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Aliphatic or Open chain compounds :
Those compounds in which first & last carbon atoms are not connected with each other. Branched or unbranched
chains are possible in these compounds.
For example :
CH3
CH3–CH2–CH2–CH3, CH3–CH2– CH–CH3, CH3–C–CH3
CH3 CH3
(Unbranched) (Branched)
There are two varieties in these compounds -
Saturated Hydrocarbons :
(a) In such type, adjacent carbon are attached with single bonds.
Example - CH3–CH2–CH3
(b) General formula of these compounds are CnH2n+2
(c) These are also called as paraffins (Parum + Affins i.e. little reactivity) because these are less reactive
due to absence of -bonds.
Unsaturated Hydrocarbons :
(a) There will be a double bond or a triple bond between any two carbon atoms,
CH2 = CH – CH3 Propene
CH C – CH3 Propyne
(b) General formula is CnH2n or Cn H2n–2
(c) These are also called as olefins because they reacts with halogens to form oily substances olefins
(Oleum + fines i.e. Oil forming).
(d) Due to presence of bonds these are more reactive.
Closed chain compounds :
In these compounds first & last carbon are attached with each other.
CH2
Example. CH2 CH2 cyclopropane.
Homocyclic compounds :
These are the compounds in which the complete ring is formed by carbon atoms only. These are also of
two types
( A ) Alicyclic compounds : These are the compounds having the properties like aliphatic compounds.
These may be saturated or unsaturated like aliphatic compounds.
cyclopropane cyclopropene cyclobutene
( B ) Aromatic compounds : Conditions for a compound to be aromatic -
(i) Compound should be cyclic.
(ii) Compound should be planar. (All carbon in ring should be sp2 hybridised)
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(iii) It follow Huckel's Rule :- [4n + 2] electrons. (Odd number of electron pairs)
n = 0 2 electrons or 1 pair
n = 1 6 electrons or 3 pairs
n = 2 10 electrons or 5 pairs
n = 3 14 electrons or 7 pairs
(iv) There should be cyclic resonance in ring.
Heterocyclic Compounds :
These are cyclic compounds having ring and rings builts up of more than one kind of atoms.
O S N
Furan |
H
Thiophene Pyrrole
Normal Groups :
(a) It is represented by 'n' :
(b) Straight chain of carbon atoms is known as normal group.
(c) Free bond will come either on Ist carbon atom or on last carbon atom.
n – propyl CH3–CH2–CH2–
n – butyl CH3–CH2–CH2–CH2–
Iso group :
(a) It is represented by following structure
CH3–CH–
CH3
(b) When methyl groups are attached to the second last carbon atom, group is named as iso.
CH3–CH– CH3–CH–CH2– CH3–CH–CH2–CH2–
CH3 CH3
CH3
Iso propyl Iso butyl Isopentyl
Neo group :
(a) When two methyl group are attached to second last carbon atom group is named neo group.
(b) It is represent by following structure -
CH3
for Ex. CH3–C–CH2– Neo pentyl
CH3
Secondary group :
(a) When two alkyl groups attached to the same carbon atom, group is named as secondary.
Ex.
CH3–CH2–CH– CH3–CH2–CH2–CH–
CH3
CH3
Secondary butyl Active Secondary pentyl
(b) It is represented by following structure.
CH3–CH2–CH–CH3
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Ter t iar y group :
(a) When three alkyl groups (similar or dissimilar) are attached to the same carbon atom, group is name
as tertiary.
CH3 CH3
CH3–C–
CH3–CH2–C–
CH3 CH3
Tertiary butyl Tertiary pentyl
(b) It is represented by following structure -
CH3
CH3–C–
CH3
Groups :
When a hydrogen is removed from saturated hydrocarbon then alkyl group is formed. It is represented by
R & its general formula is CnH2n+1. A bond is vacant on alkyl group, on which any functional group may
come.
Alkyl groups :
Alkane H Alkyl (monovalent radical) H Bivalent radical H Trivalent radical
CH4 CH3 Methyl C2H6 C2H5 Ethyl n–propyl
(i) CH3 CH2 CH2 Iso–propyl
CH3 CH2 CH3 (ii) CH3 CH CH3
Propane
CH3 CH2 CH2 CH3 (i) CH3 CH2 CH2 CH2 n–butyl
Butane (ii) CH3 CH2 CH CH3 sec–butyl
CH3 CH CH3 (i) CH3 CH CH2 Isobutyl
CH3 CH3
Isobutane (ii) CH3 C CH3 tert.–butyl
CH3
CH3CH2CH2CH2CH3 n - pentyl
n — Pentane (a) CH3 CH2 CH2 CH2 CH2 Active sec. pentyl
(b) CH3 CH2 CH2 CH CH3 1 - Ethyl propyl
(c) CH3 CH2 CH CH2 CH3 or sec. pentyl
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CH3 CH CH2 CH3 (a) CH3 CH CH2 CH2 Iso pentyl or
CH3 3–Methyl butyl
CH3
Iso pentane (b) CH3 CH CH CH3 1,2–dimethyl propyl
CH3 or active iso pentyl.
(c) CH3 C CH2 CH3 tert. pentyl or
CH3 1,1–dimethyl propyl
or tert. amyl
(d) CH2 CH CH2 CH3
CH3 Active pentyl or
active amyl
CH3 CH3
CH3 C CH2
CH3 C CH3
CH3
CH3
neo-pentane neo-pentyl
Note : Pentyl is also called amyl group.
( a ) Alkene H Alkenyl
E x . CH2 CH2 CH2 CH Ethenyl (vinyl)
CH3 CH CH2 (1) CH3 CH CH 1–propenyl
|
Iso propenyl or
(2) CH3 C CH2 1–methyl ethenyl
2–Propenyl (Allyl)
(3) CH2 CH CH2
( b ) Alkyne H Alkynyl
E x . CH CH CH C Ethynyl
1 – Propynyl
CH3 C CH CH3 C C 2 - Propynyl (Propargyl)
CH2 C CH
Aryl Radical -
(i) – H – C6H5 – H
Phene Phenyl Phenylene
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CH2 CH C
(ii) – H – H
CH3
Benzyl Benzal or Benzo (Benzylidyne)
Toluene Benzylidene
CH3 CH3 CH3
o – Tollyl m – Tollyl p – Tollyl
CH2OH CHO COOH
Ex.
Benzyl alcohol Benzaldehyde Benzoic acid
NOMENCLATURE :
Mainly three systems are adopted for naming an organic compound -
(i) Common names or Trivial system
(ii) Derived system
(ii) IUPAC system or Jeneva system
Trivial System :Initially organic compounds are named on the basis of source from which they were obtained for
S . No . Or ganic Compound Trivial Nam e S ourc e
1 C H3OH W o o d s pi rit or M e th y l Obta ined by destructive distillation
sp irit of w o o d
2 NH CONH Ur ea Obta ined from urine
22 M ars h ga s (f ire d am p) It w as p ro du ced in m a rs h y pla c es
V in e g a r Obta ined from Acetum –i.e.
3 CH V in e g a r
4 Oxalic acid
Obta ined from oxalis pla nt
4 CH COOH F orm i c acid
3 Lac tic a c id Obta ined from formicus [Red ant]
C OOH Obta ined from sou r milk
5 |
C OOH
6 HCOOH
CH CH COO H
|
7 3
OH
CH2 –COOH M alic a c id Obta ied from apples
8
C H( O H) C OO H
9 CH CH CH COOH Bu ty ric aci d Obta ined from butter
32 2 C apro ic ac id Obta ined from goats
1 0 C H (C H ) COO H
3 24
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Some typical compounds in which common & trivial names are also differ.
S. No. Com pou nd Trivial Nam e Com m on nam e
1 CH 4 M ars h ga s Methane
2 CH 3OH W o o d s p i rit M e th yl alco h o l
3 CH 3COOH Vinegar Acetic a cid
Acetone Dim ethyl ketone
4 CH3 C C H 3 A c rol e in Acryl Aldehyd e
||
O Pyvalde hyde Te rtiary valer ald ehyde
5 O
||
CH2 CH C H
H3C O
6 CH3–C–C–H
CH
3
Trivial Names :
Ex : The trivial name of the following compounds is :
CH3
CH3–C–CHO
CH3
(A) Pyvaldehyde (B) Trimethyl acetaldehyde
(D) , , - trimethylacetaldehyde (C) t-butyl formaldehyde
Sol. (A) (B) A saturated aldehyde
(C) An alkene
Ex : Acrolein is :
(A) An unsaturated aldehyde
(C) A polymer
Sol. (A)
Comman Name : R is termed as alkyl.
S . No . Com pou nd Na m e
1 R – X A lky l h a lid e
2 R – OH A lky l a lc o h ol
A lk y l t hi o alc oh o l
3 R – SH
A lky l am in e
4 R – N H D ialkyl e ther
2 Dia l kyl th io e th e r
5 R – O – R Dialk yl keone
6 R – S – R
R–C–R
7
O
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S . No . Com pou nd Na m e
8 D ialkyl amine
R–NH –R
9 R–N –R T ria lky l a m i n e
10 R Alkyl alkyl’ ether
11 R–O –R’ Alk yl alkyl’ ketone
12 R–C–R' Alk yl alkyl’ thio e ther
13 O Alkyl a lkyl’ amine
14 R –S– R’ A lkyl alkyl’ alkyl’’ amine
R –N H– R’
R–N –R'
R''
Ex : The common name of the compounds CH2 = CH – CH2 – NH2 is -
(A) Vinyl amine (B) Allyl amine (C) Divinyl amine (D) Diallyl amine
Sol. (B)
Ex : Ethyl methyl ether is :
(A) CH3 –CH2– O –CH3 (B) CH3 –O –CH2– CH3
(C) Both A & B (D) CH3 –CH2– O –CH2–CH3
Sol (C)
Position of double bond :
In an unsaturated hydrocarbon if the position of double bond is on Ist or last carbon then it's prefix will be
(alpha) if it is on 2nd carbon it is termed as (Beta) & then (gamma) & (delta) and so on.
Example :
H2C=CH–CH2–CH3 -butylene
H3C–CH=CH–CH3 -butylene
H3C–CH2–CH=CH2 -butylene
H2C=CH–CH3 or propylene
CH3–C=CH2
Both are same positions
CH3
propylene, isobutylene
Isobutylene
CH3–CH2–CH=CH–CH2–CH3 -hexylene
CH3–CH2–CH2–CH=CH–CH2–CH2 –CH3 -octylene
Common - Naming of dihalides :
(a) When two same halogen atoms are attached to the same carbon such compounds are called
Gemdihalides.
(b) Common names of such compounds are alkylidene halides.
Example : I
Cl CH3–CH–CH
CH3–CH I
Cl CH3
Ethylidene chloride Isobutylidene Iodide
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Exception : X Methylidene halide (wrong)
CH2
X Methylene halide (right)
(c) When two same halogen atoms are attached to adjacent carbon, these are called as vicinal dihalides.
Common names of such compounds are alkylene halide.
Cl
CH3–CH–CH2 H3C–C–CH2–Cl
II
CH3
Propylene Iodide Isobutylene chloride
(d) When two same halogen atoms are attached at the two ends of a carbon chain its common naming
will be polymethylene halide.
'poly' word indicates the number of –CH2– groups.
–CH2– 2 3 45 6
Hexa
Poly di tri tetra penta
Example :
CH2–CH2–CH2 CH2–CH2–CH2–CH2–CH2
I I , Br Br
Trimethylene Iodide Pentamethylene Bromide
Exception : CH2–X Dimethylene halide (wrong)
CH2–X Ethylene halide (right)
Common - Naming of di-hydroxy compounds :
(a) When two –OH groups are attached to adjacent carbon's they are termed as alkylene glycol.
OH
CH3–CH2–CH–CH2 CH3–CH2–C–CH2–OH
OH OH CH3
Butylene glycol Secondary pentylene glycol
(b) When two –OH groups are attached at the two ends of a carbon chain, these compounds are named
as polymethylene glycol.
Poly Number of >CH2 groups.
Example :
CH2–CH2–CH2–CH2–CH2–CH2 CH2–CH2–CH2–CH2
OH OH OH OH
Tetra methylene glycol
Hexamethylene glycol
Exception : CH2–OH Dimethylene glycol (wrong) 3. Trimethylene glycol
CH2–OH Ethylene glycol (right)
3. CH2–CH2–CH2
Ex : Make the structure of following organic compounds - OH OH
1. Isopropylidene Bromide 2. Isobutylene glycol
Br OH
2. H3C–C–CH2–OH
S o l . 1. CH3–C
Br CH3
CH3
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Common - Naming of the functional group having carbon :
Chart - 1
S . No . Fu nct iona l Group S u ffix
1 A ldehyde
2 O
3 i c acid
4 –C–H yl halide
5 O A m id e
o- ni tr i le
–C–OH
O
–C–X
O
–C–NH2
–C N
6 –N = C o -i so n it rile
a te
O
7 ic-anhydride
–C–O–R
O
–C
8 O
–C
O
Prefix :
1 Carbon Form
2 Carbon Acet
3 Carbon Propion
4 Carbon Butyr Normal
Iso
5 Carbon Valer Normal
Iso
Secondary
Tertiary
3C + (=) double bond = Acryl
4C + double bond = Croton
Example :
O O O
H–C–H , CH3–C–O–H , CH3–CH2–C–Cl ,
Acetic Acid Propionyl chloride
Formaldehyde
CH3 O O
CH3–CH–C–NH2 , CH3–C–H
Isobutyramide Acetaldehyde
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O
Ex : Common name of the compound : CH3–CH=CH–C–OH is -
(A) Crotonic acid (B) Acrylic acid
(C) Allylic acid (D) None
Sol. (A)
O
Ex : Common name of the compound : CH2–CH=C–H is -
(A) Croton aldehyde (B) Acryl aldehyde
(C) Propion aldehyde (D) Butyr aldehyde
Sol. (B)
O
Nomenclature of Ester : –C–O–R
The group which is attached to the oxygen is written as alkyl & the remaining structure is named same
as defined in chart-1.
Example :
O O OO O
CH3–C–O–CH3, CH3–CH2–C–O–CH2–CH3 , CH3–C–O–CH2–CH3, H–C–O–CH3 , CH3–O–C–H ,
Methyl acetate Ethyl propionate Ethyl acetate Methyl formate Methyl formate
OO O
CH3–C–O–H , CH2=CH–C–O–CH2–CH3, CH3–CH=CH–C–O–CH3
Acetic acid Ethyl acrylate Methyl crotonate
O
Nomenclature of Anhydride : R–C O
R–C
O
Rule : Add the total number of carbon atoms & divide by 2, the quotient will give you the number of carbon
atom now name it according to Chart-1.
Total = Quotient = Number of C atom
2
O O
CH3–C O 4 2 CH3–CH2–C O 6 3
CH3–C 2 CH3–CH2–C 2
O O
Propionic anhydride
Acetic anhydride
O
In R–C O If R R', You need not to find out Quotient. Divide it in two parts as above
R'–C & name it by suffixing ic anhydride (alphabetically)
O
O Acetic propionic anhydride (right) O
Propionic acetic anhydride (wrong)
CH3–C CH3–CH2–C
O O
Ex. : CH3–CH2–C CH3–CH2–CH2–C
O O
Butyric propionic anhydride
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O
CH3–CH–C O
CH3 O CH2=CH –C
,
eg. : CH3–CH2–CH–C O
CH2=CH–C
CH3 O O
Isobutyric secondary valeric anhydride Acrylic anhydride
Derived System : According to this system any compound is given name according to the parent name
of the homologous series. This system is reserved for the following nine homologous series.
Chart - 2
S . No . Nam e of H o m olo g o us Der ived Nam e Stru cture of grou p
S eries
|
1 A lkane Me thane
–C–
2 A lkene E th y le n e
|
> C=C<
3 A lkyne A cetylene – C C –
4 A lkanol C arbinol |
5 A lkanal A cetaldehyde
6 A lkanoic acid A cetic a cid – C– OH
7 A lkanoyl ha lide A cetyl
8 A lkanamide A cetamide |
9 A lkanone A cetone
|
– C– CHO
|
|
– C– COOH
|
|
– C– COX
|
|
– C – CO NH2
|
||
–C– C– C–
| || |
O
IUPAC system of Nomenclature :
The basic criterion for naming a structure by IUPAC system is choice of a parent name of the basic carbon
skeleton.
Nomenclature of alkanes is fundamental to naming whole class of organic compounds because it helps us
identify the basic carbon skeleton.
General rules for IUPAC nomenclature :
The IUPAC system is the most rational and widely used system of nomenclature in organic chemistry. The
most important feature of this system is that any given molecular structure has only one IUPAC name and
any given IUPAC name denotes only one molecular structure.
The IUPAC name of any organic compound essentially consists of five parts, i.e.
1. Word root 2. Primary Suffix 3. Secondary Suffix 4. Primary Prefix
5. Secondary Prefix
Thus, a complete IUPAC name of an organic compound consists of the following par ts :
Secondary prefix +Primary prefix + Word root + Primary suffix + Secondary suffix
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1 . Word root : It is the basic unit of the name. It denotes the number of carbon atoms present in the principal
chain (the longest possible continuous chain of carbon atoms including the functional group and based upon
the common names of alkanes) of the organic molecules.
Root word : According to number of carbon's in parent C–chain.
Number Root Number Root Number Root
of carbons word of carbons word of carbons word
1 Meth 6 Hex 11 Undec
2 Eth 7 Hept 12 dodec
3 Prop 8 Oct 13 tridec
4 But 9 Non 20 Eicos
5 Pent 10 Dec
2 . Primary Suffix : A primary suffix is always added to the word root to indicate whether the carbon chain
is saturated or unsaturated. The three basic primary suffixes are given below :
S . N o . Type of c arb on ch ain Pr im ary Su ffix General Nam e
1 (a) S atura te d -a n e A lk a n e
2 (b) U n s aturat ed w i th o n e do u ble b on d -e n e A lk e n e
3 (c) Un s atura ted w ith o n e trip le b o nd -y n e A lk y n e
If the parent carbon chain contain two, three or more double or triple bond, numerical prefix such as di
(for two), tri (for three), tetra (for four) etc. are added to the primary suffix. For example.
S. No . Type of carb on chain Pr im ary Su ffix Gen eral Nam e
1 (a) Unsaturated with two double bonds -d ie n e A lka d ie n e
2 (b) Unsaturated with two triple bonds -diyne Alkadiyne
3 . Secondary Suffix : A secondary suffix is always added to the primary suffix to indicate the nature of the
functional group present in the organic compounds. Secondary suffix of some important functional groups
are given below.
S . N o . Class of org anic com pou nds Functional gr oup S econdar y S uffix
1 A lcohols
2 A ldehydes – OH - o l
3 K e t on e s
4 C arboxylic acids –CHO - a l
5 A cid amides
6 A cid chlorides > C = O - one
7 E sters
8 N itriles – CO OH - o i c ac id
9 T h i o a lco h o ls
1 0 A mines –CONH - a m i de
2 - oyl halide
– COX
– COO R alka noate
– CN - ni tril e
– S H - t hi o l
– N H - a m in e
2
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The following examples illustrate the use of word root, primary suffix and secondary suffix in naming of
organic compounds.
S . Or ganic W o r d r o ot Prima ry Sec o nd ary IUP AC nam e
No. Com pou nd s Eth s u ffix s uffix Ethanol
CH3C H2O H Pr op a n (e ) ol
1 CH3C H2CH 2NH 2 B ut a n (e ) Amine P ro p an a m in e
2 CH CH CH COOH Pr op a n (e ) O ic a ci d Bu tan o ic aci d
3 Pr op P ro p a n e n itr i le
4 322 Pr op an(e) N i tri le
5 en(e) al Propenal
6 CH3C H2CN y n( e ) Pr o py n o ic a ci d
CH = CH CHO o i c a c id
2
HC CCOOH
4 . Primary prefix : A primary prefix is used simply to distinguish cyclic from acyclic compounds. For example,
in case of carbocyclic compounds.(cyclic compounds containing only carbon atoms in the ring.), a primary
prefix, cyclo is used immediately before the word root. Thus.
CH2 Cyclo + Pent + ane = Cyclopentane
CH2 CH2
eg. : CH2 CH2 Primary prefix + Word root + primary suffix = IUPAC
If the prefix cyclo is not used, it simply indicates that the compound is acyclic or open chain.
5 . Secondar y Prefix : In IUPAC system of nomenclature, certain groups are not considered as functional
groups but instead are treated as substituents. These are called secondary prefixes and are added immediately
before the word root (or the primary prefix in case of carbocyclic compounds) in alphabetical order to denote
the side chains or substituent groups. The secondary prefixes for some groups which are always treated as
substituents groups (regardless of the fact whether the organic compound is monofunctional or polyfunctional)
are given below :
S . O r gan ic Second ary W o rd ro o t IUP AC n am e
No . C o m p o un d s pr efix
Bromo eth W or d r oo t B ro m o e th an e
1 CH C H –Br m e th N itrom etha ne
3 2 Nitro eth ane E thoxyethane
ane
2 CH –NO E th o xy ane
32
3 C2H5 –OC2H 5
In case of carbocylic compounds, primary prefixes are also used.
Br
4
CH
5 3 4-Bromo + Cyclo + hex + an (e) + 1- ol
Ex : H2C CH2 Secondary Primary Word Primary Secondary
2 prefix prefix root suffix suffix
H2C6
CH2
CH
1
OH
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E x . Write the IUPAC name of the compound
CH3
OH
CH
CH3 CH3
S o l . 2 - Isopropyl-5-methylcyclohexanol or 2-(1-methylethyl)-5-methyl cyclohexanol
Here
Secondary prefix = 2 - Isoprypyl 5–methyl
Prim aryprefix = Cyclo
Word root = hex
Primary suffix = an (e)
Secondary suffix = ol
E x . The correct IUPAC of the following compound is -
(A) 1, 3, 4-trimethyl cyclopentane (B) 1, 3, 5-trimethyl cyclopentane
(C) 1, 3, 5-trimethyl cyclobutane (D) 1, 2, 4-trimethyl cyclopentane
Sol. (D)
E x . The correct statement is about following compound is -
OH
(A) word root is But (B) secondary prefix is cyclo
(C) primary suffix is ol (D) primary prefix is cyclo
Sol. (D)
IUPAC Nomenclature of Branched/Complex Alkanes :
( 1 ) (a) Select the longest chain of carbon atoms in the molecule.
(b) Count the number of carbon atoms in that chain and name according to the following rules.
Example :
CH2–CH3
45 6 7
CH3–C–CH2–CH2–CH3
32 1
CH2–CH2–CH3
Longest chain has 7 carbons.
It is a hept + ane
word root primary suffix
When chains of equal lengths are competing for selection, that chain is selected which has more number
of subtituents.
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CH3
CH3–H2C–CH–CH–CH3
CH–CH2–CH2–CH3
CH2–CH2–CH3
Here the chain shown is selected.
( 2 ) Carbon atoms in the longest chain selected as above in numbered consecutively form one end to the other
such that the substituents attached get the lowest number.
In the above example, according to this rule, the numbering will be done as :
CH3
32 1
CH3–H2C–CH–CH–CH3
45 6 7
CH–CH2–CH2–CH3
CH2–CH2–CH3
By this numbering, locant (substituents) get the number 2, 3 and 4 compared to 4, 5 and 6 if numbering
is done from other end.
( 3 ) Each substituent, which obviously, is an alkyl group is named according to number of carbon atoms present
in it and it is prefixed by the number to which it is located in the main chain. In the above example, substituents
are as following:
– CH3 (methyl) group at carbon NO. 2 2-methyl
3-ethyl
– C2H5 (ethyl) group at carbon NO. 3 4-propyl
– CH2CH2CH3 (propyl) group at carbon NO. 4
Hence, the above compound is named as :
3-Ethyl-2-methyl-4-propylheptane
( 4 ) If the same substituent occurs more than once in the molecule, the prefix di (for two), tri (for three), etc.
used to indicate how many times it appears.
The above example can be written with a little modification as :
Example :
CH3CH3
CH3–H2C–3C – C2H – C1 H3
45 67
CH–CH2–CH2–CH3
CH2–CH2–CH3
Methyl at No. 2, 3, Ethyl at no. 3, propyl at no.4
This will be named as : 3-Et hyl-2,3-dimet hyl-4-propylheptane
( 5 ) The name of the compound is composed in such a manner that each substituent with its number and name
is written alphabetically just before the parent name. Prefixes di, tri, tetra etc. are not considered in deciding
alphabetical order.
Ethyl will be written before methyl which will be written before propyl.
Note that in the above examples, this pattern has been compiled with.
*Also, as per convention,
(i) numbers are separated each other by commas.
(ii) numbers are separated from words by hyphens and
(iii) write the name of the compound as a single word (with no space between)
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E x . Write the IUPAC name of
1234 56
H3C–HC–HC–HC–H2C–CH3
CH3 CH2CH3
CH3
1. Primary suffix is ane as all are single bonds.
2. Chain is numbered as shown.
3. Root word is hex
4. Prefixes methyl appears twice It is 2, 4-dimethyl and 3-ethyl
5. While arranging in alphabetical order Replicators di, tri, tetra, are not considered.
3-Ethyl-2,4-dimethylhexane
Ex : Write the IUPAC name of the following compounds.
CH3
54 3 21 1 2 3 4 56 78 9
(i) CH3–CH2–CH–C–CH3 (ii) CH3–CH2–CH2–CH2–CH–CH2–CH2–CH2–CH3
CH3 CH3 1
CH–CH3
2
CH–CH3
3
CH3
S o l . (i) 2, 2, 3-trimethylpentane
(ii) 5-(1,2-dimethylpropyl)nonane
Ex : Write IUPAC name of the following compounds :-
CH3 CH2–CH3
(a) CH3–CH2–CH–CH2CH–CH2–CH2–CH3 (b) CH3–C–CH2–CH–CH2–CH–CH3
CH3 CH2–CH3 CH3 CH3
(c)
S o l . (a) 5-Ethyl-3-methyloctane
(b) 4-Ethyl-2, 2, 6-trimethylheptane
(c) 3-Methylhexane
IUPAC NOMENCLATURE OF ALKENES :
Functional group : –C=C–
(1) Select the longest chain containing carbon-carbon double bond. This need not be the longest chain in the
compound as a whole. Parent name will be alkene corresponding to number of carbon atoms in the longest
chain. CH3
CH3–CH2–C–CH=CH2
CH2
CH2
CH3
Longest chain is as shown above it has 6 atoms hexene = parent name
(2) Carbon atoms in the longest chain is numbered so that doubly bonded carbon atom gets the lowest number.
The position of double bond is indicated by the smaller of the numbers assigned to two carbon atoms of
double bond.
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The above example can be rewritten as,
CH3
32 1
CH3–CH2–C–CH=CH2
4CH2
5 CH2
6 CH3
Position of double bond will be indicated as no. 1.
Hence, name will be, 3-Ethyl–3–Methylhex–1–ene
CH3 CH3
Example : 6 54 3 2 1
CH3–C–CH=CH–C–CH3
CH3 CH3
2, 2, 5, 5-tetramethylhex-3-ene
Ex : Write the IUPAC name of the following compounds :
CH3 CH3 CH2–CH3 CH3
(a) CH3–CH2–CH–CH=CH–CH2–CH3 (b) CH3–CH2–CH–CH–CH–CH=C–CH3
CH2
CH2
CH–CH3
CH3
Ans. (a) 5–Methyl–3–heptene
(b) 5–Ethyl–2,6–dimethyl–4–(3–methylbutyl)oct–2–ene
Ex : Draw the bond line structures of the following compounds.
(a) 2–Methyl–3–heptene (b) 2, 6–Dimethyl hept –1, 5–diene
Sol. (a) (b)
IUPAC nomenclature of alkynes (– C C – group)
Numbering of longest chain is exactly same as that for naming alkenes.
Example
CH3
CH3–C–CH2–CCH
CH3CC–CH3 CH3
But–2–yne 4,4–dimethylpent–1–yne
Ex. : Write the IUPAC name of the following compounds :
(a) CH3–CH–CC–CH3 (b)
(b) 4–Propyl–2–heptyne
CH3
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Ex. : Write the IUPAC name of the following compounds :
(a) CH3–C CCH(CH3)2 CH3
(b) H3C–CH2–C – CH–CCH
CH3CH3
S o l . (a) 4–methyl–2–pentyne, (b) 3, 4, 4–trimethyl–1–hexyne
IUPAC nomenclature of hydrocarbons containing both double and triple bonds occurring only
once :
(i) Such hydrocarbon is named as alkenyne (not alkynene).
(ii) Numbering is done in a manner that double and triple bonds get the lowest possible number. In case
of a choice, the double bond is given preference over triple bond.
Example : CH3–CH=CH–CCH multiple bonds at (1) & (C)
5 43 21
Note 1 23 45 multiple bonds at (B) & (D)
Name will be Pent –3–en–1–yne
HC C – CH2– CH = CH2 Pent–1–en–4–yne
5 4 3 2 1
(Here there is a choice : if we number from other side)
HC C – CH2– CH = CH2
1 2 3 4 5
again multiple bonds are at numbers (1) and (D)
So, here we will give preference to double bond over triple bond.
Ex : Write IUPAC name of the following compounds.
(a) CH3–CH2–CC–CH–CH=CH2 (b)
CH2
CH–CH3
CH3
S o l . (a) 3–(2–Methyl propyl)–1–hepten–4–yne
(b) Oct–1–en–4–yne
Ex : Write IUPAC name of the following compounds.
(a) H–CCCH2CH=CH2 (b)
pent–1–en–4–yne
Sol. (a) 1,4–heptadiene–6–yne
(b)
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IUPAC NOMENCLATURE OF ALICYCLIC COMPOUNDS :
( 1 ) The names of alicylic compounds are obtained by adding the prefix "cyclo"
Cyclobutane Cyclopentene
( 2 ) The numbering of the carbon atoms in the ring is done in such a way that the substituent which comes
first in the alphabetical order is given the lowest possible number provided it does not violate the lowest
set of locants rule
Example :
CH3 CH3 C2H5 I
4
3 53 3 2 Br
42 4
2 CH3
6 1 CH2CH3 CH3
5 1 51
6 CH2CH3 CH3 Cl
6
1–Ethyl–3–methyl 2–Ethyl–1,4–dimethyl 3–Ethyl–1,1–dimethyl 2–Bromo–1–chloro
cyclohexane cyclohexane –3–iodocyclohexane
cyclohexane
( 3 ) When the ring contains more or equal number of carbon atoms than the alkyl group attached to it, then
it is named as a derivative of cycloalkane and the alkyl group is treated as substituent
Example :
CH2–CH2–CH3 (CH2)5CH3
3
2
4
CH3(CH2)5 51 (CH2)5CH3
6
Propylcyclopropane 1, 3, 5–Trishexylcyclohexane Cyclohexylcyclohexane
( 4 ) The alkane chain contains greater number of carbon atoms than present in the ring, the compound is considered
as the derivative of alkane and the ring is designated as substituent.
Example :
13 CH3–CH2–CH––CH2–CH2–CH3
2
4
2-Cyclopropylbutane 3–Cyclopentylhexane
( 5 ) If ring has unsaturation and side chain is saturated then ring is selected as parent chain.
If side chain has unsaturation and ring is saturated then side chain is selected as parent chain.
If both have unsaturation the chain with maximum unsaturation has selected as parent chain.
If equal unsaturation then longest chain is selected as parent chain.
If unsaturation and number of carbon atoms both are equal then ring is selected as parent chain.
Example :
6 3
51 42
4 2 5 1
3 6
1–Ethyl Cyclohex–1–ene 6–Ethyl–3,3–dimethyl cyclohex–1–ene
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32 3 21
=1 CH2 CH2–CH=CH
Methylene Cyclohexane 3–Cyclopropyl prop–1–ene
6 CH2–CH2–CH= CH–CH2–CH3
51
42
3
1–(Hex–3–ene) Cyclohex–1–ene
( 6 ) If, more than one alicyclic ring is attached to a single chain, the compound is named as a derivative of alkane
and the ring is treated as a substituent group.
Example
CH2
Dicyclopropylmethane 1,3-Dicyclohexyl propane 1–Cyclohexyl–4–cyclopropylbutane
( 7 ) If a multiple bond and some other substituents are present in the ring, the numbering is done in such a
way that the multiple bond gets the lowest number. Example :
NO2
3
4 2
1
5
6
3–Nitrocyclohex–1–ene
( 8 ) If a compound contains an alicyclic ring directly linked to the benzene ring. It is named as a derivative of
benzene. Example :
56 23
11 4
NO4
2
Cyclo hexyl benzene 3 2 65
CH3
1–(2–Methylcyclohexyl)–4–nitrobenzene
( 9 ) If functional group is present in cyclic compounds the main chain is taken there principal functional is lie,
if the principal functional group is present in ring also then main chain will be taken for the maximum no.
of carbon atoms.
OH 1
3
1
62 2
53 OH
4 1–Cyclohexyl propan–2–ol
2–propylcyclohexan–1–ol
( 1 0 ) When chain terminating functional group is directly attached with ring then ring is taken as parent chain
& special suffix used for functional group.
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S . No . Fu nct iona l Group S u ffix
1 — CHO C arb alde h y de
2 — COOH C arboxylic acid
3 — COX Carb onyl halide
4 — COOR Alkyl C arboxylate
5 — CONH2 Carbox amide
6 — CN Carbonitrile
Example :
CN CHO O
2 COOC2H5
1
Cyclohexane Carbonitrile Cyclohexane Carbaldehyde Ethyl–(2–oxo)cyclohexane–1–carboxylate
Ex : Write the IUPAC name of the following compound :
CH= CH–COCH3 CH3
CH3
(i) (ii)
O CH3
3 CH3
4
42
CH=C3 H–C2 –C1 H3
(ii)
S o l . (i)
51
4–Cyclohexylbut–3–en–2–one 2,3–Dimethyl cyclopent–1–ene
Ex : The correct IUPAC name of the following compound is :
OH OH
CH2–CH–CH2–CH3
(A) 1–(2–hydroxy cyclohexane) butan–2–ol
(B) 4–(2–hydroxy cyclohexane) butan–3–ol
(C) 1–(2–hydroxy but–1–yl) cyclohexan–2–ol
(D) 2–(2–hydroxy butyl) cyclohexan–1–ol
Sol. (D)
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IUPAC NOMENCLATURE OF COMPOUNDS CONTAINING FUNCTIONAL GROUPS
Funtional Groups
Non chain terminating Chain terminating
(i) –SO3H
O
(i) –C–OH
(ii) –C– (ii) –C–O–C–
O OO
(iii) –OH (iii) –C–OR
(iv) –NH2 O
(v) –SH
(iv) –C–X
O
(v) –C–NH2
O
(vi) –CN
(vii) –CHO
Rules for non chain terminating functional groups :
(A ) Parent chain :
Select the longest possible chain with maximum functional group and maximum unsaturation with out caring
whether it also denotes the longest possible chain or not.
Example : 432
CH3–CH2–CH–CH2–CH3
1
CH2OH
(Parent chain contains four rather than five carbon atoms)
( B ) Lowest number for the functional group :
Numbering is done from that side of the chain which gives lowest locant to the principle functional group
followed by double and triple bonds.
O O
6 5 4 32 1 1 2 3 45 6
CH3–CH–CH2–C–CH2–CH3 CH3–CH–CH2–C–CH2–CH3
Example : CH3 CH3
(II) wrong
(I) correct
( C=O group gets lowest number 3 ) ( C=O group gets number 4 which is not lowest)
Rules for chain terminating functional groups :
( 1 ) When a chain terminating functional group such as –CHO, –COOH, – COOR, –CONH2, –COCl, – CN
etc. is present, it is always given number 1 (one.)
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Example : :
O O
4 3 21 5 4 32 1
CH3–CH2–CH–C–OH CH3 –CC–CH2–C–H
CH3 Pent–3–yn–1–al
2–Methylbutan–1–oic acid
( 2 ) If a compound contains two or more like groups, the numerical prefixes di, tri, tetra etc. are used
Example : :
CH2 CH CH2 CH3–C–CH2–C–CH3
OH OH OH
Propane –1,2,3–triol OO
Pentane–2, 4–dione
( 3 ) The name for benzene as substituent is phenyl. In case the phenyl ring is further substituted, the carbon
atoms of the ring directly attached to the parent chain in such a ways that the substituent on the ring gets
the least possible number.
Example : :
21 CH3O
CH–CCl3 CH3–C2 – C1 –OC2H5
1
2
1,1,1–Trichloro–2,2–diphenyl ethane 3 NO2
Ethyl–2–methyl–2–(3–nitrophenyl) propanoate
( 4 ) If the organic molecule contain more than one similar complexes subtitutents, then the numerical prefixes
such as di, tri, tetra etc. are replaced by bis, tris, tetrakis etc. respectively.
Example : :
HO–CH2–CH2–O CH–COOH
HO–CH2–CH2–O
2,2–Bis–(2–hydroxyethoxy) ethanoic acid
Ex : Write IUPAC name of the following compounds :
O (iii) CH3–CH–CH2–COOH
CH3
(i) CH3CH2–CH–C–OCH3 (ii) (CH3)3COH
CH2
CH3
S o l . (i) Methyl–2–ethylbutanoate
(ii) 2–Methylpropan–2–ol
(iii) 3–Methylbutanoic acid
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Rules for IUPAC nomenclature of polyfunctional compounds :
1 . When an organic compound contains two or more different functional groups is selected as the principal
functional group while other groups are treated as substituents.
S. NO. Functional group Prefix Suffix
1. — (C) OOH (carboxylic acid) × oic acid
— COOH carboxy carboxylic acid
2. — SO3H (sulphonic acid) sulpho sulphonic acid
O
× oic anhydride
(C)
3 . O(anhydride)
(C)
O
4. — (C)OOR (ester) × alkyl ------ oate
— COOR alkoxy carbonyl alkyl ----- carboxylate
or carbalkoxy
5. — (C)OX (acid halide) × oyl halide
— COX halo formyl carbonyl halide
× amide
6. — (C)ONH2 (amide) carbamoyl carboxamide
— CONH2 × Nitrile
cyano carbonitrile
7. — (C)N (cyanide) × isonitrile
— CN isocyano/carbyl amino ×
oxo al
8. — N (C) (isocyanide) formyl carbaldehyde
— NC
9. — (C)HO (aldehyde)
— CHO
10. (C) (Ketone) keto/oxo one
O hydroxy ol
mercapto thiol
11. — OH (alcohol) amino amine
12. — SH (thio alcohol) alkoxy ×
13. — NH2 (amine)
14. — OR (ether)
2 . Some functional group such as all halo groups. (Fluoro, bromo, chloro, iodo) nitrosol, (NO) nitro (–NO2)
Example : NH2
5 43 2 1
CH3–CH–CH–CH–CH3
Cl OH
4–Amino–3–chloropentan–2–ol
(–NH2 & –Cl group treat as substituent )
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Numbering the principal chain order is
[Principal functional group > double bond > triple bond > substituents]
Example : O
CH3–C–CH2–COOH 5 43 2 1
CH3–C–CH2–CH2–CHO
O 4–Oxopentan–1–al
3–Oxobutan–1–oic acid [–CHO > C=O]
[–COOH > – CO]
O
65 4 32 1
O = CH–CH2–CH2–C–CH2–COOH
3,6–Dioxohexanoic acid
or 5-formyl–3–oxopentanoic acid
[COOH > C & CHO]
O
3 . The longest possible chain of carbon atoms containing the functional group the maximum number of
multiple bonds is selected as parent chain.
Example :
4 32
(a) CH3–CH2–CH–CH2–CH3
CH2OH
1
parent chain contains four rather than five carbon atoms.
O
(b) CH3–CH–CH2–C–O–C2H5
3 21
CH=CH2
45
parent chain contains four rather than six carbon atoms.
O
4
O CH3 C–NH2
1
(c) CH3–CH–CH2–C–O–C2H5
3 21 (d) 4 3 2
CH=CH2
45 CH3–CH–CH–CHCH3
Ethyl–3–methyl–4–pentenoate
CH3 CH3
3,3–Dimethyl–2–(1–methylethyl) butanamide
4 . If more than one same chain terminating group are present then the principal chain is selected including
the functional groups and numbering is done from that side which gives lowest locant to unsaturation substituent.
Example : HOOC–CH2–CH2–COOH 12 3 4 5
12 3 4
Butan–1,4–dioic acid NC–CH–CH2–CH2–CN
CH3
2-Methylpentanedinitrile
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Example : Write the IUPAC name of
34 5
CH3–CH2–CH–CH2–CH–CH3
12 67
CN–CH2 CH2–CH3
1. The longest chain containing functional group is of 7 carbon atoms. Therefore, the word root is hept
& the chain is numbered as shown.
2. There is no multiple bond in it. Hence, the primary suffix is ane.
3. The functional groups is –CN. Hence , secondary suffix is nitrile.
4 . Moreover, there is a methyl groups on carbon 5 and ethyl group on carbon 3.
5. The IUPAC name is ,therefore, 3–Ethyl–5–methylheptanenitrile
Example : Write the IUPAC name of
76 54 32 1
CH3–CH2–CH–CH=CH–CH2–CHO
CH3
1 . The longest chain containing functional group is of seven carbon atoms. Therefore, word root is hept.
2. As C=C double bond is present in the molecule. Thus, primary suffix is ene.
3. The secondary suffix is al because of presence of –CHO group.
4. The chain is numbered as shown so that carbon atoms of –CHO group gets number 1.
The methyl group is present on carbon 5 while position of double bond is 3. Thus , IUPAC name is
5–Methylhept–3–en–1–al
Example : Write the IUPAC name of
NH2
11 9 3 2 1
CH3–CH–CH2 CH3 CH2–CH–CH3
10 87 4
HC CH CH OH
65
Br HC–CH
NO2
1. Primary suffix is ene, due to presence of double bond between C4 & C5
2. Senior functional group is alcohol hence secondary suffix is –ol
3. Root word is undec.
4. Chain is numbered as shown.
5. 6–Nitro–7–methyl–8–bromo–10–amino are prefixes. Arrange them in alphabetical order & give the
name
10–Amino–8–bromo–7–methyl–6–nitroundec–4–en–2–ol
Nomenclature of Aromatic Compounds :
The aromatic compounds are cyclic compounds contains one or more benzene type rings. Benzene is the
simplest hydrocarbon of aromatic series which has planar cyclic ring of six carbon atoms having three double
bonds in alternate positions as shown below.
CH 1
HC CH 62
HC CH or 5 3
CH 4
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(A) Nuclear Substituted –
The functional group is directly attached to benzene ring in the IUPAC system, they are named as derivative
of benzene. The position of the substituents in disubstituted benzenes are indicates either by prefixes such
as o–(ortho) for 1, 2, m–(meta) for for 1, 3 and p (para) for 1, 4 position. However, many of their common
names have also been adopted by the IUPAC system.
( B ) Side–Chain Substituted –
The functional group is present in the side chain of the benzene ring in the IUPAC systems, these are usually
named as phenyl derivatives of the corresponding aliphatic compounds.
The IUPAC and common names of a few impor tant members of each formly are given below :
(a) Aromatic hydrocarbons (arenes) : Hydrocarbons which contain both aliphatic and aromatic units are
called arenes. These are of two types
(i) Hydrocarbon containing one ring only.
Example :
CH3 CH3 CH3 123
1 CH3 1 1 CH3–CH–CH3
2
2 2
3
, 3 CH3 , 4 ,
CH3
1,2–Dimethyl benzene 1,3–Dimethyl benzene 1,4–Dimethyl benzene Isopropyl benzene
(o–Xylene) (m–Xylene) (p–Xylene) (Cumene)
CH=CH2 32 1 CCH 3 21
CH2CH=CH2 CH2C CH
, , ,
Ethenynl benzene 3–propenyl benzene Ethynyl benzene 3–propynyl benzene
(Styrene) (Allyl benzene) (Phenyl acetylene) (Propargyl benzene)
(ii) Hydrocarbon containing condensed or fused ring : 3
4 2
1
8 1 5 9 1 5
7 2 72 6
6 36 3 10 ,
5
, , 7 9
4 5 10 4 8
Naphthalene Anthracene Phenanthrene
Aryl Groups :
CH2– CH C CH3 CH3 CH3
1 1 1
22
2
3
, , , , 2–Tolyl , 3 , 4
Phenyl Benzo or o–Tolyl
Benzyl Benzal 3–Tolyl 4–Tolyl
or m–Tolyl or p–Tolyl
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Halogen derivatives : Cl
1
Cl
Cl 1 Cl
12
, , Cl
1,2–Dichlorobenzene 1,4–Dichlorobenzene
Chloro benzene or o–Dichlorobenzene or p–Dichlorobenzene
CHCl2 12 1 CH=CH–Cl
CH2–CH2–CH2–Br
, ,
Phenyldicholoromethane 1–Bromo–3–phenyl propane 1–chloro–2–phenyl ethene
(Benzyl chloride)
Hydroxy derivatives :
The nuclear hydroxy derivatives are called phenols while the side chain substituted hydroxy derivatives are
called aromatic alcohols.
(i) Phenols–monohydric OH
OH
1
2
3
, 4 ,
Hydroxybenzene
CH3
(phenol)
4–methyl phenol
(p-cresol)
(ii) Dihydric and polyhydric phenols
OH OH OH
1 OH
1 OH
2 2 Benzene–1,4–diol(Quinol)
Benzene–1,2–diol 3 OH
(Catechol) Benzene–1,3–diol
(Resorcinol)
(iii) Aromatic Alcohols : 21
CH2OH
C H3CH–OH
Phenyl methanol 1–phenyl ethanol
(Benzyl alcohol) (–phenyl ethyl alcohol)
(iv) Aromatic ethers
O–C6H5
OCH3
Phenoxy benzene
(Diphenyl ether)
Methoxy benzene
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(v) Aldehydes CHO
CHO 1 OH
CH2CH2–CHO
Benzaldehyde 2
(vi) Ketones
12 2–Hydroxy benzaldehyde 3–phenylpropanal
COCH3 (Salicylaldehyde) (–phenylpropionaldehyde)
COC6H5
1–phenyl ethanone Diphenylmethanone
(Acetophenone) (Benzophenone)
(vii) Nitro Compounds NO2
NO2
1
Nitrobenzene 2
(viii) Amines
(a) Aryl amines 3 NO2
1, 3–Dinitrobenzene
NH2 (m-Dinitrobenzene)
Benzenamine NH2 NH2
(Aniline)
Benzene–1,2–diamine
(b) Aryl alkyl amine (o-phenylenediamine)
CH2NH2
CH2–CH2–NH2
Phenyl methanamine 2–Phenyl ethanamine
(Benzylamine) (–phenyl ethyl amine)
(ix) Arenediazonium Salts :
N NHSO4
NN.Cl Benzene diazonium hydrogen sulphate
Benzene diazonium chloride N= C
(x) Cyanides and Isocyanides
CN
Benzonitrile Phenyl isocyanide or
or Phenyl Cyanide Phenyl carbylamine
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(xi) Carboxylic Acids COOH COOH
COOH
1 1
Benzoic acid
(xii) Anhydrides CH3 COOH
2 2
2–Methyl benzoic acid Benzene–1,2–dicarboxylic acid
(o–toluic acid) (Pthalic acid)
OO
C6H5–C–O–C–C6H5
Benzoic anhydride
(xiii) Esters (xiv) Amides
CH3 4 3 O
C–NH2
2 O
1 O–C–CH3
4–Methyl phenyl ethanoate Benzamide
E x . Write IUPAC name of the aromatic compounds
CH3 CH2OCH3
CH2–CH–CHO
(i) (ii)
S o l . (i) 2-methyl -3-phenylpropanal, (ii) Methoxyphenylmethane (Benzylmethyl ether)
Some Impor tant 1993 Recommendations of IUPAC Nomenclature of Organic Compounds :
1 . Locants (numerals and / or letters) are placed immediately before the part of the name to which they relate.
For example :
CH3CH2CH = CH2 should be named as but–1–ene
CH3CH2OH should be named as ethan–1–ol
Similarly , a few more examples are given as following :
OH CH3 CH3
1 4 3 2 1 3 2 1
2
CH3–CH=C–CH2OH CH3–C–CH2OH
3
CH3
Cyclopent–2–en–1–ol
2–Methylbut–2–en–1–ol 2,2–Dimethylpropan–1–ol
2 . The locant 1 is often omitted when there is no ambiguity. For example.
CH3CH2CH2COOH CH3CH2CHO CH3CH2CH2CN
Butanoic acid Propanal Butanentrile
In all the above examples locant 1 for the functional group is omitted because the position of the functional
group is unambiguous. However, in the following cases the position of the functional group must be mentioned.
CH3CH2CH2OH CH3CH2CH2NH2
Propan–1–ol Propan-1- amine
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Here, we cannot write simply propanol (or propanamine) because there are two propanols ; propan–1–ol
and propan–2–ol.
3 . Arrangement of Prefixes :
Simple prefixes such as methyl, ethyl chloro, nitro, hydroxy, etc. are arranged alphabetically.
The prefixes di, tri, etc. are however not considered for comparison.
1 2 3 4 5 6 7 8 2 1
CH3CH2CHCH2CHCH2CH2CH3 CH2CH2
Example : CH3 C2H5 Cl Br
5–Ethyl–3–methyl octane 1–Bromo–2–chloroethane
(ii) The name of a prefix for a substituted substituent is considered to begin with the first letter of its
complete name.
Example :
Cl
CH–CH2–CH3
8 7 6 5 4 3 2 1
CH3–CH2––CH2–CH2–CH–CH–CH2–CH3
CH3
4–(1–Chloropropyl)–3–methyloctane
for the substituted 1–chloropropyl, 'C' is taken as the first letter.
(iii) When two or more prefixes consist of identical roman letters priority for citation is given to the group
which contains the lowest locant at the first point of difference.
For example
Cl–CH–CH3
1
2
3
4
CH2–CH2Cl
1–(chloroethyl)–4–(2–chloroethyl) cyclohexane
Here, 1–chloroethyl gets priority over 2–chloroethyl.
Bicyclic :
Bicyclo : When two rings are fused at two carbon then prefix Bicyclo is used.(Carbon chain should be taken
in decreasing order)
( i ) Two fused or bridged rings are called bicycloalkanes.
( i i ) Total number of carbon atoms present in both the rings is considered as parent alkane.
(ii i) Common carbon atoms present in both the rings are referred as principal points of the bridge.
( i v ) The line joining the principal points is called the bridge line. Bridge line can have 0. 1. 2 etc carbon atoms.
( v ) The name is written as bicyclo [x. y. z] alkane. x. y. z are in the decreasing order.
( v i ) The numbers are separated by full stops.
Bicyclo [4.4.0] decane Bicyclo [4.3.0] nonane
Bicyclo [2.2.0] hexane Bicyclo [1.1.0] butane
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Bicyclo [2.2.1] heptane Bicyclo [2.2.2] octane
Spiro : When two rings are fused at one carbon the prefix spiro is used (Carbon chain should be taken
in increasing order)
1. A molecule that has two rings sharing a single atom is called spirocyclic.
2. The numbers of skeletal atoms linked to the spiro atom are indicated by arabic numbers, separated by
a full stop.
3. The numbers are written in ascending order and enclosed in square brackets.
4. Numbering of a spiro bicyclic hydrocarbon starts with a ring carbon next to the spiro atom and proceeds
first through the smaller ring and then through the spiro atom and around the second ring.
Example :
6 89 1 6 71
4 5 432
75
41 72
8 6 5 3
32
Spiro[3.5] nonane Spiro[2.4] heptane
Spiro[3.4] octane
Spiro [4.4] nonane Spiro [2.4] heptane
Spiro [2.2] pentane 7
61
3
52
4O
4–oxa spiro [2.4] heptane
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SOLVED EXA MPLES
Ex.1 The correct IUPAC name of the following compound is O CH CH2 CH CHO
(A) 1,1–diformyl propanal HC O
(C) 2–formyl butanedial
(B) 3–formyl butanedial
(D) 1,1,3–ethane tricarbaldehyde
43 21
Sol. (C) The principal functional group is – CHO. O CH CH2 CH CHO .
CHO
Ex.2 2–formyl butanedial
The correct IUPAC name of compound CH3 CH2 C CH CHO is
O CN
(A) 2–cyano–3–oxopentanal (B) 2–formyl–3–oxopentanenitrile
(C) 2–cyano–1, 3–pentanedione (D) 1, 3–dioxo–2–cyanopentane
Sol. (B) Here the main functional group is – CN, which had nitrile suffix and CHO and CO are taken as substituents.
54 32 CHO (2-formyl-3-oxopentanenitrile)
CH3 CH2 C CH
O 1CN
Ex.3 IUPAC name of CH3 C CH C OCH3
O C OO (B) 2, 2-acetyl-1-methoxy ethanone
CH3 (D) none of these
(A) Methyl-2, 2-acetyl ethanoate
(C) Methyl-2-acetyl-3-oxobutanoate
Sol. (C) The principal functional group is ester group. CH3 C CH C OCH3 (Methyl-2-acetyl-3-oxobutanoate)
O C OO
CH3
E x . 4 The IUPAC name of compound HO C O CH3 is
CH3 C C C H
NH2 Cl
(A) 2-amino-3-chloro-2-methyl-2-pentenoic acid (B) 3-amino-4-chloro-2-methyl-2-pentenoic acid
(C) 4-amino-3-chloro-2-methyl-2-pentenoic acid (D) none of these
Sol. (B) The principal functional group is carboxylic acid (–COOH)
15
HO C O CH3
234
CH3 C C C H
NH2 Cl
3-amino-4-chloro-2-methyl-2-pentenoic acid
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Ex.5 How many carbons are in simplest alkyne having two side chanis ?
(A) 5 (B) 6 (C) 7 (D) 8
(D) Orlone
C (D) ,
Sol. (B) H C C C C
C
Ex.6 The compound name trichloroethene is
(A) Westron (B) Perclene (C) Westrosol
Sol. (C) Trichloroethene is westrosol Cl Cl
CC 1,1,2-trichlorethene(westrosol)
H Cl
E x . 7 The type of unsaturation present in crotonic acid is -
(A) , (B) , (C) ,
Sol. (A) The type of unsaturation present in crotonic acid is ,
O
CH3 CH CH C OH
4 3 21
Crotonic acid or (2-Butenoic acid) O
Ex.8 IUPAC name of compound CH3CH2OCCH2CH2CH3 is
(A) Propyl propanoate (B) Ethyl butanoate
(C) Propyl butanoate (D) Ethyl propanoate
12 3 4
S o l . (B) CH3 CH2 O C CH2 CH2 CH3 Ethyl butanoate
O
E x . 9 The IUPAC name of the compound given below is
(A) Bicyclo [3.2.1] octane (B) Bicyclo [3.2.2] octane
(C) Spiro [2.2] octane (D) None of these
Sol. (A)
Ex. 10 The structure of spiro [3.3] heptane is
(A) (B) (C) (D)
Sol. (B)
E x . 1 1 The structure of bicyclo [1.1.0] butane is
(A) (B) (C) (D)
Sol. (D)
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PURIFICATION METHODS
Distillation Techniques :
Type Conditions Examples
(A) Simple distillation
(i) When liquid sample has (i) Mixture of chloroform
(B) Fractional distillation non volatile impurities (BP = 334K) and Aniline
(C) Distallation under (BP = 457K)
(ii) When boiling point
reduced pressure difference is 80° K or more. (ii) Mixture of Ether (BP = 308K) &
(Vacuum distillation) Toluene (BP = 384K)
(D) Steam distillation
(iii) Hexane (342K) and Toulene(384K)
When BP difference is 10° (i) Crude oil in petroleum industry
(ii) Acetone (329) and Methyl alcohol(338K)
When liquid boils at higher (i) Concentration of sugar juice
temperature and it may (ii) Recovery of glycerol from spent lye.
decompose before BP is attained. (iii) Glycerol
When the substance is immiscible (i) Aniline is separated from water
with water and steam volatile. (ii) Turpentine oil
(iii) Nitro Benzene
(iv) Bromo Benzene
(v) Naphthalene
(vi) o-Nitrophenol
SIMPLE DISTILLATION TECHNIQUE
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FR ACTIONAL DISTILLATION
DISTILLATION UNDER REDUCED PRESSURE
STEA M DISTILLATION
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LASSAIGNE METHOD :
1 . Nitrogen (N) : Na + C + N NaCN
(Sodium extract)
Te st : NaCN + FeSO4 + NaOH
boil & cool
FeCl3 + conc. HCl
Blue or green colour [Fe4[Fe(CN)6]3
Prussian blue
2 . Sulphur (S) : 2Na + S Na2S
(Sodium extract)
Te st (1) Na2S
Sodium nitro prusside
A deep voilet colour
Te st (2) Na2S + CH3COOH + (CH3COO)2Pb
Black colour (PbS)
3 . Halogen (X) : Na + Cl NaCl
(Sodium extract)
Te st : NaCl + HNO3 + AgNO3
(a) White ppt soluble in aq. NH3 confirms Cl
(b) Yellow ppt partially soluble in aq. NH3 confirms Br
(c) yellow ppt insoluble in aq. NH3 confirms I
4 . Nitrogen and Sulphur together :
Na + C + N + S NaC NS
(Sodium thiocynate)
As in test of nitrogen, instead of green or blue colour,
blood red coloration confirms presence of N and S both.
5 . Phosphorous (P) :
P N a 2O2 Na3PO4
boils,
Solution in boiled with nitric acid and then treated
with ammonium molybdate (NH4)2 MoO4
Formation of yellow ppt indicate presence of phosphate
hence phosphorous present in organic compounds.
THE QUANTITATIVE ANALYSIS :
Quantitative analysis involves the estimation of percentage composition of various element by suitable method.
The molecular mass of the compound is also determined by suitable methods. The knowledge of molecular
mass and percentage composition help us to determine the molecular formula of the compound.
ESTIMATION OF CARBON AND HYDROGEN OR LIEBIG COMBUSTION METHOD :
Organic compound + dry, black CuO
(w g) Heat strongly in combustion tube
mixture of oxide
Pass through
(i) anhydrous CuSO4
(ii) anhydrous CaCl2
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say increase in weight = a g
Pass through
(i) KOH (aq)
(ii) Saphnolite resin
say increase in weight = b g
For % of H - The increase in weight is 'a' g due to the formation of H2O
18 g H2O has H = 2 g
2a
a g H2O has H g
18
2a
Since w g organic compound has = 18 g hydrogen.
2a 100
100 g organic compound has= 18 w g hydrogen
% H 2 weight of H2O formed 100
18 weight of subs tan ce
For % of C -
The increase in wt is b g due to formation of CO2
44 g CO2 has C = 12 g
12
b g CO2 has C = b g
44
Since w g organic compound has 12 b g carbon
44
100 g organic comound has 12 b 100 g carbon
44 w
% C 12 weight of CO2 formed 100
44 weight of subs tan ce
Note : This method is suitable for estimation if organic compound contains C and H only. In case if other
elements e.g., N,S, halogens are also present the organic compound will also give their oxides which on
being absorbed in KOH will increase the percentage of carbon and therefore following modification
should be made.
(a) If N is also present : The gaseous oxide mixture is first passed over heated Cu gauze which reduces all
oxides of N to N2 which are neither absorbed by H2O nor by KOH
2NO + 2Cu N2 + 2CuO
(b) If halogens are present : A roll of silver gauze is placed at the exit end of combustion tube which retains
all the halogens on itself.
2Ag + X2 2AgX
2Ag + CuX2 2AgX + Cu
(c) If S is present : A layer of fused lead chromate is placed near the exit end, all the oxides of sulphur are
oxidised to PbSO4 & left in tube it self.
Cr+6 + 3e– Cr+3
S+4 S+6 + 2e–
(in SO2) (in SO4–2)
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GENER AL CONCEPT FOR DRYING AND DEHYDR ATING AGENTS
(1) Acidic oxides ( non metals oxides such as CO2, NO2, SO2 P2O5 etc.) are absorbed by alkali (KOH,
NaOH, Ca(OH)2 etc.)
(ii) Basic oxides (Na2O, K2O etc.) are dissolved in acids (H2SO4, HCl etc.)
(iii) Acidic oxides can not be dried by basic dehydrating agent (e.g CaO) but they are dried by acid dehydrat-
ing agent (e.g H2SO4, P2O5 etc). However H2S can be dried by H2SO4 because it reacts with H2SO4.
H2S + H2SO4 2H2O + S + SO2
(iv) Basic substances can not be dried by acidic dehydrating agent but are dried by basic dehydrating agent
(e.g CaO). It is because NH3 is dried by CaO but not by H2SO4.
ESTIMATION OF NITROGEN
(a) Duma's method :
Organic compound heateCdusOtrongly Mixture of oxides Pass over Cu gauze N2+ Other oxides
(w g)
Dry N2 dryingagent N2 + Moisture PKasOs tHhr(oaqu.g)h
(Let Vml at N.T.P.)
22400 ml N2 weigh at N.T.P. = 28 g
V ml N2 weigh at NTP = 28 V g
22400
since w g organic compound gives 28 V 100 g
22400 w
% N 28 Volume of N2 at NTP 100
22400 weight of the compound
Note : This method can be used to estimate nitrogen in all types of organic compounds.
KJELDAHL'S METHOD :
This method is based on the principle that a nitrogenous organic compound on heating with conc. H2SO4
converts all its nitrogen quantitatively to ammonium sulphate ;
organic compound + conc. H2SO4 + K2SO4 + CuSO4
(w g)
(raises the B.P. of H2SO4) (catalyst)
Heating in Kjeldahl flask
(NH 4 )2 SO 4 draodpdbKyOdrHop NH 3 is form ed
Pass this gas through V1 ml of N1 H2SO4
Now titrate the H2SO4 by another alkali say of N1 H2SO4 (NH3 is absorbed here)
V2 ml of N2 ,KOH are used
Meq of H2SO4 taken = N1V1
Meq. of KOH used for H2SO4 = N2V2
Meq. of H2SO4 for NH3 = N1V1 – N2V2
Meq. of NH3 formed = (N1V1 – N2V2) or say NV)
(the difference obtained or V ml of N H2SO4 are used to absorb NH3)
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WNH3 1000 NV
17
WNH3 17 NV
1000
Now 17 g NH3 has 14 g Nitrogen
17 NV g NH3 has 14 17 NV g Nitrogen
1000 17 1000
14NV
= 1000 g Nitrogen
w g organic compound has 14NV g nitrogen
1000
14NV 100
.100 g organic compound has w 1000 g nitrogen.
1.4NV
= w g nitrogen
% Nitrogen 1.4 Normality of the acid volume of the acid
weight of the compound
Note : This method is simpler and more convenient and is mainly used for finding out the percentage of nitrogen in
food stuffs, soil, fertilizers and various agricultural products. This method cannot be used for compound having
nitro groups, azo gp. (–N = N–) and nitrogen in the ring (pyridine, quinole etc.). Since nitrogen in these
compounds is not quantitatively converted in to ammonium sulphate.
ESTIMATION OF SULPHUR (CARIUS METHOD) :
Organic compound + con. HNO3 + BaCl2 ppt (BaSO4) is dried and weighed say "a" g
(w g)
S Furning.HNO3 H2SO4 BaCl2 BaSO4 + HCl
233 g BaSO4 has 32 g sulphur (a g)
32 a
a g BaSO4 has 233 g sulphur
% of Sulphur = 32 a 100
233 w
%S 32 weight of BaSO4 formed
100
233 weight of compound
ESTIMATION OF HALOGENS ( CARIUS METHOD) :
Organic compound + con HNO3 + AgNO3 ppt (AgX) is dried and weighed say a g
% of Cl = 35.5 weight of AgCl 100
143.3 weight of compound
80 weight of AgBr
% of Br = 100
188 weight of compound
% of I= 127 weight of AgI 100
235 weight of compound
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ESTIMATION OF PHOSPHORUS - (CARIUS METHOD) :
Organic compound + con. HNO3 + Magnesia mixture (MgSO4 + NH4OH + NH4Cl)
(w g)
2 MgNH4PO4 Mg2P2O7 + 2NH3 + H2O
Precipitate is dried and ignited to give magnesium pyrophosphate (Mg2P2O7) weighed say a g
% of P 62 weight of Mg2 P2 O 7 formed 100
222
weight of compound
Atomic weight of P = 31 × 2 = 62 g
molecular weight of Mg2P2O7 = 222 g
ESTIMATION OF OXYGEN :
There is no direct formula and method for estimation of oxygen however, percentage of oxygen is calculated by
% of oxgyen = 100 – [Sum of the % of all other elements]
Note - A direct method for estimation of oxygen has been given by Alusive in 1947 known as Alusive
method.
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