General Organic

MUNISH KAKARs INSTITUTE OF CHEMISTRY
NAMING OF COMPOUNDS CONTAINING FUNCTIONAL GROUPS Functional group is group of atoms which when attached to compound changes its chemical as well as physical properties. These group of atoms also have characteristic qualitative tests associated them . NOTE: Functional group present in compound some times may also behave as substituent and its name can be generalized as stated below ;
Type of group ACID CHLORIDE
Structure
Secondary suffix ( as functional gp) oyl chloride
Primary Suffix ( as subst.) Formyl chloride
O C Cl
ALCOHOL AMINE ALDEHYDE
O H
ol amine al
Hydroxy Amino Aldo or formyl
NH2
O C H
AMIDE
O C NH2
amide
Carbamoyl
ANHYDRIDE
O C O
C
O C
N
anhydride
CYANIDE CARBOXYLIC ACID
nitrile oic acid
Cyano Carboxy
O C OH
ESTER
O C OR
oate
Alkoxycarbonyl
ETHER KETONE
ether one
Alkoxy Keto
O C C C
NOTE: All functional groups can be classified as terminal and non terminal functional groups. Examples of non terminal groups are alcohol , amine , ether and ketones only whereas rest all are terminal functional groups.
SCO # 40 , SECTOR 11 , PANCHKULA ; 3298728 (O) , 9888019721

( RULES OF NOMENCLATURE )
(HYDROCARBONS OPEN CHAIN)
RULES FOR SELECTION OF LONGEST CHAIN :
1. Always that chain is considered as parent chain in which carbons are connected in continuity for example ;
CH 2CH 3 CH 3 CH 2 CH CH 2 CH CH 3 CH 2 CH 2 CH 3
2. In case of saturated hydrocarbons, that chain will be selected as longest chain which contains maximum number of carbon irrespective of its shape .
3.
In case compound contains un saturation ( C
C or C
C only ) , that chain will be
considered as longest chain which contain un saturation along with maximum number of carbons e.g
4.
In case compound contains un saturation twice (which means two double bond , two triple bond or one double and one triple bond ) , that chain will be considered as longest chain which contains both un saturation. Such chain may or may not have maximum number of carbon atoms e.g
and

5. In case compound contains un saturation of any type ( C
C or C
C only ) more than
two times, that chain will be selected as longest chain which contains maximum number of un saturation with maximum number of carbons e.g
6.
Incase a compound has two or more cha9ins of same length , that chain will be selected as a longest chain which contains larger number of substituents e.g
Br
RULES FOR SELECTION & NAMING OF OF SUBSTITUENT : 7.

Substituent is identified as atom or group of atoms directly attached to carbon of longest chain by displacing hydrogen e.g
NO2 CH3 CH2 CH CH2 CH CH2CH3 CH3

in above structure, 8.
NO2 and CH3 are considered as substituents

yl
In case substituent is of hydrocarbon in nature, name of substituent will end with
whereas if attachment atom of substituent is more electronegative than carbon, name of substituent will have an ending with o named as chloro etc.) 9. In case substituent is further substituted , it will be named according to following rules ; (a) Carbon in substituent will be numbered in a manner , that carbon directly bonded to carbon of longest chain is numbered 1 under all condition. (b) Carbon of functional group will not be counted in longest chain of substituent for example ; (a) ( for example
NO2 is named as nitro , Cl
CH2
CH2
CH CH2CH3 CH3
named as
3 - Methylpentyl

CH3
(b)
CH2
CH2
C CH CH3 named as 3,3,4 trimethylpentyl CH3 CH3
(c)
CH2
CH2
CH
C CH2CH3 CH3
named as 4 Methylhex 3 enyl
NAMING OF SUBSTITUET DIRECTLY ATTACHED TO NITROGEN IN AMINE AND AMIDES

10. Both hydrogens present in amine as well as amide are replaceable. Hence an atom or group of atoms which has replaced hydrogen from nitrogen are considered as substuents on nitrogen. (a) Such a substituent will be named as per previous rules bur will be denoted by N (name of substituent)
CH3
CH2
CO N
CH2CH3 H
N Ethyl propan-1-amide (b) For each hydrogen displaced from same nitrogen , N presentation will be stated separately e.g
CH3
CH2
CO N
CH2CH3 Br
N Bromo N ethyl propan 1 amide RULES FOR NUMBERING OF LONGEST CHAIN 11. 12. While numbering longest chain the correct decreasing order of preference is as functional group > unsaturation > substiuent While numbering longest chain, the following sequential rule ( in given sequence only ) must be used ;
(a) (c)
Position rule Alphabetical rule
(b) (d)
Lowest Sum rule Numeric rule
POSITION RULE : According to this rule, the position of desired preference is seen from two
extreme ends e.g

CH3 CH3 CH CH CH2 CH CH3
LOWEST SUM RULE : In case, position rule can not be used , all carbon atoms only present
in longest chain in continuity are numbered from both extreme ends and number of carbon is noted and added which contain respective substituent , unsaturation or functional groups respectively. An end from where this sum comes to be minimum is considered to be correct e.g
CH3 CH3 C CH CH3 CH CH CH3 CH3
ALPHABETIC RULE : In case, lowest sum rule cannot be used, then numbering will be done
from that end from where desired preference appears alphabetically first e.g
CH
C CH2
CH2
CH
CH CH3
NUMERIC RULE : In case alphabetical rule can not be used, numbering will be done from that
end from where a substituent having identical name but involving smaller number is nearer e.g
CH2
C CH2CH2 CH2CH2Br
CH2
CH(Br) CH3
Rules for naming of compounds containing non terminal functional groups

13. In case compound contains non terminal functional group is present once, longest chain will be selected in such a manner that carbon to which functional group is attached must be a part of longest chain e.g
OH
14.
In case a non terminal functional group comes twice, longest chain will be selected in such a manner that both carbons which contain functional group must be included in longest chain e.g
NH2
H2N

15. In case non-terminal functional group comes more than two times, longest chain will be selected in such a manner that maximum carbons containing functional group must come in selected longest chain e.g
O
Rules for naming of compounds containing terminal functional groups 16.

In case a compound contains terminal functional group only once, longest chain will be selected always by considering carbon of functional group as first carbon e.g
CH3 CH2 CH CH2 CH3 CH2 CH2 CH3 CH COOH
17.
In case in a compound, terminal functional group comes twice , longest chain will be selected in a manner that first and last carbons of longest chain are always carbon of terminal functional group e.g
CH3
18.
CH CH2 CHO
CH2
CH CH CHO
CH2
In case terminal functional group is present more than two times longest chain will be selected as a chain which contains maximum number of carbons without considering carbons of functional group ( This rule will only be applicable if on selected longest chain terminal functional group is present more than two times ) e.g
CH3
CH CH2 COOH
CH CH2 COOH
CH CH3 COOH
SECONDARY SUFFIX
S.No 1 2 3 4 5
FUNCTIONAL GROUP
COOH CHO C N COOR CONH2
Carboxylic acid Carbaldehyde Carbonitrile Carboxylate Carboamide

Selection of Principal Functional group In case a compound contains multiple functional groups ( more than one type), in such case only one functional group will be named as Principal functional group ( as sec. suffix) while rest all be named as substituent. The decreasing preference order of selection of principal functional group will be as stated below ;
COOH ( carboxylic acid ) > > COCl ( acid chloride ) > ( aldehyde ) > ketone >
SO3H ( sulphonic acid) > CONH2 ( amide) > NH2 ( amine ) >
COOR ( ester) CHO O ( ether )
CN ( nitrile) >
OH ( alcohol) >
( Selection of terminal functional group as a substituent )

19. In case a terminal functional group in any case behave as a substituent, its carbon will be never considered in word root e.g
OHC CH CH2 CH3
CH2
CH2
COOH
&
NC CH2
CH CH2 CH2 CN
CN
NAMING OF CYCLIC COMPONDS

A cyclic compound has two parts as ; 1. Nucleus other as shown ; 2. Side chain Nucleus: It corresponds to closed ring structure in which every atom is bonded to each
etc.
Side Chain: A group of atoms ( hydrocarbon in nature at attachment site ) which has
displaced hydrogen directly attached to atom in nucleus is called side chain e.g
CH2
CH2
CH(CH3 )2
CH(CH3 ) CH
CH2
20.
Selection of parent compound ( cyclic compound ) :

In case number of carbon atoms in nucleus exceeds carbon in longest side chain, nucleus will be considered as parent compound and side chain as a substituent. In such compound , name will be presented as ; Prefix + cyclo word root + primary suffix. E.g
21.
Numbering of carbon atoms in nucleus

In such case, while numbering decreasing order of preference will be Functional group > unsaturation > substituent . In such case while numbering the following rules will be used in sequential order ; (a) Lowest sum Rule (b) Alphabetical rule (c) Numeric rule
22.
Selection of parent compound ( open chain & cyclic as substituent )

In case number of carbon atoms in longest side chain exceeds the number of carbons in nucleus, the longest side chain will be considered as substitent e.g
Cyclic compound containing functional group

23. In case nucleus contains a principal functional group and side chain does not. In such case nucleus will be considered as parent compound and side chain as substituent and vice versa also e.g
O
3-(3-Methyl-butyl)-cyclopent-2-enone
3-cyclopentyl pent-4-en-2-one
24.
In case side chain as well as nucleus both contains functional group, selection of parent compound will be done on basis of carbon content in nucleus or preference of selection of principal functional group
OH
O
O OH
NH2
OHC
3-(2-formylethyl) cyclopentan carbo amide , 2-(carboxymethyl)-cyclobutanecarboxylic acid

Cyclic compound containing functional group ( terminal functional group directly attached to cyclic structure )
25. In case a terminal functional group is directly attached to ring structure, in order to include carbon of functional group in word root , secondary suffix will change. Insuch case, new secondary suffix will be ;
S.No 1 2 3 4 5
FUNCTIONAL GROUP
SECONDARY SUFFIX
CH3
OHC
H2N
1-methyl cyclopentancarbaldehyde , 4-methyl cyclohex-2-en-1-carboamide

( Naming of cyclic compounds containing multiple cyclic structures )
26. If two cyclic structures are directly connected through single bond, one of cyclic structure will be named as substituent while other as parent compound. The decision regarding selection of parent compound can be taken on basis of ; (a) Functional group (c) number of substituents
OH O
(b) unsaturation (d) number of carbons in nucleus
3-cyclohexylcyclohexancarboxylic acid
2-cyclopentylcyclopent-1-ene
Br
1-bromo-3-cyclobutylcyclobutane
cyclobutyl cyclopentane

27. In case a carbon ( or carbons ) are present within two or more cyclic structures, in such case cyclic structures will be considered as substituents while longest chain will be selected by considering carbon ( or carbons ) present between cyclic structures e.g
Cl Cl Cl
Cl
Cl
1,1-dicyclobutylmethane
2-cyclobutyl-4-cyclopentylhexane
1,1,1-trichloro-2,2-bis-(4-chlorocyclopentyl)ethane
Write IUPAC name of the following organic compounds ;

HO O
NH2 O
OH
H 2N
Cl
O
Br
O O
O
Cl
O
HO
6
HO
O OH
OH
OH
O
HO HO O OH
HO O
HO
9
HO
10
HO
11
O
OH O HO
O
O
12
HO O
13
14
15
OHC
16
17
19
OH

O
O
O
N
O
20
21
CHO
22
HO
O
23
CHO
NC
24
25
OH
O
O
26
O
HO OH
27
H2N
O OH
28
OH
29 HO
OH
30 N
HO
O
HO O OH
31
O
O O
32 O
O
OH
33
O
O
OH
O
34
35
36
NAMING OF CYCLIC COMPONDS

A cyclic compound has two parts as ; 1. Nucleus other as shown ; 2. Side chain Nucleus: It corresponds to closed ring structure in which every atom is bonded to each
etc.
Side Chain: A group of atoms ( hydrocarbon in nature at attachment site ) which has
displaced hydrogen directly attached to atom in nucleus is called side chain e.g
CH2
CH2
CH(CH3 )2
CH(CH3 ) CH
CH2
Selection of parent compound ( cyclic compound ) : In case number of carbon atoms in nucleus exceeds carbon in longest side chain, nucleus will be considered as parent compound and side chain as a substituent. In such compound , name will be presented as ; Prefix + cyclo word root + primary suffix. E.g
Numbering of carbon atoms in nucleus In such case, while numbering decreasing order of preference will be Functional group > unsaturation > substituent . In such case while numbering the following rules will be used in sequential order ; (a) Lowest sum Rule (b) Alphabetical rule (c) Numeric rule Selection of parent compound ( open chain & cyclic as substituent ) In case number of carbon atoms in longest side chain exceeds the number of carbons in nucleus, the longest side chain will be considered as substituent e.g
Rules for naming of compounds containing terminal functional groups

(A)
In case a compound contains terminal functional group only once, longest chain will be selected always by considering carbon of functional group as first carbon e.g

CH3 CH2 CH CH2 CH3 CH2 CH2 CH3 CH COOH
(B)
In case in a compound, terminal functional group comes twice , longest chain will be selected in a manner that first and last carbons of longest chain are always carbon of terminal functional group e.g
CH3
(C)
CH CH2 CHO
CH2
CH CH CHO
CH2
In case terminal functional group is present more than two times longest chain will be selected as a chain which contains maximum number of carbons without considering carbons of functional group ( This rule will only be applicable if on selected longest chain terminal functional group is present more than two times otherwise statement (B) will be used ) e.g
CH3
CH CH2 COOH
CH CH2 COOH
CH CH3 COOH
&
HOOC
CH2
CH CH2 CH2 CH2
COOH COOH
(Change of Secondary Suffix)

According to statement (C) , if terminal functional group is present more than two times, in such case secondary suffix will change. New secondary suffix will be as stated below ;
S.No 1 2 3 4 5
FUNCTIONAL GROUP
SECONDARY SUFFIX
(D)
In case terminal functional group is directly attached to closed ring structure in nay number, even than new secondary suffix
O
CH3
H2N
& PROBLEM SHEET 2.
OHC
1. CH3 3. CH3
CH2 CH2
CH
CH CH(OH) CH3 CH CH2
CH3
CH2
CH
CH CH(CHO) CH3
CH(OH) CH2
4. (CH3 )2 CH C(NH2 )(CH3 )2

O
CH2 CH2
COOH
CH2
CH2OH CH2OH
5. CH CH2CH3
COOH
6.
7. CH CH2OH
CH2
OH
OH
HN OH
8. N
10.
Br
Br
11.
12.
13.
14.
15.
16..
17.
18
19
20
21
22
23
Br
24
25
26
27
Cl
28
29
30
WRITE IUPAC NAMES OF THE FOLLOWING COMPOUNDS

O
O
OHC
OH
HO
1.
OH
2.
O
H2N
3.
4.
O
NH2
H3C
O
5.
6.
7.
HO
8.
O
O
O
9.
O
O O
10
11
O
O
OHC
12
O HO
OH
13
13
HO
14
OHC
O
N
O OH
OHC
15
HO
16
Br
CHO
17
18 CHO COOH
19
20
21
22
HO
H2N
HO
OH
O OH
NO2
23
24
25
26
OH

HO
O
NO2
27 H3C
OH
28
O
Cl Cl Cl
29
NO2
CHO
O2N
30 H3C
OH
31
Cl
Cl
32
HO
NO2
OH
33
34
35
CH3
O
O
OH
O Cl
36
37
38
O O
39
40
41
OH
Br N
OH HO
HO
HO
OH
O O HO
OH
42
43
OH
44
45 O
OH

Write the IUPAC names of the following compounds ;
HO
OHC
OH O
1.
2.
O
3.
Cl
NH2
CHO
4.
Cl
6.
Cl
O HN
CHO
HO
HO
10
NH2
11
O
O
O
Br
12
O
HO O
13
14
15
OH
Br
16
17
Br
OH
18
19
O
OH
Br
Br
Cl
OHC NO2
O
20
21
22
Br

O O
O
23
Br
24
25
O Br
O
26
27
29
30
31
O
H
O
32
Br
33
34
HN
35

PROBLEM SHEET # 3 Write IUPAC names of the following compounds having multiple functional groups along with esters and ethers ; 1.
CH3
CH2
CH CH2 OH
CH(Br) CHO
2.
CH3
CH CH2 CHO
CH(Br) CONH2
OH
OH
OHC
HO Br
HO
3.
HOOC CH2 HO
C COOH NH2
4.
5. 7. CH2
6. N
C CH2
OH
CH(OH) CH2
CH CO CH2
CH2OH
C CH
CH3 CH CH2CH3
8.
NH2
9. CH3
Br
CO CH2
CHO
10
CH3
CH2
CH CH COOH OH F
O
O
11
12
13
O Br
O
O OH
14 17
CH3 CH2
15
CH CH(CH2 COOH
16 18
COOH
CH CH2 COOH
COOH) CH3
CHO CH CH2 CHO
CHO
19 (COOH)3 C CH3
20
CH3
CH CH2 COOC2H5
-------SCO # 40 , SECTOR 11 , PANCHKULA ; 3298728 (O) , 9888019721

PROBLEM SHEET Write the IUPAC names of the following organic compounds
1.
2.
Br
3.
Cl
4.
5.
6.
7.
8.
10.
11

13
12
15
14
16
17
18
19
20
21
22
23
Cl
24
25

Problem Sheet ( Naming of cyclic compounds )
Br
1.
2.
3.
4.
5.
6..
7.
10
11
12
13
Br
14
15
16
17
Cl
18
19
20

General Organic

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MUNISH KAKARs INSTITUTE OF CHEMISTRY

Type of group ACID CHLORIDE

Secondary suffix ( as functional gp) oyl chloride

Primary Suffix ( as subst.) Formyl chloride

ALCOHOL AMINE ALDEHYDE

Hydroxy Amino Aldo or formyl

CYANIDE CARBOXYLIC ACID

nitrile oic acid

SCO # 40 , SECTOR 11 , PANCHKULA ; 3298728 (O) , 9888019721

MUNISH KAKARs INSTITUTE OF CHEMISTRY

In case compound contains un saturation ( C

C only ) , that chain will be

SCO # 40 , SECTOR 11 , PANCHKULA ; 3298728 (O) , 9888019721

MUNISH KAKARs INSTITUTE OF CHEMISTRY

C only ) more than

RULES FOR SELECTION & NAMING OF OF SUBSTITUENT : 7.

NO2 CH3 CH2 CH CH2 CH CH2CH3 CH3

NO2 and CH3 are considered as substituents

In case substituent is of hydrocarbon in nature, name of substituent will end with

NO2 is named as nitro , Cl

SCO # 40 , SECTOR 11 , PANCHKULA ; 3298728 (O) , 9888019721

MUNISH KAKARs INSTITUTE OF CHEMISTRY

C CH CH3 named as 3,3,4 trimethylpentyl CH3 CH3

named as 4 Methylhex 3 enyl

NAMING OF SUBSTITUET DIRECTLY ATTACHED TO NITROGEN IN AMINE AND AMIDES

Position rule Alphabetical rule

Lowest Sum rule Numeric rule

SCO # 40 , SECTOR 11 , PANCHKULA ; 3298728 (O) , 9888019721

MUNISH KAKARs INSTITUTE OF CHEMISTRY

CH3 CH3 C CH CH3 CH CH CH3 CH3

Rules for naming of compounds containing non terminal functional groups

SCO # 40 , SECTOR 11 , PANCHKULA ; 3298728 (O) , 9888019721

MUNISH KAKARs INSTITUTE OF CHEMISTRY

Rules for naming of compounds containing terminal functional groups 16.

COOH CHO C N COOR CONH2

Carboxylic acid Carbaldehyde Carbonitrile Carboxylate Carboamide

SCO # 40 , SECTOR 11 , PANCHKULA ; 3298728 (O) , 9888019721

MUNISH KAKARs INSTITUTE OF CHEMISTRY

COOR ( ester) CHO O ( ether )

( Selection of terminal functional group as a substituent )

OHC CH CH2 CH3

NAMING OF CYCLIC COMPONDS

Selection of parent compound ( cyclic compound ) :

SCO # 40 , SECTOR 11 , PANCHKULA ; 3298728 (O) , 9888019721

MUNISH KAKARs INSTITUTE OF CHEMISTRY

Numbering of carbon atoms in nucleus

Selection of parent compound ( open chain & cyclic as substituent )

Cyclic compound containing functional group

3-(2-formylethyl) cyclopentan carbo amide , 2-(carboxymethyl)-cyclobutanecarboxylic acid

SCO # 40 , SECTOR 11 , PANCHKULA ; 3298728 (O) , 9888019721

MUNISH KAKARs INSTITUTE OF CHEMISTRY

COOH CHO C N COOR CONH2

Carboxylic acid Carbaldehyde Carbonitrile Carboxylate Carboamide

1-methyl cyclopentancarbaldehyde , 4-methyl cyclohex-2-en-1-carboamide

(b) unsaturation (d) number of carbons in nucleus

SCO # 40 , SECTOR 11 , PANCHKULA ; 3298728 (O) , 9888019721

MUNISH KAKARs INSTITUTE OF CHEMISTRY

SCO # 40 , SECTOR 11 , PANCHKULA ; 3298728 (O) , 9888019721

MUNISH KAKARs INSTITUTE OF CHEMISTRY

Write IUPAC name of the following organic compounds ;

SCO # 40 , SECTOR 11 , PANCHKULA ; 3298728 (O) , 9888019721

MUNISH KAKARs INSTITUTE OF CHEMISTRY

NAMING OF CYCLIC COMPONDS