2NO8