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Nomenclature of Organic Compounds Organic Chemistry

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Salient Features of IUPAC System


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Rule For Naming CART20
Arrangement of Prefixes, Root Word and Suffixes

Nomenclature Alkanes
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Nomenclature of Alkenes connected with IITian
Nomencalture of Alkyne
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Nomencalture of Aromatic Hydrocarbons

Nomenclature of Alkyl Halide


Name
Nomenclature of Alcohols

Nomenclature of Ether (R-O-R) Email


Nomenclature of Aldehydes
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Nomenclature of Ketones

Nomenclature of Carboxylic Acid Select Grade

Naming Acyl Groups- Acid halide and Anhydrides


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Nomenclature of Amines

Nomenclature of Nitro Alkane

Nomenclature of Alkyl Cyanide

IUPAC System [International union of pure and applied chemistry]

The most important feature of this system is that any given molecular structure has
only one IUPAC name which denotes only one molecular structure.

Related Resources

Salient Features of IUPAC System


1.A given compound can be assigned only one name. Electronic Displacement in
Covalent Bonds
2. A given name can clearly direct in writing of one and only one molecular
structure. Electronic Displacement in
Covalent Bonds Table of...
3. The system can be applied in naming complex organic compounds.

4. The system can be applied in naming multifunctional organic compounds.

Solved Examples

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5. This is simple, systematic and scientific method of nomenclature of organic Question 1: Arrange the
compounds. following in the...

Rule For Naming


Reaction Intermediates
Prefix (alphabetically) root word (alk) primary suffix (ene, yne) secondary suffix
Reactive Intermediates
(main functional group)
Table of Content...
So IUPAC name of any organic compounds essentially consists of two or three parts.
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(i) Root word (ii) Suffix (iii) Prefix

(i) Root Words Classification of organic


compounds
The basic unit is a series of root words which indicate linear or continuous chains of
carbon atoms. Chains containing one to four carbon atoms are known by special root Classification of Organic
words while chains from C5onwards are known by Greek number roots. Comounds Table of...

Chain Length Root word Chain Length Root word

C1 Meth- C11 Undec-

C2 Eth- C12 Dodec- Latest articles from


C2 Prop- C13 Tridec- Blog
C4 But- C14 Tetradec-

C5 Pent- C15 Pentadec- Department of Textile


Technology, IIT Delhi
C6 Hex- C16 Hexadec-

C7 Hept- C20 Eicos- Complete Information about


Bachelor of Technology in Civil...
C8 Oct- C30 Triacont-

C9 Non- C40 Tetracont- Everything about B. Tech and


Dual Degree (B.tech + M.tech)
C10 Dec- C50 Pentacont- in...

In general, the root word for any carbon chain in alk-.


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(ii) Primary Suffix GUIDELINES

Primary suffix are added to the root words to show saturation or unsaturation in a
carbon chain. NEET Exam preparation? Avoid
these 6 mistakes
Nature of carbon chain Primary suffix Generic name
See More
Saturated (C C) -ane Alkane

Unsaturated (C = C) -ene Alkene

with one double bond

Unsaturated (C C) with one triple -yne Alkyne


bond

Unsaturated with two C = C bonds -diene Akladiene

Unsaturated with two C C bonds -diyne Alkadiyne

Unsaturated with three C = C bonds -triene Alkatriene

(iii) Secondary Suffixes

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Suffixes added after the primary suffix to indicate the presence of a particular
functional group in the carbon chain are known as secondary suffixes.

Functional Group Secondary suffix

Alcohol (-OH) -ol

Aldehyde (-CHO) -al

Ketone (>CO) -one-


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Carboxylic acid (-COOH) -oic acid

Sulphonic (-SO3H) -sulphonic acid

Amine (-NH2) -amine

Thioalcohol (-SH) -thiol

Cyanide (-CN) -nitrile

Ester (-COOR) -oate

Amide (-CONH2) -amide

Acid halide (-COX) -oyl halide

Note:

The terminal e of the primary suffix is removed when initial letter of secondary suffix
is vowel. To illustrate the application of above basic rule, the generic names of few
classes of organic compounds are given below:

Homologous Root word Primary Secondary suffix Generic name


series suffix

Alcohols Alk -ane -ol Alkanol


(saturated)

Alcohols Alk -ene -ol Alkenol


(unsaturated) one
double bond

Alcohols Alk -yne -ol Alkynol


(Unsaturated) one
triple bond

Aldehydes Alk -ane -al Alkanal


(saturated)

Ketones Alk -ane -one Alkanone


(saturated)

Carboxylic acids Alk -ane -oic acid Alkanoic acid


(Saturated)

Acid chlorindes Alk -ane -oyl chloride Alkanoyl


(saturated) chloride

Prefix:

It should always be kept in mind that alkyl groups forming branches of the parent
chain are considered as side chains. Atoms of groups of atoms such as fluoro (-F),

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chloro (-Cl), bromo


(-Br), iodo (-I), nitro (-NO2), nitroso (-NO) and alkoxy (-OR) are referred to as
substituents. Roots words are prefixed with the name of the substituent or side chain.

Arrangement of Prefixes, Root Word and Suffixes


These are arranged as follows while writing the name.

Prefix (es) + Root word + Primary suffix + Secondary suffix

For Example:
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Prefix = Bromo (at position 3),

Root word = But,

Primary suffix = -ane

Secondary suffix = -oic acid

Hence, the name of the compound is,

3 Bromo butanoic acid

Prefix = Methyl (at position 4)

Root word = Pent,

Primary suffix = -ene (at position 2),

Secondary suffix = -ol

Hence, the name of the compound is,

4 Methyl pent 2 en 1 ol

The names of simple aliphatic organic compounds containing only straight chains
atoms of various homologous series are described in table as to explain the basic
rules of IUPAC system. In case of compounds. Other than hydrocarbons, only the
saturated compounds have been considered.

Nomenclature Alkanes
The IUPAC system of alkane nomenclature is based on the simple fundamental
principle of considering all compounds to be derivatives of the longest single carbon
chain present in the compound. The chain is then numbered from one end to the
other, the end chosen as number 1 is that which gives the smaller number at the first
point of difference.

When there are two or more identical appendages - the modifying prefixes di-, tri-,
tetra-, penta-, hexa-, and so on are used, but every appendage group still gets its own
number.

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When two or more appendage locants are employed, the longest chain is numbered
from the end which produces the lowest series of locants. When comparing one
series of locants with another, that series is lower which contains thelower number at
the first point of difference.
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Several common groups have special names that must be memorized by the student.

A more complex appendage group is named as a derivative of the longest carbon


chain in the group starting from the carbon that is attached to the principal chain. The
description of the appendage is distinguished from that of the principal chain by
enclosing it in parentheses.

When two or more appendages of different nature are present, they are cited as
prefixes in alphabetical order. Prefixes specifying the number of identical appendages
(di, tri, tetra and so on) and hyphenated prefixes (tert-or t, sec-) are ignored in
alphabetizing except when part of a complex substituent. The prefixes cyclo-, iso-, and
neo-count as a part of the group name for the purposes of alphabetizing.

When chains of equal length compete for selection as the main chain for purposes of
numbering, that chain is selected which has the greatest number of appendage
attached to it.

5-(2-ethylbutyl) 3, 3 dimethyl decane

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When two or more appendages are in equivalent positions, the lower number is
assigned to the one that is cited first in the name (that is one that comes first in the
alphabetic listing).

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Nomenclature of Alkenes
and have the general formula CnH2n. These unsaturated hydrocarbons are isomeric
with the saturated cycloalkanes. The IUPAC rules for naming alkenes are similar in
many respects to those for naming alkanes.

1. Determine the root word by selecting the longest chain that contains the
double bond and change the ending of the name of the alkane of identical
length fromanetoene.
2. Number the chain so to include both carbon atoms of the double bond, and
begin numbering at the end of the chain nearer the double bond. Designate the
location of the double bond by using the number of the first atom of the
double bond as prefix :Indicate the locations of this substituent groups by the
numbers of the carbon atoms to which they are attached.


3. Two frequently encountered alkenyl groups are the vinyl group and the allyl
group.
CH2= CH CH2= CH CH2

The vinyl group The allyl group (are not included in IUPAC
system)

The following examples illustrate how these names are employed

CH2= CH Br CH2= CH CH2Cl

vinyl bromide allyl chloride (are not IUPAC name)

4. The geometry of the double bond of a disubstituted alkene is designated with


the prefixes, cis and trans. If two identical group are on the same side of the
double bond, it is cis, if they are on opposite sides; it is trans.

Nomencalture of Alkyne
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In the IUPAC system the compounds are named as alkynes in which the final ane of
the parent alkane is replaced by the suffix yne. The position of the triple bond is
indicated by a number when necessary.

When both a double and triple bond are present, the hydrocarbon is named
analkenynewith numbers as low as possible given to the multiple bonds. In case of a
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choice, the double bond gets the lower number.

In complex structures the alkynyl group is used as a modifying prefix.

Nomencalture of Aromatic Hydrocarbons


These compounds consists of at least one benzene ring, i.e., a six membered
carbocylic ring having alternate single and double bonds.

Nomenclature of Alkyl Halide


The alkyl halides have the general formula CnH2n+1X or Rx, where X denotes fluorine,
chlorine bromine or iodine.

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Nomenclature of Alcohols
General formula [CnH2n+1.OH], IUPAC name is alkanol.

For the simpler alcohols the common names, are most often used. These consist
simply of the name of the alkyl group followed by the word alcohol. For example:

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We should notice that similar names do not always mean the same classification;for
example, isopropyl alcohol is a secondary alcohol, whereas isobutyl alcohol is a primary
alcohol.

Finally, there is the most versatile system, the IUPAC. The rules are:

. Select as the parent structure the longest continuous carbon chain that contains the -
OH group; then consider the compound to have been derived from this structureby
replacement of hydrogen by various groups. The parent structure is known as
ethanol, propanol, butanol, etc., depending upon the number of carbon atoms; each
name is derived by replacing the terminal-eof the corresponding alkane name by-ol.
. Indicate by a number the position of the -OH group in the parent chain, generally
using the lowest possible number for this purpose.
. ndicate by numbers the positions of other groups attached to the parent chain.

Alcohols containing two hydroxyl groups are called glycols. They have both
common names andIUPACnames.

Note:

2 or 3 OH group can not present on same carbon atom, decomposes to give


aldehyde/ketone or carboxylic acid respectively.

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Nomenclature of Ether (R-O-R)
Ethers are compounds in which two C atoms are connected to a single O atom. In
IUPAC nomenclature, name one of the alkyl group plus the O atom (RO-) as an alkoxy
and comes as a prefix to the parent hydrocarbon. (Oxygen is to be counted with least
number of carbon atom)

IUPAC name of ether is alkoxy alkane

CH3OCH(CH3)2 2 Methoxy propane (isopropyl methlyl ether)



1 isopropoxy 2 methaoxy cyclohexane

Methoxy ethane

Nomenclature of Aldehydes
IUPAC names the longest continuos chain including the C of CH = O and replaces e
of the alkane name by the suffix al i.e. alkanal. The C of CHO is number 1. For
compounds with two CHO groups, the suffix dial is added to the alkane name.
When other functional groups have naming priority, CHO is called formyl.

Common names replace the suffix ic (oic or oxylic) and the word acid of the
corresponding carboxylic acids by aldehyde. Locations of substituents on chains are
designated by Greek letters e.g.

The terminal C of a long chain is designated w (omega)

The IUPAC names of aldehydes follow the usual pattern. The longest chain containing
the CHO group is considered the parent structure and named by replacing e of the
corresponding alkane by al. The position of the substituent is indicated by a number,
the carbonyl carbon always being considered C-1. Here, as with the carbonyl acids,
the C-2 of the IUPAC name corresponds to alpha of the common name.

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Nomenclature of Ketones
Common names use the names of R or Ar as separate words, along with the word
ketone. The IUPAC system replaces the e of the name of the longest chain by the
suffix one. In molecules with functional groups such as COOH, that have a higher
naming priority, the carbonyl group is indicated by the prefix keto or oxo. Thus,
CH3COCH2CH2COOH is 4-ketopentanoic acid.

The simplest aliphatic ketone has the common name acetone. For most other
aliphatic ketones we name the two groups that are attached to carbonyl carbon and
follow these names by the word ketone. A ketone in which the carbonyl group is
attached to a benzene ring is named as phenone, all illustrated below. The positions
of various groups are indicated by numbers.

Nomenclature of Carboxylic Acid


(i)Common or Trivial names:

The names of lower members are derived from the Latin or Greek word that indicate
the source of the particular acid.

Formula Source Common or trivial


names

HCOOH Red ant (Latin ant formica) Formic acid

CH3COOH Vinegral (Latin vinegar acetum) Acetic acid

CH3 CH2 COOH Proton-pion Propionic acid


(Greek = Proton = first, pion = fat)

(ii)Derived System:

Monocarboxylc acid may be named as alkyl derivative of acetic acid.

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(iii)IUPAC System:

Acids are named as alkanoic acids. The name is derived by replacing e of the
corresponding alkane by oic acid.

HCOOH Methanoic acid


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CH3COOH Ethanoic acid

CH3CH2COOH Propanoic acid

In case of substituted acids, the longest chain including carboxyl group is selected and
numbering is done from the carbon of carboxylic group.7. Derivative of Carboxylic acid

Naming Acyl Groups- Acid halide and Anhydrides


The group obtained from a carboxylic acid by the removal of the hydroxyl portion is
known as an acyl group. The name of an acyl group is created by changing the - ic acid
at the end of the name of the carboxylic acid to yl, examples:

(a)Acid Halide

IUPAC name of acid halide is alkanoyl halide.

where X may be Cl, Br, I

Acid chlorides are named systematically as acyl chlorides.

(b)Acid anhydride

An acid anhydride is named by substituting anhydride for acid in the name of the acid
from which it is derived.

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IUPAC name of acid anhydride is alkanoic anhydride.

Example:

Butanoic, ethanoic anhydride

(ii) Naming Salts and Esters

General formula of ester RCOOR

IUPAC name: Alkyl alkanoate

Example:

CH3COOC2H5 (Ethyl ethanoate)

The name of the cation (in the case of a salt) or the name of the organic group
attached to the oxygen of the carboxyl group (in the case of an ester) precedes the
name of the acid.

(iii) Name of Amides and Imides

The names of amides are formed by replacing oic acid (or ic acid for common
names) by amide or carboxylic acid by carboxamide.

IUPAC name of acid amide is alkanamide

Example:

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If the nitrogen atom of the amide has any alkyl groups as substitutents, the name of
the amide is prefixed by the capital letter N; to indicate substitution on nitrogen,
followed by the name(s) of alkyl group(s).
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If the substituent on the nitrogen atom of an amide is a phenyl group, the ending for
the name of the carboxylic acid is changed to anilide

Nomenclature of Amines
Nomenclature of amines is quite simple. Aliphatic amines are named by naming the
alkyl group (or) groups attached to nitrogen , and following that by the word amine.

More complicated amines are often named as prefixing amino - (or-N-methylamino -,


N-N, diethyl amino -, etc) to the name of the parent chain.

Aromatic amines - those in which nitrogen is attached to an aromatic ring - are


generally named as derivatives of the simplest aromatic amine, aniline.

Salts of amines are generally named by replacing - amine by - ammonium (or - aniline
by - anilinium), and adding the name of the anion.

Nomenclature of Nitro Alkane


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General formual CnH2n+1.NO2

Nitro alkane

Example:

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2 nitro 3, 3 dimethyl pentane 1800-2000-838


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Alkyl nitrites Login | Register


Common name is alkyl nitrite there is no IUPAC name of nitrite.

R O N = O Alkyl nitrite

CH CH2 O NO Ethyl nitrite


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Nomenclature of Alkyl Cyanide


Past Papers Notes NCERT Solutions Blog
RC N Alkane nitrile

Example:

CH3 C N Ethane nitrile

2 methyl propane nitrile

Alkyl iso cyanide RNC

Alkyl iso nitrile or alkyl iso cyanide.

There is no specific IUPAC name for alkyl iso cyanide or isonitrile.

CH3NC Ethyl isonitrile

When a compound contains more than one functional group, the numbering and the
suffix in the name of multifunctional compound are determined by nomenclature
priority.

Preference Order

Class Formula Suffix Prefix

(if present as a (if present as a


functional group) substituent)

Carboxylic acid -oic acid Carboxy

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Acid ahydrides -oic anhydride

Eaters Alkyl alkanoate Alkoxycarbonyl

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Acyl halides -oyl halide Haloalkanoyl

Amides -amide Carbamoyl

Nitriles -CN Nitrile Cyano

Aldehydes -al Formyl

Ketones -one Oxo

Alcohols -OH -ol Hydroxy

Amines Amine Amino

Ethers -O- Alkoxy alkane -oxy

Alkenes -ene Alkenyl

Alkynes -CC- -yne Alkynyl

Halides -X - Halo

Nitro -NO2 - Nitro

Alkanes -ane Alkyl

Benzene Benzene Phenyl

Refer the below mentioned links to get an immediate solution to all queries on
Organic chemistry:

JEE Organic Chemistry Syllabus

Organic Chemistry Revision Notes

Reference books of Organic Chemistry

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