Chapter 06

6
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ORGANIC COMPOUNDS - NAMING AND ISOMERISM

WHAT WE HAVE LEARNT The valency of carbon is four. Carbon forms covalent bonds in its compounds. Carbon atom can form single bonded, double bonded and triple bonded compounds. Carbon forms chain compounds and ring compounds. Carbon atoms exhibit the property of 'catenation'. Hydrocarbons are divided into 'alkanes, alkenes and alkynes'. Different carbon compounds can have the same molecular formula. This phenomenon is called isomerism.

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Organic compounds - naming and isomerism

ORGANIC COMPOUNDS - NAMING AND ISOMERISM

have that useful proper operties ou have seen that the periodic table is useful in studying the proper ties of

more hundred elements. Surely, classification urely for more than hundred elements. Surely, classification is essential for the study also. general proper operties oxides, hydrides drides, of compounds also. Studying the general pr oper ties of oxides, hydrides,

chlorides and such compounds of each element is a method familiar to you. The howev ever follow ollowed organic same method however cannot be followed in the case of organic compound since discover ered. organic are more are about 40 lakhs of organic compounds are known and more are being discovered. Not only the classification, but the naming of these compounds is also a difficult task. The confusion that happens when the same compound is denoted by differ erent differ erent organisa ganisation different names in different languages can be imagined. An organisation was give uniform compounds. IUPA (International formed to give uniform names to compounds. IUPAC (International Union of ure Chemistry) international organisa ganisation formula ormulates Pure and Applied Chemistr y) is the international organisation which formulates egulations for compounds. organic chemistry regula the rules and regulations for naming chemical compounds. In organic chemistr y important have for organic it is important to have a clear naming system for the 40 lakh organic compounds now known and to have suitable rules for naming compounds that may be discover ered future organic discovered in future. Understanding the naming system of organic compounds organic chemistry is the first step in the study of organic chemistr y.

Naming of Organic compounds

Examine the structural formulae of the two compounds given below. CH3 - CH2 - CH2 - CH3 CH3 - CH - CH3 | CH3 Write down their molecular formulae. Are they the same? Is there any difference in their structural formulae? What is the phenomenon of compounds having same molecular formulae and different structural formula? Each of these chain isomers, formed due to the difference in the structure of the chains, is a different compound. Therefore they differ in their names also.
Standard 10

Let us now examine how these compounds can be named. IUPAC has made certain rules for naming elements and compounds. This chapter deals with the rules relating to the naming of organic compounds.

Hydrocarbons
a. Unbranched alkanes You know that uni, bi and tri indicate the numbers 1, 2 and 3 respectively. Similarly some word roots are used to denote number of carbon atoms in the hydrocarbon. They are C 1 - Meth C 2 - Eth C 3 - Prop C6 C7 C8 - Hex - Hept - Oct

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C 4 - But C 5 - Pent
1.

C9

- Non

C 1 0 - Dec

Select the suitable word root based on the number of carbon atoms in the chain. By adding '-ane' to the word root of the saturated hydrocarbon, its name can be derived. For example, consider the following. CH3 - CH2 - CH3

Here there is a branch in the 2nd carbon. Such branched compounds may have more than one carbon chain. Of these, the number of carbon atoms in the longest chain is taken as the basis for writing the word root. The word root of the above hydrocarbon can then be written as 'prop' and when '-ane' is added you get its name. The name of the group from the branch should also be a part of the name. How many carbon atoms are there in the branch? If there is one carbon then what should be the word root? '-meth', add -yl to it, to get 'methyl'. This may be added as prefix to the name written above. The position number of the carbon atom in the main chain from which the branch arises should also be written at the beginning of the name and put a '---' after this number. 2 - methylpropane Word rood ............ ............ ............ ............ Suffix ............ ............ -ane ............ Name ............ ............ ethane ............

2.

In this compound the number of carbon atoms is 3. Therefore the word root is 'prop'. Now add 'ane' to the word root and write the name. prop + ane = propane wordroot + ane = alkane Now fill up table 6.1 given below. Compound CH4 CH3 - CH2 - CH2 - CH3 ......................................... CH3 - CH2 - CH2 - CH2 - CH3
b. Branched alkanes

Table 6.1 Write the IUPAC names of alkanes with upto 10 carbons. Try to write the name of the following compound. position of the branch + hyphen + the adjective denoting the branch + word root + suffix Try writing the name of the following compound. CH3 - CH2 - CH - CH2 - CH3 | CH2 | CH3
Chemistry

C H 3 C H C H3 | CH3
What is the difference between this hydro carbon and those which we named earlier?

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Organic compounds - naming and isomerism

Examine the compounds and their names in table 6.2 below. I.

1

CH3 - 2CH - 3CH 2 - 4CH 3 | CH3 CH3 - 4CH2 - 3CH2 - 2CH - 1CH 3 | CH3 CH3 - 2CH2 - 3CH - 4CH2 5CH 3 | CH3 CH3 - 2CH2 - 3CH - 4CH2 5CH 3 | CH2 CH3 CH 3 - 7 CH 2 - 6CH 2 - 5 CH 2 - 4CH- 3 CH 2 - 2 CH 2 - 1 CH 3 | CH2 - CH2 - CH3 Table 6.2

2 - methyl butane

II.

2 - methyl pentane

III.

3 - methyl pentane

IV.

3 - ethyl pentane

V.

4 - propyl octane

Consider the following examples. I.

1

CH 3 - 2CH2 - 3CH2 - 4CH - 5CH3 | CH3

Ia. 1CH 3 - 2 CH 2- 3CH - 4CH 2- 5CH 2- 6CH 3 | CH 3 b.

6

II. 5CH 3 - 4CH2 - 3CH2 - 2CH - 1CH3 | CH3 I and II are the same compounds. The longest carbon chain has 5 carbon atoms. So the word root is 'pent' and the suffix is '-ane'. In compound I the methyl group is attached to the 4th carbon but in compound II, methyl group is attached to the 2nd carbon. While naming a compound as specified by the IUPAC, the branched carbon should be given the lowest number when counted from either ends. Therefore the naming is done correctly in the 2nd compound. The compound is 2 - methylpentane. Find the appropriate position number for the carbon chains given below.
Standard 10

CH 3 - 5CH 2- 4CH- 3 CH 2 - 2 CH 2- 1CH 3 | CH 3

IIa. 1CH 3 - 2CH 2- 3CH 2- 4 CH 2 - 5 CH-6CH 3 | CH 3 b.

6

CH 3- 5 CH 2 - 4CH 2 - 3 CH 2 - 2 CH- 1 CH 3 | CH 3

Write the structural formula of the following: a. 3 - ethylhexane b. 4 - propylheptane

c. Hydrocarbon with more than one branched carbon

When molecules with more than one branch in a single group is named, before the branch name, di, tri, tetra etc. were added to indicate 2, 3, 4 etc. The numbers indicating position number should be separated by comma.

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Analyse table 6.3. Compound CH 3 | CH3 - C - CH3 | CH 3 CH3 - CH - CH - CH3 | | CH3 CH3 CH 3 | CH3 - CH2 - C - CH3 | CH 3 CH3 - CH - CH - CH - CH3 | | | CH3 CH3 CH3 Table 6.3 Now write names of the following: CH 3 | CH3 - CH -C - CH3 | | CH 3 CH 3 CH3 | CH3 - CH - C ----- CH - CH3 | | | CH 3 CH3 CH3 Table 6.4 Consider the structural formula of the following:
1 6 2 5 3 4 4 3 5 2 6 1

Name

2,2 - dimethylpropane

2,3 - dimethylbutane

2,2 - dimethylbutane

2,3,4 - trimethylpentane

...................................................................

...................................................................

C H3 - C H - C H 2 - C H - C H 2 - C H3 | CH 3 | CH 3

What will be the position number of carbon atom if we number from left to right? The sum of the position number of the carbon atom is 2 + 4 = 6. If we number from right to left, then the sum of the position numbers is 3+5=8. Here we will have to select that option where the sum of position numbers is less.
Chemistry

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Organic compounds - naming and isomerism

i.e., the name of the compound is 2, 4 - dimethylpentane. In molecules having more than one branch, when the position numbers are different when counting from right to left and left to right, find out the sum of position numbers. And select the one where the sum is less. Complete table 6.5.

Naming of unsaturated hydrocarbons

a. Alkenes

While naming unsaturated hydrocarbons with double bond, the longer chain with double bond is taken as the basis. Add the suffix '-ene' to this. The position number of the double bond is shown before the word root. The position which gives the smallest number for the carbon carbon double bond is to be chosen. Name

Compound
CH 3 CH 2 - CH 3

| | CH 3 - CH - CH 2 - CH - CH 2 - CH 2 - CH 3

..................................................

.........................................................
CH 2 - CH 3 CH 3 CH 3

5 - ethyl - 3,3 - dimethyl heptane

| | | CH 3 - CH 2 - C - CH 2 - CH - CH - CH 2 - CH 3

......................................................................

Table 6.5 Now try to write the names of the chain isomers given below: a. CH 3 - CH 2 - CH 2 - CH 3 b.
CH 3 | CH 3 - CH - CH 3

Eg:

1 2 C H2 = C H2

Since there are 2 carbon atoms the word root is 'eth'. As there is a double bond '-ene' may be added. The IUPAC name of CH2 -- CH2 is eth + ene ethene

c.
CH 3 | CH 3 - C - CH 3 | CH 3

Consider the following. a. b.

1

CH3 - 2CH = 3CH 2 CH3 - 2CH = 1CH 2

2- propene 1- propene

Observe how the names are written. You can see that the two carbon chains are named in two different ways.

Standard 10

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Which way of naming is correct? Can you explain why?

CH 3
__

H H C H H

H H C H Cl

CH 2

__

CH = CH

__

CH 3

What is the name of this compound? 2 - pentene or 3 - pentene? Justify your answer. Write down the names of the following: CH 3 __ CH 2 __ CH = CH 2 CH 3 __ CH2 __ CH2 __ CH = CH __ CH3 CH 3 __ CH2 __ CH = CH __ CH2 __ CH3 CH 2= CH
b. Alkynes
__

To get the name of the compound in which the hydrogen atom of methane is substituted by chlorine, add the prefix chloro - to the word 'methane'. In general, to get the name of compounds in which hydrogen atom of the hydro carbon is substituted by a halogen, add the prefix halo (halo- fluoro, chloro, bromo, iodo). Name the following compounds. CH 3 - CH 2 - Cl CH 3 - CH 2 - CH 2 - Cl CH3 - CH - CH 3 | Cl Can you explain why the chemical properties of chloro methane is different from that of methane.

CH 2

__

CH 3

While naming hydrocarbons with triple bond after the word root '-yne' (alk + yne) is added. The rules for naming double bonded hydrocarbons are applicable to triple bonded hydrocarbons also. Write names of the following. ethyne
CH CH C CH 3 2 CH C C CH 3 3 CH CH C C CH CH 3 2 2 3

The atoms or atom groups that get substituted for the hydrogen atom in the hydrocarbons determine the property of that compound. These atoms or atom groups are called functional groups. The names of some compounds, functional group, name of the functional group and general name are given below in table 6.6.

II. Compounds with functional groups

a. Halogen compounds

Consider the compounds CH4, CH3Cl.

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Compound

Functional group -OH -COOH -CO -CHO - O -NH 2 -NO2

Name of the functional group hydroxyl carboxyl carbonyl aldehyde ether amino nitro

Common name alcohol acid ketones aldehydes ether amines nitro compound

CH 3-CH 2-OH CH 3-CH 2-COOH CH 3-CO-CH 3 CH 3-CH 2-CH 2-CHO CH 3-O-CH 3 CH 3-CH 2 -NH 2 CH 3-CH 2 -CH 2 -NO 2

Table 6.6
b. Alcohols

c. Ether Now we shall find out how to write the name of the following compounds. CH 3 - O - CH 2 - CH 3 The longest alkyl chain on either side of oxygen should be considered for determining the word root. CH3 - O - CH2 - CH3, Here there are two alkyl groups -CH 3 and -CH2-CH3. The longest chain is the ethyl group. Since it is a saturated hydrocarbon it can be called ethane. The CH3 - O - group is linked to the ethyl group. The CH3- O - group can be named as meth + oxy = methoxy. The IUPAC name of CH3 - O - CH2 - CH3 is meth + oxy + ethane = methoxy ethane. Now the compound CH3 - CH2 - O - CH2 - CH2 - CH3 can be considered. The name of this compound is ethoxy propane. Explain why this name is used.

Consider the compound CH3- CH2- OH. How will you name the compounds with -OH as their functional group? For naming such compounds the following procedure can be adopted. Consider the compound CH3- CH2- OH. Since there are 2 carbon atoms, the word root can be 'eth'. Since this is a saturated hydrocarbon the prefix '-ane' should be added and 'ol' is to be added to indicate the functional group -OH. i.e., eth + ane -- e + ol ethanol. Alkane --- e + ol Ethane --- e + ol Alkanol Ethanol

Name the following compounds. a. CH 3 - CH 2 - CH 2 - CH 2 - OH b. CH 3OH c . CH 3 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -OH

Standard 10

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Match properly the columns A and B in table 6.7 below. A Methoxy propane Ethoxy ethane Ethoxy butane Methoxy methane Methoxy hexane B CH3 CH2 CH2 CH2 O CH2 CH3 CH3 O CH2 CH2 CH3 CH3 CH2 CH2 CH2 CH2 CH2 O CH3 CH3 O CH2 CH3 CH3 CH2 CH2 CH3 CH3 O CH3 CH3 CH2 O CH2 CH3 CH3 O CH3 Table 6.7

Isomerism
You are familiar with compounds with same molecular formula, but having different structural formula. Such compounds are called isomers. Based on the differences in the structures, isomers can be classified into various types.
a. Chain isomerism

Ethanol and dimethyl ether are examples of functional group isomers. Now can you write out a definition for functional group isomerism? From those given below find out functional group isomers and note them in your science diary. CH3O CH2CH3 CH3CH2CH2OH CH3 CH2 CH2 CH3 CH3 CHCH3 | CH3 CH 3CH2CHO

Chain isomerism occurs due to the difference in the carbon chain. Butane and 2-methyl propane are examples.
b. Functional group isomerism

CH 3COCH 3

Find out the names of CH3-CH2-OH, CH 3 -O-CH 3 . Do they have the same molecular formula and structural formula? What is the functional group in the compounds CH3-CH2-OH and CH3-O-CH3? Are they the same?

CH3 | CH 3CH 2CH 2CH 2CH 3 CH3 - C - CH3 | CH3

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Organic compounds - naming and isomerism

c.

Position isomerism

d. Metamerism

The following compounds are examples of position isomerism.

4

Compare the two compounds. CH3 CH2OCH2CH3 CH3OCH2CH2CH3 Are the alkyl groups on either side of the ether group and their molecular formula the same? Here are some examples of metamerism which arises due to the difference in the number of carbon atoms in the alkyl groups on either sides of a functional group.

CH33CH22CH2 1CH2 OH : 1- butanol

OH | 1 2 CH3 - CH - 3CH2 - 4CH3 : 2- butanol Is there any difference in the carbon chain structure, functional group and the position of the functional groups? Thus those isomers which differ in the position of the functional groups in the same carbon chain are termed as position isomers.
CH 3 __CH 2 __CH 2__CH 2 __CH 2 __CH 2 __CH 2__OH

CH 3__ CH 2 CH3
_ _

__

CH 2 __ O

__

CH 2__ CH 2__ CH 3
_ _

CH2__ O__ CH2

_ _

_ _

CH2 CH2

CH 2

_ _

CH3

CH3__ O

CH2

_ _

CH2

_ _

_ _

CH2__ CH3

What is the name of this compound? Write all the possible position isomers and their names.

Write the names of the above compounds.

SUMMARY

Organic compounds are named according to the rules and conventions formulated by IUPAC.

Compounds having the same molecular formula, but different structural formulae are called isomers.

Isomers are of different types - chain isomers, functional group isomers, position isomers, metamers etc.

Standard 10

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Chapter 06

MORE ACTIVITIES FOR YOU

1. Write the structure and name of the isomers of chloro propane (C3H7Cl). 2. Write a note on isomerism. 3. Write the IUPAC names of the following: a. CH3 - CH - CH2 - CH2 - CH3 | CH3 b. CH3 | CH3 - C - CH3 | CH3 OH | CH3 - CH2 - CH - CH2 - CH3 4. Write the structures of the following
a . 2,2 - dimethylheptane b. methylpropane c . 3-ethyl - 2-methyl - 5-propyl

nonane
d. 2-ethyl - 3-methyloctane e . 3-methyl - 1-butene.

5. Write the name of isomers of the following compounds and to which type of isomerism is shown by them. $ $ $ ethanol methoxy ethane 2 - chloro butane 2 - propanol 1 - propanol 1 - butanol ethoxyethane 2-methyl - 1-chloropropane

c.

d. CH3 - CH2 - CH - CH2 - CH2 - Cl | CH3 e. Cl Cl | | CH3-CH2-CH-CH2-CH-CH2-CH-CH3 | Cl

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f. CH3 - CH - CH - CH2-CH2-CH2- CH3 | | CH 3 CH 2-CH 3 g. CH3-CH2-CH=CH-CH2-CH2-CH2-CH3

$$$$$$

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Chemistry