Chapter 2 nomenclature of organic compounds
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Transcript of Chapter 2 nomenclature of organic compounds
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Alkanes Alkenes Alkynes Arenes
Methane, ethane, propaneSimplest
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When a hydrogen atom is removed from an alkane the remaining group of atoms is called
alkyl group or alkyl radical.
CH4 -CH3
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CH4 CH3
C2H6 C2H5
C3H8 C3H7
Methane Methyl
Ethyl Ethane
Propane Propyl
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A carbon atom attached to three other carbon atoms
A carbon atom attached to four othercarbon atoms
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CH3 C
CH3
CH3
C
CH3
CH2 CH3
H secondary
tertiary
primery
quaternary
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This method of nomenclature was used before 1892.
In this system of nomenclature, the compounds were named on the basis of
their history, such as source of origin etc.
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A method known as the Geneva system was suggested in 1892 by the International Chemical
Congress at Geneva for naming organic compounds.
Later the International Union of Chemistry at Liege (Belgium) developed it into IUPAC system of
nomenclature in 1930.
In 1958, the IUPAC system was modified by the International Union of Pure and Applied Chemistry
(IUPAC) into the present day IUPAC system of nomenclature.
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Select the longest continuous chain of carbon atoms as the parent chain and name the
hydrocarbon.
CH3 CH CH2 CH3
CH3
The longest continuous chain has four carbon atoms, thus the compound is named as butane.
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Number the carbon atoms in the longest continuous chain in such a way as to give lowest possible number to
carbons atoms carrying substituents.
CH3 CH CH2 CH2 CH3
CH3
1 2 3 4 5
CH3 CH CH2 CH2 CH3
CH3
234 15
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CH3 CH CH2 CH3
CH3
1234
CH3 CH CH2 CH3
CH3
1 2 3 4
Incorrect numbering
Correct numbering
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Name the substituent. Indicate its position by the number of the carbon
atom to which it is attached.
CH3 CH CH2 CH3
CH3
1 2 3 4
The attached group is located on carbon 2 of the chain, and it is a
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Prefix the position number and name of the substituent onto the parent name.
The whole name is written as one word.
Note that the number and name of the substituent are separated by a hyphen.
CH3 CH CH2 CH3
CH3
1 2 3 4
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2- ButaneMethyl
Position of alkyl group
Attached alkyl group Longest chain
CH3 CH CH2 CH3
CH3
1 2 3 4
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If identical substituents are present more than once in the molecule, then use prefixes di- tri-tetra-,penta-, etc.
CH3 CH
CH3
CH2 CH
CH3
CH3
2,4-Dimethylpentane
Position of each substituent is indicated by a separate number.
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When two or more different substituents are present, their names are arranged in alphabetic
order and added to the name of the parent alkane, again as one word.
CH3 CH2 CH
CH3
CH2 CH
CH2
CH2 CH2 CH3
CH3
5-Ethyl-3-methyloctane
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CH3 CH
CH3
HC
CH3
HC
H2C
CH2 CH3
CH2 CH3
1.
2.
CH3 CH2 C
CH2
CH2
CH2
H3C
CH3
CH
CH3
CH2 CH2 CH2 CH2 CH33.
CH3 CH2 CH2 C
H
CH2 CH2 CH3
CH3
4.CH3 CH CH2 CH CH2 CH2 CH3
C2H5
CH2
CH3
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Numbers are separated from each other by commas;
Numbers are separated from names by hyphens;
Prefixes di-, tri-, are not taken into account in alphabetizing substituent
names.
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Step-by-step procedure to draw structural formulas from the IUPAC names.
Consider the following IUPAC name:
3,3-Diethyl-5-methyldecane
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C C C C C C C C C C1 2 3 4 5 6 7 8 9 10
Draw a decane skeleton and number it.
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Attach two ethyl groups at C-3
C2H5
C C C C C C C C C C1 2 3 4 5 6 7 8 9 10
C2H5
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Attach a methyl group at C.5
C C C CH2C C C C C C
CH2
CH2
CH3
H3C
1 2 3 4 5 6 7 8 9 10
CH3
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Supply hydrogen atoms so that each carbon atom has four bonds.
CH3 CH2 C
CH2
CH2
CH2
H3C
CH3
CH
CH3
CH2 CH2 CH2 CH2 CH3
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Draw structural formulas for the following compounds
1.
2.
3.
4.
5.
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•They are named by attaching the prefix cyclo- to the name of the alkane having the same number of
carbons as in the ring.
•Alkanes whose carbon atoms are joined in rings are called cycloalkanes.
•They have the general formula CnH2n
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Cycloalkanes are often represented by simple geometrical figures.
is represented by a
is represented by a
is represented by a
is represented by a
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H2C
CH2
H2C
CH2
H2C
CH2
H2C
H2C
Cyclopropane Cyclopentane
It is understood that each corner represents CH2 group.
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Substituted Cycloalkanes are named as
•The substituent's on the ring are named and their position is indicated by
numbers.
•The ring is numbered so that the substituent's are given the lowest possible
numbers.
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CH CH3H3CCH3
CH2 CH3
Isopropylcyclohexane 1-Ethyl-3-methylcyclohexane
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CH2 CH2 CH2 CH3
1-Cyclopropylbutane and NOT Butylcyclopropane
The ring is designed as a substituent if the alkane chain contains a greater number of
carbon atoms than the ring.
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Alkenes have the general formula CnH2n
Contain at least one carbon-carbon double bond. They are also called olefins
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CH2 CH CH2 CH3 CH3 CH CH CH3
CH2 CH2 CH3 CH CH2
Ethene Propene
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Select the longest continuous chain of carbon atoms containing the double bond, as the parent
chain.
CH3 C
CH3
CH CH2 CH3
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Name the longest chain. The name is obtained by replacing “ane” of alkane with “ene”.
-ane
+ene
Pentene
CH3 C
CH3
CH CH2 CH3
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Number the chain from the end closer to the double bond.
CH3 C
CH3
CH CH2 CH31 2 3 4 5
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Indicate the position of the double bond by the number of the first (lowest numbered) carbon
atom involved in the double bond.
CH3 C
CH3
CH CH2 CH31 2 3 4 5
Carbon-2
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Alkyl groups and other substituent's are numbered , named and placed as prefixes in
alphabetical order.
CH3 C
CH3
CH CH2 CH31 2 3 4 5
2-Methyl-2-pentene or 2-Methylpent-2-ene
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If more than one double bonds are found then use the prefixes di,tri,tetra,for 2,3 and 4.
Alkenes containing two double bonds are named as
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H2C C CH2
1,2-Propadiene
H2C CH CH CH2
1,3-Butadiene or But-1,3-diene
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In naming Cycloalkenes, number the ring to give the double bonded carbons the numbers 1 and 2 , choose the direction of numbering so that the substituents
also get the lowest numbers.
CH3
Cyclohexene
12
3
45
3-Methylcyclopentene
The position of the double bond is not indicated because it must be between
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Alkynes are hydrocarbons have the general formula CnH2n-2 where
Alkynes contain at least one carbon-carbon triple bond
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HC CH
The simplest alkynes is Ethyne commonly called
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HC CH CH3 C CH CH3 C C CH3
Ethyne Propyne 2-Butyne or But-2-yne
CH3 C C CH2 CH
CH3
CH3
5-Methyl-2-hexyne or 5-Methyl-hex-2-yne
and NOT 2-Methyl-4-hexyne2
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Select the longest continuous carbon chain containing at least one triple bond, as the parent
chain.
CH3 C C CH2 CH
CH3
CH3
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Name the longest chain. The name is obtained by replacing ane of alkane with yne.
-ane
+yne
CH3 C C CH2 CH
CH3
CH3
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Number the chain from the end closer to the triplebond.
CH3 C C CH2 CH
CH3
CH3
653 421
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Indicate the position of the triple bond by the number of the first (lowest numbered) carbon atom
involved in the triple bond.
CH3 C C CH2 CH
CH3
CH3
653 421
Carbon -2
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Alkyl groups and other substituents are numbered, named and placed as prefixes in
alphabetical order.
CH3 C C CH2 CH
CH3
CH3
653 421
5-methyl-2-hexyne
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If more than one triple are found then use the prefixes di,tri,tetra,for 2,3 and 4.
Alkynes containing two triple bonds are named as
HC C C CH
1,3-Butadiyne or But-1,3-diyne
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They are classified as primary (1°), secondary (2°) and tertiary ( 3°) alkyl halides.
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Alkyl halides are named in the same way as alkanes
by treating the halogen as substituent on a parent
alkane chain.
CH3CHCHCHCH2CH3
Cl Cl
CH3
2,3-Dichloro-4-methylhexane
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If different halogens are present, number each
according to its position on the chain and list them in
alphabetical order when writing the name.
BrCH2CH2CHCHCH3
Cl
CH3
1-Bromo-3-chloro-4-methylpentane
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In addition to their systematic names, many simple
alkyl halides are also named by identifying first the
alkyl group and then the halogen.
For example,
CH3I can be called methyl iodide.
Such names are well entrenched in the chemical
literature and in daily usage.
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CH3I
Iodomethane
CH3CHCH3
Cl
2-Chloropropane
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Br
Bromocyclohexane
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Alcohols are compounds in which a hydroxyl group (-OH) is bonded to a saturated carbon.
H3C OH
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They are classified as primary (1°), secondary (2°) and tertiary ( 3°) alcohols.
H3C CH2 OHPrimary alcohol
CH3 CH
CH3
OH
CH3 C
CH3
OH
CH3
Secondary alcohol
Tertiary alcohol
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Select the longest continuous carbon chain to which the hydroxyl group is attached as the
parent chain.
CH3CHCHCHCH2CH3
CH3
OH
CH3
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-e
+ol
Name the longest chain
The name is obtained by replacing the final -e with-
ol.
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Number the chain to give the lowest number to
carbon attached to the hydroxyl group.
CH3 CH
CH3
CH2 CH2 OH
3-Methyl-1-butanol or 3-Methyl-but-1-ol
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Other substituents are numbered, named, and
placed as prefixes in alphabetic order. For
example:
CH3 OH CH3 CH2 OH CH3 CH
OH
CH3
Methanol Ethanol2-Propanol
CH3 CH
CH3
CH2 CH OHCH3 CH
CH3
CH2 CH2 OH
CH3
3-Methyl-1-butanol or 3-Methyl-but-1-ol 4-Methyl-2-butanol or 4-Methyl-but-2-ol
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Alcohols containing two or three –OH groups are
named as Alkanediols and Alkanetriols respectively.
Note that “–e” of the corresponding alkane name is
retained.
CH2 OH
CH2
CH2 OH
CH2 OH
CH
CH2 OH
OH
1,3-Propranediol or Propan-1,3-diol 1,2,3-Propanetriol or propan-1,2,3-triol
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Select the longest chain containing the aldehyde
group.
CH3 CH2 CH
Br
CH2 C
O
H
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Name the longest chain.
The name is obtained by dropping the final “-e”
from the name of the corresponding alkane, and
adding “-al” to the end.
CH3 CH2 CH
Br
CH2 C
O
H
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Number the chain by assigning the number 1 to the
aldehyde carbon.
CH3 CH2 CH
Br
CH2 C
O
H
5 4 3 2 1
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Other substituents are numbered, named, and
placed as prefixes in alphabetic order.
CH3 CH
CH3
CH2 C
O
H
3-Methyl
CH3 CH2 CH
Br
CH2 C
O
H
3-Bromo
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When there are two aldehyde groups in a molecule, it is named as “Alkanedial”.
Note that “-e” of the corresponding alkane name is retained.
H C
O
CH2 CH2 CH2 C
O
H
1,5-Hexanedial
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Ketones are compounds in which carbonyl group
(C=O) is bonded to two organic groups.
CH3 C
O
CH2 CH3
Butanone
CH3 C
O
CH3
Propanone
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Select the longest chain
containing the carbonyl carbon atom.
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Name the longest chain by dropping “-e” fromthe name of the corresponding alkane, andAdding “-one” at the end.
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Number the chain to give the lowest number to the carbonyl carbon.
CH3 CH2 C
O
CH2 CH3
5 4 3 2 1
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Other substituent's are numbered, named, and placed as prefixes in alphabetic order.
CH3 CH
CH3
CH2 C CH3
O
5 4 3 2 1
4-Methyl-2-pentanone OR 4-Methyl pentan-2-one
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CH3 C
O
CH2 C
O
CH2 CH3
When there are two carbonyl groups in a molecule, it is named as Alkanedione.
2,4-Hexanedione
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1. Select the longest chain containing the acid group -COOH.
2. Start numbering from the end where the –COOH group is.
3. Remove “-e” from the parent alkane and add “_oic acid”.Eg.:-CH3CH2COOH Propanoic acid
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4. If two carboxylic acid groups are present, it should be named as alkanedioic acidEg.:-
HOOC-CH2-CH2-COOH Butanedioic acid
Other substituents are numbered, named, and placed as prefixes in alphabetic order.
CH3CHCH2COOH
CH3
3-Methylbutanoic acid
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Esters
They are the condensation products of alcohols and acids.CH3CH2COO H + HO CH2CH3 CH3CH2COO CH2CH3 + H2O
Fraction contains –COO- group will have the name end with “ate”.
Fraction carries no –COO- group will have the name end with “yl”and will be written first.
The molecule is Ethyl propanoate