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
New Way Chemistry for Hong Kong A-Level Book 3A
1.
Hydrocarbons
Organic compounds containing carbon and
hydrogen only.
3
New Way Chemistry for Hong Kong A-Level Book 3A
(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
New Way Chemistry for Hong Kong A-Level Book 3A
The first 10 members of the unbranched (acyclic)
alkane series are :
CH4
Methane
C6H14 Hexane
C 2H 6
Ethane
C7H16 Heptane
C 3H 8
Propane
C8H18 Octane
C4H10
Butane
C9H20 Nonane
C5H12
Pentane
C10H22 Decane
5
New Way Chemistry for Hong Kong A-Level Book 3A
Cycloalkanes are alkanes in which all or some
of the carbon atoms are arranged in a ring
6
New Way Chemistry for Hong Kong A-Level Book 3A
Cycloalkanes in skeletal forms
Angle strain arises from repulsions between
adjacent bond pairs
Most stable due to less angle strain
7
New Way Chemistry for Hong Kong A-Level Book 3A
Cycloalkanes in skeletal forms
8
New Way Chemistry for Hong Kong A-Level Book 3A
Alkanes and Cycloalkanes
• General formula of acyclic alkanes: CnH2n+2
• General formula of cycloalkanes: Q.1
CnH2n
9
New Way Chemistry for Hong Kong A-Level Book 3A
The First Three Members of Alkanes
Methane
(CH4)
Ethane
(CH3CH3)
10
New Way Chemistry for Hong Kong A-Level Book 3A
Propane
(CH3CH2CH3)
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
New Way Chemistry for Hong Kong A-Level Book 3A
Q.2 C4H10
All carbon atoms are sp3 hybridized - zigzag
H2
C
H3C
CH3
CH3
C
H2
CH
H3C
CH3
12
New Way Chemistry for Hong Kong A-Level Book 3A
Q.2 C5H12
H2
C
H2
C
H 3C
C
H2
CH3
CH3
CH
H 3C
CH3
C
H2
CH3
C
H 3C
CH3
CH3
13
New Way Chemistry for Hong Kong A-Level Book 3A
Q.2 C6H14
14
New Way Chemistry for Hong Kong A-Level Book 3A
Nomenclature of
Alkanes
IUPAC Conventions
15
New Way Chemistry for Hong Kong A-Level Book 3A
Straight-Chain Alkanes
16
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
New Way Chemistry for Hong Kong A-Level Book 3A
Branched-Chain Alkanes
1. Name the longest possible straight chain
 give the parent name for the alkane
17
New Way Chemistry for Hong Kong A-Level Book 3A
Branched-Chain Alkanes
2. Name the substituent groups – the branches
CnH2n+1– Alkyl groups (derived from alkanes)
CH3 –
methyl
C2H5 –
ethyl
18
New Way Chemistry for Hong Kong A-Level Book 3A
C 3H 7 –
H2
C
propyl
H3C
C
H2
H3C
CH
isopropyl
H3C
19
New Way Chemistry for Hong Kong A-Level Book 3A
C 4H 9 –
H3C
H2
C
H3C
H2
C
C
H2
sec-butyl
CH
H2C
butyl
CH3
H3C
secondary, 2
carbon
tert-butyl
H3C
CH
C
H2
H3C
H3C
C
H3C
isobutyl
20
New Way Chemistry for Hong Kong A-Level Book 3A
tertiary, 3
carbon
3.
Number the positions of the substituent
groups with the smallest possible numbers
2
2-methyl
2-methylbutane
21
New Way Chemistry for Hong Kong A-Level Book 3A
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
New Way Chemistry for Hong Kong A-Level Book 3A
tetramethyl
tetramethylmethane
23
New Way Chemistry for Hong Kong A-Level Book 3A
2
propane
2,2-dimethylpropane
24
New Way Chemistry for Hong Kong A-Level Book 3A
Cl
Cl
1
5
Cl
1,5,5-trichloro
1,5,5-trichlorohexane
25
New Way Chemistry for Hong Kong A-Level Book 3A
Cl
Cl
6
1
2
5
Cl
1,5,5-trichloro
2,2,6-trichloro


‘Lowest numbers’ does NOT refer to the
smallest sum
26
New Way Chemistry for Hong Kong A-Level Book 3A
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
2
3-ethyl-2,2-dimethylpentane
prefix is not
considered
27
New Way Chemistry for Hong Kong A-Level Book 3A
3
tert-butyl
3-ethyl-2,2-dimethylpentane
3-tert-butylpentane
28
New Way Chemistry for Hong Kong A-Level Book 3A


(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
New Way Chemistry for Hong Kong A-Level Book 3A
(b) Alkenes (CnH2n)
First member is ethene (ethylene)
Cyclic structures are possible
cyclopropene
cyclobutene
30
New Way Chemistry for Hong Kong A-Level Book 3A
(b) Alkenes (CnH2n)
First member is ethene (ethylene)
Cyclic structures are possible
Q.3
CnH2n-2
cyclopentene
cyclohexene
31
New Way Chemistry for Hong Kong A-Level Book 3A
Starting from C4H8, isomerism occurs
Structural isomerism :
• same molecular formula
• different linking orders of atoms
32
New Way Chemistry for Hong Kong A-Level Book 3A
Structural
isomerism
Different
functional groups
Chain
isomerism
Different
carbon
skeletons
Position
isomerism
Functional groups
in different
positions
Functional group
isomerism
33
New Way Chemistry for Hong Kong A-Level Book 3A
Same linking order
of atoms
Geometrical
isomerism
Stereoisomerism
Different spatial
arrangements of
atoms
Optical isomerism
34
New Way Chemistry for Hong Kong A-Level Book 3A
Geometrical Isomerism
e.g. cis-but-2-ene and trans-but-2-ene
35
New Way Chemistry for Hong Kong A-Level Book 3A
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
New Way Chemistry for Hong Kong A-Level Book 3A
cannot be inter-converted
at lower temperatures
37
New Way Chemistry for Hong Kong A-Level Book 3A
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
38
New Way Chemistry for Hong Kong A-Level Book 3A
Geometrical Isomerism
Arises from restricted rotation about the
axis of the C=C double bond.
39
New Way Chemistry for Hong Kong A-Level Book 3A
Position isomers
Q.4
Chain isomerism
40
position isomers
trans
cis
New Way Chemistry for Hong Kong A-Level Book 3A
Geometrical
isomers
Position isomers
Q.4
Chain isomerism
41
New Way Chemistry for Hong Kong A-Level Book 3A
Q.4
Functional group
isomerism
42
New Way Chemistry for Hong Kong A-Level Book 3A
Q.4
Chain isomerism
A total of 11
isomers
43
New Way Chemistry for Hong Kong A-Level Book 3A
Q.4
C5H8
C5H6
44
New Way Chemistry for Hong Kong A-Level Book 3A
pent-1-ene
1
2
pent-2-ene
45
New Way Chemistry for Hong Kong A-Level Book 3A
2
pent-2-ene
(2E)-pent-2-ene
trans
cis
Geometrical Isomerism
(2Z)-pent-2-ene
46
New Way Chemistry for Hong Kong A-Level Book 3A
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
New Way Chemistry for Hong Kong A-Level Book 3A
CH3
2
3
(2Z)-3-methylpent-2-ene
1
H3C
CH3
CH3
2
1
H3C
3
(2E)-3-methylpent-2-ene
CH3
48
New Way Chemistry for Hong Kong A-Level Book 3A
Q.4
1
2
2
2-methylbut-1-ene
2-methylbut-2-ene
3-methylbut-1-ene
1
3
Functional group has a higher priority than
branches
49
New Way Chemistry for Hong Kong A-Level Book 3A
Q.4
cyclopentane
methylcyclobutane
50
New Way Chemistry for Hong Kong A-Level Book 3A
Q.4
1,2-dimethylcyclopropane
ethylcyclopropane
1,1-dimethylcyclopropane
51
New Way Chemistry for Hong Kong A-Level Book 3A
bicyclo[1.1.1]pentane
bicyclo[2.1.0]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
52
New Way Chemistry for Hong Kong A-Level Book 3A
tricyclo[1.1.1.11,3]hexane
tricyclo[2.1.0.01,3]pentane
53
New Way Chemistry for Hong Kong A-Level Book 3A
(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
New Way Chemistry for Hong Kong A-Level Book 3A
(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
New Way Chemistry for Hong Kong A-Level Book 3A
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

56
New Way Chemistry for Hong Kong A-Level Book 3A
In naming alkenes and alkynes,
the ‘longest’ carbon chain need NOT be the
one that contains the multiple bond.
3
1
3-methylenehexane

57
New Way Chemistry for Hong Kong A-Level Book 3A
Q.5(a)
2
5
(2E)-5-methylhex-2-ene
Functional group has the higher priority
than branch.
58
New Way Chemistry for Hong Kong A-Level Book 3A
Q.5(b)
1
3
(3E)-penta-1,3-diene
59
New Way Chemistry for Hong Kong A-Level Book 3A
Q.5(c)
5
1
2
4
2
5
3
1
1,3 > 2,4
60
New Way Chemistry for Hong Kong A-Level Book 3A
4
3
Q.5(c)
1
3
(3E)-pent-3-en-1-yne
NOT ene
61
New Way Chemistry for Hong Kong A-Level Book 3A
Q.5(d)
5
1
5
4
3
2
1
2
3
4
1,3 > 2,4
although -yne has the smaller number
62
New Way Chemistry for Hong Kong A-Level Book 3A
Q.5(d)
1
5
4
3
2
pent-1-en-3-yne
NOT ene
63
New Way Chemistry for Hong Kong A-Level Book 3A
Q.5(e)
4
4
1
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
New Way Chemistry for Hong Kong A-Level Book 3A
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
New Way Chemistry for Hong Kong A-Level Book 3A
8
Q.5(f)
7
5-ethyl
3
6-ethynyl
4
5 6
1
3,7-dimethyl
octa-1,6-diene
4-methylidene
5-ethyl-6-ethynyl-3,7-dimethyl-4-methylideneocta-1,6-diene
66
New Way Chemistry for Hong Kong A-Level Book 3A
8
Q.5(g)
8
6
7
1
octa-1,6-diene

octa-1,7-diene

67
New Way Chemistry for Hong Kong A-Level Book 3A
8
Q.5(g)
7
5-ethyl
3
3,7-dimethyl 1
4
5
6
octa-1,6-diene
4-methylidene
6-vinyl
5-ethyl-3,7-dimethyl-4-methylidene-6-vinylocta-1,6-diene
68
New Way Chemistry for Hong Kong A-Level Book 3A
Q.5(h)
3
1
4
5
8
6
7
octa-1,7-diene substituents at 3,4,5,6
69
New Way Chemistry for Hong Kong A-Level Book 3A
Q.5(h)
7
8
6
5
4
1
3
octa-1,7-diene substituents at 3,4,5,6
70
New Way Chemistry for Hong Kong A-Level Book 3A
8
Q.5(h)
7
3
4
5
6
1
octa-1,7-diene substituents at 3,4,5,6,7
71
New Way Chemistry for Hong Kong A-Level Book 3A
1
Q.5(h)
2
7
6
5
4
3
8
octa-1,7-diene substituents at 2,3,4,5,6

72
New Way Chemistry for Hong Kong A-Level Book 3A
1
Q.5(h)
2
7
4-ethyl
6
2,6-dimethyl
5-methylidene
8
5
4
3
octa-1,7-diene
3-ethenyl
3-ethenyl-4-ethyl-2,6-dimethyl-5-methylideneocta-1,7-diene
vinyl
methylene
73
New Way Chemistry for Hong Kong A-Level Book 3A
Q.5(i)
2
3 4
5
8
6
7
1
octa-1,7-diene
substituents at 3,4,5,6
74
New Way Chemistry for Hong Kong A-Level Book 3A
Q.5(i)
7
6 5
4
1
3
2
8
octa-1,7-diene
substituents at 3,4,5,6
75
New Way Chemistry for Hong Kong A-Level Book 3A
Q.5(i)
2
3 4
5
8
6
7
1
octa-1,7-diene
substituents at 3,4,5,6
5-ethyl
3,6-dimethyl
4-methylidene
76
New Way Chemistry for Hong Kong A-Level Book 3A
Q.5(i)
7
6 5
4
1
3
2
8
octa-1,7-diene
4-ethyl
3,6-dimethyl
substituents at 3,4,5,6
4,3,6,5 > 5,3,6,4
5-methylidene
4-ethyl-3,6-dimethyl-5-methylideneocta-1,7-diene
77
New Way Chemistry for Hong Kong A-Level Book 3A
In naming hydrocarbons, cyclic structures
always have higher priority than C=C, CC.
ethenylcyclohexane
ethynylcyclohexane
78
New Way Chemistry for Hong Kong A-Level Book 3A
Also, cyclic structure rather than the length
of the carbon chain is first considered.
heptylcyclohexane
79
New Way Chemistry for Hong Kong A-Level Book 3A
1
3
but-3-en-1-ylcyclohexane
The C directly bonded to the ring is
assigned the lowest possible number
80
New Way Chemistry for Hong Kong A-Level Book 3A
2
1
but-1-en-2-ylcyclohexane
2
3
but-3-en-2-ylcyclohexane
New Way Chemistry for Hong Kong A-Level Book 3A
In naming cyclic hydrocarbons, the side branches
are numbered in alphabetical order.
2
1-ethyl
1
2-methyl
1-ethyl-2-methylcyclohexane
82
New Way Chemistry for Hong Kong A-Level Book 3A
In naming cyclic hydrocarbons, the side branches
are numbered in alphabetical order.
1
2
2
1-methyl
2-(propan-2-yl)
1-methyl-2-(propan-2-yl)cyclohexane
83
New Way Chemistry for Hong Kong A-Level Book 3A
In naming cyclic hydrocarbons, the side branches
are numbered in alphabetical order.
2
1-butan-2-yl
1
2-methyl
1-(butan-2-yl)-2-methylcyclohexane
84
New Way Chemistry for Hong Kong A-Level Book 3A
Q.6
propan-2-ylcyclopropane
1,2-dimethyl-3-(propan-2-yl)cyclopropane
85
New Way Chemistry for Hong Kong A-Level Book 3A
Q.6
3
1
2
prop-1-en-1-yl
(2-methylprop-1-en-1-yl)
(2-methylprop-1-en-1-yl)cyclobutane
86
New Way Chemistry for Hong Kong A-Level Book 3A
Q.6
1
1-methylcyclobutene
2
2
2-methylcyclobutene
1
87
New Way Chemistry for Hong Kong A-Level Book 3A
Q.6
3
2
3-methylcyclobutene
1
4
1
4-methylcyclobutene
2
88
New Way Chemistry for Hong Kong A-Level Book 3A
Q.6
3
2
3-methylcyclobutene
1
2
1
3
4
89
New Way Chemistry for Hong Kong A-Level Book 3A
(d) Aromatic hydrocarbons
With a total of (4n + 2)  electrons in the
conjugated system
(alternating single and double bonds)
90
New Way Chemistry for Hong Kong A-Level Book 3A
(d) Aromatic hydrocarbons
Extra stability (aromaticity) due to
delocalization of  electrons
Also called arenes
91
New Way Chemistry for Hong Kong A-Level Book 3A
(d) Aromatic hydrocarbons
C6H5 –  phenyl group
C10H7 –  naphthyl group
Both are aryl groups
92
New Way Chemistry for Hong Kong A-Level Book 3A
Q.7
6 = 41+2
aromatic
methylbenzene
93
New Way Chemistry for Hong Kong A-Level Book 3A
Q.7
10 = 42+2
aromatic
naphthalene
94
New Way Chemistry for Hong Kong A-Level Book 3A
Q.7
14 = 43+2
aromatic
anthracene
95
New Way Chemistry for Hong Kong A-Level Book 3A
Q.7
8  4n+2
NOT aromatic
cyclooctatetraene
96
New Way Chemistry for Hong Kong A-Level Book 3A
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
New Way Chemistry for Hong Kong A-Level Book 3A
2.
Hydroxy compounds
Organic compounds with one or more
hydroxyl groups, –OH.
98
New Way Chemistry for Hong Kong A-Level Book 3A
(a) Alkanols (alcohols)
Derived from alkanes
Contain one or more –OH groups attached
to an alkyl group.
R – OH
Alkyl group
Hydroxyl group
99
New Way Chemistry for Hong Kong A-Level Book 3A
(a) Alkanols (alcohols)
Hydroxy derivative of alkane
Alkyl derivative of water
RH
H replaced
by OH
ROH
H replaced
by R
100
New Way Chemistry for Hong Kong A-Level Book 3A
HOH
(a) Alkanols (alcohols)
General formula : CnH2n+1OH (acyclic)
Three classes :
R
C
R''
H
H
OH
R
C
OH
R
C
OH
H
R'
R'
Primary,
1
Secondary,
2
Tertiary,
3
101
New Way Chemistry for Hong Kong A-Level Book 3A
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
New Way Chemistry for Hong Kong A-Level Book 3A
5
4
3
2
1
OH
pentane
pentan-2-ol
103
New Way Chemistry for Hong Kong A-Level Book 3A
OH
5
4
3
2
1
pentane
pentan-3-ol
104
New Way Chemistry for Hong Kong A-Level Book 3A
1
5
2
OH
3
4
OH
pentane
pentane-2,4-diol
‘e’ is retained in diol
105
New Way Chemistry for Hong Kong A-Level Book 3A
(b) Phenols
Derived from aromatic hydrocarbons
Contain one or more –OH groups attached
to an aryl group
Ar – OH
Aryl group
Hydroxyl group
106
New Way Chemistry for Hong Kong A-Level Book 3A
OH
OH
1
OH
2
phenol

Benzene-1,2-diol 
2-hydroxyphenol
107
New Way Chemistry for Hong Kong A-Level Book 3A
OH
1
Cl
OH
OH
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
New Way Chemistry for Hong Kong A-Level Book 3A
Q.8
1
2
4-methylhexan-2-ol
4
OH
6
5
1
4
2
4-methylpentan-2-ol
OH
109
New Way Chemistry for Hong Kong A-Level Book 3A
Q.8
5
3
2
1
trans-
4
OH
- OH has a higher priority than C=C
pent-3-en-2-ol
(3E)-pent-3-en-2-ol
110
New Way Chemistry for Hong Kong A-Level Book 3A
Q.8
Menthol
(薄荷醇)
Propan-2-yl
2
OH
cyclohexanol
with
TWO branches
methyl
111
New Way Chemistry for Hong Kong A-Level Book 3A
Q.8
menthol
2
6
OH
OH
3
1
5
1
4
6
4
2
5
2,5 > 3,6
3
5-methyl-2-(propan-2-yl)cyclohexanol
112
New Way Chemistry for Hong Kong A-Level Book 3A
3.
Ethers
Contain the oxy, –O-, group or
alkoxy, R-O- group
R
O
oxy group
R
113
New Way Chemistry for Hong Kong A-Level Book 3A
3.
Ethers
Contain the oxy, –O-, group or
alkoxy, R-O- group
R
O
Alkoxy group
R
114
New Way Chemistry for Hong Kong A-Level Book 3A
3.
Ethers
Alkyl derivatives of water
H
O
H
2H replaced
by 2R
R
O
R
115
New Way Chemistry for Hong Kong A-Level Book 3A
3.
Ethers
Three classes of ethers : R
a
'R
Ar
O
b
R
Ar
O
c
H
O
o
105
'Ar
O
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
New Way Chemistry for Hong Kong A-Level Book 3A
3.
Ethers
Naming : The alkoxy groups are always treated as
substituents and expressed as prefixes.
117
New Way Chemistry for Hong Kong A-Level Book 3A
Q.9
O
ethane
methoxy
methoxyethane

118
New Way Chemistry for Hong Kong A-Level Book 3A
Q.9
methane
O
ethoxy
ethoxymethane

119
New Way Chemistry for Hong Kong A-Level Book 3A
Q.9
benzene
O
methoxy
methoxybenzene
120
New Way Chemistry for Hong Kong A-Level Book 3A

Q.9
O
phenoxy
methane
phenoxymethane

121
New Way Chemistry for Hong Kong A-Level Book 3A
Q.9
1
2
propane
3
O
methoxy
2-methoxypropane

122
New Way Chemistry for Hong Kong A-Level Book 3A
4.
Carbonyl compounds
Organic compounds with the carbonyl group,
C
O
123
New Way Chemistry for Hong Kong A-Level Book 3A
4.
Carbonyl compounds
(a) Aldehydes
Products of dehydrogenation of alcohols
H
R
C
R
O
C
H
H
H
At least ONE H attached to C
R : alkyl, aryl or H
124
New Way Chemistry for Hong Kong A-Level Book 3A
O
+
H2
(a) Aldehydes
Examples : O
O
O
O
H
H
H
H
methanal
ethanal
H
propanal
–ane replaced by –anal
125
New Way Chemistry for Hong Kong A-Level Book 3A
benzaldehyde
(a) Aldehydes
Examples : O
propan-1-al
O
O
O
H
H
H
H
methanal
ethanal
H
propanal
benzaldehyde
The aldehye group, –CHO, always occupies
the terminal position
 No need to specify its position
126
New Way Chemistry for Hong Kong A-Level Book 3A
4.
Carbonyl compounds
(b) Ketones
No H atom is directly attached to the
carbonyl group
R
C
'R
O
R, R’ : alkyl or aryl group
127
New Way Chemistry for Hong Kong A-Level Book 3A
(b) Ketones
Examples : O
propanone
O
butanone
–ane replaced by –anone
128
New Way Chemistry for Hong Kong A-Level Book 3A
(b) Ketones
Examples : O
3
2
O
pentan-2-one
pentan-3-one
129
New Way Chemistry for Hong Kong A-Level Book 3A
(b) Ketones
Examples : O
O
4
2
2
3
4-methylpentan-2-one
2-methylpentan-3-one
130
New Way Chemistry for Hong Kong A-Level Book 3A
(b) Ketones
Examples : -
3
O
O
O
2
4
2
O
pentane-2,4-dione
pentane-2,3-dione
131
New Way Chemistry for Hong Kong A-Level Book 3A
5.
Carboxylic acids
Organic compounds with the carboxyl group,
O
C
OH
132
New Way Chemistry for Hong Kong A-Level Book 3A
5.
Carboxylic acids
Organic compounds with the carboxyl group,
O
C
carbonyl
carboxyl
OH
hydroxyl
133
New Way Chemistry for Hong Kong A-Level Book 3A
5.
Carboxylic acids
Organic compounds with the carboxyl group,
O
R
R : alkyl, aryl or H
C
OH
If R is an alkyl group, the compound is an
alkanoic acid, CnH2n+1COOH.
134
New Way Chemistry for Hong Kong A-Level Book 3A
Carboxylic acids
Examples : O
O
O
OH
OH
OH
H
methanoic acid
ethanoic acid
propanoic acid
–ane replaced by –anoic acid
135
New Way Chemistry for Hong Kong A-Level Book 3A
Carboxylic acids
Examples : O
O
O
OH
OH
OH
H
methanoic acid
ethanoic acid
propanoic acid
The carboxyl group, –COOH, always occupies
the terminal position
 No need to specify its position
136
New Way Chemistry for Hong Kong A-Level Book 3A
Carboxylic acids
Examples : COOH
COOH
COOH
1
1
OH
2
3
benzoic acid
2-hydroxybenzoic
acid
3-methylbenzoic
acid
137
New Way Chemistry for Hong Kong A-Level Book 3A
Carboxylic acids
Examples : COOH
benzoic acid
138
cyclohexanecarboxylic
acid
COOH
COOH
cyclohexylethanoic
acid
cyclohexylacetic
acid
New Way Chemistry for Hong Kong A-Level Book 3A
Carboxylic acids
Examples : HOOC
COOH
hexanedioic acid
139
New Way Chemistry for Hong Kong A-Level Book 3A
Carboxylic acids
Examples : HOOC
6
1
COOH

hexane-1,6-dioic acid 
hexanedioic acid
140
New Way Chemistry for Hong Kong A-Level Book 3A
Carboxylic acids
Examples : HOOC
1
4
COOH

hexane-1,6-dioic acid 
hexane-1,4-dioic acid 
hexanedioic acid
141
New Way Chemistry for Hong Kong A-Level Book 3A
6.
Acids derivatives
acyl group
FOUR types : -
O
O
OH replaced by Cl
R
R
C
Cl
OH
carboxylic acid
C
acyl(acid) chloride
142
New Way Chemistry for Hong Kong A-Level Book 3A
6.
Acids derivatives
FOUR types : -
acid anhydride
O
O
R
C
O
H
R
H2O
C
O
OH
'R
'R
C
O
R  R’ for mixed acid
anhydride
143
New Way Chemistry for Hong Kong A-Level Book 3A
C
O
6.
Acids derivatives
FOUR types : O
R
C
+
O
HO
R'
H2O
H
O
R
C
O
ester
R : alkyl, aryl or H
R’ : alkyl or aryl
144
New Way Chemistry for Hong Kong A-Level Book 3A
R'
6.
Acids derivatives
FOUR types : O
R
C
+
H
NH2
H2O
O
R
C
NH2
OH
1° amide
N links to only ONE C
145
New Way Chemistry for Hong Kong A-Level Book 3A
6.
Acids derivatives
FOUR types : O
R
+
C
OH
H
NH
H2O
R'
1o amine
O
R
C
HN
R'
2° amide
N links to TWO C atoms
146
New Way Chemistry for Hong Kong A-Level Book 3A
6.
Acids derivatives
FOUR types : O
R''
O
R
+
C
H
N
H2O
R
C
N
R'
R'
OH
2o
amine
''R
3° amide
N links to THREE C atoms
147
New Way Chemistry for Hong Kong A-Level Book 3A
Naming of acids derivatives
Acyl chloride : oic acid to oyl chloride
O
ethanoyl chloride
Or
Cl
acetyl chloride
148
New Way Chemistry for Hong Kong A-Level Book 3A
Naming of acids derivatives
Acyl chloride : oic acid to oyl chloride
O
ethanoyl chloride
Cl
spacing
149
New Way Chemistry for Hong Kong A-Level Book 3A
Naming of acids derivatives
Acid anhydride : oic acid to oic anhydride
O
O
ethanoic anhydride
spacing
O
150
New Way Chemistry for Hong Kong A-Level Book 3A
Naming of acids derivatives
Acid anhydride : oic acid to oic anhydride
O
ethanoic propanoic
anhydride
O
O
For mixed anhydride, the
parent acids are named in
alphabetical order
151
New Way Chemistry for Hong Kong A-Level Book 3A
Naming of acids derivatives
Ester : oic acid to oate preceded by R
group of ROH
O
O
methyl ethanoate
spacing
152
New Way Chemistry for Hong Kong A-Level Book 3A
Naming of acids derivatives
Ester : oic acid to oate preceded by R
group of ROH
O
ethyl propanoate
O
153
New Way Chemistry for Hong Kong A-Level Book 3A
Naming of acids derivatives
Ester : oic acid to oate preceded by R
group of ROH
O
ethyl propenoate
Or, ethyl acrylate
O
154
New Way Chemistry for Hong Kong A-Level Book 3A
Naming of acids derivatives
Ester : oic acid to oate preceded by R
group of ROH
O
2
ethyl 2-methylpropenoate
Or
1
O
ethyl 2-methylacrylate
155
New Way Chemistry for Hong Kong A-Level Book 3A
Naming of acids derivatives
Amides : oic acid to amide
O
ethanamide
NH2
156
New Way Chemistry for Hong Kong A-Level Book 3A
Naming of acids derivatives
Amides : oic acid to amide
O
Or, N-methylacetamide
N-methyl ethanamide
HN
NO spacing
157
New Way Chemistry for Hong Kong A-Level Book 3A
Naming of acids derivatives
Amides : oic acid to amide
O
N,N-dimethylethanamide
N
158
New Way Chemistry for Hong Kong A-Level Book 3A
Naming of acids derivatives
Amides : oic acid to amide
O
N-ethyl-N-methylethanamide
N
Or
N-ethyl-N-methylacetamide
159
New Way Chemistry for Hong Kong A-Level Book 3A
7.
Halogeno hydrocarbons
Hydrocarbons containing at least one
halogen atom
R–X
X : halogens
160
New Way Chemistry for Hong Kong A-Level Book 3A
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)
161
New Way Chemistry for Hong Kong A-Level Book 3A
7.
Halogeno hydrocarbons
Examples : H
H
C
H
Br
H
C
Br
H
Br
bromomethane
dibromomethane
162
New Way Chemistry for Hong Kong A-Level Book 3A
7.
Halogeno hydrocarbons
Examples : F
F
C
BTM
Br
Both are used in
fire extinguishers
F
Br
Cl
C
F
bromotrifluoromethane
F
bromochlorodifluoromethane
BCF
163
New Way Chemistry for Hong Kong A-Level Book 3A
7.
Halogeno hydrocarbons
Examples : Br
Br
Br
bromobenzene
1,2-dibromobenzene
164
New Way Chemistry for Hong Kong A-Level Book 3A
7.
Halogeno hydrocarbons
Examples : -
165
Br
Br
1
4
4
1
Cl
Cl
1-bromo-4-chlorobenzene
4-bromo-1-chlorobenzene


New Way Chemistry for Hong Kong A-Level Book 3A
7.
Halogeno hydrocarbons
Examples : Br
Br
1
Cl
2
Cl
1
2
4
Cl
5
Cl

2-bromo-1,5-dichlorobenzene 
1-bromo-2,4-dichlorobenzene
166
New Way Chemistry for Hong Kong A-Level Book 3A
7.
Halogeno hydrocarbons
Examples : Br
Br
1
4
3
4
Cl
2
Cl
1
Cl

Cl
4-bromo-1,2-dichlorobenzene
167
New Way Chemistry for Hong Kong A-Level Book 3A
7.
Halogeno hydrocarbons
Examples : Br
Br
Br
Br
Br
Br
hexabromobenzene
168
New Way Chemistry for Hong Kong A-Level Book 3A
Q.10
All acyclic structures of C4H8Cl2
Cl
1,1-dichlorobutane
Cl
Cl
2,2-dichlorobutane
Cl
169
New Way Chemistry for Hong Kong A-Level Book 3A
Q.10
Cl
1,2-dichlorobutane
Cl
*
Cl
1,3-dichlorobutane
*
Cl
Cl
1,4-dichlorobutane
Cl
Cl
2,3-dichlorobutane
Cl
* chiral centre, optical isomers exist
170
New Way Chemistry for Hong Kong A-Level Book 3A
Q.10 Cl
1
2
Cl
Cl
3
Cl
1,1-dichloro-2-methylpropane

2-(dichloromethyl)propane

1
2
3
171
New Way Chemistry for Hong Kong A-Level Book 3A
Q.10 Cl
1
2
Cl
Cl
1,1-dichloro-2-methylpropane
3
1
1,2-dichloro-2-methylpropane
2
3
Cl
Cl
1
1,3-dichloro-2-methylpropane
2
Cl
3
172
New Way Chemistry for Hong Kong A-Level Book 3A
8.
Amines
Derivatives of ammonia
H
N
H
R
Primary(1°) amine
H
NH3
N
R
Secondary(2°) amine
'R
''R
N
R
Tertiary (3°) amine
'R
173
New Way Chemistry for Hong Kong A-Level Book 3A
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
NH2
NH2
NH2
ethenamine (ethylenamine)
ethynamine (acetylenamine)
174
New Way Chemistry for Hong Kong A-Level Book 3A
8.
Amines
Naming amines with functional groups
other than CC, C=C, X- and ROThe amino group, is always treated as the
substituent and expressed as prefix,
amino2
HO
1
NH2
2-aminoethanol
175
New Way Chemistry for Hong Kong A-Level Book 3A
8.
Amines
Examples : -
2° amine
N-methylmethanamine
NH
N-methylethanamine
NH
176
New Way Chemistry for Hong Kong A-Level Book 3A
8.
Amines
N
N
3° amine
N,N-dimethylethanamine
N,N-dimethylmethanamine
177
New Way Chemistry for Hong Kong A-Level Book 3A
8.
Amines
NH2
NOT benzenamine
phenylamine or aniline
178
New Way Chemistry for Hong Kong A-Level Book 3A
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
New Way Chemistry for Hong Kong A-Level Book 3A
8.
Amines
NH2
NH
2-methylaniline
N-methylaniline

N-phenylmethanamine
180
New Way Chemistry for Hong Kong A-Level Book 3A

8.
Amines
1-phenylmethanamine
NH2
181
New Way Chemistry for Hong Kong A-Level Book 3A
8.
Amines
2
NH2
1
3
Prop-2-en-1-amine
NH2
Prop-1-en-2-amine
2
1
3
182
New Way Chemistry for Hong Kong A-Level Book 3A
8.
Amines
linear
4
3
2
1
NH2
NH2
but-3-yne-1,2-diamine
183
New Way Chemistry for Hong Kong A-Level Book 3A
8.
Amines
NH
3
2
1
NH2
N2-ethylpropane-1,2-diamine
184
New Way Chemistry for Hong Kong A-Level Book 3A
Q.11
NH2
OH
2-aminophenol
NH2
NH2
benzene-1,2-diamine
NH2
COOH
2-aminobenzoic acid
185
New Way Chemistry for Hong Kong A-Level Book 3A
Q.11
1
2
3
N-methylbutan-1-amine
N
H
4
1
pentan-2-amine
4
3
5
2
NH2
186
New Way Chemistry for Hong Kong A-Level Book 3A
Q.11
1
NH2
2
butan-1-amine
butan-2-amine
NH2
187
New Way Chemistry for Hong Kong A-Level Book 3A
Q.11
propane-1,2-diamine
N1-ethylpropane-1,2-diamine
NH2
H
N
2
3
1
1
3
2
N-methylbutan-2-amine
4
NH
188
New Way Chemistry for Hong Kong A-Level Book 3A
Q.11
N-ethyl
2
N
1
N-methyl
O
ethanamine
2-methoxy
N-ethyl-2-methoxy-N-methylethanamine
189
New Way Chemistry for Hong Kong A-Level Book 3A
Q.11
N-methyl
ethanamine
2
N
1
O
N-(2-methoxyethyl)
N-(2-methoxyethyl)-N-methylethanamine
3 substituents > 2 substituents
190
New Way Chemistry for Hong Kong A-Level Book 3A

Q.11
3
propan-1-amine
2
1
N-methyl
2
N
1
O
N-(2-methoxyethyl)
N-(2-methoxyethyl)-N-methylpropan-1-amine
191
New Way Chemistry for Hong Kong A-Level Book 3A
Q.11
1
N-methyl
2
N
3
1
propan-2-amine
2
O
N-(2-methoxyethyl)
N-(2-methoxyethyl)-N-methylpropan-2-amine
192
New Way Chemistry for Hong Kong A-Level Book 3A
9.
Nitriles
Containing the cyano group, -CN
193
New Way Chemistry for Hong Kong A-Level Book 3A
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
New Way Chemistry for Hong Kong A-Level Book 3A
9.
Nitriles
Examples : C
1
3
2
ethanenitrile
N
C
N
2-methylpropanenitrile
The carbon of the -CN group is counted
as part of the longest carbon chain.
195
New Way Chemistry for Hong Kong A-Level Book 3A
9.
Nitriles
Examples : C
1
3
2
ethanenitrile
N
C
N
2-methylpropanenitrile
The -CN group always occupies
the terminal position.
No need to specify its position.
196
New Way Chemistry for Hong Kong A-Level Book 3A
9.
Nitriles
OH
5
4
3
2
1
C
N
4-hydroxypentanenitrile
197
New Way Chemistry for Hong Kong A-Level Book 3A
9.
Nitriles
N
1
HOOC
2
3
C
3-cyano-2-methylpropanoic acid
If used as prefix, its carbon is not counted
as part of the main carbon chain
198
New Way Chemistry for Hong Kong A-Level Book 3A
9.
Nitriles
3
N
1
2
C
HOOC
2-(cyanomethyl) propanoic acid
Only one substituent 

199
New Way Chemistry for Hong Kong A-Level Book 3A
10. Poly-functional compounds
With two or more functional groups
200
New Way Chemistry for Hong Kong A-Level Book 3A
10. Poly-functional compounds
With identical functional groups
2
1
1
4
buta-1,3-diene
3
2
3
4
buta-1,3-diyne
201
New Way Chemistry for Hong Kong A-Level Book 3A
CH3
H3C
H3C
CH3
(2Z,4Z)-hexa-2,4-diene
(2E,4E)-hexa-2,4-diene
CH3
＝
H3C
CH3
H3C
(2Z,4E)-hexa-2,4-diene
(2E,4Z)-hexa-2,4-diene
2Z > 2 E
202
New Way Chemistry for Hong Kong A-Level Book 3A
10. Poly-functional compounds
With identical functional groups
O
O
ethanedioic acid
HO
O
H
OH
O
pentanedial
H
-COOH and –CHO groups always occupy the
terminial positions.
203
No need to specify its position
New Way Chemistry for Hong Kong A-Level Book 3A
10. Poly-functional compounds
With identical functional groups
H2N
hexane-1,6-diamine
O
O
NH2
O
heptane-2,4,6-trione
204
New Way Chemistry for Hong Kong A-Level Book 3A
10. Poly-functional compounds
With identical functional groups
1
HO
2
3
OH
OH
propane-1,2,3-triol
205
New Way Chemistry for Hong Kong A-Level Book 3A
xylitol
OH
HO
1
2
OH
3
4
5
OH
OH
pentane-1,2,3,4,5-pentol
206
New Way Chemistry for Hong Kong A-Level Book 3A
10. Poly-functional compounds
With different functional groups
2
H2N
1
COOH
2-aminoethanoic acid
or glycine
OH
3
2
1
COOH
2-hydroxypropanoic acid
207
New Way Chemistry for Hong Kong A-Level Book 3A
10. Poly-functional compounds
With different functional groups
2
7
4
6
1
3
5
(2E)-hept-2-en-6-yn-1-ol
208
New Way Chemistry for Hong Kong A-Level Book 3A
OH
10. Poly-functional compounds
Naming : 1. The functional group with the highest
priority (the principal functional group) is
expressed as the suffix.
209
New Way Chemistry for Hong Kong A-Level Book 3A
+
>
N
C
O
>
HO
O
O
R
>
C
O
-CN
O
>
C
C
O
>
C
C
H2N
X
RO
>
>
O
O
>
H
-OH > -NH2 > CC > C=C > -OR = X
210
New Way Chemistry for Hong Kong A-Level Book 3A
O
>
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
p.5
211
3-methylidenehexane
New Way Chemistry for Hong Kong A-Level Book 3A
10. Poly-functional compounds
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
New Way Chemistry for Hong Kong A-Level Book 3A
Q.5(e)
4
4
1
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
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (a)
4
5
3
2
1
COOH
OH
(2Z)-3-hydroxypent-2-enoic acid
C2 : COOH > H
C3 : OH > CH2C
atomic masses are compared
214
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (b)
5
linear
4
3
2
1
COOH
OH
(2Z)-3-hydroxypent-2-en-4-ynoic acid
C2 : COOH > H
C3 : OH > CC
215
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (c)
5
HOOC
4
3
2
1
COOH
OH
(2Z)-3-hydroxypent-2-enedioic acid
C2 : COOH > H
C3 : OH > CH2C
216
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (d)
O
1
HOOC
5
2
4
3
3
4
2
5
COOH
1
OH

(2Z)-3-hydroxy-4-oxopent-2-enedioic acid

(3Z)-3-hydroxy-2-oxopent-3-enedioic acid
217
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (e)
CN
5
HOOC
4
3
2
1
COOH
OH
(2Z)-4-cyano-3-hydroxypent-2-enedioic acid
218
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (f)
O
5
H
4
3
2
1
C
N
4-formylpentanenitrile
219
New Way Chemistry for Hong Kong A-Level Book 3A

Worked examples : (f)
O
H
5
4
3
2
1
C
N
4-methyl-5-oxopentanenitrile
220
New Way Chemistry for Hong Kong A-Level Book 3A

Worked examples : (g)
O
5
H
4
2
3
1
COOH
OH
Carbonyl C is counted as part
of the main carbon chain

3-hydroxy-4-formylbutanoic acid 
3-hydroxy-5-oxopentanoic acid
The one with the longer C chain is preferred
221
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (h)
H
O
O
5
HOOC
4
3
2
1
COOH
OH
(2Z)-2-formyl-3-hydroxy-4-oxopent-2-enedioic acid
222
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (h)
H
O
O
5
HOOC
4
3
2
1
COOH
OH
(2Z
Z)-2-formyl-3-hydroxy-4-oxopent-2-enedioic acid
C3 : OH > COC;
C2 : COOH = CHO; COOH = CHO; COOH > CHO
223
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (i)
4
O
5
3
2
1
COOH
NH2
5-amino-5-oxopentanoic acid
4-(aminocarbonyl)butanoic acid
224
New Way Chemistry for Hong Kong A-Level Book 3A


Worked examples : (j)
O
NH2
O
5
4
HOOC
2-(aminocarbonyl)
3
2
1
COOH
OH
3-hydroxy
4-oxo
2A4O > 4A2O
2-(aminocarbonyl)-3-hydroxy-4-oxopentanedioic acid
225
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (j)
O
NH2
O
5
4
HOOC
2-(aminocarbonyl)
3
2
1
COOH
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
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (k)
O
5
4
2
3
1
COOH
Cl
5-chloro-5-oxopentanoic acid
227
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : O
(l)
Cl
O
5
HOOC
4
2-(chlorocarbonyl)
3
2
1
COOH
OH
3-hydroxy
4-oxo
2C4O > 4C2O
2-(chlorocarbonyl)-3-hydroxy-4-oxopentanedioic acid
228
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (m)
4
O
5
3
2
1
COOH
O
5-methoxy-5-oxopentanoic acid
229
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : O
(n)
O
O
5
HOOC
2-(methoxycarbonyl)
4
3
2
1
COOH
OH
3-hydroxy
4-oxo

3-hydroxy-2-(methoxycarbonyl)-4-oxopentanedioic acid
230
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (o)
4
O
5
O
3
2
1
COOH
O
5-(ethanoyloxy)-5-oxopentanoic acid
231
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (p)
1
2
HOOC
3
O
3-carbonyl
4
pentanedioic acid
5
COOH
O
O
3-(oxycarbonyl)
3-[(ethanoyloxy)carbonyl]
3-[(ethanoyloxy)carbonyl]pentanedioic acid
232
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (p)
1
2
3
4
HOOC
3-(oxycarbonyl)
5
COOH
O
3-carbonyl
pentanedioic acid
O
O
O
3-[(carbonyloxy)carbonyl]
3-{[(methoxycarbonyl)oxy]carbonyl}
3-{[(methoxycarbonyl)oxy]carbonyl}pentanedioic acid
233
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (q)
+
N
COOH
N-carboxy-N,N-dimethyl ethanaminium ion
6B
234
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (r)
COOH
+
N
COOH
N,N-dicarboxy- N-methylethanaminium ion
235
New Way Chemistry for Hong Kong A-Level Book 3A
Worked examples : (s)
1
HOOC
2
1
3
2
4
3
Citric acid
5
COOH
COOH
3-carboxypentanedioic acid

Propane-1,2,3-tricarboxylic acid
Or
Propane-1,2,3-trioic acid
236
New Way Chemistry for Hong Kong A-Level Book 3A

Worked examples : (t)
COOH
3
HOOC
2
1
COOH
COOH
propane-1,1,2,3-tetracarboxylic acid
237
New Way Chemistry for Hong Kong A-Level Book 3A
O
OH
OH
HO
5
3
4
OH
1
2
O
O
(4Z)-5-hydroxypenta-1,4-diene-1,1,5-tricarboxylic acid
238
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(a)
H2N
COOH
O
3-amino-3-oxopropanoic acid
239
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(a)
COOH
HOOC
O
NH2
3-(aminocarbonyl)pentanedioic acid
240
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(b)
O
H
COOH
4-oxobutanoic acid
241
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(b)
COOH
HOOC
H
O
3-formylpentanedioic acid
242
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(c)
O
C
H
N
3-oxopropanenitrile
243
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(c)
N C
COOH
4-cyanobutanoic acid
244
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(c)
N
C
COOH
4-cyanopentanoic acid
245
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(d)
COOH
HOOC
O
O
3-(methoxycarbonyl)pentanedioic acid
246
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(d)
O
O
COOH
4-methoxy-4-oxobutanoic acid
247
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(d)
O
O
COOH
3-(acetyloxy)propanoic acid
248
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(e)
Cl
O
COOH
5-chloro-4-methyl-5-oxopentanoic acid
249
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(e)
HO
Cl
O
COOH
2-methylpentanedioic acid
O
COOH
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
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(e)
HOOC
COOH
O
Cl
3-(chlorocarbonyl)pentanedioic acid
251
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(e)
Cl
O
COOH
HOOC
O
Br
3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid
252
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(f)
O
Cl
Cl
O
hexanedioyl dichloride
253
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(e)
O
Cl
1
6
2
5
3
4
4
3
5
2
6
1
Br
O

6-chloro-6-oxohexanoyl bromide 
6-bromo-6-oxohexanoyl chloride
254
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(e)
Cl
O
COOH
HOOC
O
Br
3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid
255
New Way Chemistry for Hong Kong A-Level Book 3A
Q.12(e)
Cl
O
COOH
HOOC
O
Br
3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid
256
New Way Chemistry for Hong Kong A-Level Book 3A
Q.13(a)
Cyclohexylamine
NH2
257
New Way Chemistry for Hong Kong A-Level Book 3A
Q.13(b)
Benzene-1,3-dioic acid
COOH
1
3
COOH
258
New Way Chemistry for Hong Kong A-Level Book 3A
Q.13(c)
(3E)-hept-3-ene-2,5-diol
HO
5
3
2
1
OH
259
New Way Chemistry for Hong Kong A-Level Book 3A
Q.13(d)
Propane-1,2,3-triol
OH
HO
OH
2
1
3
260
New Way Chemistry for Hong Kong A-Level Book 3A
Q.13(e)
1,2-dichloro-1,1,2,2-tetrafluoroethane
Cl Cl
F
1
2
F
F F
261
New Way Chemistry for Hong Kong A-Level Book 3A
Q.13(f)
Methyl 2-methylpropenoate
2
1
O
O
262
New Way Chemistry for Hong Kong A-Level Book 3A
Q.13(g)
3-hydroxy-2,4-dioxohex-5-enal
O
H
O
2
1
3
4
5
O
OH
263
New Way Chemistry for Hong Kong A-Level Book 3A
Q.13(h)
3-ethoxypentanedioic acid
HOOC
3
COOH
O
264
New Way Chemistry for Hong Kong A-Level Book 3A
Q.13(i)
(5E)-5,6-dibromo-4-hydroxyhex-5-en-2-ynoic acid
Br
6
Br
5
2
COOH
1
4
OH
265
New Way Chemistry for Hong Kong A-Level Book 3A
Q.13(j)
Cyclohexa-2,5-dien-1-ol
OH
1
2
5
266
New Way Chemistry for Hong Kong A-Level Book 3A
Q.13(k)
4-bromo-5,5-dichlorocyclohex-2-en-1-ol
OH
1
Cl
Cl
5
4
Br
267
New Way Chemistry for Hong Kong A-Level Book 3A
Q.13(l)
1-butyl-2,4,5-trimethylbenzene
1
2
5
4
268
New Way Chemistry for Hong Kong A-Level Book 3A
Q.13(m)
Pentan-2-ylbenzene
269
New Way Chemistry for Hong Kong A-Level Book 3A
H3C
CH3
(2Z)-pent-2-en-2-ylbenzene
H2C
CH3
pent-1-en-2-ylbenzene
CH3
CH3
(1Z)-pent-1-en-1-ylbenzene
(3Z)-pent-3-en-1-ylbenzene
270
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
HO
aspirin
O
All C atoms are
sp2 hybridized
O
O
271
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
HO
Analgesic
O
C9H8O4
carboxyl
O
Ester
O
272
New Way Chemistry for Hong Kong A-Level Book 3A
Caffeine
Q.14
O
H3C
CH3
N
N
H
N
O
N
sp3 hybridized
CH3
sp2 hybridized
273
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
C8H10N4O2
Tertiary
amide
CH3
O
C=C bond
H3C
Tertiary amino
N
N
H
carbonyl
N
O
N
CH3
Tertiary amino
274
New Way Chemistry for Hong Kong A-Level Book 3A
C=N bond
Q.14
Acetaminophen
HO
NH
O
sp2 hybridized
sp3 hybridized
275
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Acetaminophen
Secondary amide
HO
NH
O
hydroxyl
C8H9NO2
276
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Adrenalin
OH
HO
NH
HO sp2 hybridized
sp3 hybridized
277
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Adrenalin
hydroxyl
C9H13NO3
OH
HO
NH
HO
Secondary amino
278
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
A neurotransmitter – A deficiency is
associated with Parkinson’s disease
HO
sp2 hybridized
sp3 hybridized
HO
NH2
Dopamine
279
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
A neurotransmitter – A deficiency is
associated with Parkinson’s disease
HO
hydroxyl
Primary amino
HO
NH2
Dopamine
C8H11NO2
280
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Menthol – from peppermint oil
sp3 hybridized
OH
281
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Menthol – from peppermint oil
C10H20O
hydroxyl
OH
282
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
sp2 hybridized
Insecticide
sp3 hybridized
Cl
Cl
Cl
Cl
283
Cl
DDT
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Insecticide
Chloro
Cl
Cl
C14H9Cl5
Cl
Cl
284
Cl
DDT
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
HO
OH
O
sp2 hybridized
sp3 hybridized
O
phenolpht halein
285
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
hydroxyl
HO
OH
C20H14O4
O
Ester
O
phenolpht halein
286
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Insecticide
N
sp2 hybridized
N
nicotine
sp3 hybridized
287
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Insecticide
N
N
C=N
nicotine
288
New Way Chemistry for Hong Kong A-Level Book 3A
Tertiary amino
C10H14N2
Q.14
2,3,7,8-tetrachlorodibenzo-p-dioxin
(TCDD)
Cl
O
Cl
Cl
O
Cl
dioxin
sp2 hybridized
289
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
One of the most toxic chemical
known – A class 1 carcinogen
Ether
Cl
O
Cl
Cl
O
Cl
Chloro
Chloro
C12H4O2Cl4
290
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Anti-hypertensive
O
N
N
H
O
HO
O
O
sp2 hybridized
sp3 hybridized
291
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Anti-hypertensive
C20H28N2O5
O
N
N
H
O
HO
O
O
292
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Anti-hypertensive
C20H28N2O5
Tertiary amide
Ester
N
O
N
H
O
HO
O
O
Secondary amino
Carboxyl
enalapril
293
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
A local anesthetic
O
sp2 hybridized
O
sp3 hybridized
O
N
294
O
cocaine
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
A local anesthetic
O
C17H21NO4
O
O
Tertiary amino
295
N
O
cocaine
New Way Chemistry for Hong Kong A-Level Book 3A
Ester
Addictive cough medicine
Q.14
N
sp2 hybridized
sp3 hybridized
O
O
OH
codeine
296
New Way Chemistry for Hong Kong A-Level Book 3A
Addictive cough medicine
Q.14
N
C18H21NO3
Tertiary amino
C=C bond
Hydroxyl
O
Ether
O
OH
codeine
297
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14 A potent addictive analgesic from opium
N
sp2 hybridized
sp3 hybridized
HO
298
O
morphine
OH
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14 A potent addictive analgesic from opium
N
C17H19NO3
Tertiary amino
C=C bond
Hydroxyl
Hydroxyl
HO
O
OH
Ether
299
morphine
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Acetylated morphine
N
sp2 hybridized
sp3 hybridized
O
O
O
300
O
O
heroin
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Acetylated morphine
N
C21H23NO5
Tertiary amino
C=C bond
Ester
Ester
O
O
O
O
O
Ether
301
heroin
New Way Chemistry for Hong Kong A-Level Book 3A
Tranquilizer for elephants – 2000 times more potent
than morphine
N
sp2 hybridized
sp3 hybridized
OH
HO
302
O
O
etorphine
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Tranquilizer for elephants – 2000 times more potent
than morphine
Tertiary amino
N
C25H33NO4
Hydroxyl
OH
Hydroxyl
HO
O
O
Ether
303
etorphine
C=C
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Q.14
Narcotic analgesic
O
sp2 hybridized
sp3
304
hybridized
N
methadone
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
Narcotic analgesic
C21H27NO
Carbonyl
O
N
305
methadone
New Way Chemistry for Hong Kong A-Level Book 3A
Tertiary amino
Q.14
You don’t need it !
N
N
O
O
S
N
N
N
NH
O
O
viagra
sp2 hybridized
sp3 hybridized
306
New Way Chemistry for Hong Kong A-Level Book 3A
Q.14
C=C
O
O
S
N
C=N
N
N
N
N
NH
O
Tertiary
amino
O
Ether
Secondary amide
307
viagra
C22H30N6O4S
New Way Chemistry for Hong Kong A-Level Book 3A
OH
1
2
O
Aspirin
O
Analgesics and antipyretics
O
CH3
2-(acetyloxy)benzoic acid
308
New Way Chemistry for Hong Kong A-Level Book 3A
1
HO
4
NH
CH3
O
Acetaminophen
Analgesics and antipyretics
N-(4-hydroxyphenyl)acetamide
309
New Way Chemistry for Hong Kong A-Level Book 3A
Vitamin C
OH
3
HO
2
4
HO
5
1
2
O
1
O
Helps maintain elasticity of
the skin, aids the absorption
of iron and improves
resistance to infection.
HO
5-(1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one
O
O
furan
O
furan-2(3H)-one
O
O
furan-2(5H)-one
310
New Way Chemistry for Hong Kong A-Level Book 3A
Albuterol
CH3
H3C
2
HO
1
CH3
NH
4
Treating asthma, emphysema
and chronic bronchitis
2
OH
1
OH
4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
311
New Way Chemistry for Hong Kong A-Level Book 3A
Camphor(樟腦)
7
5
6
4
1
3
2
1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
New Way Chemistry for Hong Kong A-Level Book 3A
Ketamine(氯胺酮)
C13H16ClNO
2
Cl
2-(2-chlorophenyl)
1
NH
2
1
CH3 2-(methylamino)
O
2-(2-chlorophenyl) -2-(methylamino) cyclohexanone
313
New Way Chemistry for Hong Kong A-Level Book 3A
2
1
Cl
NH
CH3
3
2
O
1
O
3-(2-chlorophenyl)-3-(methylamino)cyclohexane-1,2-dione
314
New Way Chemistry for Hong Kong A-Level Book 3A
2
1
Cl
NH
6
CH3
1
3
O
2
O
6-(2-chlorophenyl)-6-(methylamino)cyclohex-3-ene-1,2-dione
315
New Way Chemistry for Hong Kong A-Level Book 3A
O
Name it !
Cl
Cl
O
O
C24H15Cl2NO8
O
H3C
O
O
N
O
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
New Way Chemistry for Hong Kong A-Level Book 3A