Nomenclature and introduction of major functional groups

New Way Chemistry for Hong Kong A-Level Book 3A
1
Nomenclature &Nomenclature &
Introduction ofIntroduction of
Major Families ofMajor Families of
OrganicOrganic
CompoundsCompounds

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

3
Organic compounds containing carbon and
hydrogen only.
1.1. HydrocarbonsHydrocarbons

4
(a)(a) Alkanes (CAlkanes (CnnHH2n+22n+2))
Alkanes are hydrocarbons that contain only
C – C and C – H single bonds(except CH4)
Relatively inert as the σ bonds are strong
→ saturated hydrocarbons
contain the maximum possible number
of hydrogen atoms per molecule

5
The first 10 members of the unbranched (acyclic)
alkane series are :
CH4 Methane C6H14 Hexane
C2H6 Ethane C7H16 Heptane
C3H8 Propane C8H18 Octane
C4H10Butane C9H20 Nonane
C5H12Pentane 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
Most stable due to less angle strain
Angle strain arises from repulsions between
adjacent bond pairs

8
Cycloalkanes in skeletal forms

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

10
The First Three Members of AlkanesThe 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
H3C
H2
C
C
H2
CH3
H3C
CH
CH3
CH3
All carbon atoms are sp3
hybridized - zigzag

13
Q.2 C5H12
H3C
H2
C
C
H2
H2
C
CH3
H3C
CH
C
H2
CH3
CH3
H3C
C
CH3
CH3
CH3

14
Q.2 C6H14

15
Nomenclature ofNomenclature of
AlkanesAlkanes
IUPAC Conventions

16
Straight-Chain AlkanesStraight-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 AlkanesBranched-Chain Alkanes
1. Name the longest possible straight chain
 give the parent name for the alkane

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

19
C3H7 –
H3C
H2
C
C
H2
propyl
H3C
CH
H3C
isopropyl

20
C4H9 –
H3C
H2
C
C
H2
H2
C
butyl
H3C
CH
H2C
CH3
sec-butyl
secondary, 2°
carbon
CH C
H2
H3C
H3C
isobutyl
C
H3C
H3C
H3C
tert-butyl
tertiary, 3°
carbon

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

22
4. 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
propane
2
2,2-dimethylpropane

25
Cl
Cl
Cl
1 5
1,5,5-trichloro
1,5,5-trichlorohexane

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

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

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

29
(b)(b) Alkenes (CAlkenes (CnnHH2n2n))
One C=C double bond
More reactive than alkanes due to weaker π
bond
→ unsaturated hydrocarbons
NOT contain the maximum possible
number of hydrogen atoms per molecule

30
First member is ethene (ethylene)
Cyclic structures are possible
cyclopropene cyclobutene

31
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
Structural
isomerism
Chain
isomerism
Position
isomerism
Functional group
isomerism
Different
carbon
skeletons
Functional groups
in different
positions
Different
functional groups

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

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

36
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
Rotation about the axis of a double bond through an
angle of 90o
results in the breaking of the π bond
maximum overlap of
pz orbitals
minimum overlap of
pz orbitals

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

40
Q.4
Position isomersChainisomerism
position isomers
Geometrical
isomers
trans cis

41
Q.4 Position isomers
Chainisomerism

42
Q.4
Functional group
isomerism

43
Q.4
Chain isomerism
A total of 11
isomers

44
Q.4 C5H8
C5H6

45
pent-1-ene1
pent-2-ene
2

46
2
pent-2-ene
(2E)-pent-2-ene
(2Z)-pent-2-ene
trans
cis

47
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
http://en.wikipedia.org/wiki/Cahn-Ingold-Prelog_priority_rule

48
CH3
CH3
CH3
(2Z)-3-methylpent-2-ene
CH3 CH3
CH3
(2E)-3-methylpent-2-ene
1
2 3
1
2 3

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

50
cyclopentane
methylcyclobutane
Q.4

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

52
bicyclo[2.1.0]pentane
bicyclo[1.1.1]pentane
spiro[2.2]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[2.1.0.01,3
]pentane
tricyclo[1.1.1.11,3
]hexane

54
(c)(c) Alkynes (CAlkynes (CnnHH2n-22n-2))
One C≡C triple bond
Reactive (unsaturated) due to weak π bonds
First member is ethyne (acetylene), C2H2
Cycloalkenes and alkadienes have the same
general formula as alkynes

55
(c)(c) Alkynes (CAlkynes (CnnHH2n-22n-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
(2E)-5-methylhex-2-ene
Functional group has the higher priority
than branch.
2
5
Q.5(a)

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

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

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

62
Q.5(d
)
3
1
45
2
1
2 4
5
3
1,3 > 2,4
although -yne has the smaller number

63
pent-1-en-3-yne
NOT ene
Q.5(d)
3
1
45
2

64
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)
Q.5(e)

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

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

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

68
1
8
63 4 5
7
octa-1,6-diene
5-ethyl
6-vinyl
3,7-dimethyl
4-methylidene
5-ethyl-3,7-dimethyl-4-methylidene-6-vinylocta-1,6-diene
Q.5(g)

69
1
8
63 4 5
7
octa-1,7-diene substituents at 3,4,5,6
Q.5(h)

70
1
8
6 34
5
7
Q.5(h)

71
1
8
63 4 5
7
octa-1,7-diene substituents at 3,4,5,6,7
Q.5(h)

72
octa-1,7-diene substituents at 2,3,4,5,6
1
8
6 345
7
2

Q.5(h)

73
Q.5(h)
octa-1,7-diene
4-ethyl
3-ethenyl
2,6-dimethyl
5-methylidene
3-ethenyl-4-ethyl-2,6-dimethyl-5-methylideneocta-1,7-diene
1
8
6 345
7
2
vinyl methylene

74
1
2
3 4 5 6
7
8
Q.5(i
)

75
8
7
6 5 4 3
2
1
Q.5(i)

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

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

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

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

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

2
3
2
1

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

83
2
1-methyl
1
2-(propan-2-yl)
1-methyl-2-(propan-2-yl)cyclohexane
2

84
1
1-butan-2-yl
2
2-methyl
1-(butan-2-yl)-2-methylcyclohexane

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

86
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
3-methylcyclobutene
1
23
4-methylcyclobutene
2
14

89
Q.6
3-methylcyclobutene
1
23
4
12
3

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

91
Extra stability (aromaticity) due to
delocalization of π electrons
Also called arenes

92
C6H5 – → phenyl group
C10H7 – → naphthyl group
Both are aryl groups

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

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

95
14 = 4×3+2
aromatic
anthracene
Q.7

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

97
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 π electrons
Q.7
>120
o

98

99
2.2. Hydroxy compoundsHydroxy compounds
Organic compounds with one or more
hydroxyl groups, –OH.

100
(a)(a) Alkanols (alcohols)Alkanols (alcohols)
Derived from alkanes
Contain one or more –OH groups attached
to an alkyl group.
R – OH
Alkyl group Hydroxyl group

101
Hydroxy derivative of alkane
RH ROH
H replaced
by OH
HOH
H replaced
by R
Alkyl derivative of water

102
General formula : CnH2n+1OH (acyclic)
Three classes :
Primary,
1°
Tertiary,
3°
Secondary,
2°
R C
H
H
OH R C
H
R'
OH R C
R''
R'
OH

103
Naming of alkanols : -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.

104
OH
pentane
1
234
5
pentan-2-ol

105
OH
pentane
1
2345
pentan-3-ol

106
OH OH
1
2 3 4
5
pentane
pentane-2,4-diol
‘e’ is retained in diol

107
(b)(b) PhenolsPhenols
Derived from aromatic hydrocarbons
Contain one or more –OH groups attached
to an aryl group
Ar – OH
Aryl group Hydroxyl group

108
phenol
OH OH
OH1
2
2-hydroxyphenol 
Benzene-1,2-diol 

109
OH
Cl
OH
Cl
OH
Cl
o-chlorophenol
o → ortho
m-chlorophenol
m → meta
p-chlorophenol
p → para
2-chlorophenol 3-chlorophenol 4-chlorophenol
1 1 1
2
3
4

110
Q.8
OH
1
6
4
2
4-methylhexan-2-ol
OH
1
5 4 2 4-methylpentan-2-ol

111
OH
1
23
4
5
- OH has a higher priority than C=C
pent-3-en-2-ol
trans-
(3E)-pent-3-en-2-ol
Q.8

112
OH
Menthol
( 薄荷
醇 )
cyclohexanol
with
TWO branches
Propan-2-yl
methyl
Q.8
2

113
OH
menthol
1
2
4
3
5
OH
1
24
5
3
6
6
2,5 > 3,6
5-methyl-2-(propan-2-yl)cyclohexanol
Q.8

114
3.3. EthersEthers
Contain the oxy, –O-, group or
alkoxy, R-O- group
R
O
R
oxy group

115
3.3. EthersEthers
Contain the oxy, –O-, group or
alkoxy, R-O- group
R
O
R
Alkoxy group

116
3.3. EthersEthers
Alkyl derivatives of water
H
O
H
R
O
R
2H replaced
by 2R

117
3.3. EthersEthers
Three classes of ethers : -
R
O
'R
Ar
O
R
Ar
O
'Ar
H
O
H
a b c 105
o
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

118
3.3. EthersEthers
Naming : -
The alkoxy groups are always treated as
substituents and expressed as prefixes.

119
Q.9
O
methoxy
ethane
methoxyethane


120
O
methane
ethoxy
ethoxymethane 
Q.9

121
O
benzene
methoxy
methoxybenzene 
Q.9

122
O
phenoxy
methane
phenoxymethane

Q.9

123
O
propane
methoxy
2
1
3
2-methoxypropane

Q.9

124
4.4. Carbonyl compoundsCarbonyl compounds
Organic compounds with the carbonyl group,
C O

125
(a) Aldehydes
Products of dehydrogenation of alcohols
R C O
H
H
H
R
C
H
O + H2
At least ONE H attached to C
R : alkyl, aryl or H

126
(a) Aldehydes
Examples : -
H H
O
H
O
H
O
H
O
methanal ethanal propanal benzaldehyde
–ane replaced by –anal

127
(a) Aldehydes
Examples : -
H H
O
H
O
H
O
H
O
methanal ethanal propanal benzaldehyde
The aldehye group, –CHO, always occupies
the terminal position
⇒ No need to specify its position
propan-1-al

128
(b) Ketones
No H atom is directly attached to the
carbonyl group
R
C
'R
O
R, R’ : alkyl or aryl group

129
O
(b) Ketones
Examples : -
O
propanone butanone
–ane replaced by –anone

130
(b) Ketones
Examples : -
O
O
pentan-2-one pentan-3-one
2
3

131
(b) Ketones
Examples : -
O O
4-methylpentan-2-one
24 2 3
2-methylpentan-3-one

132
(b) Ketones
Examples : -
O
O
OO
pentane-2,3-dione
pentane-2,4-dione
23 24

133
5.5. Carboxylic acidsCarboxylic acids
Organic compounds with the carboxyl group,
C
OH
O

134
C
OH
O
hydroxyl
carbonyl
carboxyl

135
R C
OH
O
If R is an alkyl group, the compound is an
alkanoic acid, CnH2n+1COOH.

136
Carboxylic acids
Examples : -
H
OH
O
OH
O
OH
O
methanoic acid ethanoic acid propanoic acid
–ane replaced by –anoic acid

137
Carboxylic acids
Examples : -
H
OH
O
OH
O
OH
O
methanoic acid ethanoic acid propanoic acid
The carboxyl group, –COOH, always occupies
the terminal position
⇒ No need to specify its position

138
Carboxylic acids
Examples : -
benzoic acid
COOH COOH
OH
COOH
2-hydroxybenzoic
acid
3-methylbenzoic
acid
1
3
1
2

139
Carboxylic acids
Examples : -
COOH COOH
COOH
benzoic acid
cyclohexanecarboxylic
acid
cyclohexylethanoic
acid
cyclohexylacetic
acid

140
COOH
HOOC
Carboxylic acids
Examples : -
hexanedioic acid

141
COOH
HOOC
Carboxylic acids
Examples : -
hexanedioic acid
16
hexane-1,6-dioic acid 


142
COOH
HOOC
Carboxylic acids
Examples : -
hexanedioic acid
1
4


143
6.6. Acids derivativesAcids derivatives
FOUR types : -
OH replaced by Cl
R C
OH
O
R C
Cl
O
carboxylic acid acyl(acid) chloride
acyl group

144
FOUR types : -
R C
O
O
'R C
O
OH
H
R C
O
O
C
O
'R
−H2O
acid anhydride
R ≠ R’ for mixed acid
anhydride

145
FOUR types : -
−H2OR C
O
O
H
R'HO+ R C
O
O
R'
ester
R’ : alkyl or aryl

146
FOUR types : -
R C
OH
O
NH2H+ R C
NH2
O
−H2O
1° amide
N links to only ONE C

147
R C
OH
O
NHH
R'
+
FOUR types : -
R C
HN
O
R'
−H2O
2°
amide
N links to TWO C atoms
1o
amine

148
FOUR types : -
R C
OH
O
NH
R'
+
R''
−H2O
3° amide
R C
N
O
''R
R'
N links to THREE C atoms
2o
amine

149
Naming of acids derivativesNaming of acids derivatives
Acyl chloride : −oic acid to −oyl chloride
Cl
O
ethanoyl chloride
Or
acetyl chloride

150
Acyl chloride : −oic acid to −oyl chloride
Cl
O
ethanoyl chloride
spacing

151
Acid anhydride : −oic acid to −oic anhydride
O
O
O
ethanoic anhydride
spacing

152
Acid anhydride : −oic acid to −oic anhydride
O
O
O
ethanoic propanoic
anhydride
For mixed anhydride, the
parent acids are named in
alphabetical order

153
Ester : −oic acid to −oate preceded by R
group of ROH
O
O methyl ethanoate
spacing

154
O
O
group of ROH
ethyl propanoate

155
O
O
group of ROH
ethyl propenoate
Or, ethyl acrylate

156
O
O
group of ROH
ethyl 2-methylpropenoate
2 1
Or
ethyl 2-methylacrylate

157
Amides : −oic acid to −amide
NH2
O
ethanamide

158
HN
O
N-methylethanamide
NO spacing
Or, N-methylacetamide

159
N
O
N,N-dimethylethanamide

160
N
O
N-ethyl ethanamide-N-methyl
Or
N-ethyl-N-methylacetamide

161
7.7. Halogeno hydrocarbonsHalogeno hydrocarbons
Hydrocarbons containing at least one
halogen atom
R – X
X : halogens

162
-F fluoro
-Cl chloro
-Br bromo
-I iodo
Hydrocarbons containing at least one
halogen atom
Always treated as
substituents
(shown by
prefixes)

163
Examples : -
C Br
H
H
H
C Br
H
H
Br
bromomethane dibromomethane

164
Examples : -
C Br
F
F
F
C F
Br
Cl
F
bromotrifluoromethane
bromochlorodifluoromethane
BTM
BCF
Both are used in
fire extinguishers

165
Examples : -
Br Br
Br
bromobenzene 1,2-dibromobenzene

166
Examples : -
Br
Cl
Br
Cl
1
41
4
1-bromo-4-chlorobenzene 4-bromo-1-chlorobenzene
 

167
Examples : -
Br
Cl
Cl1
2
4
Br
Cl
Cl
1
2
5
1-bromo-2,4-dichlorobenzene



168
Examples : -
Br
Cl
Cl
1
3
4
Br
Cl
Cl
4
2
1


169
Examples : -
Br
Br
Br
Br
Br
Br
hexabromobenzene

170
1,1-dichlorobutane
2,2-dichlorobutane
Cl
Cl
Cl
Cl
Q.10 All acyclic structures of C4H8Cl2

171
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
1,2-dichlorobutane
1,3-dichlorobutane
1,4-dichlorobutane
2,3-dichlorobutane
*
*
* chiral centre, optical isomers exist
Q.10

172
Cl Cl
1,1-dichloro-2-methylpropane
1
2 3
Q.10
2-(dichloromethyl)propane
Cl Cl
1
2
3



173
Cl Cl
Cl
Cl
Cl
Cl
1
1
1
2
2
2
3
3
3
Q.10

174
8.8. AminesAmines
Derivatives of ammonia
NH3
H
N
H
R
H
N
'R
R
''R
N
'R
R
Primary(1°) amine
Secondary(2°) amine
Tertiary (3°) amine

175
8.8. AminesAmines
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
)
NH2
NH2
NH2 ethynamine (acetylenamine)

176
8.8. AminesAmines
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-
NH2
HO
2-aminoethanol1
2

177
8.8. AminesAmines
Examples : -
NH
NH
N-methylmethanamine
ethanamineN-methyl
2° amine

178
8.8. AminesAmines
N
N
3° amine
ethanamineN,N-dimethyl
methanamineN,N-dimethyl

179
8.8. AminesAmines
NH2 NOT benzenamine
phenylamine or aniline

180
8.8. AminesAmines
NH2
NH2
NH2
2
1
3
4
1
1
2-methylaniline
3-methylaniline
4-methylaniline
or o-toluidine
or m-toluidine
or p-toluidine

181
8.8. AminesAmines
NH2 2-methylaniline
NH N-methylaniline
N-phenylmethanamine


182
8.8. AminesAmines
NH2
1-phenylmethanamine

183
8.8. AminesAmines
NH2
NH2
1
2
3
3
2
1
Prop-2-en-1-amine
Prop-1-en-2-amine

184
8.8. AminesAmines
NH2
NH2
linear
1
23
4
but-3-yne-1,2-diamine

185
8.8. AminesAmines
NH2
NH
12
3
propane-1,2-diamineN2-ethyl

186
Q.11
NH2
OH
NH2
NH2
NH2
COOH
2-aminophenol
benzene-1,2-diamine
2-aminobenzoic acid

187
Q.11
N
H
NH2
1
23
4
1
23
4
5
N-methylbutan-1-amine
pentan-2-amine

188
Q.11
NH2
NH2
1
butan-1-amine
2 butan-2-amine

189
Q.11
H
N
NH2
NH
1
2
3
propane-1,2-diamine
N1-ethylpropane-1,2-diamine
1
23
4 N-methylbutan-2-amine

190
N
O
Q.11
N-ethyl
ethanamine 2-methoxy
N-methyl
1
2
N-ethyl-2-methoxy-N-methylethanamine

191
N
O
Q.11
ethanamine
1
2
N-(2-
methoxyethyl)
N-methyl
N-(2-methoxyethyl)-N-methylethanamine 
3 substituents > 2 substituents

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

193
Q.11
N
O
1
2
3 propan-2-amine
1 2
N-(2-methoxyethyl)
N-methyl
N-(2-methoxyethyl)-N-methylpropan-2-amine

194
9.9. NitrilesNitriles
Containing the cyano group, -C≡N

195
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−.

196
Examples : -
C N
C
N
ethanenitrile
1
2
3
2-methylpropanenitrile
The carbon of the -C≡N group is counted
as part of the longest carbon chain.

197
Examples : -
C N
C
N
ethanenitrile
1
2
3
2-methylpropanenitrile
No need to specify its position.
The -C≡N group always occupies
the terminal position.

198
C
N
OH
12345
4-hydroxypentanenitrile

199
HOOC
C
N
21 3
propanoic acid3-cyano-2-methyl
If used as prefix, its carbon is not counted
as part of the main carbon chain

200
HOOC
C
N
21
3
propanoic acid2-(cyanomethyl)
Only one substituent →


201
10.10. Poly-functional compoundsPoly-functional compounds
With two or more functional groups

202
With identical functional groups
buta-1,3-diene
buta-1,3-diyne1
1
2
2
3
3
4
4

203
CH3
CH3
CH3
CH3
CH3
CH3
(2E,4E)-hexa-2,4-diene
(2E,4Z)-hexa-2,4-diene(2Z,4E)-hexa-2,4-diene
(2Z,4Z)-hexa-2,4-diene
＝
CH3
CH3
2Z > 2E

204
OH
O
HO
O
H H
OO
ethanedioic acid
pentanedial
-COOH and –CHO groups always occupy the
terminial positions.
No need to specify its position

205
NH2
H2N
OOO
hexane-1,6-diamine
heptane-2,4,6-trione

206
propane-1,2,3-triol
HO OH
OH
1
2
3

OH OH
OH
OH OH
xylitol
1 2 3 4 5
pentane-1,2,3,4,5-pentol
207

208
With different functional groups
H2N COOH
COOH
OH
2-aminoethanoic acid
or glycine
2-hydroxypropanoic acid
1
2
12
3

209
With different functional groups
(2E)-hept-2-en-6-yn-1-ol
OH
1
6
2
3
4
5
7

210
Naming : -
1. The functional group with the highest
priority (the principal functional group) is
expressed as the suffix.

211
N
+
C
HO
O
> >
-OH > -NH2 > C≡C > C=C > -OR = X
C
H
O C O
-C≡N > > >
O
OO
R
C
RO
O C
X
O C
H2N
O> >> >

212
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

213
Naming : -
3. The position(s) of the principal functional
group(s) is/are given the lowest possible
number(s)
Exception : p.5 Q.5(e)

214
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.
Q.5(e)

215
(2Z)-3-hydroxypent-2-enoic acid
Worked examples : -
(a)
COOH
OH
12
3
4
5
C2 : COOH > H
atomic masses are compared
C3 : OH > CH2C
Z

216
Worked examples : -
(b)
COOH
OH
linear
1
2
3
4
5
(2Z)-3-hydroxypent-2-en-4-ynoic acidZ
C2 : COOH > H
C3 : OH > CC

217
Worked examples : -
(c)
HOOC COOH
OH
1
2
3
4
5
(2Z)-3-hydroxypent-2-enedioic acidZ
C2 : COOH > H
C3 : OH > CH2C

218
Worked examples : -
(d)
HOOC COOH
OH
O
1
2
3
4
5
(3Z)-3-hydroxy-2-oxopent-3-enedioic acid
1
24
3
5
(2Z)-3-hydroxy-4-oxopent-2-enedioic acid



219
HOOC COOH
OH
CN
Worked examples : -
(e)
1
2
345
(2Z)-4-cyano-3-hydroxypent-2-enedioic acid

220
Worked examples : -
(f)
C
N
O H
1
2
34
5
4-formylpentanenitrile 

221
Worked examples : -
(f)
C
N
O H
4-methyl-5-oxopentanenitrile 
1
2
34
5

222
COOH
OH
O
H
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

223
HOOC COOH
OH
O
OH
Worked examples : -
(h)
5 1
234
(2Z)-2-formyl-3-hydroxy-4-oxopent-2-enedioic acid

224
HOOC COOH
OH
O
OH
Worked examples : -
(h)
5 1
234
(2Z)-2-formyl-3-hydroxy-4-oxopent-2-enedioic acid
C2 : COOH =
CHO;
COOH = CHO; COOH > CHO
C3 : OH > COC;
Z

225
Worked examples : -
(i) O
COOH
NH2
1
2
3
4
5
5-amino-5-oxopentanoic acid
4-(aminocarbonyl)butanoic acid



226
HOOC COOH
OH
O
NH2O
Worked examples : -
(j)
12345
2-(aminocarbonyl)
3-hydroxy
4-oxo
2-(aminocarbonyl)-3-hydroxy-4-oxopentanedioic acid
2A4O > 4A2O

227
HOOC COOH
OH
O
NH2O
Worked examples : -
(j)
12345
2-(aminocarbonyl)
3-hydroxy
4-oxo 2A4O > 4A2O
If the same set of numbers is obtained from either
direction, substituents are numbered in alphabetical order

228
COOH
O
Cl
Worked examples : -
(k)
2
13
4
5
5-chloro-5-oxopentanoic acid

229
HOOC COOH
OH
O
ClO
Worked examples : -
(l)
12345
2-(chlorocarbonyl)
3-hydroxy
4-oxo
2-(chlorocarbonyl)-3-hydroxy-4-oxopentanedioic acid
2C4O > 4C2O

230
Worked examples : -
(m)
COOH
O
O
1
2
3
4
5
5-methoxy-5-oxopentanoic acid

231
HOOC COOH
OH
O
OO
Worked examples : -
(n)
5 1234
2-(methoxycarbonyl)
3-hydroxy
4-oxo
3-hydroxy-2-(methoxycarbonyl)-4-oxopentanedioic acid


232
Worked examples : -
(o)
COOH
O
OO
1
2
3
4
5
5-(ethanoyloxy)-5-oxopentanoic acid

233
Worked examples : -
(p)
HOOC COOH
O O
O
1
2
3
4
5
3-carbonyl
3-(oxycarbonyl)
3-[(ethanoyloxy)carbonyl]
pentanedioic acid
3-[(ethanoyloxy)carbonyl]pentanedioic acid

234
HOOC COOH
O
O
O
O
Worked examples : -
(p) 1
2
3
4
5
3-carbonyl
3-(oxycarbonyl)
3-[(carbonyloxy)carbonyl]
pentanedioic acid
3-{[(methoxycarbonyl)oxy]carbonyl}pentanedioic acid
3-{[(methoxycarbonyl)oxy]carbonyl}

235
N
COOH
+
Worked examples : -
(q)
ethanaminium ionN-carboxy-N,N-dimethyl
6B

236
N
COOH
COOH
+
Worked examples : -
(r)
ethanaminium ionN,N-dicarboxy-N-methyl

237
Propane-1,2,3-tricarboxylic acid
Or
Propane-1,2,3-trioic acid
HOOC COOH
COOH
Worked examples : -
(s) 1
2
3
4
51
2
3
3-carboxypentanedioic acid 

Citric acid

238
Worked examples : -
(t)
HOOC COOH
COOH
COOH
3
2 1
propane-1,1,2,3-tetracarboxylic acid

O
OH
OH
O
OH
O OH
1
2
3
4
5
1,1,5-tricarboxylic acid5-hydroxypenta-1,4-diene-(4Z)-
239

240
COOH
O
H2N
3-amino-3-oxopropanoic acid
Q.12(a
)

241
HOOC COOH
O NH2
3-(aminocarbonyl)pentanedioic acid
Q.12(a
)

242
COOH
O
H
4-oxobutanoic acid
Q.12(b
)

243
HOOC COOH
H O
3-formylpentanedioic acid
Q.12(b
)

244
O
C
H
N
3-oxopropanenitrile
Q.12(c
)

245
N C
COOH
4-cyanobutanoic acid
Q.12(c
)

246
COOH
C
N
4-cyanopentanoic acid
Q.12(c
)

247
HOOC COOH
O O
3-(methoxycarbonyl)pentanedioic acid
Q.12(d
)

248
O COOH
O
4-methoxy-4-oxobutanoic acid
Q.12(d
)

249
O
O
COOH
3-(acetyloxy)propanoic acid
Q.12(d
)

250
COOH
OCl
5-chloro-4-methyl-5-oxopentanoic acid
Q.12(e
)

251
2-methylpentanedioic acid
4-(chlorocarbonyl)pentanoic acid is wrong since
the structure should be viewed as the
derivative of 2-methylpentanedioic acid.
COOH
OHO
COOH
OCl
5-chloro-4-methyl-5-oxopentanoic acid
Q.12(e
)

252
HOOC COOH
O Cl
3-(chlorocarbonyl)pentanedioic acid
Q.12(e
)

253
HOOC COOH
OCl
O Br
3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid
Q.12(e
)

254
hexanedioyl dichloride
Q.12(f
)
Cl
O
Cl
O

255
6-bromo-6-oxohexanoyl chloride
Q.12(e
)
Cl
O
Br
O
1
2
3
4
5
66
5
4
3
2
1
6-chloro-6-oxohexanoyl bromide 


256
HOOC COOH
OCl
O Br
Q.12(e
)

257
HOOC COOH
OCl
O Br
Q.12(e
)

258
Cyclohexylamine
NH2
Q.13(a)

259
Benzene-1,3-dioic acid
COOH
COOH
1
3
Q.13(b)

260
OH
HO
(3E)-hept-3-ene-2,5-diol
1
2
3
5
Q.13(c)

261
Propane-1,2,3-triol
OH
OH
HO
1
2
3
Q.13(d)

262
1,2-dichloro-1,1,2,2-
tetrafluoroethane
ClCl
F
F
F
F
1 2
Q.13(e)

263
Methyl 2-methylpropenoate
O
O1
2
Q.13(f)

264
3-hydroxy-2,4-dioxohex-5-enal
H
O
OH
O
O
3
2
4
5
1
Q.13(g)

265
3-ethoxypentanedioic acid
HOOC COOH
O
3
Q.13(h)

266
OH
Br
Br
COOH
(5E)-5,6-dibromo-4-hydroxyhex-5-en-2-ynoic acid
1
2
56 4
Q.13(i)

267
Cyclohexa-2,5-dien-1-ol
OH
1
2
5
Q.13(j)

268
4-bromo-5,5-dichlorocyclohex-2-en-1-ol
OH
Cl
Cl
Br
1
4
5
Q.13(k)

269
1-butyl-2,4,5-trimethylbenzene
1
2
4
5
Q.13(l)

270
Pentan-2-ylbenzene
Q.13(m)

271
CH3 CH3
(2Z)-pent-2-en-2-ylbenzene
CH2 CH3
pent-1-en-2-ylbenzene
CH3
CH3

272
O
O
HO O
aspirin
Q.14
All C atoms are
sp2
hybridized

273
O
O
HO O
Analgesic
O
O
HO O
Ester
carboxyl
C9H8O4
Q.14

274
N
N
N
N
H
CH3
O
O
H3C
CH3
CaffeineQ.14
sp3
hybridized
sp2
hybridized

275
N
N
N
N
H
CH3
O
O
H3C
CH3
N
N
N
N
H
CH3
O
O
H3C
CH3
Tertiary
amide
carbonyl
Tertiary amino
Tertiary amino
C=N bond
C=C bond
C8H10N4O2
Q.14

276
HO NH
O
Acetaminophen
Q.14
sp2
hybridized
sp3
hybridized

277
HO NH
O
Acetaminophen
HO NH
Ohydroxyl
Secondary amide
C8H9NO2
Q.14

278
HO
HO
NH
OH
AdrenalinQ.14
sp2
hybridized
sp3
hybridized

279
HO
HO
NH
OH
Adrenalin
HO
HO
NH
OH
hydroxyl
Secondary amino
C9H13NO3
Q.14

280
HO
HO
NH2
Dopamine
A neurotransmitter – A deficiency is
associated with Parkinson’s disease
Q.14
sp2
hybridized
sp3
hybridized

281
HO
HO
NH2
Dopamine
A neurotransmitter – A deficiency is
associated with Parkinson’s disease
HO
HO
NH2
hydroxyl
Primary amino
C8H11NO2
Q.14

282
OH
Menthol – from peppermint oil
Q.14
sp3
hybridized

283
OH
Menthol – from peppermint oil
OH
hydroxyl
C10H20O
Q.14

284
ClCl
Cl
ClCl
DDT
Insecticide
Q.14
sp2
hybridized
sp3
hybridized

285
ClCl
Cl
ClCl
DDT
Insecticide
ClCl
Cl
ClCl
Chloro
C14H9Cl5
Q.14

286
HO OH
O
O
phenolphthalein
Q.14
sp2
hybridized
sp3
hybridized

287
HO OH
O
O
phenolphthalein
HO OH
O
O
hydroxyl
Ester
Q.14
C20H14O4

N
N
nicotine
288
Insecticide
Q.14
sp2
hybridized
sp3
hybridized

289
N
N
N
N
nicotine
Insecticide
Tertiary amino
C=N
Q.14
C10H14N2

290
2,3,7,8-tetrachlorodibenzo-p-dioxin
(TCDD)
Q.14
sp2
hybridized
O
O
Cl
Cl
Cl
Cl
dioxin

O
O
Cl
Cl
Cl
Cl
291
One of the most toxic chemical
known – A class 1 carcinogen
Ether
Chloro Chloro
C12H4O2Cl4
Q.14

292
N
O
N
H
O
O
HO
O
Anti-hypertensive
Q.14
sp2
hybridized
sp3
hybridized

293
N
O
N
H
O
O
HO
O
Anti-hypertensive
C20H28N2O5
Q.14

N
H
O
O
N
O
O
HO
enalapril
294
Ester
Carboxyl
Tertiary amide
Secondary amino
Anti-hypertensive
C20H28N2O5
Q.14

O
O
N O
O
cocaine295
A local anestheticQ.14
sp2
hybridized
sp3
hybridized

296
A local anesthetic
Tertiary amino
O
O
N O
O
O
O
N O
O
cocaine
Ester
C17H21NO4
Q.14

O OHO
N
codeine
297
Addictive cough medicineQ.14
sp2
hybridized
sp3
hybridized

O OHO
N
codeine
O OHO
N
298
Addictive cough medicine
Ether
Tertiary amino
Hydroxyl
C=C bond
C18H21NO3
Q.14

O OHHO
N
morphine299
A potent addictive analgesic from opiumQ.14
sp2
hybridized
sp3
hybridized

O OHHO
N
morphine300
O OHHO
N
A potent addictive analgesic from opium
Ether
HydroxylHydroxyl
Tertiary amino
C=C bond
C17H19NO3
Q.14

301
O OO
N
O O
heroin
Acetylated morphineQ.14
sp2
hybridized
sp3
hybridized

302
O OO
N
O O
heroin
Acetylated morphine
O OO
N
O O
Tertiary amino
Ester
Ester
Ether
C=C bond
C21H23NO5
Q.14

303
O OHO
N
etorphine
OH
Tranquilizer for elephants – 2000 times more potent
than morphine
Q.14
sp2
hybridized
sp3
hybridized

304
O OHO
N
etorphine
OH
O OHO
N
OH
Tranquilizer for elephants – 2000 times more potent
than morphine
Hydroxyl
Hydroxyl
Ether
C=C
Tertiary amino
C25H33NO4
Q.14

305
O
N
methadone
Narcotic analgesicQ.14
sp2
hybridized
sp3
hybridized

306
O
N
methadone
Narcotic analgesic
O
N
Tertiary amino
Carbonyl
C21H27NO
Q.14

307
S
O
O
N
N
O
N
NH
O
N
N
S
O
O
N
N
O
N
NH
O
N
N
viagra
You don’t need it !Q.14
sp2
hybridized
sp3
hybridized

308
S
O
O
N
N
O
N
NH
O
N
N
S
O
O
N
N
O
N
NH
O
N
N
viagra
Ether
Tertiary
amino
C=C
Secondary amide
C=N
C22H30N6O4S
Q.14

309
O
O
OH
O CH3
Aspirin
Analgesics and antipyretics
2-(acetyloxy)benzoic acid
1
2

310
OH
NH CH3
O Acetaminophen
Analgesics and antipyretics
N-(4-hydroxyphenyl)acetamide
1
4

311
O
O
OH
OH
OH
OH
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
5-(1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one
O
furan
O
O
furan-2(3H)-one
O
O
furan-2(5H)-one

312
OH
OH
OH
NH
CH3 CH3
CH3 Albuterol
Treating asthma, emphysema
and chronic bronchitis
4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
1
24
1
2

Camphor
1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
1
2
345
6
7

NH
CH3
O
Cl
KetamineKetamine
C13H16ClNO
1
2
1
2
314
cyclohexanone
2-(2-
chlorophenyl)
2-(methylamino)
2-(2-
chlorophenyl)
-2-(methylamino)

NH
CH3
O
O
Cl
1
2
3
12
315
3-(2-chlorophenyl)-3-(methylamino)cyclohexane-1,2-dione

NH
CH3
O
O
Cl
1
2
3
6
12
316
6-(2-chlorophenyl)-6-(methylamino)cyclohex-3-ene-1,2-dione

317
C24H15Cl2NO8
(2Z)-3-(acetyloxy)-2-(4-chloro-5-cyano-2-formylspiro[2.2]pent-1-yl)-3-(3'-chloro-4,6-dioxospiro[bicyclo[3.1.0]hexane-3,
1'-cyclobutane]-1,3'-dien-2'-yl)prop-2-enoic prop-2-enoic anhydride
Cl
O
O
O
O
O
CH2
Cl
N
O
O
O
CH3
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Nomenclature and introduction of major functional groups

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Nomenclature and introduction of major functional groups