Nomenclature and Introduction of Major Functional Groups - 2011

Nomenclature &
Introduction of
Major Families of
Organic
Compounds
1
New Way Chemistry for Hong Kong A-Level Book 3A
Classification of Hydrocarbons
alkadienes, etc.
cycloalkadienes, etc.
Huckel rule
2
1. Hydrocarbons
Organic compounds containing carbon and
hydrogen only.
3
(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
4
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
5
Cycloalkanes are alkanes in which all or some
of the carbon atoms are arranged in a ring
6
Cycloalkanes in skeletal forms
Angle strain arises from repulsions between

adjacent bond pairs
Most stable due to less angle strain

7
Cycloalkanes in skeletal forms
8
Alkanes and Cycloalkanes
• General formula of acyclic alkanes: CnH2n+2

• General formula of cycloalkanes: Q.1
CnH2n
9
The First Three Members of Alkanes
Methane Ethane Propane

(CH4) (CH3CH3) (CH3CH2CH3)
10
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.
11
Q.2 C4H10
All carbon atoms are sp3 hybridized - zigzag
H2
C CH3
H3C C
H2
CH3
CH
H3C CH3
12
Q.2 C5H12
H2 H2
C C
H3C C CH3
H2
CH3
CH CH3
H3C C
H2
CH3
C
H3C CH3
CH3
13
Q.2 C6H14
14
Nomenclature of
Alkanes
IUPAC Conventions
15
Straight-Chain Alkanes
Number of Condensed
Name
carbon atoms structural formula
CH4
Methane 1
CH3CH3
Ethane 2
Propane 3 CH3CH2CH3
Butane 4 CH3(CH2)2CH3
Pentane 5 CH3(CH2)3CH3
Hexane 6 CH3(CH2)4CH3
Heptane 7 CH3(CH2)5CH3
Octane 8 CH3(CH2)6CH3
Nonane 9 CH3(CH2)7CH3
16 Decane 10
CH3(CH2)8CH3
Branched-Chain Alkanes
1. Name the longest possible straight chain
 give the parent name for the alkane
17
Branched-Chain Alkanes
2. Name the substituent groups – the branches
CnH2n+1– Alkyl groups (derived from alkanes)

CH3 – methyl
C2H5 – ethyl
18
C3H7 –
H2
C propyl
H3C C
H2
H3C
CH isopropyl
H3C
19
C4H9 –
H3C
H2 H2 CH
sec-butyl
C C
H3C C
H2 H2C secondary, 2
carbon
butyl CH3
H3C
H3C tert-butyl
CH C
H2 H3C C
H3C tertiary, 3
H3C
carbon
isobutyl
20
3. Number the positions of the substituent
groups with the smallest possible numbers
2-methyl
2-methylbutane
21
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
22
tetramethyl
tetramethylmethane
23
2
propane
2,2-dimethylpropane
24
Cl
Cl
1 5
Cl
1,5,5-trichloro
1,5,5-trichlorohexane
25
Cl
Cl
6 2
1 5
Cl
1,5,5-trichloro 
2,2,6-trichloro 
‘Lowest numbers’ does NOT refer to the
smallest sum
26
5. If two or more different substituent groups
exist, they are named in alphabetical order
but NOT in numerical order of their positions.
2,2-dimethyl
3-ethyl
3 3-ethyl-2,2-dimethylpentane
2
prefix is not
considered
27
3
tert-butyl
3-ethyl-2,2-dimethylpentane 
3-tert-butylpentane 
28
(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
29
(b) Alkenes (CnH2n)
First member is ethene (ethylene)

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

Cyclic structures are possible
Q.3
CnH2n-2
cyclopentene cyclohexene
31
Starting from C4H8, isomerism occurs
Structural isomerism :
• same molecular formula
• different linking orders of atoms
32
Chain Different
isomerism carbon
skeletons
Structural Position Functional groups

in different
isomerism isomerism positions
Different Functional group

functional groups isomerism
33
Geometrical
Same linking order isomerism
of atoms
Stereoisomerism
Different spatial
arrangements of Optical isomerism
atoms
34
GeometricalIsomerism
Geometrical Isomerism
e.g. cis-but-2-ene and trans-but-2-ene
35
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
36
cannot be inter-converted
at lower temperatures
37
maximum overlap of minimum overlap of
pz orbitals pz orbitals
Rotation about the axis of a double bond through an

angle of 90o results in the breaking of the π bond
38
Arises from restricted rotation about the

axis of the C=C double bond.
39
Q.4
Chain isomerism Position isomers
position isomers
Geometrical
isomers
40 trans cis
Q.4 Position isomers
Chain isomerism
41
Q.4
Functional group
isomerism
42
Q.4
Chain isomerism
A total of 11
isomers
43
Q.4 C5H8
C5H6
44
1 pent-1-ene
2
pent-2-ene
45
2
pent-2-ene
trans (2E)-pent-2-ene
cis
(2Z)-pent-2-ene
46
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
47
CH3
2 3
(2Z)-3-methylpent-2-ene
1
H3C CH3
CH3
2 3
(2E)-3-methylpent-2-ene
1
H3C CH3
48
Q.4
2-methylbut-1-ene
1 2
2-methylbut-2-ene
2
3-methylbut-1-ene
3 1
Functional group has a higher priority than
branches
49
Q.4
cyclopentane
methylcyclobutane
50
Q.4
1,2-dimethylcyclopropane
ethylcyclopropane
1,1-dimethylcyclopropane
51
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
52
tricyclo[1.1.1.11,3]hexane
tricyclo[2.1.0.01,3]pentane
53
(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
54
(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
55
In naming alkenes and alkynes,
the ‘longest’ carbon chain need NOT be the
one that contains the multiple bond.
2-ethylpent-1-ene 
56
In naming alkenes and alkynes,
the ‘longest’ carbon chain need NOT be the
one that contains the multiple bond.
1
3
3-methylenehexane 
57
Q.5(a)
2
5
(2E)-5-methylhex-2-ene
Functional group has the higher priority

than branch.
58
Q.5(b
)
1
3
(3E)-penta-1,3-diene
59
Q.5(c)
1 5
4 2
2 4
5 3 1 3
1,3 > 2,4
60
Q.5(c
1
)
3
(3E)-pent-3-en-1-yne
NOT ene
61
Q.5(d
)
1 5
4 3
5 1 4
2 2 3
1,3 > 2,4

although -yne has the smaller number
62
Q.5(d)
1
4 3
5
2
pent-1-en-3-yne
NOT ene
63
Q.5(e)
1
4 4
1
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)
64
Q.5(f) 8 
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 !
65
8
Q.5(f) 7
5-ethyl 3 5 6
4
6-ethynyl 1
3,7-dimethyl octa-1,6-diene
4-methylidene
5-ethyl-6-ethynyl-3,7-dimethyl-4-methylideneocta-1,6-diene
66
8
Q.5(g)
8
6
1 7
octa-1,6-diene octa-1,7-diene
 
67
8
Q.5(g) 7
5-ethyl 3 5
4 6
3,7-dimethyl 1 octa-1,6-diene
4-methylidene
6-vinyl
5-ethyl-3,7-dimethyl-4-methylidene-6-vinylocta-1,6-diene
68
Q.5(h)
8
3 4 5 6
1 7
octa-1,7-diene substituents at 3,4,5,6
69
Q.5(h)
7 1
6 4 3
8 5
70
8
Q.5(h) 7
3 4 5 6
1
octa-1,7-diene substituents at 3,4,5,6,7
71
1
Q.5(h) 2
7
6 5 4 3
8
octa-1,7-diene substituents at 2,3,4,5,6


72
1
Q.5(h)
2
7
4-ethyl 6 4
5 3
2,6-dimethyl 8
octa-1,7-diene
5-methylidene
3-ethenyl
3-ethenyl-4-ethyl-2,6-dimethyl-5-methylideneocta-1,7-diene
vinyl methylene
73
Q.5(i
) 2 8
3 4 5 6
1 7
74
Q.5(i)
7 1
6 5 4 3
8 2
75
Q.5(i)
2 8
3 4 5 6
1 7

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

4-ethyl
3,6-dimethyl 4,3,6,5 > 5,3,6,4
5-methylidene
4-ethyl-3,6-dimethyl-5-methylideneocta-1,7-diene
77
In naming hydrocarbons, cyclic structures
always have higher priority than C=C, CC.
ethenylcyclohexane ethynylcyclohexane
78
Also, cyclic structure rather than the length
of the carbon chain is first considered.
heptylcyclohexane
79
1
3
but-3-en-1-ylcyclohexane
The C directly bonded to the ring is

assigned the lowest possible number
80
1
2
3
2

In naming cyclic hydrocarbons, the side
branches are numbered in alphabetical order.
1-ethyl
2
1 2-methyl
1-ethyl-2-methylcyclohexane
82
2 1-methyl
1
2 2-(propan-2-yl)
1-methyl-2-(propan-2-yl)cyclohexane
83
1-butan-2-yl
2
1 2-methyl
1-(butan-2-yl)-2-methylcyclohexane
84
Q.6
propan-2-ylcyclopropane
1,2-dimethyl-3-(propan-2-yl)cyclopropane
85
Q.6 3
1 2
prop-1-en-1-yl
(2-methylprop-1-en-1-yl)
(2-methylprop-1-en-1-yl)cyclobutane
86
Q.6
1-methylcyclobutene
2-methylcyclobutene
87
Q.6
3 2
3-methylcyclobutene
4 1
4-methylcyclobutene
88
Q.6
3 2
3-methylcyclobutene
2 1
3 4
89
(d) Aromatic hydrocarbons
With a total of (4n + 2)  electrons in the

conjugated system
(alternating single and double bonds)
90
Extra stability (aromaticity) due to

delocalization of  electrons
Also called arenes
91
C6H5 –  phenyl group
C10H7 –  naphthyl group
Both are aryl groups
92
Q.7
6 = 41+2
aromatic
methylbenzene
93
Q.7
10 = 42+2
aromatic
naphthalene
94
Q.7
14 = 43+2
aromatic
anthracene
95
Q.7
8  4n+2
NOT aromatic
cyclooctatetraene
96
Q.7
o
>120 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
97
2. Hydroxy compounds
Organic compounds with one or more

hydroxyl groups, –OH.
98
(a) Alkanols (alcohols)
Derived from alkanes

Contain one or more –OH groups attached
to an alkyl group.
R – OH
Alkyl group Hydroxyl group
99
Hydroxy derivative of alkane

Alkyl derivative of water
H replaced H replaced
by OH by R
RH ROH HOH
100
General formula : CnH2n+1OH (acyclic)

Three classes :
H H R''
R C OH R C OH R C OH
H R' R'
Primary, Secondary, Tertiary,

1 2 3
101
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.
102
5 1
4 3 2
OH
pentane
pentan-2-ol
103
OH
5 1
4 3 2
pentane
pentan-3-ol
104
1 5
2 3 4
OH OH
pentane
pentane-2,4-diol
‘e’ is retained in diol

105
(b) Phenols
Derived from aromatic hydrocarbons

Contain one or more –OH groups attached
to an aryl group
Ar – OH
Aryl group Hydroxyl group
106
OH OH
1 OH
phenol 2-hydroxyphenol 
Benzene-1,2-diol 
107
OH OH OH
1 Cl 1 1
2
3
Cl 4
Cl
2-chlorophenol 3-chlorophenol 4-chlorophenol

o-chlorophenol m-chlorophenol p-chlorophenol
o  ortho m  meta p  para
108
Q.8
1
2
4 4-methylhexan-2-ol
OH
6
1
5 4 2 4-methylpentan-2-ol
OH
109
Q.8 trans-
5 1
3 2
4
OH
- OH has a higher priority than C=C

pent-3-en-2-ol
(3E)-pent-3-en-2-ol
110
Q.8 Propan-2-yl
2
Menthol
( 薄荷 OH cyclohexanol
醇)
with
TWO branches
methyl
111
Q.8
menthol
2 OH 6 OH
3 1 5 1
4 6 4 2
5 3
2,5 > 3,6
5-methyl-2-(propan-2-yl)cyclohexanol
112
3. Ethers
Contain the oxy, –O-, group or
alkoxy, R-O- group
O oxy group
113
3. Ethers
Contain the oxy, –O-, group or
alkoxy, R-O- group
O Alkoxy group
114
3. Ethers
Alkyl derivatives of water
H 2H replaced R
by 2R
O O
H R
115
3. Ethers
Three classes of ethers : -
R Ar Ar H
a O b O c O o O
105
'R R 'Ar H
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
116
3. Ethers
Naming : -
The alkoxy groups are always treated as

substituents and expressed as prefixes.
117
Q.9
O
methoxy
ethane
methoxyethane

118
Q.9
methane
ethoxy
ethoxymethane 
119
Q.9
O
benzene
methoxy
methoxybenzene 
120
Q.9
O
phenoxy
methane
phenoxymethane

121
Q.9
1
2
3 O methoxy
propane
2-methoxypropane

122
4. Carbonyl compounds
Organic compounds with the carbonyl group,
C O
123
(a) Aldehydes
Products of dehydrogenation of alcohols
H
R
R C O H C O + H2
H
H
At least ONE H attached to C

R : alkyl, aryl or H
124
(a) Aldehydes
Examples : -
O
O O O
H
H H H H
methanal ethanal propanal benzaldehyde
–ane replaced by –anal
125
(a) Aldehydes
Examples : - propan-1-al O
O O O
H
H H H H
methanal ethanal propanal benzaldehyde
The aldehye group, –CHO, always occupies

the terminal position
 No need to specify its position
126
(b) Ketones
No H atom is directly attached to the
carbonyl group
R
C O
'R R, R’ : alkyl or aryl group
127
(b) Ketones
Examples : -
O O
propanone butanone
–ane replaced by –anone
128
(b) Ketones
Examples : -
O
3
2
O
pentan-2-one pentan-3-one
129
(b) Ketones
Examples : -
O O
4 2 2 3
4-methylpentan-2-one
2-methylpentan-3-one
130
(b) Ketones
Examples : -
O O O
3 2 4 2
O
pentane-2,4-dione
pentane-2,3-dione
131
5. Carboxylic acids
Organic compounds with the carboxyl group,
O
OH
132
5. Carboxylic acids
O
carbonyl
C
carboxyl
OH hydroxyl
133
5. Carboxylic acids
O
R C R : alkyl, aryl or H
OH
If R is an alkyl group, the compound is an
alkanoic acid, CnH2n+1COOH.
134
Carboxylic acids
Examples : -
O O O
OH OH OH
methanoic acid ethanoic acid propanoic acid
–ane replaced by –anoic acid
135
Carboxylic acids
Examples : -
O O O
OH OH OH
methanoic acid ethanoic acid propanoic acid
The carboxyl group, –COOH, always occupies

the terminal position
 No need to specify its position
136
Carboxylic acids
Examples : -
COOH COOH COOH
1 OH
1
2
3
benzoic acid 2-hydroxybenzoic 3-methylbenzoic

acid acid
137
Carboxylic acids
Examples : - cyclohexanecarboxylic
acid COOH
COOH COOH
benzoic acid cyclohexylethanoic

acid
cyclohexylacetic
acid
138
Carboxylic acids
Examples : -
HOOC
COOH
hexanedioic acid
139
Carboxylic acids
Examples : -
HOOC
6 1
COOH
hexanedioic acid
hexane-1,6-dioic acid 
140
Carboxylic acids
Examples : -
1
HOOC
4
COOH
hexanedioic acid
141
6. Acids derivatives
FOUR types : - acyl group
O O
OH replaced by Cl
R C R C
OH Cl
carboxylic acid acyl(acid) chloride
142
FOUR types : - acid anhydride
O
O
R C
R C
O H
H2O
O
OH
'R C
'R C
R  R’ for mixed acid O
O
anhydride
143
FOUR types : -
O O
H2O
R C + HO R' R C
O H O R'
ester
R : alkyl, aryl or H
R’ : alkyl or aryl
144
FOUR types : -
O O
H2O
R C + H NH2 R C
OH NH2
1° amide
N links to only ONE C
145
FOUR types : -
O O
H2O
R C + H NH R C
OH R' HN R'
1o amine
2°
amide
N links to TWO C atoms
146
FOUR types : -
O
O R''
H2O R C
R C + H N
N R'
OH R'
''R
2 amine
o
3° amide
N links to THREE C atoms
147
Naming of acids derivatives
Acyl chloride : oic acid to oyl chloride
O
ethanoyl chloride
Or
Cl
acetyl chloride
148
Acyl chloride : oic acid to oyl chloride
O
ethanoyl chloride
Cl
spacing
149
Acid anhydride : oic acid to oic anhydride
O
O ethanoic anhydride
spacing
O
150
Acid anhydride : oic acid to oic anhydride
O
ethanoic propanoic
anhydride
O
For mixed anhydride, the
parent acids are named in
alphabetical order
O
151
Ester : oic acid to oate preceded by R
group of ROH
O methyl ethanoate
O spacing
152
group of ROH
O ethyl propanoate
153
group of ROH
O ethyl propenoate
Or, ethyl acrylate
O
154
group of ROH
O ethyl 2-methylpropenoate
2 1
Or
O ethyl 2-methylacrylate
155
Amides : oic acid to amide
O
ethanamide
NH2
156
O Or, N-methylacetamide
N-methyl ethanamide
HN
NO spacing
157
O
N,N-dimethylethanamide
158
O
N-ethyl-N-methylethanamide
N
Or
N-ethyl-N-methylacetamide
159
7. Halogeno hydrocarbons
Hydrocarbons containing at least one
halogen atom
R–X
X : halogens
160
Hydrocarbons containing at least one
halogen atom
-F fluoro
-Cl chloro Always treated as
substituents
-Br bromo (shown by
-I iodo prefixes)
161
Examples : -
H H
H C Br H C Br
H Br
bromomethane dibromomethane
162
Examples : -
F
BTM
F C Br bromotrifluoromethane
F Both are used in
fire extinguishers
Br
Cl C F bromochlorodifluoromethane
BCF
F
163
Examples : -
Br Br
Br
bromobenzene 1,2-dibromobenzene
164
Examples : -
Br Br
1 4
4 1
Cl Cl
1-bromo-4-chlorobenzene 4-bromo-1-chlorobenzene
165
 
Examples : -
Br Br
1 Cl
2 Cl
2 1
4 5
Cl Cl
1-bromo-2,4-dichlorobenzene 
2-bromo-1,5-dichlorobenzene 
166
Examples : -
Br Br
1 4
4
3
Cl
1
2
Cl

Cl Cl
4-bromo-1,2-dichlorobenzene
167
Examples : -
Br
Br Br
Br Br
Br
hexabromobenzene
168
Q.10 All acyclic structures of C4H8Cl2
Cl
Cl 1,1-dichlorobutane
Cl
2,2-dichlorobutane
Cl
169
Cl
Q.10
Cl
1,2-dichlorobutane
*
Cl
* 1,3-dichlorobutane
Cl Cl
Cl 1,4-dichlorobutane
Cl
2,3-dichlorobutane
Cl
* chiral centre, optical isomers exist

170
Q.10 Cl 1
Cl
1,1-dichloro-2-methylpropane
2 
3
2-(dichloromethyl)propane
Cl Cl

2
1 3
171
Q.10 Cl 1
Cl
2 3
Cl
1
2
3
Cl
Cl
1
2 Cl
3
172
8. Amines
Derivatives of ammonia
H
N R Primary(1°) amine
H
H
NH3 N R Secondary(2°) amine

'R
''R
N R Tertiary (3°) amine

'R
173
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
NH2 methanamine
NH2 ethenamine (ethylenamine

)
NH2 ethynamine (acetylenamine)
174
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-
2
HO
1 2-aminoethanol
NH2
175
8. Amines
Examples : - 2° amine
NH N-methylmethanamine
N-methylethanamine
NH
176
8. Amines
3° amine
N N,N-dimethylethanamine
N N,N-dimethylmethanamine
177
8. Amines
NH2 NOT benzenamine
phenylamine or aniline
178
8. Amines
1 NH2 2-methylaniline or o-toluidine

2
1 NH2 3-methylaniline or m-toluidine

3
4 1 NH2 4-methylaniline or p-toluidine
179
8. Amines
NH2 2-methylaniline
NH N-methylaniline 
N-phenylmethanamine 
180
8. Amines
1-phenylmethanamine
NH2
181
8. Amines
2 NH2
1
3 Prop-2-en-1-amine
NH2
Prop-1-en-2-amine
2
1 3
182
8. Amines
4 linear
1
3 2 NH2
NH2
but-3-yne-1,2-diamine
183
8. Amines
NH
NH2
2 1
3
N2-ethylpropane-1,2-diamine
184
NH2
Q.11
OH
2-aminophenol
NH2
NH2
benzene-1,2-diamine
NH2
COOH
2-aminobenzoic acid
185
Q.11
1
3 2
N
4 H N-methylbutan-1-amine
1
4 pentan-2-amine
3 2
NH2
5
186
Q.11
1
butan-1-amine
NH2
2 butan-2-amine
NH2
187
Q.11 propane-1,2-diamine
NH2
N1-ethylpropane-1,2-diamine
H
N
2
3 1
1
3 2
4 N-methylbutan-2-amine
NH
188
Q.11
N-ethyl
N 2
O
1
N-methyl
ethanamine 2-methoxy
N-ethyl-2-methoxy-N-methylethanamine
189
Q.11
ethanamine
N-methyl N 2
O
1
N-(2-
methoxyethyl)
N-(2-methoxyethyl)-N-methylethanamine 
3 substituents > 2 substituents
190
Q.11 3
2 propan-1-amine
1
N-methyl N
2
O
1
N-(2-
methoxyethyl)
N-(2-methoxyethyl)-N-methylpropan-1-amine
191
Q.11
1 3 propan-2-amine
2
N-methyl
N
1 2
O
N-(2-methoxyethyl)
N-(2-methoxyethyl)-N-methylpropan-2-amine
192
9. Nitriles
Containing the cyano group, -CN
193
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.
194
9. Nitriles
Examples : -
C N ethanenitrile
N
3 1
C
2 2-methylpropanenitrile
The carbon of the -CN group is counted

as part of the longest carbon chain.
195
9. Nitriles
Examples : -
C N ethanenitrile
N
3 1
C
2 2-methylpropanenitrile
The -CN group always occupies

the terminal position.
No need to specify its position.
196
9. Nitriles
OH
5 4 3 2 1
C
N
4-hydroxypentanenitrile
197
9. Nitriles
N
2
C
1 3
HOOC
3-cyano-2-methylpropanoic acid
If used as prefix, its carbon is not counted

as part of the main carbon chain
198
9. Nitriles
3
N
2
C
1
HOOC
2-(cyanomethyl) propanoic acid
Only one substituent 


199
10. Poly-functional compounds
With two or more functional groups
200
With identical functional groups
2 4
buta-1,3-diene
1 3
2 3
1 4 buta-1,3-diyne
201
CH3 H3C
H3C
CH3
(2E,4E)-hexa-2,4-diene (2Z,4Z)-hexa-2,4-diene
CH3
H3C ＝ CH3
H3C
(2Z,4E)-hexa-2,4-diene (2E,4Z)-hexa-2,4-diene
2Z > 2E
202
O O
ethanedioic acid
HO OH
O O
pentanedial
H H
-COOH and –CHO groups always occupy the

terminial positions.
203
No need to specify its position
H2N
NH2
hexane-1,6-diamine
O O O
heptane-2,4,6-trione
204
1 3
2
HO OH
OH
propane-1,2,3-triol
205
OH
xylitol
1 2 3 4 5
HO OH
OH OH
pentane-1,2,3,4,5-pentol
206
With different functional groups
2
1 2-aminoethanoic acid
H2N COOH
or glycine
OH
2 2-hydroxypropanoic acid
1
3 COOH
207
With different functional groups
2 1
4 OH
7 6 3
5
(2E)-hept-2-en-6-yn-1-ol
208
Naming : -
1. The functional group with the highest

priority (the principal functional group) is
expressed as the suffix.
209
+
N > C O
>
HO
O R
> C O
> C O
> C O >
O O RO X H2N
-CN > C O > C O >

H
-OH > -NH2 > CC > C=C > -OR = X
210
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
p.5
211
3-methylidenehexane
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)
212
Q.5(e)
1
4 4
1
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.
213
Worked examples : -
(a) 4 2 1
3
COOH
5
OH
(2Z)-3-hydroxypent-2-enoic acid
C2 : COOH > H
atomic masses are compared
C3 : OH > CH2C
214
Worked examples : -
(b)
linear
5
4 2
3 1
COOH
OH
(2Z)-3-hydroxypent-2-en-4-ynoic acid
C2 : COOH > H
C3 : OH > CC
215
Worked examples : -
(c) 4 2
5 3 1
HOOC COOH
OH
(2Z)-3-hydroxypent-2-enedioic acid
C2 : COOH > H
C3 : OH > CH2C
216
Worked examples : -
(d) O
2 4
1 4 3 5
HOOC 3 2 COOH
5 1
OH
(3Z)-3-hydroxy-2-oxopent-3-enedioic acid 
(2Z)-3-hydroxy-4-oxopent-2-enedioic acid

217
Worked examples : -
(e) CN
2
5 4 3 1
HOOC COOH
OH
(2Z)-4-cyano-3-hydroxypent-2-enedioic acid
218
Worked examples : -
O H
(f)
2
4 3 1
5 C
N
4-formylpentanenitrile 
219
Worked examples : -
O H
(f)
5
2
4 3 1
C
N
4-methyl-5-oxopentanenitrile 
220
Worked examples : -
(g) O 4 2
5 3 1
COOH
H OH
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
221
Worked examples : -
(h) H O
O
5 4 3 2 1
HOOC COOH
OH
(2Z)-2-formyl-3-hydroxy-4-oxopent-2-enedioic acid
222
Worked examples : -
(h) H O
O
5 4 3 2 1
HOOC COOH
OH
(2Z)-2-formyl-3-hydroxy-4-oxopent-2-enedioic acid
C3 : OH > COC;
C2 : COOH = COOH = CHO; COOH > CHO
CHO;
223
Worked examples : -
4 2
(i) O
1
3
5 COOH
NH2
5-amino-5-oxopentanoic acid 
4-(aminocarbonyl)butanoic acid 
224
Worked examples : -
(j) O NH2
O
5 4 3 2 1
HOOC COOH
2-(aminocarbonyl) OH
3-hydroxy
4-oxo 2A4O > 4A2O
2-(aminocarbonyl)-3-hydroxy-4-oxopentanedioic acid
225
Worked examples : -
(j) O NH2
O
5 4 3 2 1
HOOC COOH
2-(aminocarbonyl) OH
3-hydroxy
4-oxo 2A4O > 4A2O
If the same set of numbers is obtained from either
direction, substituents are numbered in alphabetical order
226
Worked examples : -
4 2
(k) O
5 1
3
COOH
Cl
5-chloro-5-oxopentanoic acid
227
Worked examples : -
O Cl
(l) O
5 4 3 2 1
HOOC COOH
2-(chlorocarbonyl) OH
3-hydroxy
4-oxo 2C4O > 4C2O
2-(chlorocarbonyl)-3-hydroxy-4-oxopentanedioic acid
228
Worked examples : -
4 2
(m) O
1
3 COOH
5
5-methoxy-5-oxopentanoic acid
229
Worked examples : -
O O
(n) O
5 4 3 2 1
HOOC COOH
2-(methoxycarbonyl) OH
3-hydroxy
4-oxo

3-hydroxy-2-(methoxycarbonyl)-4-oxopentanedioic acid
230
Worked examples : -
(o) O 4 2
3 1
COOH
5
O O
5-(ethanoyloxy)-5-oxopentanoic acid
231
Worked examples : - pentanedioic acid
2 4
(p) 1 3 5
HOOC COOH
O O
3-carbonyl O
3-(oxycarbonyl)
3-[(ethanoyloxy)carbonyl]
3-[(ethanoyloxy)carbonyl]pentanedioic acid
232
Worked examples : - pentanedioic acid
2 4
(p) 1 3 5
HOOC COOH
O O
3-carbonyl
O O
3-(oxycarbonyl)
3-[(carbonyloxy)carbonyl]
3-{[(methoxycarbonyl)oxy]carbonyl}
3-{[(methoxycarbonyl)oxy]carbonyl}pentanedioic acid
233
Worked examples : -
(q) +
N
COOH
N-carboxy-N,N-dimethyl ethanaminium ion
6B
234
Worked examples : -
+
(r) COOH
N
COOH
N,N-dicarboxy- N-methylethanaminium ion
235
Worked examples : - Citric acid
2 4
(s) 1 1 3 3 5
HOOC COOH
2
COOH
3-carboxypentanedioic acid 
Propane-1,2,3-tricarboxylic acid
Propane-1,2,3-trioic acid
Or

236
Worked examples : -
COOH
(t)
3
2 1
HOOC COOH
COOH
propane-1,1,2,3-tetracarboxylic acid
237
O OH
OH
HO OH
5 3 1
4 2
O O
(4Z)-5-hydroxypenta-1,4-diene-1,1,5-tricarboxylic acid
238
Q.12(a
)
H2N
COOH
O
3-amino-3-oxopropanoic acid
239
Q.12(a
)
HOOC COOH
O NH2
3-(aminocarbonyl)pentanedioic acid
240
Q.12(b
) O
H COOH
4-oxobutanoic acid
241
Q.12(b
)
HOOC COOH
H O
3-formylpentanedioic acid
242
Q.12(c
) O
C
N
H
3-oxopropanenitrile
243
Q.12(c
)
N C
COOH
4-cyanobutanoic acid
244
Q.12(c
) N
C
COOH
4-cyanopentanoic acid
245
Q.12(d
)
HOOC COOH
O O
3-(methoxycarbonyl)pentanedioic acid
246
Q.12(d
) O
O COOH
4-methoxy-4-oxobutanoic acid
247
Q.12(d
) O
COOH
O
3-(acetyloxy)propanoic acid
248
Q.12(e
) Cl O
COOH
5-chloro-4-methyl-5-oxopentanoic acid
249
Q.12(e
)HO O
Cl O
COOH COOH
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.
250
Q.12(e
)
HOOC COOH
O Cl
3-(chlorocarbonyl)pentanedioic acid
251
Q.12(e Cl O
)
HOOC COOH
O Br
3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid
252
Q.12(f
) O
Cl
Cl
hexanedioyl dichloride
253
Q.12(e
) O
1 3 5
Br
6 2 4 4 2 6
Cl 3 1
5
6-bromo-6-oxohexanoyl chloride 
6-chloro-6-oxohexanoyl bromide 
254
Q.12(e Cl O
)
HOOC COOH
O Br
255
Q.12(e Cl O
)
HOOC COOH
O Br
256
Q.13(a)
Cyclohexylamine
NH2
257
Q.13(b)
Benzene-1,3-dioic acid
COOH
1
3
COOH
258
Q.13(c)
(3E)-hept-3-ene-2,5-diol
HO
5
3
2
1
OH
259
Q.13(d)
Propane-1,2,3-triol
OH
HO
1
2 OH
3
260
Q.13(e)
1,2-dichloro-1,1,2,2-
tetrafluoroethane
Cl Cl
F 1 2
F
F F
261
Q.13(f)
Methyl 2-methylpropenoate
2
1 O
O
262
Q.13(g)
3-hydroxy-2,4-dioxohex-5-enal
O O
H 2 4
1 3
5
O OH
263
Q.13(h)
3-ethoxypentanedioic acid
3
HOOC COOH
O
264
Q.13(i)
(5E)-5,6-dibromo-4-hydroxyhex-5-en-2-ynoic acid
Br COOH
2
1
6 5 4
Br OH
265
Q.13(j)
Cyclohexa-2,5-dien-1-ol
OH
1
2
266
Q.13(k)
4-bromo-5,5-dichlorocyclohex-2-en-1-ol
OH
1
5
Cl
4
Cl
Br
267
Q.13(l)
1-butyl-2,4,5-trimethylbenzene
1
2
5
4
268
Q.13(m)
Pentan-2-ylbenzene
269
H3C CH3 H2C CH3
(2Z)-pent-2-en-2-ylbenzene pent-1-en-2-ylbenzene
CH3
CH3
(1Z)-pent-1-en-1-ylbenzene (3Z)-pent-3-en-1-ylbenzene
270
Q.14
aspirin
HO O
All C atoms are
sp2 hybridized
O
271
Q.14
Analgesic
HO O
carboxyl
C9H8O4
O
Ester
272
Q.14 Caffeine
O CH3
H3C N
N
H
N
O N
sp3 hybridized
CH3
sp2 hybridized
273
Q.14 C8H10N4O2
Tertiary
O CH3
amide
C=C bond Tertiary amino
H3C N
N
H
carbonyl
C=N bond
N
O N
Tertiary amino
CH3
274
Q.14
Acetaminophen
HO NH
sp2 hybridized
sp3 hybridized
275
Q.14
Acetaminophen
Secondary amide
HO NH
hydroxyl O
C8H9NO2
276
Q.14 Adrenalin
OH
HO
NH
HO
sp2 hybridized
sp3 hybridized
277
Q.14 Adrenalin
hydroxyl C9H13NO3
OH
HO
NH
HO Secondary amino
278
Q.14
A neurotransmitter – A deficiency is
associated with Parkinson’s disease
HO sp2 hybridized
sp3 hybridized
HO
NH2
Dopamine
279
Q.14
A neurotransmitter – A deficiency is
associated with Parkinson’s disease
hydroxyl HO
Primary amino
HO
NH2
Dopamine
C8H11NO2
280
Q.14
Menthol – from peppermint oil
sp3 hybridized
OH
281
Q.14
Menthol – from peppermint oil
C10H20O
hydroxyl
OH
282
Q.14
Insecticide sp2 hybridized
sp3 hybridized
Cl Cl
Cl
Cl Cl
283
DDT
Q.14
Insecticide
Chloro
Cl Cl
Cl
C14H9Cl5
Cl Cl
284
DDT
Q.14
HO OH
sp2 hybridized
sp3 hybridized
O
phenolphthalein
285
Q.14
hydroxyl
HO OH
C20H14O4
O
Ester
phenolphthalein
286
Q.14
Insecticide
N sp2 hybridized
nicotine sp3 hybridized
287
Q.14
Insecticide
Tertiary amino
N C=N
nicotine C10H14N2
288
Q.14 2,3,7,8-tetrachlorodibenzo-p-dioxin
(TCDD)
Cl O Cl
Cl O Cl
dioxin
sp2 hybridized
289
Q.14 One of the most toxic chemical
known – A class 1 carcinogen
Ether
Cl O Cl
Cl O Cl
Chloro Chloro
C12H4O2Cl4
290
Q.14
Anti-hypertensive
N O
N
H
O O
HO
O
sp2 hybridized
sp3 hybridized
291
Q.14
Anti-hypertensive
C20H28N2O5
N O
N
H
O O
HO
O
292
Q.14
Anti-hypertensive
C20H28N2O5
Tertiary amide
Ester
N O
N
H
O O
HO
O
Secondary amino
Carboxyl
enalapril
293
Q.14 A local anesthetic
O
sp2 hybridized
O
sp3 hybridized
N O
294 cocaine
Q.14 A local anesthetic
O
C17H21NO4
O Ester
Tertiary amino
N O
295 cocaine
Q.14 Addictive cough medicine
N sp2 hybridized
sp3 hybridized
O O OH
codeine
296
Q.14 Addictive cough medicine
N
Tertiary amino
C18H21NO3
C=C bond
Hydroxyl
O O OH
Ether
codeine
297
Q.14 A potent addictive analgesic from opium
N sp2 hybridized
sp3 hybridized
HO O OH
298 morphine
Q.14 A potent addictive analgesic from opium
N Tertiary amino
C17H19NO3
C=C bond
Hydroxyl Hydroxyl
HO O OH
Ether
299 morphine
Q.14 Acetylated morphine
N sp2 hybridized
sp3 hybridized
O O
O O O
300
heroin
Q.14 Acetylated morphine
Tertiary amino
N
C21H23NO5
C=C bond
Ester
Ester
O O
O O O
Ether
301
heroin
Tranquilizer for elephants – 2000 times more potent
than morphine
N sp2 hybridized
sp3 hybridized
OH
HO O O
302
etorphine Q.14
Tranquilizer for elephants – 2000 times more potent
than morphine
Tertiary amino
N
Hydroxyl
C25H33NO4
OH
Hydroxyl
HO O O
Ether
303
etorphine C=C Q.14
Q.14 Narcotic analgesic
sp2 hybridized
N
sp3 hybridized
304
methadone
Q.14 Narcotic analgesic
C21H27NO
Carbonyl
O
Tertiary amino
N
305
methadone
Q.14 You don’t need it !
O
O
S
N N
N N
N
NH
O O sp2 hybridized
sp3 hybridized
viagra
306
Q.14
C=C
O
C=N O
S
N N
N N
N
NH Tertiary
O O amino
Ether
Secondary amide viagra C22H30N6O4S
307
OH
Aspirin
1
O
Analgesics and antipyretics
2 O
O CH3
2-(acetyloxy)benzoic acid
308
1 NH CH3
O Acetaminophen
HO 4
Analgesics and antipyretics
N-(4-hydroxyphenyl)acetamide
309
OH Vitamin C
3
HO
2 Helps maintain elasticity of
4 O
the skin, aids the absorption
HO 5 O
1 of iron and improves
1
resistance to infection.
2
HO
5-(1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one
O O
O O O
furan furan-2(3H)-one furan-2(5H)-one
310
CH3 Albuterol
H3C CH3
Treating asthma, emphysema
NH and chronic bronchitis
2
4 2
HO 1 OH
1 OH
4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
311
Camphor( 樟
腦) 7
5 4 3
2
6 1
1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

Ketamine(
Ketamine( 氯胺酮
氯胺酮 ))
C13H16ClNO
2
1
Cl
NH
2-(2- CH3 2-(methylamino)
2
chlorophenyl)
1 O
2-(2- -2-(methylamino) cyclohexanone

chlorophenyl)
313
2 1
Cl
NH
3 CH3
2 O
1
3-(2-chlorophenyl)-3-(methylamino)cyclohexane-1,2-dione
314
2 1
Cl
NH
6 CH3
1 O
2
3
O
6-(2-chlorophenyl)-6-(methylamino)cyclohex-3-ene-1,2-dione
315
O
Name it ! Cl
Cl
O
O
N
O O
H3C
O
C24H15Cl2NO8 O
CH2
(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
316

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Nomenclature and Introduction of Major Functional Groups - 2011

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Nomenclature &

Alkanes are hydrocarbons that contain only

CH4 Methane C6H14 Hexane

Angle strain arises from repulsions between

Most stable due to less angle strain

• General formula of acyclic alkanes: CnH2n+2

Methane Ethane Propane

All carbon atoms are sp3 hybridized - zigzag

CnH2n+1– Alkyl groups (derived from alkanes)

One C=C double bond

First member is ethene (ethylene)

First member is ethene (ethylene)

Structural Position Functional groups

Different Functional group

e.g. cis-but-2-ene and trans-but-2-ene

Both substituent groups are

Rotation about the axis of a double bond through an

Arises from restricted rotation about the

Polycyclic hydrocarbons contain two or more

One CC triple bond

Cycloalkenes and alkadienes have the same

C atoms in triple bond are sp hybridized

90 << 180

Functional group has the higher priority

1,3 > 2,4

1,3 > 2,4

octa-1,7-diene substituents at 3,4,5,6

octa-1,7-diene substituents at 3,4,5,6

octa-1,7-diene substituents at 3,4,5,6,7

octa-1,7-diene substituents at 2,3,4,5,6

octa-1,7-diene substituents at 3,4,5,6

octa-1,7-diene substituents at 3,4,5,6

octa-1,7-diene substituents at 3,4,5,6

octa-1,7-diene substituents at 3,4,5,6

The C directly bonded to the ring is

New Way Chemistry for Hong Kong A-Level Book 3A

With a total of (4n + 2)  electrons in the

Extra stability (aromaticity) due to

C6H5 –  phenyl group

C10H7 –  naphthyl group

Both are aryl groups

The molecular is not planar

Organic compounds with one or more

Derived from alkanes

Hydroxy derivative of alkane

General formula : CnH2n+1OH (acyclic)

Primary, Secondary, Tertiary,

The longest C chain containing the –OH

‘e’ is retained in diol

Derived from aromatic hydrocarbons

2-chlorophenol 3-chlorophenol 4-chlorophenol

o  ortho m  meta p  para

- OH has a higher priority than C=C

a,b,c,are all greater than 105 due to

The alkoxy groups are always treated as

At least ONE H attached to C

methanal ethanal propanal benzaldehyde