• Written By Sushmita Rout
  • Last Modified 25-01-2023

Homologous Series: Definition, Process, Functional Groups

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Just like we have the first name that differentiates us from the others but our surnames that groups us with our family, organic compounds too can be classified into families. Organic compounds are divided into several groups depending on the general formula, properties, structures, etc. The series differentiating the organic compounds are known as Homologous series.

Methane is used as a fuel in the form of natural gas. Similarly, Propane is also used as a fuel in cooking gas. These have similar properties, but do they belong to the same family? Let’s dive in to discover this widespread family tree of organic chemistry. Continue reading to learn more!

What is a Homologous Series?

Organic compounds are divided into different groups having the same general formula, properties, and related structures. Such a series of organic compounds are known as homologous series.

A homologous series is a series of organic compounds whose members can be denoted by a single general formula and differ from each other by a CH2 group. The individual members of a homologous series are called homologues. While transforming a compound into its next homologue, CH2 group gets added to the chain.

Process of Homologous Series

The name or the nomenclature of an organic compound is written out with the substituents in an alphabetical order followed by the base name (derived from the number of carbon atoms in the parent chain). Commas are used between numbers, and dashes are used between letters and numbers.

There are no spaces in the name. The most frequently used nomenclature worldwide is the one created and developed by the International Union of Pure and Applied Chemistry (IUPAC). The basename or the parent name of an organic compound depends on the total number of carbon atoms. This is shown as below:

NameNumber of C’s in the Parent Chain
Meth-1
Eth-2
Prop-3
But-4
Pent-5
Hex-6
Hept-7
Oct-8
Non-9
Dec-10

Alkanes in Homologous Series

The simplest example of homologous series is the first four hydrocarbons: methane, ethane, propane, and butane.

What is the homologous series of hydrocarbons 2

Methane having one carbon atom is surrounded by four hydrogen atoms. Hence, its molecular formula is CH4. The chemical formula of ethane differs from that of methane by the CH2 group. Similarly, the propane formula differs from the ethane by the CH2 group. This shows that the homologous series occurs in succession.

The general formula of this homologous series Alkanes is Cn H2n+2 where n=1,2,3
The combustion of all the above hydrocarbons produces carbon dioxide and water. This means that the organic compounds in the homologous series have similar chemical properties.

CH4(g)+2O2(g)CO2(g)+2H2O(g)
2CH3CH3(g)+7O2(g) 4CO2(g)+6H2O(g)

The table above shows that with the addition of the CH2 group, there is an increase in the boiling point of the respective hydrocarbon.

Alkenes in Homologous Series

The homologous series of alkenes consists of ethene, propene, butene, pentene and so on. Ethene has two carbon atoms bonded to each other through a double bond and is surrounded by four hydrogen atoms. Hence, its molecular formula is C2H4. The chemical formula of propene differs from that of ethene by the CH2 group. Similarly, the butene formula differs from the propene by the CH2 group.

This shows that the homologous series of alkenes occurs in succession. The general formula of this homologous series alkynes is CnH2n, where n=1,2,3

What is the homologous series of hydrocarbons 3

Alkynes in Homologous Series

The homologous series of alkynes consists of ethyne, propyne, butyne, pentyne and so on. Ethyne has two carbon atoms connected by a triple bond. The two carbon atoms are surrounded by two hydrogen atoms. Hence, its molecular formula is C2H2. The chemical formula of propyne differs from that of ethyne by the CH2 group.

Similarly, the butyne formula differs from the propyne by the CH2 group. This shows that the homologous series of alkynes occurs in succession.
The general formula of this homologous series alkynes is CnH2n2, where n=1,2,3

What is the homologous series of hydrocarbons 4

The chemical formula of propyne differs from that of ethyne by the CH2 group. Similarly, the butyne formula differs from the propyne by the CH2 group. This shows that the homologous series of alkynes occurs in succession.

Cycloalkane in Homologous Series

Carbon atoms can join to form rings of carbons. Cycloalkanes are simply cyclic alkanes. The simplest cycloalkane is cyclopropane. There are two hydrogen atoms less in a cycloalkane than its respective straight chain.

This is because the two ends of the molecule are joined together. These are saturated hydrocarbons, and the carbon atom is bonded to the maximum number of hydrogen atoms. As there is an additional bond present, cycloalkanes will have higher boiling points than their corresponding straight-chain partner.

The general formula of this homologous series cycloalkanes is CnH2n, where n=1,2,3

Functional Groups in Homologous Series

When the H atom in methane is replaced by some other group such as hydroxyl group OH, then methane is converted into methanol, a type of alcohol with the formula CH3OH. This hydroxyl group is the functional group that, when attached to an alkyl carbon such as methyl- CH3 or ethyl C2H5, forms a new class of organic compounds called alcohols.

Hence, a functional group is an atom or a group of atoms that replaces hydrogen in an organic compound and is responsible for the characteristic chemical properties of such compounds. These functional groups are the site of chemical reactions in an organic compound.

For example, primary alcohols get oxidised into carboxylic acids when heated in the presence of alkaline KMnO4. On the other hand, when alcohol is heated with concentrated sulfuric acid, it undergoes dehydration, i.e., removal of water, to produce an alkene:

CH3CH2OHCH3COOH( in the presence of alkaline KMnO4)
CH3CH2OHC2H2+H2O( in the presence of conc. H2SO4 at 443 K)

The table below lists the general formula and the functional groups for various categories of organic compounds such as halides, alcohols, aldehydes, ketones, and organic carboxylic acid.

It can be observed from the above table that the functional groups for alkyl halides, alcohols, aldehydes, ketones, and carboxylic acids are the halogen atom, hydroxyl group, aldehydic group, ketonic group, and carboxyl group, respectively. Now, how is the naming for these organic compounds done, and what can be their homologous series? Read on to find out.

Alkyl Halides in Homologous Series

The alkyl halides have the general formula of RX where R is some alkyl group, such as methyl CH3 or ethyl C2H5, and X is a halogen atom fluorine F, chlorine Cl, bromine Br, and iodine I.
Ethyl chloride C2H5Cl and butyl chloride CH3CH2CH2CH2Cl are examples of alkyl halides.
In alkyl halides, the halogen atom is bonded to an alkyl group (R) Thus, they form a homologous series represented by the general formula CnH2n+1X.

They are further classified as primary, secondary, or tertiary according to the nature of carbon to which halogen is attached. When naming an alkyl halide, the name of the alkyl residue or the longest parent chain carbon is written first, followed by the respective halide name. For example, CH3CH2CH2Cl is a three-carbon chain; therefore, the alkyl residue is propyl, and the halide is chloride and the name of the compound is propyl chloride.

Alkyl halideCarbon numberFormula
Structure1CH3Br
ethyl bromide2CH3CH2Br
propyl bromide3CH3CH2CH2Br
butyl bromide4CH3CH2CH2CH2Br

Methyl bromide, ethyl bromide, propyl bromide, and butyl bromide have chemical formulas of CH3Br,CH3CH2Br,CH3CH2CH2Br, and CH3CH2CH2CH2Br, respectively.
This homologous series of alkyl bromides differs from each successive compound by a CH2 group.

Alcohols in Homologous Series

Alcohols have the same general formula as alkanes except that they have the functional group OH, called the hydroxyl group. The most common alcohol, known as ethanol, is used in alcoholic drinks, as fuel (gasoline), as a preservative for biological specimens, and as a solvent for paints and drugs.

In naming alcohols, the suffix of the name ol, is added to the parent chain of the alkane name. The position of the OH functional group is indicated in the name. The numbering of the parent chain is done at the end closest to where the OH is located.
The general formula of alcohols homologous series is CnH2n+1OH, where n=1,2,3..

The example of homologous series in alcohol can be methanol, ethanol, propanol, and butanol with chemical formulas of CH3OH,CH3CH2OH,CH3CH2CH2OH, and CH3CH2CH2CH2OH, respectively, where each successive compound differs from the previous one by a CH2 group.

Aldehydes and Ketones in Homologous Series

The aldehydes and ketones contain a carbonyl group. A carbonyl group is a carbon atom double-bonded to an oxygen atom C=O while the carbon is also bonded to two other atoms or groups.
In an aldehyde, the carbonyl group is always on an end carbon.

To name aldehydes, use the longest parent chain name of the alkane and replace ‘e’ of ‘ane’ with the suffix ‘-al’. Thus, the name of CH3CHO is ethanal, and CH3CH2CHO is propanal. A homologous series for aldehydes is methanal, ethanal, propanal, and butanal with chemical formulas of HCHO,CH3CHO,CH3CH2CHO, and CH3CH2CH2CHO, respectively, where each successive compound differs from the previous one by a CH2 group.

Aldehyde Carbon number Formula Structure
Methanal 1 HCHO
Ethanal 2 CH3CHO
Propanal 3 CH3CH2CHO

The general formula of the homologous aldehyde series is CnH2nO, where n=1,2,3
In a ketone, the carbonyl group is never on an end carbon. Acetone, for example, is a ketone and is the main component in nail polish remover, while cumin aldehyde is an aldehyde present in cumin seeds.
In order to name ketones, use the longest parent chain name of the alkane and replace ‘e’ of ‘-ane’ by the suffix ‘-one’. For parent chains with more than four carbon atoms, the position of the carbonyl group must be indicated.

For example, the name of the compound CH3COCH2CH2CH2CH3 is 2 -hexanone. The longest parent chain is six carbon atoms; thus, the name of the parent chain alkane is hexane, and since it is a ketone, the suffix -one is added in place of ‘e’ in ‘-ane’.

Now, the position of the ketonic group is determined to be in the second position as it is attached to the second carbon in the chain. Therefore, while writing the name of a ketone, first indicate the position of the ketone group, followed by a hyphen, and then write the parent chain name with the suffix ‘-one’.

A homologous series of ketones can include propanone, butanone, and 2 -pentanone with chemical formulas of CH3COCH3,CH3CH2COCH3, and CH3CH2CH2COCH3, respectively, where each successive compound differs from the previous one by a CH2 group.

KetoneCarbon numberFormula
Propanone1CH3COCH3
Butanone2CH3CH2COCH3
Pentanone3CH3CH2CH2COCH3

The general formula of the homologous ketone series is CnH2nO, where n=1,2,3

Carboxylic Acids in Homologous Series

The organic acids (or carboxylic acids) contain the carboxyl group. A carboxyl group is a carbon atom double-bonded to an oxygen atom C=O, and a hydroxyl group OH, attached to a hydrogen atom or an alkyl group. Vinegar, chemical formula CH3COOH, is a common carboxylic acid called ethanoic acid and known as acetic acid.

When naming organic acids, use the parent chain name of the alkane, and add the suffix ‘oic acid’ by replacing the ‘e’ of the ‘-ane’.
For example, the organic compound with the chemical formula of CH3CH2COOH is propanoic acid, and CH3CH2CH2COOH is butanoic acid. The first compound contains a three-carbon chain; therefore, the parent chain name of the alkane is propane. Since it is a carboxylic acid, the ‘e’ of ‘-ane’ is replaced by ‘-oic acid’, making the name of the compound propanoic acid. Similarly, the name of the carboxylic acid with the four-carbon chain is butanoic acid.

Carboxylic acidCarbon numberFormula
Methanoic acid1HCOOH
Ethanoic acid2CH3COOH
Propanoic acid3CH3CH2COOH
Butanoic acid4CH3CH2CH2COOH

The general formula of the carboxylic acid homologous series is CnH2nO2, where n=1,2,3
A homologous series of carboxylic acids can include pentanoic acid, hexanoic acid, and heptanoic acid with chemical formulas of CH3CH2CH2CH2COOH,CH3CH2CH2CH2CH2COOH and CH3CH2CH2CH2CH2CH2COOH, respectively, where each successive compound differs from the previous one by a CH2 group.

Esters in Homologous Series

An ester is a chemical compound derived from an acid (organic or inorganic) in which at least one OH hydroxyl group is replaced by an Oalkyl (alkoxy) group, as in the substitution reaction of a carboxylic acid and an alcohol.

Esters are named as if the alkyl chain from the alcohol is a substituent. No number is assigned to this alkyl chain. This is followed by the name of the parent chain from the carboxylic acid part of the ester with an -e removed and replaced with the ending -oate.

EsterFormula
Methyl acetateCH3COOCH3
Ethyl acetateCH3COOCH2CH3
Ethyl propionateCH3CH2COOCH2CH3

The general formula of the homologous ester series is CnH2nO2 where n=1,2,3
In the table given above, ethyl acetate differs from methyl acetate by a CH2 unit. Hence, they belong to the same homologous series.

Amides in Homologous Series

Amides are derived from carboxylic acids. A carboxylic acid contains the COOH functional group, and in an amide, the OH part of that group is replaced by an NH2 group. So, amides contain the CONH2 group.

AmidesCardon numberFormula
Methanamide1HCONH2
Ethanamide2CH3CONH2
Propanamide3CH3CH2CONH2

The general formula of the homologous amide series is CnH2n+1NO, where n=1,2,3
A homologous series of amides include methanamide, ethanamide and propanamide, where each successive compound differs from the previous one by a CH2 group.

Nitroalkane in Homologous Series

The organic compounds that contain one or more nitro (NO2) functional groups are called nitroalkanes. These compounds are named by placing the ‘nitro’ as a prefix to the alkanes.

NitroalkanesCarbon numberFormulaStructure
Nitromethane1CH3NO2
Nitroethane2CH3CH2NO2
Nitropropane3(CH3)2CHCH2NO2

The general formula of the nitroalkanes homologous series is CnH2n+1NO2, where n= 1,2,3
A homologous series of nitroalkanes include nitromethane, nitroethane, nitropropane, where each successive compound differs from the previous one by a CH2 group.

Amines in Homologous Series

Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. The amines are named as a derivative of the alkane (or cycloalkane), having the appropriate number of carbon atoms by deleting the terminal e of the alkane and replacing it with the suffix –amine.

AminesCarbon numberFormulaStructure
Methenamine1CH3NH2
Ethanamine2CH3CH2NH2
Propanamine3CH3CH2CH2NH2

The general formula of the homologous amine series is CnH2n+3N, where n=1,2,3

Order in Physical and Chemical Properties

What will happen to a train if an extra compartment is added to it? With every addition of a compartment to the train, its speed decrease by 15% but its use remains the same. In a similar way, the homologous series is a series of molecules that have similar chemical properties but show a trend in their physical properties.

1. The physical properties of members of a homologous series change gradually as the number of carbon atoms increases.

Order in Physical and Chemical Properties

2. Each homologous series has its own functional group. These functional groups determine the chemical reactions that an organic molecule can undergo. Hence, all members of a homologous series have very similar chemical properties.
For example,

  1. The carbon-carbon double bond allows all members of the homologous alkene series to undergo addition reactions.
  2. Acidic properties of carboxylic acids are due to the presence of the carboxyl group,
  3. The order in the physical and chemical properties of organic molecules in a homologous series makes it easy to predict the properties and behaviour of unknown members of the series. By studying the properties of a few members of a homologous series, it is possible to deduce the properties of the other members in the same series.

Characteristic Properties of Homologous Series

A homologous series is a group or family of organic compounds that have certain characteristics:
(a) Members of the series can be represented by a general formula.
(b) Successive members differ from each other by CH2 or 14 amu.
(c) Physical properties change gradually with an increasing number of carbon atoms per molecule.
(d) Members have similar chemical properties because they have the same functional group.
(e) Members can be prepared by similar methods.

Summary

Alkanes, alkenes, alcohols, carboxylic acids and esters belong to different homologous series. Organic compounds’ organisation into the various homologous series makes the study of organic chemistry more systematic, orderly and effective. The members of any homologous series have properties that vary in a regular and predictable manner. There is order in all homologous series with respect to the nomenclature, physical properties and chemical properties. Furthermore, each homologous series has its own functional group. It helps in determining the chemical reactions that an organic molecule can undergo.

Study Classification of Organic Compounds

FAQs on Homologous Series

Q.1. What are the four characteristics of homologous series?
Ans: Four characteristics of a homologous series are:
(i) The general formula of all compounds in the series is the same.
(ii) They have the same functional group.
(iii) Their physical properties, such as melting point, boiling point, density, generally show a gradual change with an increase of molecular formula in the series.

Q.2. What is the importance of homologous series?
Ans: Homologous series is the characteristic feature of carbon compounds in which carbon and hydrogen atoms in hydrocarbons are varying by a single parameter. Homologous series helps in the determination of the structure of the successive member of the series, and the property of those members can also be predicted by their series.

Q.3. Why are cyclopropane and cyclopentane members of the same homologous series?
Ans: Even though they have the same general formula as the alkenes, the cycloalkanes are saturated and contain only single bonds. This means that they do not quickly decolourise bromine solution. Cyclopropane and cyclopentane differ by two CH2 units. Hence, they belong to the same homologous series.

Q.4. How many compounds are present in the homologous series of nitroalkanes?
Ans: A homologous series of nitroalkanes involve nitromethane, nitropropane, nitroethane, where each successive compound differs from the previous one by a CH2 group.

Q.5. List down the examples of Homologous series.
Ans:
Some of the examples of homologous series are methane, ethane, propane, and butane.

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