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Файл:Ординатура / Хирургия / Библиотека им академика М.И. Перельмана / Книга_5574_Библиотеки_им_академика_М_И_Перельмана.pdf
c h A P T e r 2 u nomenclature of Organic compounds
Cl
N
—
—
N
Cl
4
3
2
2
3
1
1
(4-Chlorophenyl)
(3-Chlorophenyl)diazene
3
6
1234
54
21
CH
3
—— CH —— CH —— CH —— CH2 —— CH2OH
OH
3-(4-Chlorobutyl)-hexane-1,4,5-triol
OH
CH
2
—— CH2 —— CH2 —— CH2 —— Cl
HO——CH2——CH CH——CH——CH CH——CH2——CH2OH
3
CH CH——CH
2
——CH2——OH
21 5
6
5-(3-Hydroxy-1-propenyl)-non-3,6-diene-1,9-diol
78 9
432 1
9
5-(4-Hydroxy-yny)-non-2,6-diene-1,9-diol
123 4
876 54321
HO
—CH2—CH2—CH
—
—
CH—CH—CH—CH
—
—
CH—CH
2
OH
CH
—
—
CH—CH
2
—CH2—OH
When it is present as a principal functional group, it is named by placing the name ‘hydrazone’ as a
separate word after the name of the corresponding aldehyde or ketones. For example,
CH3CH2CH
N
NH
2
Propanal hydrazone
3. The compound is named as the derivative of diazene. For example,
2.6.1 Some Additional Rules for Solving Complex Compounds
1. select that chain as the principal chain which contains maximum number of radicals of secondary
sufx.
111
2. When the number of radicals of the principal functional group are same in different chains, select the
longest possible chain.
3. All things being equal, the principal chain must contain maximum number of double bonds.
112
||
||
H C (CH2)3 C H
O
O
Acyclic principal chain
Pentanedial
||
|
H —— C —— CH2 —— CH —— CH2 —— CHO
CH
2
CHO
54 32 1
O
3-(Formyl-methyl)-pentane-1,5-dial
Parent hydrocarbon
Pentane-1,3,5-tricarbaldehyde
H C CH2 CH2 C CH2 CH2 C H
CHOO
54 32 1
O
PhArmAceuTicAl OrgAnic chemisTry
2.6.2 Specific Classes of Organic Compounds
Besides the usual IUPAC system of nomenclature, there is another IUPAC system of naming sec-
ondary and tertiary amines as follows:
1. symmetrical secondary and tertiary amines are named as the substituted alkyl groups preceded by
‘di-’ or ‘tri-’ as appropriate and followed without a space by the sufx ‘amine’. For example,
(Br
CH2
Bis(2-bromoethyl)-amine
CH2)
2
NH
2. substituent group names of unsymmetrical secondary and tertiary amines are written alphabetically.
For example,
CH3
CH
Ethyl methyl propanamine
CH
2
N
CH
CH2
3
2
CH
3
Polyfunctional compounds containing more than two like functional groups: According to latest convention
(1993), if an unbranched carbon chain is directly linked to more than two like functional groups, the organic
compound is named as a derivative of the parent hydrocarbon (parent hydride), which does not include the
carbon atoms of the functional groups.
1. Aldehydes: Acyclic mono- and dialdehydes are named by adding sufxes ‘-al’ or ‘dial’ to the name of
the acyclic principal chain with the same number of carbon atoms.
if an unbranched chain is directly linked to more than two aldehyde groups, these aldehyde groups
are named from the parent hydrocarbon the substitutive use of a sufx such as tricarbaldehyde, etc. For
example,
c h A P T e r 2 u nomenclature of Organic compounds
H
CHO
Cyclohexane carbaldehyde
HOOC CH2 C CH2COOH
COOH
Heptanedioic acid Propane-1,2,3-tricarboxylic acid
HOOC (CH2)5 COOH
H
COOH
Cyclohexane carboxylic acid
Butane dionyl chloride
Cl C CH
2
CH2 C Cl
O
4-(Bromocarbonyl)-butanoyl-chloride
Br C CH2 CH2 CH2 C Cl
54 321
O O O
Cl C CH2 CH CH2 C Cl
CH
2
COCI
O
3-(Chlorocarbonyl-methyl)-pentane dionyl chloride Propane-1,2,3-tricarbonyl-chloride
CICO CH
2
CH CH2 COCl
COCl
121
O
Other aldehydes are named as adding the sufx ‘-carbaldehyde’ to the name of a parent hydride. For
example,
2. Mono and diacarboxylic acids are named in usual manner as –oic acid and –di-
oic acid. if an unbranched chain is directly linked to more than two carboxy groups, these carboxy
groups are named from the parent hydrocarbon by substitutive use of a sufx as tricarboxylic acid etc.
For example,
Other carboxylic acids are named by adding the sufx ‘-carboxylic acid’ to the name of the parent hydride. For example,
113
3. These are also named on the same pattern as discussed in aldehydes and acids. some
typical examples are:
114
H
COCl
Cyclohexane carbonyl chloride
C2H5 � O � C � CH2 � CH2 � CH � CH2 � CH2 � COOC2H
5
CH2COOC2H
5
Diethyl-4-(ethoxy carbonyl methyl)-heptanedioate
O
CH2CN
NC——CH
2
——CH2——CH——CH2——CN
4 3 2 1
3-(Cyanomethyl)-hexanedinitrile
CN
NC——CH
2
——CH2——C——CH2——CN
4 3 2 1
Butane-1,2,4-tricarbonitrile
CH3 CH2 N C
Ethyl isocyanide
3-Isocyano-benzoic acid
NC
COOH
PhArmAceuTicAl OrgAnic chemisTry
4. some typical examples are:
C2H5COOC
COOC2H
CH
2
CH
5
CH
2
CH
2
COOC
2H5
COOCH
H
3
1 2 3 4
Triethyl-butane-1,2,4-tricarboxylate Carboxylate
5. mono- and dinitriles are named in the usual manner as nitriles and
dinitriles. if an unbranched chain is directly linked to more than two cyanide groups, these cyanide
groups are named from the parent hydrocarbon by substitutive use of a sufx such as tricarbonitrile,
etc.
N C
CH
1 2 3 4 5
CH
2
Pentane dinitrile
2
CH
C
2
N
6. Compounds with the structure R–N c are called isocyanides or isonitriles and may
be named as follows:
c h A P T e r 2 u nomenclature of Organic compounds
C
–
–
–
N
CH
3
1
2
3
O
COOH
4
3
2
1
COOC H
2
5
O
2
1
3-Methyl-cyclohexane
-1-carbonitrile
4-Oxocyclohexane-1-
carboxylic acid
Ethyl-(2-oxocyclohexane)
-1-carboxylate
|
CH
3
|
CONH
2
|
||
CH
3
CH
3
O
1
2
3
6
5
4
HC
3
CH CHO
2
1
2
1
2
|
2-Methylcyclohexane
-1-carboxamide
5,6-Diethylcyclohex-2-
en-1-one
2-(2-Methyl cyclobut-1-enyl)-
ethanal
O
|
CH CH COCH
22 3
1234
2-(3-Oxobutyl)-cyclohexan-1-one
2.7 NOMENCLATURE OF SUBSTITUTED ALICYCLIC COMPOUNDS HAVING SOME
FUNCTIONAL GROUP ALONG WITH OTHER SUBSTITUENTS
if some functional group along with the other substituents groups are present in the ring, it is indicated by
some appropriate prex or sufx and its position is indicated by numbering the carbon atoms of the ring in
such a way that the functional group gets the lowest number. For example,
115
it is very simple and convenient method of representing the structure of organic
compound. in this notation, bonds are represented by lines and the carbon atom by line terminals and intersections. required numbers of hydrogen atoms are assumed to be present wherever they are necessary to
satisfy the tetravalency of carbon. The following examples will help to understand the notation.
116
(i)CHCHCHCHCH
22223
CH –––––
3
1
2
3
4
5
6
1.
CH(CH) CH(CH)CH CH
3323
CH –––
3
1
2
3
4
5
1
2
3
4
5
–
3.
CH =CHCCH CH
223
–– –
CH –
2CH3
|
|
CH
3
1
2
3
4
5
1234
5
4.
CH∫C CH=CH
2
–
1
12
3
4
4
2
3
6.
CH CH CH
23
CH –– –
3
|
CH
3
112
2
3
4
3
4
2.
CH =C CH=CH
22
–
|
CH
3
1
2
3
4
1234
5.
PhArmAceuTicAl OrgAnic chemisTry
2.8 NOMENCLATURE OF AROMATIC COMPOUNDS
like the aliphatic compounds, aromatic compounds have also been divided into various homologous series
or families such as hydrocarbons, halogen derivatives, hydroxyl compounds, nitro compound, aldehydes,
ketones, acids, etc. The nomenclature of these compounds is discussed below.
Hydrocarbons:
Benzene C
or dimethyl benzene c6h4(ch3)2 is the third member.
Isomerism of benzene derivatives
1. When two hydrogen atoms in benzene are replaced by two univalent
radicals (which may be same or different), three isomers are possible (position isomerism) named as
Aromatic hydrocarbons have the general formula cnh
is the rst member, toluene or methyl benzene C6h5–CH3 is the second member while xylene
6h6
ortho, meta and para.
C6H
4
CH
CH
where n equals 6 or more than 6.
2n–6
3
3
C H A P T E R 2 u Nomenclature of Organic Compounds
Br Br
Br
Br
Br
Br
o-Dibromobenzene m-Dibromobenzene
p-Dibromobenzene
NO
2
Cl
m-Chloronitrobenzene
NO
2
CH
3
NO
2
COOH
o-Nitrotoluene m-Nitrobenzoic acid
A
A
A
A
A
A
A
A
A
vic- or adjor 1, 2, 3
unsym or
1, 2, 4
sym or 1, 3, 5
This,becauseallthecarbon–carbonbondsinbenzeneareequivalent.
Ifthetwogroupsaredifferent,andneitherisagroupthatgivesaspecialnametothemoleculewesimply
namethetwogroupssuccessivelyandendthewordwith‘benzene’.Forexample,
Ifoneofthetwogroupsisthekindthatgivesaspecialnametothemolecule,thenthecompoundisnamed
117
2. Isomerism in tri-derivatives:Thenumberoftri-substitutedderivativesofbenzenedependsuponthe
nature of substituents groups.
a. Ifthethreesubstituentgroupsareidentical,thenthreeisomersarepossible.Thesearenamedas
vicinal or adjacent (vic- or adj-),unsymmetrical(unsym-) and symmetrical (sym- or s-).
118
Br
Br
Br
Br
Br Br
NO
2
ON
2
CH
3
NH
2
Cl
NO
2
Br
1,2,4-Tribromobenzene
2-Chloro-4-nitrobromobenzene
2,6-Dinitrotoluene 2,4,6-Tribromoaniline
CH Cl
2
Side chain
CH OH
2
Side chain
Monovalent: CH—— or
65
........Phenyl radial
PhArmAceuTicAl OrgAnic chemisTry
b. if two substituent groups are identical and the third is different, then six isomers are possible.
c. if all the three substituent groups are different, then 10 isomers are possible.
When two more groups are attached to the benzene ring, the positions are better indicated by numbering
their relative positions.
if all groups are same, each is given a number, the sequence being the one that gives the lowest combina-
tion of numbers. if the groups are different, then the last named group is understood to be in position 1 and
the other numbers conform to that, for example, 2-chloro-4-nitro-bromo benzene. if one of the groups that
give a special name is present, then the compound is named as having the special group in position, e.g., in
2,6-dinitrotoluene, the methyl group is considered to be at that position 1.
Benzene nucleus and side chain: The benzene molecule represented by a regular hexagon made of six
carbons (each carrying one hydrogen atom) linked by alternate single and double bonds or solid circle is
called benzene nucleus. An alkyl radical or any other group containing at least one carbon atom, attached
to the nucleus, is called a side chain. The side chain is aliphatic in nature and shows reactions of aliphatic
compounds. Thus the methyl group in xylene constitute two side chains attached to the benzene nucleus.
Similarly the aliphatic groups such as –CH
Cl, –CH2Oh, etc., attached to the nucleus are termed as side
2
chains. Thus,
It must be clearly understood that groups such as –NO2, –OH, –NH2 are not regarded as side chains,
though they may be directly linked to the nucleus, as they do not contain a carbon atom.
Aromatic or aryl groups: The groups or radicals obtained after the removal of one, two or three hydrogen
atoms of the aromatic hydrocarbons are called aromatic or aryl radicals. Thus benzene forms monovalent
and divalent radicals:
c h A P T e r 2 u nomenclature of Organic compounds
Divalent: CH—— or
64
o-
p-
m-
Phenylene radical
From nucleus: CH
64
CH
3
o-
p-
m-
......Tolyl radical
or
CH
3
CH
3
CH
3
From the side chain:
CHCH
65 2
or
CH2 –
....Benzyl (Monovalent)
CHCH
65
or
CH
......Benzal (Divalent)
CHCH
65
Or
C
......Benzo (Trivalent)
CH=CH CH Br
2
––
1.
3-Bromo-1-Phenyl prop-1-ene
or cinnamyl bromide
12
3
OH
CH
3
2.
2-Methyl phenol or o-cresol
119
some typical examples:
120
OH
OH
5.
1,4-Dihydroxy benzene
or hydroquinone or quinol
OH
OH
OH
6.
1,2,3-Trihydroxy benzene
or pyrogallol
3.
OH
OH
1,2-Dihydroxy benzene
or catechol
4.
1,3-Dihydroxy benzene
or resorcinol
OH
OH
OH
OH
OH
7.
1,2,4-Trihydroxy benzene
or hydroxyquinol
OH
OH
HO
8.
1,3,5-Trihydroxy benzene
or phloroglucinol
9.
CH ––
2
CH OH
2
β
α
21
2-Phenyl ethanol or
β-phenyl ethyl alcohol
3-Phenyl propanol or
β-phenyl propionaldehyde
CH ––
2
CH CHO
2
α
β
321
10.
11.
COCH
3
12
1-Phenylethanone
or methyl phenyl ketone
12.
COCH2–CH
3
12
3
1-Phenyl propanone or propiophenone
or ethyl phenyl ketone
PhArmAceuTicAl OrgAnic chemisTry