new way chemistry for hong kong a-level book 3a 1 nomenclature & introduction of major families...
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New Way Chemistry for Hong Kong A-Level Book 3A1
Nomenclature Nomenclature & Introduction & Introduction
of Major of Major Families of Families of
Organic Organic CompoundsCompounds
New Way Chemistry for Hong Kong A-Level Book 3A2
Classification of Classification of HydrocarbonsHydrocarbons
alkadienes, etc.
cycloalkadienes, etc.
Huckel rule
New Way Chemistry for Hong Kong A-Level Book 3A3
Organic compounds containing carbon and hydrogen only.
1.1. HydrocarbonsHydrocarbons
New Way Chemistry for Hong Kong A-Level Book 3A4
(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 bonds are strong
saturated hydrocarbons
contain the maximum possible number of hydrogen atoms per molecule
New Way Chemistry for Hong Kong A-Level Book 3A5
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
New Way Chemistry for Hong Kong A-Level Book 3A6
Cycloalkanes are alkanes in which all or some of the carbon atoms are arranged in a ring
New Way Chemistry for Hong Kong A-Level Book 3A7
Cycloalkanes in skeletal forms
Most stable due to less angle strain
Angle strain arises from repulsions between adjacent bond pairs
New Way Chemistry for Hong Kong A-Level Book 3A8
Cycloalkanes in skeletal forms
New Way Chemistry for Hong Kong A-Level Book 3A9
Alkanes and CycloalkanesAlkanes and Cycloalkanes
• General formula of acyclic alkanes: CnH2n+2
• General formula of cycloalkanes: Q.1
CnH2n
New Way Chemistry for Hong Kong A-Level Book 3A10
The First Three Members of The First Three Members of Alkanes Alkanes
Methane (CH4)
Ethane (CH3CH3)
Propane(CH3CH2CH3)
New Way Chemistry for Hong Kong A-Level Book 3A11
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.
New Way Chemistry for Hong Kong A-Level Book 3A12
Q.2 C4H10
H3C
H2C
CH2
CH3
H3C
CH
CH3
CH3
All carbon atoms are sp3 hybridized - zigzag
New Way Chemistry for Hong Kong A-Level Book 3A13
Q.2 C5H12
H3C
H2C
CH2
H2C
CH3
H3C
CH
CH2
CH3
CH3
H3C
C
CH3
CH3
CH3
New Way Chemistry for Hong Kong A-Level Book 3A14
Q.2 C6H14
New Way Chemistry for Hong Kong A-Level Book 3A15
Nomenclature Nomenclature of Alkanesof Alkanes
IUPAC Conventions
New Way Chemistry for Hong Kong A-Level Book 3A16
Straight-Chain Straight-Chain Alkanes Alkanes
NameNumber of
carbon atomsCondensed
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 3A17
Branched-Chain Branched-Chain Alkanes Alkanes 1. Name the longest possible straight
chain
give the parent name for the alkane
New Way Chemistry for Hong Kong A-Level Book 3A18
Branched-Chain Branched-Chain Alkanes Alkanes 2. Name the substituent groups – the
branchesCnH2n+1– Alkyl groups (derived from alkanes)
CH3 – methyl
C2H5 – ethyl
New Way Chemistry for Hong Kong A-Level Book 3A19
C3H7 –
H3C
H2C
CH2
propyl
H3C
CH
H3C
isopropyl
New Way Chemistry for Hong Kong A-Level Book 3A20
C4H9 –
H3C
H2C
CH2
H2C
butyl
H3C
CH
H2C
CH3
sec-butyl
secondary, 2 carbon
CH CH2
H3C
H3C
isobutyl
C
H3C
H3C
H3C
tert-butyl
tertiary, 3 carbon
New Way Chemistry for Hong Kong A-Level Book 3A21
3. Number the positions of the substituent groups with the smallest possible numbers
2
2-methyl
2-methylbutane
New Way Chemistry for Hong Kong A-Level Book 3A22
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
New Way Chemistry for Hong Kong A-Level Book 3A23
tetramethyltetramethylmethane
New Way Chemistry for Hong Kong A-Level Book 3A24
propane
2
2,2-dimethylpropane
New Way Chemistry for Hong Kong A-Level Book 3A25
Cl
Cl
Cl
1 5
1,5,5-trichloro
1,5,5-trichlorohexane
New Way Chemistry for Hong Kong A-Level Book 3A26
Cl
Cl
Cl
1 5
1,5,5-trichloro
2,2,6-trichloro
6 2
‘Lowest numbers’ does NOT refer to the smallest sum
New Way Chemistry for Hong Kong A-Level Book 3A27
5. If two or more different substituent groups exist, they are named in alphabetical order but NOT in numerical order of their positions.
23
2,2-dimethyl
3-ethyl
3-ethyl-2,2-dimethylpentane
prefix is not considered
New Way Chemistry for Hong Kong A-Level Book 3A28
3-ethyl-2,2-dimethylpentane
3
3-tert-butylpentane
tert-butyl
New Way Chemistry for Hong Kong A-Level Book 3A29
(b)(b) Alkenes (CAlkenes (CnnHH2n2n))
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
New Way Chemistry for Hong Kong A-Level Book 3A30
(b)(b) Alkenes (CAlkenes (CnnHH2n2n))
First member is ethene (ethylene)
Cyclic structures are possible
cyclopropene
cyclobutene
New Way Chemistry for Hong Kong A-Level Book 3A31
(b)(b) Alkenes (CAlkenes (CnnHH2n2n))
First member is ethene (ethylene)
Cyclic structures are possible
cyclopentene
cyclohexene
Q.3
CnH2n-2
New Way Chemistry for Hong Kong A-Level Book 3A32
Starting from C4H8, isomerism occurs
Structural isomerism :
• same molecular formula
• different linking orders of atoms
New Way Chemistry for Hong Kong A-Level Book 3A33
Structural isomeris
m
Chain isomerism
Position isomerism
Functional group
isomerism
Different carbon
skeletons
Functional groups in different positions
Different functional
groups
New Way Chemistry for Hong Kong A-Level Book 3A34
Stereoisomerism
Geometrical isomerism
Optical isomerism
Same linking order of atoms
Different spatial arrangements of
atoms
New Way Chemistry for Hong Kong A-Level Book 3A35
Geometrical IsomerismGeometrical Isomerism
e.g. cis-but-2-ene and trans-but-2-ene
New Way Chemistry for Hong Kong A-Level Book 3A36
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
New Way Chemistry for Hong Kong A-Level Book 3A37
cannot be inter-converted at lower
temperatures
New Way Chemistry for Hong Kong A-Level Book 3A38
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
New Way Chemistry for Hong Kong A-Level Book 3A39
Arises from restricted rotation about the axis of the C=C double bond.
Geometrical IsomerismGeometrical Isomerism
New Way Chemistry for Hong Kong A-Level Book 3A40
Q.4 Position isomers
Chain
isom
erism
position isomers
Geometrical isomers
trans cis
New Way Chemistry for Hong Kong A-Level Book 3A41
Q.4 Position isomers
Chain
isom
erism
New Way Chemistry for Hong Kong A-Level Book 3A42
Q.4
Functional group isomerism
New Way Chemistry for Hong Kong A-Level Book 3A43
Q.4
Chain isomerism
A total of 11 isomers
New Way Chemistry for Hong Kong A-Level Book 3A44
Q.4 C5H8
C5H6
New Way Chemistry for Hong Kong A-Level Book 3A45
pent-1-ene1
pent-2-ene2
New Way Chemistry for Hong Kong A-Level Book 3A46
2
pent-2-ene
(2E)-pent-2-ene
(2Z)-pent-2-ene
Geometrical IsomerismGeometrical Isomerism
trans
cis
New Way Chemistry for Hong Kong A-Level Book 3A47
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 cishttp://en.wikipedia.org/wiki/Cahn-Ingold-Prelog_priority_rule
New Way Chemistry for Hong Kong A-Level Book 3A48
CH3
CH3
CH3
(2Z)-3-methylpent-2-ene
CH3 CH3
CH3
(2E)-3-methylpent-2-ene
1
2 3
1
2 3
New Way Chemistry for Hong Kong A-Level Book 3A49
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
New Way Chemistry for Hong Kong A-Level Book 3A50
cyclopentane
methylcyclobutane
Q.4
New Way Chemistry for Hong Kong A-Level Book 3A51
Q.4
ethylcyclopropane
1,2-dimethylcyclopropane
1,1-dimethylcyclopropane
New Way Chemistry for Hong Kong A-Level Book 3A52
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 atomsA spiro compound is a bicyclic compound with rings connected through just one atom
New Way Chemistry for Hong Kong A-Level Book 3A53
tricyclo[2.1.0.01,3]pentane
tricyclo[1.1.1.11,3]hexane
New Way Chemistry for Hong Kong A-Level Book 3A54
(c)(c) Alkynes (CAlkynes (CnnHH2n-22n-2))
One CC triple bond
Reactive (unsaturated) due to weak bonds
First member is ethyne (acetylene), C2H2
Cycloalkenes and alkadienes have the same general formula as alkynes
New Way Chemistry for Hong Kong A-Level Book 3A55
(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 strain90 << 180
New Way Chemistry for Hong Kong A-Level Book 3A56
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
New Way Chemistry for Hong Kong A-Level Book 3A57
In naming alkenes and alkynes,
the ‘longest’ carbon chain need NOT be the one that contains the multiple bond.
13
3-methylenehexane
New Way Chemistry for Hong Kong A-Level Book 3A58
(2E)-5-methylhex-2-ene
Functional group has the higher priority than branch.
25
Q.5(a)
New Way Chemistry for Hong Kong A-Level Book 3A59
13
(3E)-penta-1,3-diene
Q.5(b)
New Way Chemistry for Hong Kong A-Level Book 3A60
Q.5(c)
3
14
52
1
2
4
5
3
1,3 > 2,4
New Way Chemistry for Hong Kong A-Level Book 3A61
3
1
(3E)-pent-3-en-1-yne
NOT ene
Q.5(c)
New Way Chemistry for Hong Kong A-Level Book 3A62
Q.5(d)
31
452
12 4
5
3
1,3 > 2,4although -yne has the smaller
number
New Way Chemistry for Hong Kong A-Level Book 3A63
pent-1-en-3-yne
NOT ene
Q.5(d)
31
452
New Way Chemistry for Hong Kong A-Level Book 3A64
14
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)
New Way Chemistry for Hong Kong A-Level Book 3A65
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)
New Way Chemistry for Hong Kong A-Level Book 3A66
1
8
34 5 6
7
octa-1,6-diene
5-ethyl
6-ethynyl
3,7-dimethyl
4-methylidene5-ethyl-6-ethynyl-3,7-dimethyl-4-methylideneocta-1,6-diene
Q.5(f)
New Way Chemistry for Hong Kong A-Level Book 3A67
1
8
67
8
octa-1,6-diene
octa-1,7-diene
Q.5(g)
New Way Chemistry for Hong Kong A-Level Book 3A68
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)
New Way Chemistry for Hong Kong A-Level Book 3A69
1
863 4 5
7
octa-1,7-diene substituents at 3,4,5,6
Q.5(h)
New Way Chemistry for Hong Kong A-Level Book 3A70
1
86 34
57
octa-1,7-diene substituents at 3,4,5,6
Q.5(h)
New Way Chemistry for Hong Kong A-Level Book 3A71
1
8
63 4 5
7
octa-1,7-diene substituents at 3,4,5,6,7
Q.5(h)
New Way Chemistry for Hong Kong A-Level Book 3A72
octa-1,7-diene substituents at 2,3,4,5,6
1
86 345
72
Q.5(h)
New Way Chemistry for Hong Kong A-Level Book 3A73
Q.5(h)
octa-1,7-diene
4-ethyl
3-ethenyl
2,6-dimethyl5-methylidene
3-ethenyl-4-ethyl-2,6-dimethyl-5-methylideneocta-1,7-diene
1
86 345
72
vinyl methylene
New Way Chemistry for Hong Kong A-Level Book 3A74
1
23 4 5 6
7
8
octa-1,7-diene substituents at 3,4,5,6
Q.5(i)
New Way Chemistry for Hong Kong A-Level Book 3A75
8
76 5 4 3
2
1
octa-1,7-diene substituents at 3,4,5,6
Q.5(i)
New Way Chemistry for Hong Kong A-Level Book 3A76
1
23 4 5 6
7
8
octa-1,7-diene substituents at 3,4,5,65-ethyl3,6-dimethyl4-methylidene
Q.5(i)
New Way Chemistry for Hong Kong A-Level Book 3A77
8
76 5 4 3
2
1
octa-1,7-diene substituents at 3,4,5,64-ethyl3,6-dimethyl5-methylidene
4,3,6,5 > 5,3,6,4
4-ethyl-3,6-dimethyl-5-methylideneocta-1,7-diene
Q.5(i)
New Way Chemistry for Hong Kong A-Level Book 3A78
ethenylcyclohexane
In naming hydrocarbons, cyclic structures always have higher priority than C=C, CC.
ethynylcyclohexane
New Way Chemistry for Hong Kong A-Level Book 3A79
Also, cyclic structure rather than the length of the carbon chain is first considered.
heptylcyclohexane
New Way Chemistry for Hong Kong A-Level Book 3A80
but-3-en-1-ylcyclohexane
13
The C directly bonded to the ring is assigned the lowest possible
number
New Way Chemistry for Hong Kong A-Level Book 3A
23
but-3-en-2-ylcyclohexane
but-1-en-2-ylcyclohexane
21
New Way Chemistry for Hong Kong A-Level Book 3A82
In naming cyclic hydrocarbons, the side branches are numbered in alphabetical order.
1
1-ethyl
1-ethyl-2-methylcyclohexane
2 2-methyl
New Way Chemistry for Hong Kong A-Level Book 3A83
In naming cyclic hydrocarbons, the side branches are numbered in alphabetical order.
2
1-methyl1
2-(propan-2-yl)
1-methyl-2-(propan-2-yl)cyclohexane
2
New Way Chemistry for Hong Kong A-Level Book 3A84
In naming cyclic hydrocarbons, the side branches are numbered in alphabetical order.
1
1-butan-2-yl22-methyl
1-(butan-2-yl)-2-methylcyclohexane
New Way Chemistry for Hong Kong A-Level Book 3A85
Q.6
1,2-dimethyl-3-(propan-2-yl)cyclopropane
propan-2-ylcyclopropane
New Way Chemistry for Hong Kong A-Level Book 3A86
Q.6
1 2
3
prop-1-en-1-yl(2-methylprop-1-en-1-yl)
(2-methylprop-1-en-1-yl)cyclobutane
New Way Chemistry for Hong Kong A-Level Book 3A87
Q.6
1
2
1-methylcyclobutene
2
1
2-methylcyclobutene
New Way Chemistry for Hong Kong A-Level Book 3A88
Q.6
3-methylcyclobutene
1
23
4-methylcyclobutene
2
14
New Way Chemistry for Hong Kong A-Level Book 3A89
Q.6
3-methylcyclobutene
1
23
4
12
3
New Way Chemistry for Hong Kong A-Level Book 3A90
(d)(d) Aromatic hydrocarbonsAromatic hydrocarbons
With a total of (4n + 2) electrons in the conjugated system
(alternating single and double bonds)
New Way Chemistry for Hong Kong A-Level Book 3A91
(d)(d) Aromatic hydrocarbonsAromatic hydrocarbons
Extra stability (aromaticity) due to delocalization of electrons
Also called arenes
New Way Chemistry for Hong Kong A-Level Book 3A92
(d)(d) Aromatic hydrocarbonsAromatic hydrocarbons
C6H5 – phenyl group
C10H7 – naphthyl group
Both are aryl groups
New Way Chemistry for Hong Kong A-Level Book 3A93
Q.7
6 = 41+2
aromaticmethylbenzen
e
New Way Chemistry for Hong Kong A-Level Book 3A94
10 = 42+2
aromaticnaphthalene
Q.7
New Way Chemistry for Hong Kong A-Level Book 3A95
14 = 43+2
aromaticanthracene
Q.7
New Way Chemistry for Hong Kong A-Level Book 3A96
8 4n+2
NOT aromatic
cyclooctatetraene
Q.7
New Way Chemistry for Hong Kong A-Level Book 3A97
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
Q.7
>120o
New Way Chemistry for Hong Kong A-Level Book 3A98
2.2. Hydroxy compoundsHydroxy compounds
Organic compounds with one or more hydroxyl groups, –OH.
New Way Chemistry for Hong Kong A-Level Book 3A99
(a)(a) Alkanols (alcohols)Alkanols (alcohols)
Derived from alkanes
Contain one or more –OH groups attached to an alkyl group.
R – OHAlkyl group
Hydroxyl group
New Way Chemistry for Hong Kong A-Level Book 3A100
(a)(a) Alkanols (alcohols)Alkanols (alcohols)
Hydroxy derivative of alkane
RH ROH
H replaced
by OH HOH
H replaced
by R
Alkyl derivative of water
(a)(a) Alkanols (alcohols)Alkanols (alcohols)
New Way Chemistry for Hong Kong A-Level Book 3A101
(a)(a) Alkanols (alcohols)Alkanols (alcohols)
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
New Way Chemistry for Hong Kong A-Level Book 3A102
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.
New Way Chemistry for Hong Kong A-Level Book 3A103
OH
pentane
1234
5
pentan-2-ol
New Way Chemistry for Hong Kong A-Level Book 3A104
OH
pentane
12345
pentan-3-ol
New Way Chemistry for Hong Kong A-Level Book 3A105
OH OH
12 3 4
5
pentanepentane-2,4-diol
‘e’ is retained in diol
New Way Chemistry for Hong Kong A-Level Book 3A106
(b)(b) PhenolsPhenols
Derived from aromatic hydrocarbons
Contain one or more –OH groups attached to an aryl group
Ar – OHAryl group Hydroxyl
group
New Way Chemistry for Hong Kong A-Level Book 3A107
phenol
OH OH
OH1
2
2-hydroxyphenolBenzene-1,2-diol
New Way Chemistry for Hong Kong A-Level Book 3A108
OH
Cl
OH
Cl
OH
Cl
o-chlorophenolo ortho
m-chlorophenolm meta
p-chlorophenolp para
2-chlorophenol 3-chlorophenol
4-chlorophenol
1 1 1
2
3
4
New Way Chemistry for Hong Kong A-Level Book 3A109
Q.8
OH
1
6
42
4-methylhexan-2-ol
OH
15 4 2 4-methylpentan-2-
ol
New Way Chemistry for Hong Kong A-Level Book 3A110
OH
123
4
5
- OH has a higher priority than C=C
pent-3-en-2-ol
trans-
(3E)-pent-3-en-2-ol
Q.8
New Way Chemistry for Hong Kong A-Level Book 3A111
OH
Menthol (薄荷醇 )
cyclohexanol
with
TWO branches
Propan-2-yl
methyl
Q.82
New Way Chemistry for Hong Kong A-Level Book 3A112
OHmenthol
1
2
4
3
5
OH
1
24
5
36
6
2,5 > 3,6
5-methyl-2-(propan-2-yl)cyclohexanol
Q.8
New Way Chemistry for Hong Kong A-Level Book 3A113
3.3. EthersEthers
Contain the oxy, –O-, group or
alkoxy, R-O- group
R
O
R
oxy group
New Way Chemistry for Hong Kong A-Level Book 3A114
3.3. EthersEthers
Contain the oxy, –O-, group or
alkoxy, R-O- group
R
O
R
Alkoxy group
New Way Chemistry for Hong Kong A-Level Book 3A115
3.3. EthersEthers
Alkyl derivatives of water
H
O
H
R
O
R
2H replaced by 2R
New Way Chemistry for Hong Kong A-Level Book 3A116
3.3. EthersEthers
Three classes of ethers : -R
O
'R
Ar
O
R
Ar
O
'Ar
H
O
H
a b c 105o
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
New Way Chemistry for Hong Kong A-Level Book 3A117
3.3. EthersEthers
Naming : -
The alkoxy groups are always treated as substituents and expressed as prefixes.
New Way Chemistry for Hong Kong A-Level Book 3A118
Q.9
Omethoxy
ethane
methoxyethane
New Way Chemistry for Hong Kong A-Level Book 3A119
O
methane
ethoxy
ethoxymethane
Q.9
New Way Chemistry for Hong Kong A-Level Book 3A120
Obenzene
methoxy
methoxybenzene
Q.9
New Way Chemistry for Hong Kong A-Level Book 3A121
O
phenoxy
methane
phenoxymethane
Q.9
New Way Chemistry for Hong Kong A-Level Book 3A122
Opropane
methoxy
2
1
3
2-methoxypropane
Q.9
New Way Chemistry for Hong Kong A-Level Book 3A123
4.4. Carbonyl compoundsCarbonyl compounds
Organic compounds with the carbonyl group,
C O
New Way Chemistry for Hong Kong A-Level Book 3A124
4.4. Carbonyl compoundsCarbonyl compounds
(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
New Way Chemistry for Hong Kong A-Level Book 3A125
(a) Aldehydes
Examples : -
H H
O
H
O
H
O
H
O
methanal
ethanal propanal
benzaldehyde
–ane replaced by –anal
New Way Chemistry for Hong Kong A-Level Book 3A126
(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
New Way Chemistry for Hong Kong A-Level Book 3A127
4.4. Carbonyl compoundsCarbonyl compounds
(b) Ketones
No H atom is directly attached to the carbonyl group
R
C
'R
O
R, R’ : alkyl or aryl group
New Way Chemistry for Hong Kong A-Level Book 3A128
O
(b) Ketones
Examples : -
O
propanone butanone
–ane replaced by –anone
New Way Chemistry for Hong Kong A-Level Book 3A129
(b) Ketones
Examples : -O
O
pentan-2-one pentan-3-one
2
3
New Way Chemistry for Hong Kong A-Level Book 3A130
(b) Ketones
Examples : -
O O
4-methylpentan-2-one
24 2 3
2-methylpentan-3-one
New Way Chemistry for Hong Kong A-Level Book 3A131
(b) Ketones
Examples : -O
O
OO
pentane-2,3-dione
pentane-2,4-dione
23 24
New Way Chemistry for Hong Kong A-Level Book 3A132
5.5. Carboxylic acidsCarboxylic acids
Organic compounds with the carboxyl group,
C
OH
O
New Way Chemistry for Hong Kong A-Level Book 3A133
5.5. Carboxylic acidsCarboxylic acids
Organic compounds with the carboxyl group,
C
OH
O
hydroxyl
carbonyl
carboxyl
New Way Chemistry for Hong Kong A-Level Book 3A134
5.5. Carboxylic acidsCarboxylic acids
Organic compounds with the carboxyl group,
R C
OH
O
R : alkyl, aryl or H
If R is an alkyl group, the compound is an alkanoic acid, CnH2n+1COOH.
New Way Chemistry for Hong Kong A-Level Book 3A135
Carboxylic acids
Examples : -
H
OH
O
OH
O
OH
O
methanoic acid
ethanoic acid
propanoic acid
–ane replaced by –anoic acid
New Way Chemistry for Hong Kong A-Level Book 3A136
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
New Way Chemistry for Hong Kong A-Level Book 3A137
Carboxylic acids
Examples : -
benzoic acid
COOH COOH
OH
COOH
2-hydroxybenzoic
acid
3-methylbenzoic acid
1
3
1
2
New Way Chemistry for Hong Kong A-Level Book 3A138
Carboxylic acids
Examples : -
COOH COOH
COOH
benzoic acid
cyclohexanecarboxylic acid
cyclohexylethanoic acid
cyclohexylacetic acid
New Way Chemistry for Hong Kong A-Level Book 3A139
COOH
HOOC
Carboxylic acids
Examples : -
hexanedioic acid
New Way Chemistry for Hong Kong A-Level Book 3A140
COOH
HOOC
Carboxylic acids
Examples : -
hexanedioic acid
16
hexane-1,6-dioic acid
New Way Chemistry for Hong Kong A-Level Book 3A141
COOH
HOOC
Carboxylic acids
Examples : -
hexanedioic acid
1
4
hexane-1,6-dioic acid
hexane-1,4-dioic acid
New Way Chemistry for Hong Kong A-Level Book 3A142
6.6. Acids derivativesAcids derivatives
FOUR types : -
OH replaced by ClR C
OH
O
R C
Cl
O
carboxylic acid acyl(acid) chloride
acyl group
New Way Chemistry for Hong Kong A-Level Book 3A143
6.6. Acids derivativesAcids derivatives
FOUR types : -
R C
O
O
'R C
O
OH
HR C
O
O
C
O
'R
H2O
acid anhydride
R R’ for mixed acid anhydride
New Way Chemistry for Hong Kong A-Level Book 3A144
6.6. Acids derivativesAcids derivatives
FOUR types : -
H2OR C
O
O
H
R'HO+ R C
O
O
R'
esterR : alkyl, aryl or H
R’ : alkyl or aryl
New Way Chemistry for Hong Kong A-Level Book 3A145
6.6. Acids derivativesAcids derivatives
FOUR types : -
R C
OH
O
NH2H+ R C
NH2
O
H2O
1° amideN links to only ONE
C
New Way Chemistry for Hong Kong A-Level Book 3A146
R C
OH
O
NHH
R'
+
6.6. Acids derivativesAcids derivatives
FOUR types : -
R C
HN
O
R'
H2O
2° amide
N links to TWO C atoms
1o amine
New Way Chemistry for Hong Kong A-Level Book 3A147
6.6. Acids derivativesAcids derivatives
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
New Way Chemistry for Hong Kong A-Level Book 3A148
Naming of acids derivativesNaming of acids derivatives
Acyl chloride : oic acid to oyl chloride
Cl
O
ethanoyl chloride
Or
acetyl chloride
New Way Chemistry for Hong Kong A-Level Book 3A149
Naming of acids derivativesNaming of acids derivatives
Acyl chloride : oic acid to oyl chloride
Cl
O
ethanoyl chloride
spacing
New Way Chemistry for Hong Kong A-Level Book 3A150
Naming of acids derivativesNaming of acids derivatives
Acid anhydride : oic acid to oic anhydride
O
O
O
ethanoic anhydride
spacing
New Way Chemistry for Hong Kong A-Level Book 3A151
Naming of acids derivativesNaming of acids derivatives
Acid anhydride : oic acid to oic anhydride
O
O
O
ethanoic propanoic anhydride
For mixed anhydride, the parent acids are named in
alphabetical order
New Way Chemistry for Hong Kong A-Level Book 3A152
Naming of acids derivativesNaming of acids derivatives
Ester : oic acid to oate preceded by R group of ROH
O
O methyl
ethanoate
spacing
New Way Chemistry for Hong Kong A-Level Book 3A153
O
O
Naming of acids derivativesNaming of acids derivatives
Ester : oic acid to oate preceded by R group of ROH
ethyl propanoate
New Way Chemistry for Hong Kong A-Level Book 3A154
O
O
Naming of acids derivativesNaming of acids derivatives
Ester : oic acid to oate preceded by R group of ROH
ethyl propenoateOr, ethyl acrylate
New Way Chemistry for Hong Kong A-Level Book 3A155
O
O
Naming of acids derivativesNaming of acids derivatives
Ester : oic acid to oate preceded by R group of ROH
ethyl 2-methylpropenoate2 1 Or
ethyl 2-methylacrylate
New Way Chemistry for Hong Kong A-Level Book 3A156
Naming of acids derivativesNaming of acids derivatives
Amides : oic acid to amide
NH2
O
ethanamide
New Way Chemistry for Hong Kong A-Level Book 3A157
Naming of acids derivativesNaming of acids derivatives
Amides : oic acid to amide
HN
O
N-methyl
ethanamide
NO spacing
Or, N-methylacetamide
New Way Chemistry for Hong Kong A-Level Book 3A158
Naming of acids derivativesNaming of acids derivatives
Amides : oic acid to amide
N
O
N,N-dimethyl
ethanamide
New Way Chemistry for Hong Kong A-Level Book 3A159
N
O
Naming of acids derivativesNaming of acids derivatives
Amides : oic acid to amide
N-ethyl ethanamide
-N-methyl
Or
N-ethyl-N-methylacetamide
New Way Chemistry for Hong Kong A-Level Book 3A160
7.7. Halogeno hydrocarbonsHalogeno hydrocarbons
Hydrocarbons containing at least one halogen atom
R – X X : halogens
New Way Chemistry for Hong Kong A-Level Book 3A161
-F fluoro
-Cl chloro
-Br bromo
-I iodo
7.7. Halogeno hydrocarbonsHalogeno hydrocarbons
Hydrocarbons containing at least one halogen atom
Always treated as substituents (shown by prefixes)
New Way Chemistry for Hong Kong A-Level Book 3A162
7.7. Halogeno hydrocarbonsHalogeno hydrocarbons
Examples : -
C Br
H
H
H
C Br
H
H
Br
bromomethane dibromomethane
New Way Chemistry for Hong Kong A-Level Book 3A163
7.7. Halogeno hydrocarbonsHalogeno hydrocarbons
Examples : -
C Br
F
F
F
C F
Br
Cl
F
bromotrifluoromethane
bromochlorodifluoromethane
BTM
BCF
Both are used in fire extinguishers
New Way Chemistry for Hong Kong A-Level Book 3A164
7.7. Halogeno hydrocarbonsHalogeno hydrocarbons
Examples : -
Br Br
Br
bromobenzene
1,2-dibromobenzene
New Way Chemistry for Hong Kong A-Level Book 3A165
7.7. Halogeno hydrocarbonsHalogeno hydrocarbons
Examples : -Br
Cl
Br
Cl
1
41
4
1-bromo-4-chlorobenzene
4-bromo-1-chlorobenzene
New Way Chemistry for Hong Kong A-Level Book 3A166
7.7. Halogeno hydrocarbonsHalogeno hydrocarbons
Examples : -Br
Cl
Cl1
2
4
Br
Cl
Cl
1
2
5
1-bromo-2,4-dichlorobenzene
2-bromo-1,5-dichlorobenzene
New Way Chemistry for Hong Kong A-Level Book 3A167
7.7. Halogeno hydrocarbonsHalogeno hydrocarbons
Examples : -Br
Cl
Cl
1
3
4
Br
Cl
Cl
4
2
1
4-bromo-1,2-dichlorobenzene
New Way Chemistry for Hong Kong A-Level Book 3A168
7.7. Halogeno hydrocarbonsHalogeno hydrocarbons
Examples : -Br
Br
Br
Br
Br
Br
hexabromobenzene
New Way Chemistry for Hong Kong A-Level Book 3A169
1,1-dichlorobutane
2,2-dichlorobutane
Cl
Cl
Cl
Cl
Q.10
All acyclic structures of C4H8Cl2
New Way Chemistry for Hong Kong A-Level Book 3A170
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
1,2-dichlorobutane1,3-dichlorobutane
1,4-dichlorobutane
2,3-dichlorobutane
**
* chiral centre, optical isomers exist
Q.10
New Way Chemistry for Hong Kong A-Level Book 3A171
Cl Cl
1,1-dichloro-2-methylpropane
1
2 3
Q.10
2-(dichloromethyl)propan
e
Cl Cl
12
3
New Way Chemistry for Hong Kong A-Level Book 3A172
Cl Cl
Cl
Cl
Cl
Cl
1,1-dichloro-2-methylpropane
1,2-dichloro-2-methylpropane
1,3-dichloro-2-methylpropane
1
1
1
2
2
2
3
3
3
Q.10
New Way Chemistry for Hong Kong A-Level Book 3A173
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
New Way Chemistry for Hong Kong A-Level Book 3A174
8.8. AminesAmines
Naming amines derived from hydrocarbonsThe amino group, is always treated as the principal functional group and expressed as suffix. e replaced by amine methanami
neethenamine
(ethylenamine)
NH2
NH2
NH2 ethynamine (acetylenamine)
New Way Chemistry for Hong Kong A-Level Book 3A175
8.8. AminesAmines
Naming amines with functional groups other than CC, C=C, X- and RO-
The amino group, is always treated as the substituent and expressed as prefix, amino-
NH2
HO2-aminoethanol
1
2
New Way Chemistry for Hong Kong A-Level Book 3A176
8.8. AminesAmines
Examples : -
NH
NH
N-methyl
methanamine
ethanamine
N-methyl
2° amine
New Way Chemistry for Hong Kong A-Level Book 3A177
8.8. AminesAmines
N
N
3° amine
ethanamine
N,N-dimethyl
methanamine
N,N-dimethyl
New Way Chemistry for Hong Kong A-Level Book 3A178
8.8. AminesAmines
NH2 NOT benzenamine
phenylamine or aniline
New Way Chemistry for Hong Kong A-Level Book 3A179
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
New Way Chemistry for Hong Kong A-Level Book 3A180
8.8. AminesAmines
NH2 2-methylaniline
NH N-methylaniline
N-phenylmethanamine
New Way Chemistry for Hong Kong A-Level Book 3A181
8.8. AminesAmines
NH2
1-phenylmethanamine
New Way Chemistry for Hong Kong A-Level Book 3A182
8.8. AminesAmines
NH2
NH2
12
3
32
1
Prop-2-en-1-amine
Prop-1-en-2-amine
New Way Chemistry for Hong Kong A-Level Book 3A183
8.8. AminesAmines
NH2
NH2
linear 1
23
4
but-3-yne-1,2-diamine
New Way Chemistry for Hong Kong A-Level Book 3A184
8.8. AminesAmines
NH2
NH
123
propane-1,2-diamine
N2-ethyl
New Way Chemistry for Hong Kong A-Level Book 3A185
Q.11NH2
OH
NH2
NH2
NH2
COOH
2-aminophenol
benzene-1,2-diamine
2-aminobenzoic acid
New Way Chemistry for Hong Kong A-Level Book 3A186
Q.11
NH
NH2
123
4
1
234
5
N-methylbutan-1-amine
pentan-2-amine
New Way Chemistry for Hong Kong A-Level Book 3A187
Q.11
NH2
NH2
1butan-1-amine
2 butan-2-amine
New Way Chemistry for Hong Kong A-Level Book 3A188
Q.11
HN
NH2
NH
1
23
propane-1,2-diamine
N1-ethylpropane-1,2-diamine
123
4 N-methylbutan-2-amine
New Way Chemistry for Hong Kong A-Level Book 3A189
N
O
Q.11N-ethyl
ethanamine 2-methoxyN-methyl
1
2
N-ethyl-2-methoxy-N-methylethanamine
New Way Chemistry for Hong Kong A-Level Book 3A190
N
O
Q.11ethanamine
1
2
N-(2-methoxyethyl)
N-methyl
N-(2-methoxyethyl)-N-methylethanamine
3 substituents > 2 substituents
New Way Chemistry for Hong Kong A-Level Book 3A191
Q.11
N
O
propan-1-amine1
2
3
1
2
N-(2-methoxyethyl)
N-methyl
N-(2-methoxyethyl)-N-methylpropan-1-amine
New Way Chemistry for Hong Kong A-Level Book 3A192
Q.11
N
O
12
3 propan-2-amine
1 2
N-(2-methoxyethyl)
N-methyl
N-(2-methoxyethyl)-N-methylpropan-2-amine
New Way Chemistry for Hong Kong A-Level Book 3A193
9.9. NitrilesNitriles
Containing the cyano group, -CN
New Way Chemistry for Hong Kong A-Level Book 3A194
9.9. NitrilesNitriles
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.
New Way Chemistry for Hong Kong A-Level Book 3A195
9.9. NitrilesNitriles
Examples : -
C N
C
N
ethanenitrile
1
23
2-methylpropanenitrile
The carbon of the -CN group is counted as part of the longest carbon chain.
New Way Chemistry for Hong Kong A-Level Book 3A196
9.9. NitrilesNitriles
Examples : -
C N
C
N
ethanenitrile
1
23
2-methylpropanenitrile
No need to specify its position.
The -CN group always occupies the terminal position.
New Way Chemistry for Hong Kong A-Level Book 3A197
9.9. NitrilesNitriles
C
N
OH
12345
4-hydroxypentanenitrile
New Way Chemistry for Hong Kong A-Level Book 3A198
9.9. NitrilesNitriles
HOOC
C
N
21 3
propanoic acid
3-cyano-2-methyl
If used as prefix, its carbon is not counted as part of the main carbon chain
New Way Chemistry for Hong Kong A-Level Book 3A199
9.9. NitrilesNitriles
HOOC
C
N
21
3
propanoic acid
2-(cyanomethyl)
Only one substituent
New Way Chemistry for Hong Kong A-Level Book 3A200
10.10. Poly-functional Poly-functional compoundscompounds
With two or more functional groups
New Way Chemistry for Hong Kong A-Level Book 3A201
10.10. Poly-functional Poly-functional compoundscompounds
With identical functional groups
buta-1,3-diene
buta-1,3-diyne1
1
2
2
3
3
4
4
New Way Chemistry for Hong Kong A-Level Book 3A202
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
New Way Chemistry for Hong Kong A-Level Book 3A203
10.10. Poly-functional Poly-functional compoundscompounds
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
With identical functional groups
New Way Chemistry for Hong Kong A-Level Book 3A204
10.10. Poly-functional Poly-functional compoundscompounds
With identical functional groups
NH2
H2N
OOO
hexane-1,6-diamine
heptane-2,4,6-trione
New Way Chemistry for Hong Kong A-Level Book 3A205
10.10. Poly-functional Poly-functional compoundscompounds
With identical functional groups
propane-1,2,3-triol
HO OH
OH
12
3
New Way Chemistry for Hong Kong A-Level Book 3A
OH OH
OH
OH OH
xylitol
1 2 3 4 5
pentane-1,2,3,4,5-pentol
206
New Way Chemistry for Hong Kong A-Level Book 3A207
10.10. Poly-functional Poly-functional compoundscompounds
With different functional groups
H2N COOH
COOH
OH
2-aminoethanoic acid
or glycine
2-hydroxypropanoic acid
12
123
New Way Chemistry for Hong Kong A-Level Book 3A208
10.10. Poly-functional Poly-functional compoundscompounds
With different functional groups
(2E)-hept-2-en-6-yn-1-ol
OH
1
6
2
34
57
New Way Chemistry for Hong Kong A-Level Book 3A209
10.10. Poly-functional Poly-functional compoundscompounds
Naming : -
1. The functional group with the highest priority (the principal functional group) is expressed as the suffix.
New Way Chemistry for Hong Kong A-Level Book 3A210
N
+
C
HO
O> >
-OH > -NH2 > CC > C=C > -OR = X
C
H
O C O-CN > > >
O
OO
R
C
RO
O C
X
O C
H2N
O> >> >
New Way Chemistry for Hong Kong A-Level Book 3A211
10.10. Poly-functional Poly-functional compoundscompounds
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
New Way Chemistry for Hong Kong A-Level Book 3A212
10.10. Poly-functional Poly-functional compoundscompounds
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)
New Way Chemistry for Hong Kong A-Level Book 3A213
14
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)
New Way Chemistry for Hong Kong A-Level Book 3A214
(2Z)-3-hydroxypent-2-enoic acid
Worked examples : -
(a)COOH
OH
1234
5
C2 : COOH > H atomic masses are
comparedC3 : OH > CH2C
Z
New Way Chemistry for Hong Kong A-Level Book 3A215
Worked examples : -
(b)
COOH
OH
linear
12
34
5
(2Z)-3-hydroxypent-2-en-4-ynoic acid
Z
C2 : COOH > HC3 : OH > CC
New Way Chemistry for Hong Kong A-Level Book 3A216
Worked examples : -
(c)
HOOC COOH
OH
12
34
5
(2Z)-3-hydroxypent-2-enedioic acid
Z
C2 : COOH > HC3 : OH > CH2C
New Way Chemistry for Hong Kong A-Level Book 3A217
Worked examples : -
(d)
HOOC COOH
OH
O
12
34
5
(3Z)-3-hydroxy-2-oxopent-3-enedioic acid
124
35
(2Z)-3-hydroxy-4-oxopent-2-enedioic acid
New Way Chemistry for Hong Kong A-Level Book 3A218
HOOC COOH
OH
CN
Worked examples : -
(e)
12
345
(2Z)-4-cyano-3-hydroxypent-2-enedioic acid
New Way Chemistry for Hong Kong A-Level Book 3A219
Worked examples : -
(f)
C
N
O H
12
345
4-formylpentanenitrile
New Way Chemistry for Hong Kong A-Level Book 3A220
Worked examples : -
(f)
C
N
O H
4-methyl-5-oxopentanenitrile
12
34
5
New Way Chemistry for Hong Kong A-Level Book 3A221
COOH
OH
O
H
Worked examples : -
(g)1
2
34
5
Carbonyl C is counted as part of the main carbon
chain3-hydroxy-5-oxopentanoic acid3-hydroxy-4-formylbutanoic acid
The one with the longer C chain is preferred
New Way Chemistry for Hong Kong A-Level Book 3A222
HOOC COOH
OH
O
OH
Worked examples : -
(h)
5 1234
(2Z)-2-formyl-3-hydroxy-4-oxopent-2-enedioic acid
New Way Chemistry for Hong Kong A-Level Book 3A223
HOOC COOH
OH
O
OH
Worked examples : -
(h)
5 1234
(2Z)-2-formyl-3-hydroxy-4-oxopent-2-enedioic acid
C2 : COOH = CHO;
COOH = CHO;
COOH > CHO
C3 : OH > COC;
Z
New Way Chemistry for Hong Kong A-Level Book 3A224
Worked examples : -
(i) O
COOH
NH2
12
34
5
5-amino-5-oxopentanoic acid4-(aminocarbonyl)butanoic acid
New Way Chemistry for Hong Kong A-Level Book 3A225
HOOC COOH
OH
O
NH2O
Worked examples : -
(j)
12345
2-(aminocarbonyl)3-hydroxy
4-oxo
2-(aminocarbonyl)-3-hydroxy-4-oxopentanedioic acid
2A4O > 4A2O
New Way Chemistry for Hong Kong A-Level Book 3A226
HOOC COOH
OH
O
NH2O
Worked examples : -
(j)
12345
2-(aminocarbonyl)3-hydroxy
4-oxo 2A4O > 4A2OIf the same set of numbers is obtained from either
direction, substituents are numbered in alphabetical order
New Way Chemistry for Hong Kong A-Level Book 3A227
COOH
O
Cl
Worked examples : -
(k)2
13
45
5-chloro-5-oxopentanoic acid
New Way Chemistry for Hong Kong A-Level Book 3A228
HOOC COOH
OH
O
ClO
Worked examples : -
(l)
12345
2-(chlorocarbonyl)3-hydroxy
4-oxo
2-(chlorocarbonyl)-3-hydroxy-4-oxopentanedioic acid
2C4O > 4C2O
New Way Chemistry for Hong Kong A-Level Book 3A229
Worked examples : -
(m) COOH
O
O
12
34
5
5-methoxy-5-oxopentanoic acid
New Way Chemistry for Hong Kong A-Level Book 3A230
HOOC COOH
OH
O
OO
Worked examples : -
(n)
5 1234
2-(methoxycarbonyl)3-hydroxy
4-oxo
3-hydroxy-2-(methoxycarbonyl)-4-oxopentanedioic acid
New Way Chemistry for Hong Kong A-Level Book 3A231
Worked examples : -
(o)COOH
O
OO
12
34
5
5-(ethanoyloxy)-5-oxopentanoic acid
New Way Chemistry for Hong Kong A-Level Book 3A232
Worked examples : -
(p)HOOC COOH
O O
O
12
34
5
3-carbonyl
3-(oxycarbonyl)3-[(ethanoyloxy)carbonyl]
pentanedioic acid
3-[(ethanoyloxy)carbonyl]pentanedioic acid
New Way Chemistry for Hong Kong A-Level Book 3A233
HOOC COOH
O
O
O
O
Worked examples : -
(p) 12
34
5
3-carbonyl
3-(oxycarbonyl)3-[(carbonyloxy)carbonyl]
pentanedioic acid
3-{[(methoxycarbonyl)oxy]carbonyl}pentanedioic acid
3-{[(methoxycarbonyl)oxy]carbonyl}
New Way Chemistry for Hong Kong A-Level Book 3A234
N
COOH
+
Worked examples : -
(q)
ethanaminium ion
N-carboxy-N,N-dimethyl
6B
New Way Chemistry for Hong Kong A-Level Book 3A235
N
COOH
COOH
+
Worked examples : -
(r)
ethanaminium ion
N,N-dicarboxy-
N-methyl
New Way Chemistry for Hong Kong A-Level Book 3A236
Propane-1,2,3-tricarboxylic acid
Or
Propane-1,2,3-trioic acid
HOOC COOH
COOH
Worked examples : -
(s) 12
34
51
2
3
3-carboxypentanedioic acid
Citric acid
New Way Chemistry for Hong Kong A-Level Book 3A237
Worked examples : -
(t)
HOOC COOH
COOH
COOH
32 1
propane-1,1,2,3-tetracarboxylic acid
New Way Chemistry for Hong Kong A-Level Book 3A
O
OH
OH
O
OH
O OH
1
2
3
4
5
1,1,5-tricarboxylic acid
5-hydroxypenta-1,4-diene-
(4Z)-
238
New Way Chemistry for Hong Kong A-Level Book 3A239
COOH
O
H2N
3-amino-3-oxopropanoic acid
Q.12(a)
New Way Chemistry for Hong Kong A-Level Book 3A240
HOOC COOH
O NH2
3-(aminocarbonyl)pentanedioic acid
Q.12(a)
New Way Chemistry for Hong Kong A-Level Book 3A241
COOH
O
H
4-oxobutanoic acid
Q.12(b)
New Way Chemistry for Hong Kong A-Level Book 3A242
HOOC COOH
H O3-formylpentanedioic acid
Q.12(b)
New Way Chemistry for Hong Kong A-Level Book 3A243
OC
HN
3-oxopropanenitrile
Q.12(c)
New Way Chemistry for Hong Kong A-Level Book 3A244
N CCOOH
4-cyanobutanoic acid
Q.12(c)
New Way Chemistry for Hong Kong A-Level Book 3A245
COOH
C
N
4-cyanopentanoic acid
Q.12(c)
New Way Chemistry for Hong Kong A-Level Book 3A246
HOOC COOH
O O
3-(methoxycarbonyl)pentanedioic
acid
Q.12(d)
New Way Chemistry for Hong Kong A-Level Book 3A247
O COOH
O
4-methoxy-4-oxobutanoic acid
Q.12(d)
New Way Chemistry for Hong Kong A-Level Book 3A248
O
O
COOH
3-(acetyloxy)propanoic acid
Q.12(d)
New Way Chemistry for Hong Kong A-Level Book 3A249
COOH
OCl
5-chloro-4-methyl-5-oxopentanoic acid
Q.12(e)
New Way Chemistry for Hong Kong A-Level Book 3A250
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)
New Way Chemistry for Hong Kong A-Level Book 3A251
HOOC COOH
O Cl
3-(chlorocarbonyl)pentanedioic acid
Q.12(e)
New Way Chemistry for Hong Kong A-Level Book 3A252
HOOC COOH
OCl
O Br
3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid
Q.12(e)
New Way Chemistry for Hong Kong A-Level Book 3A253
hexanedioyl dichloride
Q.12(f)
Cl
O
Cl
O
New Way Chemistry for Hong Kong A-Level Book 3A254
6-bromo-6-oxohexanoyl chloride
Q.12(e)
Cl
O
Br
O
12
34
566
54
32
1
6-chloro-6-oxohexanoyl bromide
New Way Chemistry for Hong Kong A-Level Book 3A255
HOOC COOH
OCl
O Br
3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid
Q.12(e)
New Way Chemistry for Hong Kong A-Level Book 3A256
HOOC COOH
OCl
O Br
3-(bromocarbonyl)-2-(chlorocarbonyl)pentanedioic acid
Q.12(e)
New Way Chemistry for Hong Kong A-Level Book 3A257
Cyclohexylamine
NH2
Q.13(a)
New Way Chemistry for Hong Kong A-Level Book 3A258
Benzene-1,3-dioic acid
COOH
COOH
1
3
Q.13(b)
New Way Chemistry for Hong Kong A-Level Book 3A259
OH
HO
(3E)-hept-3-ene-2,5-diol
12
3
5
Q.13(c)
New Way Chemistry for Hong Kong A-Level Book 3A260
Propane-1,2,3-triol
OH
OHHO
12
3
Q.13(d)
New Way Chemistry for Hong Kong A-Level Book 3A261
1,2-dichloro-1,1,2,2-tetrafluoroethane
ClCl
F
F
F
F
1 2
Q.13(e)
New Way Chemistry for Hong Kong A-Level Book 3A262
Methyl 2-methylpropenoate
O
O1
2
Q.13(f)
New Way Chemistry for Hong Kong A-Level Book 3A263
3-hydroxy-2,4-dioxohex-5-enal
HO
OH
O
O
32 4
51
Q.13(g)
New Way Chemistry for Hong Kong A-Level Book 3A264
3-ethoxypentanedioic acid
HOOC COOH
O
3
Q.13(h)
New Way Chemistry for Hong Kong A-Level Book 3A265
OH
Br
Br
COOH
(5E)-5,6-dibromo-4-hydroxyhex-5-en-2-ynoic acid
12
56 4
Q.13(i)
New Way Chemistry for Hong Kong A-Level Book 3A266
Cyclohexa-2,5-dien-1-ol
OH1
2
5
Q.13(j)
New Way Chemistry for Hong Kong A-Level Book 3A267
4-bromo-5,5-dichlorocyclohex-2-en-1-ol
OH
ClCl
Br
1
4
5
Q.13(k)
New Way Chemistry for Hong Kong A-Level Book 3A268
1-butyl-2,4,5-trimethylbenzene
1
2
4
5
Q.13(l)
New Way Chemistry for Hong Kong A-Level Book 3A269
Pentan-2-ylbenzene
Q.13(m)
New Way Chemistry for Hong Kong A-Level Book 3A270
CH3 CH3
(2Z)-pent-2-en-2-ylbenzene
CH2 CH3
pent-1-en-2-ylbenzene
CH3
(1Z)-pent-1-en-1-ylbenzene
CH3
(3Z)-pent-3-en-1-ylbenzene
New Way Chemistry for Hong Kong A-Level Book 3A271
O
O
HO O
aspirin caffeine
aspirinQ.14
All C atoms are sp2 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A272
O
O
HO O
aspirin caffeine
Analgesic
O
O
HO O
Ester
carboxylC9H8O4
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A273
N
N
N
N
H
CH3
O
O
H3C
CH3
Caffeine
Q.14
sp3 hybridized
sp2 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A274
N
N
N
N
H
CH3
O
O
H3C
CH3
N
N
N
N
H
CH3
O
O
H3C
CH3Tertiary amide
carbonyl
Tertiary amino
Tertiary amino
C=N bond
C=C bond
C8H10N4O2Q.14
New Way Chemistry for Hong Kong A-Level Book 3A275
HO NH
O
Acetaminophen
Q.14
sp2 hybridized
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A276
HO NH
O
Acetaminophen
HO NH
Ohydroxyl
Secondary amide
C8H9NO2
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A277
HO
HO
NH
OH
Adrenalin
Q.14
sp2 hybridized
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A278
HO
HO
NH
OH
Adrenalin
HO
HO
NH
OH
hydroxyl
Secondary amino
C9H13NO3
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A279
HO
HONH2
Dopamine
A neurotransmitter – A deficiency is associated with Parkinson’s disease
Q.14
sp2 hybridized
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A280
HO
HONH2
Dopamine
A neurotransmitter – A deficiency is associated with Parkinson’s disease
HO
HONH2
hydroxylPrimary amino
C8H11NO2
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A281
OH
Menthol – from peppermint oil
Q.14
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A282
OH
Menthol – from peppermint oil
OH
hydroxyl
C10H20O
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A283
ClCl
Cl
ClCl
DDT
Insecticide
Q.14 sp2 hybridized
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A284
ClCl
Cl
ClCl
DDT
Insecticide
ClCl
Cl
ClCl
Chloro
C14H9Cl5
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A285
HO OH
O
O
phenolphthalein
Q.14
sp2 hybridized
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A286
HO OH
O
O
phenolphthalein
HO OH
O
O
hydroxyl
Ester
Q.14
C20H14O4
New Way Chemistry for Hong Kong A-Level Book 3A
N
N
nicotine287
Insecticide
Q.14
sp2 hybridized
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A288
N
N
N
N
nicotine
Insecticide
Tertiary aminoC=N
Q.14
C10H14N2
New Way Chemistry for Hong Kong A-Level Book 3A289
2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)
Q.14
sp2 hybridized
O
O
Cl
Cl
Cl
Cl
dioxin
New Way Chemistry for Hong Kong A-Level Book 3A
O
O
Cl
Cl
Cl
Cl
290
One of the most toxic chemical known – A class 1 carcinogen Ether
Chloro Chloro
C12H4O2Cl
4
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A291
N
O
NH
O
OHO
O
Anti-hypertensive
Q.14
sp2 hybridized
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A292
N
O
NH
O
OHO
O
Anti-hypertensiveC20H28N2O5
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A
NH
O
O
N
O
OHO
enalapril293
Ester
Carboxyl
Tertiary amide
Secondary amino
Anti-hypertensiveC20H28N2O5
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A
O
O
N O
O
cocaine294
A local anestheticQ.14
sp2 hybridized
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A295
A local anesthetic
Tertiary amino
O
O
N O
O
O
O
N O
O
cocaine
Ester
C17H21NO4
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A
O OHO
N
codeine296
Addictive cough medicine
Q.14
sp2 hybridized
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A
O OHO
N
codeine
O OHO
N
297
Addictive cough medicine
Ether
Tertiary amino
Hydroxyl
C=C bond
C18H21NO3
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A
O OHHO
N
morphine298
A potent addictive analgesic from opium
Q.14
sp2 hybridized
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A
O OHHO
N
morphine299
O OHHO
N
A potent addictive analgesic from opium
Ether
Hydroxyl Hydroxyl
Tertiary amino
C=C bond
C17H19NO3
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A300
O OO
N
O O
heroin
Acetylated morphine
Q.14
sp2 hybridized
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A301
O OO
N
O O
heroin
Acetylated morphine
O OO
N
O O
Tertiary amino
Ester
Ester
Ether
C=C bond
C21H23NO5
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A302
O OHO
N
etorphine
OH
Tranquilizer for elephants – 2000 times more potent than morphine
Q.14
sp2 hybridized
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A303
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
New Way Chemistry for Hong Kong A-Level Book 3A304
O
N
methadone
Narcotic analgesic
Q.14
sp2 hybridized
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A305
O
N
methadone
Narcotic analgesic
O
NTertiary amino
Carbonyl C21H27NO
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A306
SO
O
NN
O
N
NHO
N
N
SO
O
NN
O
N
NHO
N
N
viagra
You don’t need it !
Q.14
sp2 hybridized
sp3 hybridized
New Way Chemistry for Hong Kong A-Level Book 3A307
SO
O
NN
O
N
NHO
N
N
SO
O
NN
O
N
NHO
N
N
viagraEther
Tertiary amino
C=C
Secondary amide
C=N
C22H30N6O4S
Q.14
New Way Chemistry for Hong Kong A-Level Book 3A308
O
O
OH
O CH3
Aspirin
Analgesics and antipyretics
2-(acetyloxy)benzoic acid
1
2
New Way Chemistry for Hong Kong A-Level Book 3A309
OH
NH CH3
O Acetaminophen
Analgesics and antipyretics
N-(4-hydroxyphenyl)acetamide
1
4
New Way Chemistry for Hong Kong A-Level Book 3A310
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
23
4
51
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
New Way Chemistry for Hong Kong A-Level Book 3A311
OH
OH
OH
NH
CH3 CH3
CH3 Albuterol
Treating asthma, emphysema and chronic
bronchitis
4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
1
241
2
New Way Chemistry for Hong Kong A-Level Book 3A
Camphor(樟腦 )
1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
12
345
6
7
New Way Chemistry for Hong Kong A-Level Book 3A
NHCH3
O
Cl
Ketamine( 氯胺酮 )Ketamine( 氯胺酮 )
C13H16ClNO
1
2
12
313
cyclohexanone
2-(2-chlorophenyl)
2-(methylamino)
2-(2-chlorophenyl)
-2-(methylamino)
New Way Chemistry for Hong Kong A-Level Book 3A
NHCH3
O
O
Cl
12
3
12
314
3-(2-chlorophenyl)-3-(methylamino)cyclohexane-1,2-dione
New Way Chemistry for Hong Kong A-Level Book 3A
NHCH3
O
O
Cl
12
3
6
12
315
6-(2-chlorophenyl)-6-(methylamino)cyclohex-3-ene-1,2-dione
New Way Chemistry for Hong Kong A-Level Book 3A316
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
OCH3
Name it !