Nomenclature in Organic Compounds

Nomenclature in
Organic Compounds
1
New Way Chemistry for Hong Kong A-Level Book 3A
Functional Groupings of Organic Compounds
alkadienes, etc.
cycloalkadienes, etc.
Huckel rule
2
Functional Grouping
• Organic compounds can be grouped according
to the functional group they possess.
• A functional group is the characteristic reaction
unit of an organic compound.
Examples include:
R-OH – alcohol R-COOH –Carboxylic acid
R-O-R – ether O O
R-NH2 – amine R-C-H; R-C-R
Alkanal; Alkanone
3
Nomenclature of
Alkanes
IUPAC Conventions
4
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
Cycloalkanes are alkanes in which all or
some of the carbon atoms are arranged in a
5
ring
Straight-Chain Alkanes
Number of Condensed
Name
carbon atoms structural formula
CH4
Methane 1
CH3CH3
Ethane 2
Propane 3 CH3CH2CH3
Butane 4 CH3(CH2)2CH3
Pentane 5 CH3(CH2)3CH3
Hexane 6 CH3(CH2)4CH3
Heptane 7 CH3(CH2)5CH3
Octane 8 CH3(CH2)6CH3
Nonane 9 CH3(CH2)7CH3
6 Decane 10
CH3(CH2)8CH3
The First Three Members of Alkanes
Methane Ethane Propane

(CH4) (CH3CH3) (CH3CH2CH3)
7
Cycloalkanes in skeletal forms
Angle strain arises from repulsions between

adjacent bond pairs
Most stable due to less

8
angle strain
All carbon atoms in alkanes are sp3 hybridized -
zigzag
H2
C CH3
H3C C
H2
CH3
CH
H3C CH3
9
C5H12
H2 H2
C C
H3C C CH3
H2
CH3
CH CH3
H3C C
H2
CH3
C
H3C CH3
CH3
10
C6H14
11
Rules for Naming Branched-Chain Alkanes
1. Name the longest possible straight chain

 give the parent name for the
alkane
2. Name the substituent groups – the branches
CnH2n+1– Alkyl groups (derived from alkanes)

CH3 – methyl
C2H5 – ethyl
12
C 3 H7 –
H2
C propyl
H3C C
H2
H3C
CH isopropyl
H3C
13
C 4 H9 –
H3C
H2 H2 CH
sec-butyl
C C
H3C C
H2 H2C secondary, 2
carbon
butyl CH3
H3C
H3C tert-butyl
CH C
H2 H3C C
H3C tertiary, 3
H3C
carbon
isobutyl
14
3. Number the positions of the substituent
groups with the smallest possible numbers
2-methyl
2-methylbutane
15
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
16
2
tetramethyl
tetramethylmethane propane
2,2-dimethylpropane
17
Cl
Cl
1 5
Cl
1,5,5-trichloro
1,5,5-trichlorohexane
18
Cl
Cl
6 2
1 5
Cl
1,5,5-trichloro 
2,2,6-trichloro 
‘Lowest numbers’ does NOT refer to the
smallest sum
19
5. If two or more different substituent groups
exist, they are named in alphabetical order
but NOT in numerical order of their positions.
2,2-dimethyl
3-ethyl
3 3-ethyl-2,2-dimethylpentane
2
prefix is not
considered
20
3
tert-butyl
3-ethyl-2,2-dimethylpentane 
3-tert-butylpentane 
21
Naming Alkenes (CnH2n)
Containing at least 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
22
First member is ethene (ethylene)
Cyclic structures are possible
cyclopropene cyclobutene
cyclopentene cyclohexene
23
1 pent-1-ene
2
pent-2-ene
24
GeometricalIsomerism
Geometrical Isomerism
e.g. cis-but-2-ene and trans-but-2-ene
25
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
26
2
pent-2-ene
trans (2E)-pent-2-ene
GeometricalIsomerism
Geometrical Isomerism
cis
(2Z)-pent-2-ene
27
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
28
CH3
2 3
(2Z)-3-methylpent-2-ene
1
H3C CH3
CH3
2 3
(2E)-3-methylpent-2-ene
1
H3C CH3
29
2-methylbut-1-ene
1 2
2-methylbut-2-ene
2
3-methylbut-1-ene
3 1
Functional group has a higher priority than
branches
30
cyclopentane
methylcyclobutane
31
1,2-dimethylcyclopropane
ethylcyclopropane
1,1-dimethylcyclopropane
32
Naming 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
33
C atoms in triple bond are sp hybridized
 Linear
 Cyclic structures are highly unstable
due to great angle strain
90 << 180
34
In naming alkenes and alkynes,
the ‘longest’ carbon chain need NOT be the
one that contains the multiple bond.
2-ethylpent-1-ene 
35
In naming alkenes and alkynes,
the ‘longest’ carbon chain need NOT be the
one that contains the multiple bond.
1
3
3-methylenehexane 
36
Q.5(a)
2
5
(2E)-5-methylhex-2-ene
Functional group has the higher priority

than branch.
37
Q.5(b
)
1
3
(3E)-penta-1,3-diene
38
Q.5(c)
1 5
4 2
2 4
5 3 1 3
1,3 > 2,4
39
Q.5(c
1
)
3
(3E)-pent-3-en-1-yne
NOT ene
40
Q.5(d
)
1 5
4 3
5 1 4
2 2 3
1,3 > 2,4

although -yne has the smaller number
41
Q.5(d)
1
4 3
5
2
pent-1-en-3-yne
NOT ene
42
Q.5(e)
1
4 4
1
pent-4-en-1-yne 
pent-1-en-4-yne 
If the same set of numbers is obtained by
counting in either direction, the number is
assigned in alphabetical order. Refer to 5(i)
43
In naming hydrocarbons, cyclic structures
always have higher priority than C=C, CC.
ethenylcyclohexane ethynylcyclohexane
44
Also, cyclic structure rather than the length
of the carbon chain is first considered.
heptylcyclohexane
45
1
3
but-3-en-1-ylcyclohexane
The C directly bonded to the ring is

assigned the lowest possible number
46
1
2
3
2

In naming cyclic hydrocarbons, the side
branches are numbered in alphabetical order.
1-ethyl
2
1 2-methyl
1-ethyl-2-methylcyclohexane
48
2 1-methyl
1
2 2-(propan-2-yl)
1-methyl-2-(propan-2-yl)cyclohexane
49
1-butan-2-yl
2
1 2-methyl
1-(butan-2-yl)-2-methylcyclohexane
50
Q.6
propan-2-ylcyclopropane
1,2-dimethyl-3-(propan-2-yl)cyclopropane
51
Q.6 3
1 2
prop-1-en-1-yl
(2-methylprop-1-en-1-yl)
(2-methylprop-1-en-1-yl)cyclobutane
52
Q.6
1-methylcyclobutene
2-methylcyclobutene
53
Q.6
3 2
3-methylcyclobutene
4 1
4-methylcyclobutene
54
Q.6
3 2
3-methylcyclobutene
2 1
3 4
55
(d) Aromatic hydrocarbons
With a total of (4n + 2)  electrons in the

conjugated system
(alternating single and double bonds)
56
(d) Aromatic hydrocarbons
C6H5 –  phenyl group
C10H7 –  naphthyl group
Both are aryl groups
57
2. Hydroxy compounds
Organic compounds with one or more

hydroxyl groups, –OH.
58
(a) Alkanols (alcohols)
Derived from alkanes

Contain one or more –OH groups attached
to an alkyl group.
R – OH
Alkyl group Hydroxyl group
59
Hydroxy derivative of alkane

Alkyl derivative of water
H replaced H replaced
by OH by R
RH ROH HOH
60
General formula : CnH2n+1OH (acyclic)

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

1 2 3
61
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.
62
5 1
4 3 2
OH
pentane
pentan-2-ol
63
OH
5 1
4 3 2
pentane
pentan-3-ol
64
1 5
2 3 4
OH OH
pentane
pentane-2,4-diol
‘e’ is retained in diol

65
(b) Phenols
Derived from aromatic hydrocarbons

Contain one or more –OH groups attached
to an aryl group
Ar – OH
Aryl group Hydroxyl group
66
OH OH
1 OH
phenol 2-hydroxyphenol 
Benzene-1,2-diol 
67
OH OH OH
1 Cl 1 1
2
3
Cl 4
Cl
2-chlorophenol 3-chlorophenol 4-chlorophenol

o-chlorophenol m-chlorophenol p-chlorophenol
o  ortho m  meta p  para
68
Q.8
1
2
4 4-methylhexan-2-ol
OH
6
1
5 4 2 4-methylpentan-2-ol
OH
69
Q.8 trans-
5 1
3 2
4
OH
- OH has a higher priority than C=C

pent-3-en-2-ol
(3E)-pent-3-en-2-ol
70
Q.8 Propan-2-yl
2
Menthol
( 薄荷 OH cyclohexanol
醇)
with
TWO branches
methyl
71
Q.8
menthol
2 OH 6 OH
3 1 5 1
4 6 4 2
5 3
2,5 > 3,6
5-methyl-2-(propan-2-yl)cyclohexanol
72
3. Ethers
Contain the oxy, –O-, group or
alkoxy, R-O- group
O oxy group
73
3. Ethers
Contain the oxy, –O-, group or
alkoxy, R-O- group
O Alkoxy group
74
3. Ethers
Alkyl derivatives of water
H 2H replaced R
by 2R
O O
H R
75
3. Ethers
Three classes of ethers : -
R Ar Ar H
a O b O c O o O
105
'R R 'Ar H
a,b,c,are all greater than 105 due to

stronger van der Waals’ repulsive forces
between bulky alkyl/aryl groups than
between H atoms
76
3. Ethers
Naming : -
The alkoxy groups are always treated as

substituents and expressed as prefixes.
77
Q.9
O
methoxy
ethane
methoxyethane

78
Q.9
methane
ethoxy
ethoxymethane 
79
Q.9
O
benzene
methoxy
methoxybenzene 
80
Q.9
O
phenoxy
methane
phenoxymethane

81
Q.9
1
2
3 O methoxy
propane
2-methoxypropane

82
4. Carbonyl compounds
Organic compounds with the carbonyl group,
C O
83
(a) Aldehydes
Products of dehydrogenation of alcohols
H
R
R C O H C O + H2
H
H
At least ONE H attached to C

R : alkyl, aryl or H
84
(a) Aldehydes
Examples : -
O
O O O
H
H H H H
methanal ethanal propanal benzaldehyde
–ane replaced by –anal
85
(a) Aldehydes
Examples : - propan-1-al O
O O O
H
H H H H
methanal ethanal propanal benzaldehyde
The aldehye group, –CHO, always occupies

the terminal position
 No need to specify its position
86
(b) Ketones
No H atom is directly attached to the
carbonyl group
R
C O
'R R, R’ : alkyl or aryl group
87
(b) Ketones
Examples : -
O O
propanone butanone
–ane replaced by –anone
88
(b) Ketones
Examples : -
O
3
2
O
pentan-2-one pentan-3-one
89
(b) Ketones
Examples : -
O O
4 2 2 3
4-methylpentan-2-one
2-methylpentan-3-one
90
(b) Ketones
Examples : -
O O O
3 2 4 2
O
pentane-2,4-dione
pentane-2,3-dione
91
5. Carboxylic acids
Organic compounds with the carboxyl group,
O
OH
92
5. Carboxylic acids
O
carbonyl
C
carboxyl
OH hydroxyl
93
5. Carboxylic acids
O
R C R : alkyl, aryl or H
OH
If R is an alkyl group, the compound is an
alkanoic acid, CnH2n+1COOH.
94
Carboxylic acids
Examples : -
O O O
OH OH OH
methanoic acid ethanoic acid propanoic acid
–ane replaced by –anoic acid
95
Carboxylic acids
Examples : -
O O O
OH OH OH
methanoic acid ethanoic acid propanoic acid
The carboxyl group, –COOH, always occupies

the terminal position
 No need to specify its position
96
Carboxylic acids
Examples : -
COOH COOH COOH
1 OH
1
2
3
benzoic acid 2-hydroxybenzoic 3-methylbenzoic

acid acid
97
Carboxylic acids
Examples : - cyclohexanecarboxylic
acid COOH
COOH COOH
benzoic acid cyclohexylethanoic

acid
cyclohexylacetic
acid
98
Carboxylic acids
Examples : -
HOOC
COOH
hexanedioic acid
99
Carboxylic acids
Examples : -
HOOC
6 1
COOH
hexanedioic acid
hexane-1,6-dioic acid 
100
Carboxylic acids
Examples : -
1
HOOC
4
COOH
hexanedioic acid
101
6. Acids derivatives
FOUR types : - acyl group
O O
OH replaced by Cl
R C R C
OH Cl
carboxylic acid acyl(acid) chloride
102
FOUR types : - acid anhydride
O
O
R C
R C
O H
H2O
O
OH
'R C
'R C
R  R’ for mixed acid O
O
anhydride
103
FOUR types : -
O O
H2O
R C + HO R' R C
O H O R'
ester
R : alkyl, aryl or H
R’ : alkyl or aryl
104
FOUR types : -
O O
H2O
R C + H NH2 R C
OH NH2
1° amide
N links to only ONE C
105
FOUR types : -
O O
H2O
R C + H NH R C
OH R' HN R'
1o amine
2°
amide
N links to TWO C atoms
106
FOUR types : -
O
O R''
H2O R C
R C + H N
N R'
OH R'
''R
2 amine
o
3° amide
N links to THREE C atoms
107
Naming of acids derivatives
Acyl chloride : oic acid to oyl chloride
O
ethanoyl chloride
Or
Cl
acetyl chloride
108
Acyl chloride : oic acid to oyl chloride
O
ethanoyl chloride
Cl
spacing
109
Acid anhydride : oic acid to oic anhydride
O
O ethanoic anhydride
spacing
O
110
Acid anhydride : oic acid to oic anhydride
O
ethanoic propanoic
anhydride
O
For mixed anhydride, the
parent acids are named in
alphabetical order
O
111
Ester : oic acid to oate preceded by R
group of ROH
O methyl ethanoate
O spacing
112
group of ROH
O ethyl propanoate
113
group of ROH
O ethyl propenoate
Or, ethyl acrylate
O
114
group of ROH
O ethyl 2-methylpropenoate
2 1
Or
O ethyl 2-methylacrylate
115
Amides : oic acid to amide
O
ethanamide
NH2
116
O Or, N-methylacetamide
N-methyl ethanamide
HN
NO spacing
117
O
N,N-dimethylethanamide
118
O
N-ethyl-N-methylethanamide
N
Or
N-ethyl-N-methylacetamide
119
7. Halogeno hydrocarbons
Hydrocarbons containing at least one
halogen atom
R–X
X : halogens
120
Hydrocarbons containing at least one
halogen atom
-F fluoro
-Cl chloro Always treated as
substituents
-Br bromo (shown by
-I iodo prefixes)
121
Examples : -
H H
H C Br H C Br
H Br
bromomethane dibromomethane
122
Examples : -
F
BTM
F C Br bromotrifluoromethane
F Both are used in
fire extinguishers
Br
Cl C F bromochlorodifluoromethane
BCF
F
123
Examples : -
Br Br
Br
bromobenzene 1,2-dibromobenzene
124
Examples : -
Br Br
1 4
4 1
Cl Cl
1-bromo-4-chlorobenzene 4-bromo-1-chlorobenzene
125
 
Examples : -
Br Br
1 Cl
2 Cl
2 1
4 5
Cl Cl
1-bromo-2,4-dichlorobenzene 
2-bromo-1,5-dichlorobenzene 
126
Examples : -
Br Br
1 4
4
3
Cl
1
2
Cl

Cl Cl
4-bromo-1,2-dichlorobenzene
127
Examples : -
Br
Br Br
Br Br
Br
hexabromobenzene
128
Q.10 All acyclic structures of C4H8Cl2
Cl
Cl 1,1-dichlorobutane
Cl
2,2-dichlorobutane
Cl
129
Cl
Q.10
Cl
1,2-dichlorobutane
*
Cl
* 1,3-dichlorobutane
Cl Cl
Cl 1,4-dichlorobutane
Cl
2,3-dichlorobutane
Cl
* chiral centre, optical isomers exist

130
Q.10 Cl 1
Cl
1,1-dichloro-2-methylpropane
2 
3
2-(dichloromethyl)propane
Cl Cl

2
1 3
131
Q.10 Cl 1
Cl
2 3
Cl
1
2
3
Cl
Cl
1
2 Cl
3
132
8. Amines
Derivatives of ammonia
H
N R Primary(1°) amine
H
H
NH3 N R Secondary(2°) amine

'R
''R
N R Tertiary (3°) amine

'R
133
8. Amines
Naming amines derived from hydrocarbons
The amino group, is always treated as the
principal functional group and expressed
as suffix. e replaced by amine
NH2 methanamine
NH2 ethenamine (ethylenamine

)
NH2 ethynamine (acetylenamine)
134
8. Amines
Naming amines with functional groups
other than CC, C=C, X- and RO-
The amino group, is always treated as the

substituent and expressed as prefix,
amino-
2
HO
1 2-aminoethanol
NH2
135
8. Amines
Examples : - 2° amine
NH N-methylmethanamine
N-methylethanamine
NH
136
8. Amines
3° amine
N N,N-dimethylethanamine
N N,N-dimethylmethanamine
137
8. Amines
NH2 NOT benzenamine
phenylamine or aniline
138
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
139
8. Amines
NH2 2-methylaniline
NH N-methylaniline 
N-phenylmethanamine 
140
8. Amines
1-phenylmethanamine
NH2
141
8. Amines
2 NH2
1
3 Prop-2-en-1-amine
NH2
Prop-1-en-2-amine
2
1 3
142
8. Amines
4 linear
1
3 2 NH2
NH2
but-3-yne-1,2-diamine
143
8. Amines
NH
NH2
2 1
3
N2-ethylpropane-1,2-diamine
144
NH2
Q.11
OH
2-aminophenol
NH2
NH2
benzene-1,2-diamine
NH2
COOH
2-aminobenzoic acid
145
Q.11
1
3 2
N
4 H N-methylbutan-1-amine
1
4 pentan-2-amine
3 2
NH2
5
146
Q.11
1
butan-1-amine
NH2
2 butan-2-amine
NH2
147
Q.11 propane-1,2-diamine
NH2
N1-ethylpropane-1,2-diamine
H
N
2
3 1
1
3 2
4 N-methylbutan-2-amine
NH
148
Q.11
N-ethyl
N 2
O
1
N-methyl
ethanamine 2-methoxy
N-ethyl-2-methoxy-N-methylethanamine
149
Q.11
ethanamine
N-methyl N 2
O
1
N-(2-
methoxyethyl)
N-(2-methoxyethyl)-N-methylethanamine 
3 substituents > 2 substituents
150
Q.11 3
2 propan-1-amine
1
N-methyl N
2
O
1
N-(2-
methoxyethyl)
N-(2-methoxyethyl)-N-methylpropan-1-amine
151
Q.11
1 3 propan-2-amine
2
N-methyl
N
1 2
O
N-(2-methoxyethyl)
N-(2-methoxyethyl)-N-methylpropan-2-amine
152
9. Nitriles
Containing the cyano group, -CN
153
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.
154
9. Nitriles
Examples : -
C N ethanenitrile
N
3 1
C
2 2-methylpropanenitrile
The carbon of the -CN group is counted

as part of the longest carbon chain.
155
9. Nitriles
Examples : -
C N ethanenitrile
N
3 1
C
2 2-methylpropanenitrile
The -CN group always occupies

the terminal position.
No need to specify its position.
156
9. Nitriles
OH
5 4 3 2 1
C
N
4-hydroxypentanenitrile
157
9. Nitriles
N
2
C
1 3
HOOC
3-cyano-2-methylpropanoic acid
If used as prefix, its carbon is not counted

as part of the main carbon chain
158
9. Nitriles
3
N
2
C
1
HOOC
2-(cyanomethyl) propanoic acid
Only one substituent 


159

Nomenclature in Organic Compounds

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Nomenclature in Organic Compounds

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Nomenclature in

Methane Ethane Propane

Angle strain arises from repulsions between

Most stable due to less

1. Name the longest possible straight chain

CnH2n+1– Alkyl groups (derived from alkanes)

Containing at least One C=C double bond

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

Both substituent groups are

One CC triple bond

Cycloalkenes and alkadienes have the same

90 << 180

Functional group has the higher priority

1,3 > 2,4

1,3 > 2,4

The C directly bonded to the ring is

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

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

C6H5 –  phenyl group

C10H7 –  naphthyl group

Both are aryl groups

Organic compounds with one or more

Derived from alkanes

Hydroxy derivative of alkane

General formula : CnH2n+1OH (acyclic)

Primary, Secondary, Tertiary,

The longest C chain containing the –OH

‘e’ is retained in diol

Derived from aromatic hydrocarbons

2-chlorophenol 3-chlorophenol 4-chlorophenol

o  ortho m  meta p  para

- OH has a higher priority than C=C

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

The alkoxy groups are always treated as

At least ONE H attached to C

methanal ethanal propanal benzaldehyde

–ane replaced by –anal

methanal ethanal propanal benzaldehyde

The aldehye group, –CHO, always occupies

'R R, R’ : alkyl or aryl group

–ane replaced by –anoic acid

The carboxyl group, –COOH, always occupies

benzoic acid 2-hydroxybenzoic 3-methylbenzoic

benzoic acid cyclohexylethanoic

carboxylic acid acyl(acid) chloride

* chiral centre, optical isomers exist

NH3 N R Secondary(2°) amine

N R Tertiary (3°) amine

NH2 ethenamine (ethylenamine

The amino group, is always treated as the

NH2 NOT benzenamine

1 NH2 2-methylaniline or o-toluidine

1 NH2 3-methylaniline or m-toluidine

4 1 NH2 4-methylaniline or p-toluidine

If acting as the principal functional group,

The carbon of the -CN group is counted

The -CN group always occupies

If used as prefix, its carbon is not counted

2-(cyanomethyl) propanoic acid

Only one substituent 

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