Organic Chemistry – Chapter Revision

 Originally, the term ‘organic chemistry’ was referred to the chemistry of those compounds
which were obtained from plants or animals. Substances obtained from living organisms
only were called organic substances and the chemistry related to them were called
organic chemistry. It is a separate branch of chemistry.
 According to the modern definition, organic compounds are the compounds which contain
carbon as their essential constituent. However, there are compounds like carbon monoxide,
carbon dioxide, metal carbonates and carbides which contain carbon but are arbitrarily
studied along with inorganic compounds.
 There are four electrons in the outermost shell of a carbon atom. It is difficult for the carbon
atom to gain or lose electrons to complete its octet. The carbon atom thus shares its valence
electrons with the electrons of other atoms of carbon or other elements. For example, to
form a molecule of methane (CH4), a carbon atom bonds covalently with four hydrogen
atoms forming four covalent bonds. This property of carbon atom is called tetravalency
of carbon.
 The self-linking capacity of carbon atom with other carbon atoms to form a giant molecule
is known catenation. It is the property of catenation which is responsible for the formation
of very large number of organic compounds. carbon atoms can combine with one another
to form long chains or rings of different shapes and sizes, such as:

C C C C

(a) Straight chain

C C C

(b) Branched chain

(c) Closed chain

 Organic compounds that contain rings of atoms in their molecules arc called cyclic
compounds. Open chain and acyclic organic compounds arc called aliphatic compounds.
 Characteristics of Organic Compounds
 All the organic compounds are covalent, i.e., all organic compounds are non-ionic in
nature.
 Most of the organic compounds are insoluble in water but soluble in organic solvents.

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  They have low melting and boiling points as compared to inorganic compounds.
 They possess the phenomenon of isomerism.
 When burnt in air, organic compounds produce carbon dioxide and water.
 The phenomenon by virtue of which two or more compounds having the same molecular
formula can be assigned different molecular structures is called isomerism.
ISOMERISM

 A functional group is an atom or a group of atoms on which most of the properties of the
compound depend and which defines the structure of a particular family of organic
compounds.
The chemical properties of the compounds containing the same functional group are
similar but their physical properties may be different.
 A homologous series is a group, or a family, of organic compounds having similar
structures and similar chemical properties in which the successive members differ by a —
CH2 group.
 Compounds that contain only the elements hydrogen and carbon are called hydrocarbons.
In general, the molecular formula of a hydrocarbon is CXHY.
 Classification of Hydrocarbons:

 The system of naming of organic compounds is called nomenclature of organic

compounds. In the case of aliphatic compounds, two systems of nomenclature are
generally used:
 Trivial or Common system — distinguished by prefixes n, iso and neo.
 IUPAC system — consists of word root, suffix and prefix.
 Alkanes
 An alkane is a hydrocarbon that contains no multiple bonds. All the four valencies of
carbon are satisfied by single bonds.

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  General formula of alkanes is CnH2n+2, where n = 1, 2, 3, ... . When n = 1, the alkane
is CH4; when n = 2, the alkane is C2H6 etc.
 Methane (CH4), ethane (C2H6), propane (C3H8), and butane (C4H10) form the
homologous series of alkanes.
 A few of them show isomerism.
 IUPAC system retains the common names for the first ten alkanes, but is used for
naming higher branched-chain alkanes.
 Alkenes
 Alkenes are a homologous series of unsaturated hydrocarbons that contain carbon-
carbon double bond.
 General formula for alkenes is CnH2n, where n = 2, 3, 4,.... When n = 2, the alkene is
C2H4; when n = 3, the alkene is C3H6; when n = 4, the alkene is C4H8, etc.
 Their IUPAC names are derived from parent alkanes by replacing the suffix ‘-ane’ of
alkane by ‘-ene’, for example, ethene (C2H4), propene (C3H8), etc.
 Alkynes
 Alkynes are a homologous series of unsaturated hydrocarbons that contain carbon-
carbon triple bond.
 General formula for alkynes is CnH2n-2, where n = 2, 3, 4,.... When n = 2, the alkyne
is C2H2; when n = 3, the alkyne is C3H4 etc.
 Their IUPAC names are derived from parent alkanes by replacing the suffix ‘-ane’ of
alkane by ‘-yne’, for example, ethyne (C2H2), propyne (C3H4), butyne (C4H6), etc.
 Alcohols
 Alcohols form a homologous series of general formula CnH2n+1OH, where OH is the
hydroxy group and n is the number of carbon atoms for molecule of the alcohol.
 For naming the alcohols according to IUPAC system, the last letter ‘e’ of the parent
alkane is replaced by the ending ol to indicate the presence of—OH group. Hence
alcohols are named as alkanols in the IUPAC system, for example, methanol
(CH3OH), ethanol L(C2H5OH), propanol (C3H7OH), etc.
 Ethanol when mixed with a certain quantity of methanol (about 5%) is called
denatured spirit or spurious alcohol.
 Aldehydes
 General formula for aldehydes is CnH2n+1CHO where n = 0, 1, 2.... when it n = 0, the
aldehyde is HCHO, when n = 1, the aldehyde is CH3CHO, etc.
 Formaldehyde (HCHO), acetaldehyde (CH3CHO), propionaldehyde (C2H5CHO), n-
butyraldehyde (C3H7CHO) form the homologous series of aldehydes.
 Their IUPAC names are derived from parent alkanes by replacing suffix ‘-e’ of alkane
by ‘-al’, for example, methanal (HCHO), ethanal (CH3CHO), etc.
 Carboxylic Acids
 General formula for carboxylic acids is R — COOH, where R is an alkyl group having
formula CnH2n+1
 Carboxylic acids are classified as monocarboxylic acids, dicarboxylic acids, etc.,
according to the number of —COOH groups present in the molecule.

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  Common names of carboxylic acids are derived from the name of source (plant or
animal) from which they were isolated, for example, formic acid (HCOOH), acetic
acid (CH3COOH), propanoic acid (C2H5COOH), etc.
 Their IUPAC names are derived from parent alkanes by replacing suffix ‘-e’ of alkane
by ‘-oic acid’, for example, methanoic acid (HCOOH), ethanoic acid (CH3COOH),
propanoic acid (C2H5COOH), etc.
Methane (CH4)
 Occurrence
Methane is the first member of alkanes having one carbon atom and four hydrogen atoms.
It has a tetrahedral structure. Methane is also called marsh gas because it is evolved in
the marshy lands. Methane also occurs in coal-mines, natural gas and coal gas.

 Preparation
In the laboratory, methane is prepared by heating a mixture of sodium acetate with soda
lime (a mixture of sodium hydroxide and calcium oxide).
∆
CH3COONa + NaOH → Na2CO3 + CH4↑
Cao
Methane is also prepared by the reduction of methyl iodide.
zn−cu
CH3I + 2[H] → HI + CH4 ↑
(nascet) Alcohol
 Physical Properties
 Methane is a colourless, odourless, tasteless and non-poisonous gas.
 Its boiling point is —164°C and melting point is —184°C.
 It is sparingly soluble in water but readily soluble in organic solvents like ether and
alcohols.
 It is 1.8 times lighter than air. Its vapour density is 8 and that of air is 14.4.
 Chemical Properties.
 Methane burns in excess of air with a bluish, non-luminous flame forming carbon
dioxide and water.
CH4 + 2O2 → CO2 + 2H2O + Heat
(excess)
In a limited supply of air, methane burns with luminous flame forming carbon monoxide
and water.
2CH4 + 3O2 → 2CO2 + 4H2O
(limited)
 Methane reacts with steam in the presence of nickel catalyst forming carbon monoxide
and hydrogen.

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 1000°C
CH4 + H2O → CO + 3H2↑
Ni
 Oxidation of methane with potassium dichromate gives alcohol, aldehyde and acid.
[O]
2CH4 + O2→ 2CH3OH
K2Cr2O7
[O]
2CH3OH + O2 → 2HCHO + 2H2O
K2Cr2O7
[O]
2HCHO + O2 → 2HCOOH
K2Cr2O7
 In the presence of diffused sunlight, methane undergoes a series of substitution
reactions with chlorine.

 In the presence of direct sunlight, methane reacts with chlorine explosively to form
carbon and hydrogen chloride.
Diffused
CH4 + 2C12 → C +4HCl
Sunlight
 At 1000°C, methane decomposes into carbon and hydrogen.
1000°C
CH4 → C + 2H2 ↑
 At 1500°C, methane decomposes into acetylene liberating hydrogen gas.
1500°C
2CH4 → HC ≡ CH + 3H2↑
Acetylene
 Uses: Methane is used:
 as a domestic fuel.
 for making carbon black.
 in automobiles as a fuel.
 for making chloroform, etc., by regulated chlorination.
 for manufacturing methanol, formaldehyde, etc.
 Ethane (C2H6)
 Occurrence
Ethane is the second member of homologous series of alkanes. It occurs in mineral oil
and natural gas.
 Preparation
 In the laboratory, ethane is prepared by heating sodium propionate with soda lime.
∆
C2H5COONa + NaOH → C2H6 + Na2CO3
CaO

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  Ethane is also Prepared by the reduction of ethyl iodide.
zn−cu
C2H5I + 2[H] → C2H6 + HI
Alcohol
 Physical Properties
 Ethane is a colourless, odourless and tasteless gas.
 Liquid ethane boils at —88.3°C and solidifies at —172°C.
 Ethane is slightly heavier than air. its vapour density is 15.
 Ethane is partially soluble in water but highly soluble in ethanol.
 Chemical Properties
 Ethane burns in excess of air to form carbon dioxide. In a limited supply of air, it
forms carbon monoxide and water. In a very limited supply of air, it forms carbon and
water.
2C2H6 + 7O2 → 4CO2 + 6H2O + Heat
(excess)
2C2H6 + 5O2→ 4CO + 6H20
(limited)
2C2H6 + 3O2 → 4C + 6H2O
(very limited)
 The oxidation of ethane with acidified potassium dichromate gives alcohol, aldehyde
and acid.
[O] [O] [O]
C2H6 → C2H5OH → CH3CHO → CH3COOH
K2Cr2O7 K2Cr2O7 K2Cr2O7
 Ethane undergoes substitution reactions. It reacts with chlorine in diffused sunlight
giving chloro-derivatives.

 At 500°C in the presence of catalyst Al2O3, ethane forms ethene and hydrogen,
500°𝐶
C2H6 → C2H4+ H2
Al2O3
 Uses: Ethane is used:
 as a gaseous fuel because of its high calorific value.
 as a fuel in automobiles.
 to prepare important compounds like ethanol, acetaldehyde, acetic acid, etc.
Ethene or Ethylene (C2H4)
 Preparation
 In the laboratory, ethene is prepared by dehydration of ethanol.

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 Conc.H2 SO4
CH3CH2OH → C2H4 + H2O
180°C
 Ethene is also prepared by dehydrohalogenation of ethyl chloride with alcoholic
potassium hydroxide.
Heat
C2H5Cl → C2H4 + KCl + H2O
Alc.KOH
 Physical Properties
 Ethene is a colourless gas with a pleasant odour.
 It is sparingly soluble in water but dissolves readily in organic solvents.
 It is slightly lighter than air. Its vapour density is 14 and that of air is 14.4.
 Liquid ethene boils at —104°C and solidifies at —169°C.
 Chemical Properties
 Ethene burns in air with a sooty flame, but when burns in excess of oxygen, it forms
carbon dioxide and water.
C2H4 + 3O2 → 2CO2 + 2H2O
(excess)
 Ethene being unsaturated undergoes addition reactions.

 Ethene reacts with a large number of other ethene molecules to give a compound of
large molecular weight.

 Uses: Ethene is used:

 as oxyethene for the manufacture of detergents.
 For artificial ripening and preservation of fruits.
 As general anaesthesia.

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  In the manufacture of synthetic chemicals.
 In the manufacture of polymers.
 Acetylene or Ethyne (C2H2)
 Preparation
 In the laboratory, ethyne is prepared by the action of water on calcium carbide.
CaC2 + 2H2O → C2H2 + Ca(OH)2
 Ethyne may be prepared by boiling ethylene dibromide with alcoholic potassium
hydroxide solution.
 C2H4Br2+ 2KOH→ C2H2+ 2KBr+ 2H2O
(alcoholic)
 Physical Properties
 Ethyne is a colourless gas with sweet smell.
 it is lighter than air. Its vapour density is 13 and that of air is 14.4.
 It liquefies at –84°C under ordinary pressure and boils at –75°C.
 It is slightly soluble in water but dissolves readily in organic solvents like acetone,
etc.
 Chemical Properties
 Ethyne burns in air to form carbon dioxide and water.
 2C2H2 + 5O2 → 4CO2↑ + 2H2O + Heat
(air)
 Ethyne gives a number of addition reactions, combining with four monovalent atoms
per molecule, for example:

 When ethyne is treated with ammoniacal silver nitrate solution or ammoniacal copper
(I) chloride solution, metal silver or copper respective precipitate.

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 Uses: Ethyne is used:
 for illumination specially in acetylene lamps.
 in the production of oxy-acetylene flame which is used for cutting and welding.
 for artificial ripening of fruits.
 in the manufacture of organic compounds.
 as a starting material to prepare plastics, synthetic rubber, etc.
 Ethanol or Ethyl alcohol (C2H5OH)
 Preparation
 Ethanol can be prepared by ethene.
H3 PO4
 CH2= CH2 + H2O → C2H5OH
300°C / 60 atm
 Ethanol is prepared by hydrolysis of ethyl halides.
H3 PO4
C2H5Br + KOH → C2H5OH + KBr
300°C / 60 atm
 Physical Properties
 Ethanol is a colourless inflammable volatile liquid soluble in water.
 It is toxic in nature.
 It is lighter than water.
 It boils at 78.3 °C.
 It is a non-conductor of electricity because it does not contain ions.
 Chemical Properties
 Ethanol is a combustible liquid which burns in air to form carbon dioxide and water.
C2H5OH + 3O2 → 2CO2 + 3H2O
(air)
 Ethanol reacts with acetic acid in the presence of concentrated sulphuric acid at a high
temperature to form ethyl acetate.
Conc.H2 SO4
C2H5OH + CH3COOH → CH3COOC2H5 + H2O
 Ethanol is oxidized to ethanol(acetaldehyde) by aqueous potassium dichromate, which
is further oxidized to ethanoic acid (acetic acid)
[O] [O]
C2H5OH → CH3CHO → CH3COOH
K 2 Cr2 O7 K 2 Cr2 O7
 Ethanol reacts with chlorides of phosphorus.
C2H5OH +PCl5 → C2H5Cl + POCl3 +HCl ↑
3C2H5OH +PCl3 → 3C2H5Cl + POCl3

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  Sodium reacts with ethanol displacing hydrogen.
 2C2H5OH + 2Na → 2C2H5ONa + H2↑
 Ethanol reacts with sulphuric acid in two ways.
H2 SO4 (limited)
 C2H5OH → C2H4 + H2O
140° C
H2 SO4 (limited)
 2C2H5OH → C2H5OC2H5 + H2O
(excess) 140° C
 uses: Ethanol is used:
 in the manufacture of beer, wine and other alcoholic beverages.
 as a solvent for paints, varnishes, oils and dyes.
 as a fuel. A mixture of 80% petrol and 20% ethanol is known as power alcohol.
 in the synthesis of many organic compounds.
ACETIC ACID OR ETHANOIC ACID (CH3COOH)
Acetic acid is the second member of carboxylic acid family. It is one of the naturally occurring
carboxylic acids.
 Preparation
 From Ethanol: In this method, fermented liquor of ethanol is oxidized by air under
the influence of bacterium aceti. The solution produced is called vinegar.
Bacterium aceti
C2H5OH + O2 → CH3COOH + H2O
 Physical Properties
 Pure acetic acid is a colourless and corrosive liquid.
 It has a pungent vinegar smell. It tastes sour.
 It has a pungent vinegar smell. It tastes sour.
 It is miscible with water and alcohol in all proportions.
 Its freezing point is 16.6°C and boiling point is 118°C.
 Chemical Properties
Acetic acid ionizes in aqueous solution, so it shows all properties of an acid.
CH3COOH ⇌ H+ CH3COO−
 It turns blue litmus paper red.
 When acetic acid is added to metallic carbonates or bicarbonates, respective metallic
ethanoates and water are formed with the liberation of carbon dioxide.
2CH3OOH + Na2CO3 → 2CH3COONa + H2O + CO2 ↑
CH3OOH + NaHCO3 → 2CH3COONa + H2O + CO2 ↑
 Acetic acid is neutralized by an alkali such as sodium hydroxide or ammonium
hydroxide.
CH3COOH + NaOH → CH3COONa + H2O
CH3COOH + NH4OH → CH3COONH4 + H2O
 When treated with active metals like sodium, magnesium and zinc, acetic acid forms
respective metallic ethanoates and hydrogen gas is evolved.
2CH3COOH + Mg → (CH3COO)2Mg + H2↑
 Acetic acid is reduced to ethanol by lithium aluminium hydride.
LiAlH4
 CH3COOH + 4H → C2H5OH +H2 ↑

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  When acetic acid reacts with alcohols like ethanol in the presence of conc. H2SO4
ethyl acetate (ester) and water are formed.
∆
 CH3COOH + C2H5OH → 2CH3COOC2H5 + H2O
Conc.H2SO4
 Acetic acid reacts with PCl5 to give acetyl chloride.
 CH3COOH + PCl5 → CH3COCl + POCl3 + HCl
 The removal of CO2 by heating a carboxylic acid is called decarboxylation.
 Uses: Acetic acid is used:
 in the manufacture of white vinegar, acetone, esters, pharmaceuticals, drugs, dyes,
perfumes, cellulose, acetate, polyvinyl acetate and metal acetate.
 as a laboratory reagent.

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