Organic compounds are the hydrocarbons and their derivatives and organic chemistry is that branch of chemistry that deals with the study of these compounds

Tetravalency of carbon

The atomic number of Carbon is 6 and its electronic configuration is 2,4 i.e. it has 4 valence electrons. Thus carbon is always tetracovalent, i.e. it forms 4 covalent bonds with other atoms

Due to tetravalency of carbon it has a tetrahedron shape.
Catenation– The self linking property of carbon is known as catenation. This is the main reason of existence of such large number of compounds

Classification of organic compounds

Functional groups:A functional group may be defined as an atom or a group of atoms present in a molecule which largely determines the chemical properties.

HOMOLOGOUS SERIES

Homologous series is defined as a family or group of structurally similar organic compounds all members of which contain the same functional group, show a gradation in physical and similarity in chemical properties and any two adjacent members of which differ by  -CH₂ group. The individual members of this group are called homologues and the phenomenon is called homology.

NOMENCLATURE OF ORGANIC COMPOUNDS

Organic chemistry deals with millions of compounds. In order to clearly identify them, a systematic method of naming known as IUPAC system of nomenclature is adopted. The names are such that the listener can deduce the structure from it. The IUPAC name consists of three parts:
refix  Word root  Suffix

EX:   3 meth lyoctane

NOMENCLATURE OF ALKANES

Straight chain alkanes: The names of such compounds is based on their chain structure , and end with suffix ‘-ane’ and carry a prefix indicating the number of carbon atoms present in the chain.

Branched chain hydrocarbons:

1.) The longest carbon chain in the molecule is identified.
2.) The numbering is done in such a way that the branched carbon atoms get the lowest possible value.
3.) The names of the alkyl groups attached as a branch are then prefixed to the name of the parent alkane and its position is indicated by numbers.
4.) The lower number is given to the first in alphabetical order.
5.) The carbon atom of the branch that attaches to the root alkane is numbered 1.

Organic compounds having Functional Groups:

The longest chain of carbon atoms containing the functional groups is numbered in such a way that the functional group attached to the carbon atom gets the lowest possible number in the chain.

When there are more functional groups then a priority order is followed as:

-COOH, -SO₃H, -COOR, COCl, -CONH₂, -CN, -HC=O, =C=O, -OH, -NH₂, =C=C=, -CΞ C-.

 

ISOMERISM

Two or more compounds having the same molecular formula but different physical and chemical properties are called isomers and this phenomenon is called isomerism.

Chain isomerism: When two or more compounds having same molecular formula but different carbon skeletons are referred to as chain isomers.

Position Isomerism : Compounds which have the same structure of carbon chain but differ in position of double or triple bonds or functional group are called position isomers and this phenomenon is called Position Isomerism. e  g
CH₃-CH₂-CH=CH₂
CH₃-CH = CH – CH₃

Functional Isomerism :Compounds which have the same molecular formula but different functional group are called functional isomers and this phenomenon is called functional Isomerism. e  g

CH₃ – CH₂ – OH
CH₃ – O – CH₃

Metamerism:It is due to the presence of different alkyl groups on either side of functional group in the molecule. Ex.  C₄H₁₀O represents C₂H₅OC₂H₅   and CH₃OC₃H₇.

FISSION OF COVALENT BOND

Heterolytic cleavage: In this cleavage the bond breaks in such a way that the shared pair of electron remains with one of the fragments.

H3C – Br          +CH3   + Br-

Homolytic Cleavage: In this cleavage the shared pair of electron goes with each of the bonded atom.

R – X              R.   + X.

Alkyl free radical

 

Nucleophiles : A reagent that brings an electron pair is called nucleophile ie nucleus seeking e g -OH , -CN

Electrophiles: A reagent that takes away electron pair is called electrophile I e electron seeking e g C= O , R₃C – X

Inductive Effect: The displacement of the electron along the chain of the carbon atoms due to presence of an atom or group  at the end of the chain.

d+++ d ++ d+
CH₃         C H₂             CH₂           Cl

Resonance Effect : The polarity produced in the molecule by the interaction of two pi bonds or between a pi bond and lone pair of electron present on an adjacent atom. There are two types of resonance effect:

1) Positive resonance effect : In this effect the transfer of electrons is away from an atom or substituent group attached to the conjugated system.
The atoms or groups which shows +R effect are halogens,-OH , OR,- NH₂

2)  Negative resonance effect : In this effect the transfer of electrons is towards the  atom or substituent group attached to the conjugated system.

The atoms or groups which shows -R effect are –COOH , -CHO , -CN

METHODS OF PURIFICATION OF ORGANIC COMPOUNDS :

Sublimation : This method is used to separate the sublimable compounds from non sublimable compounds.

Crystallisation: This method is based on the difference in the solubilities of compound and impurities in a suitable solvent. The impure compound is dissolved in solvent at heated at higher temp .on cooling the hot and conc solution pure compounds crystallizes out.

Distillation: This method is used to separate volatile liquids from non volatile liquids and liquids having sufficient difference in their boiling points.

Fractional distillation: If the boiling points of two liquids is not much , they are separated by this method.

Distillation under reduced pressure : This method is used to purify liquids having high boiling points and decomposes at or below their boiling points.

Steam distillation : This method is used to separate substances which are steam volatile and are immiscible with water.
Differential Extraction: When an organic compound is present in an aqueous medium it is separated by shaking it with organic solvent in which it is more soluble than in water. The aqueous solution is mixed with organic solvent in a separating funnel and shaken for sometimes and then allowed to stand for some time .when organic solvent and water form two separate layers the lower layer is run out by opening the tap of funnel and organic layer is separated. the process is repeated several times and pure organic compound is separated.

Chromatography :This technique is used to separate mixtures in to their components ,purify the compounds and test the purity of compounds.It is classified as

Adsorption Chromatography : It is based on the fact that different compounds are adsorbed on an adsorbent to different degrees. Silica jel or alumina is used as adsorbents.

Partition Chromatography : It is based on the continuous differential portioning of components of a mixture between stationary and mobile phase.

 

QUALITATIVE ANALYSIS OF ORGANIC COMPOUNDS

Detection of Carbon and Hydrogen: The Carbon and Hydrogen present in the Organic compound is detected by heating the compound with Copper II oxide in a hard glass tube when carbon present in the compound is oxidized to CO2 which can be tested with lime Water and Hydrogenis converted to water which can be tested with anhydrous copper sulphate which turns blue.

C + CuO –> 2Cu + CO₂

2 H +CuO –> Cu + H2O

CO₂  +Ca (OH )₂ –> CaCO₃ + H₂O

5H₂O + CuSO₄ –> CuSO₄.5H₂O

DETECTION OF OTHER ELEMENTS

Sodium Fusion Extract: A small piece of dry Sodium metal is heated with a organic compound in a fusion tube for 2 -3 minutes and the red hot tube is plunged in to distilled water contained in a china dish. The contained of the china dish is boiled, cooled and filtered. The filtrate is known as Sodium fusion extract.

Test for Nitrogen: The sodium fusion extract is boiled with iron II sulphate and then acidified with Concsulphuric acid, the formation of Prussian blue colour confirms the presence of nitrogen.

6CN^– + Fe²⁺  –>  [Fe(CN)₆] ^4-

3[Fe(CN)₆] ^4-+ 4Fe³⁺ –> Fe [Fe(CN)₆]₃ . xH O

Test for Sulphur: the sodium fusion extract is acidified with acetic acid and lead acetate is added to it. A black precipitate of lead sulphide indicates the presence of sulphur.

S^2- + Pb²⁺ –> PbS

Black

Test for halogens: The sodium fusion extract is acidified with nitric acid and then treated with silver nitrate. A white precipitate, soluble in ammonium hydroxide shows the presence of chlorine, a yellowish ppt. sparingly soluble in ammonium hydroxide shows the presence of bromine, a yellowish ppt. insoluble in ammonium hydroxide shows the presence of iodine.

X^– + Ag⁺ –> AgX

 

QUANTITIVE ANALYSIS(Carbon and Hydrogen)

Let the mass of organic compound be m g. Mass of water and carbon dioxide produced be m₁ and m₂ g respectively;

% of carbon  =   12 x m₂ x 100 / 44 x m

% of hydrogen =   2 x m₁ x 100 / 18 x m

Nitrogen

DUMAS METHOD: A known mass of organic compound is heated with excess of CuO in an atmosphere of CO₂, when nitrogen of the organic compound is converted into N₂ gas. The volume of N₂ thus obtained is converted into STP and the percentage of nitrogen determined by applying the equation:

Volume of Nitrogen at STP = P₁V₁ x 273 / 760 x T₁

%N   =      28 x vol of N₂ at STP x 100 / 22400 x mass of the substance taken

KJELDAHL’S METHOD: A known mass of the organic compound is heated with conc. H₂SO₄ in presence of K₂SO₄ and little CuSO₄ or Hg in a long-necked flask called Kjeldahl’s flask when nitrogen present in the organic compound is quantitatively converted into (NH₄)₂SO₄. (NH₄)₂SO₄ thus obtained is boiled with an excess of NaOH solution to liberate NH₃ gas which is absorbed in a known excess of a standard acid such as H₂SO₄ or HCl.

The vol of acid unused is found by titration against a standard alkali solution. From the vol of the acid used, the percentage of nitrogen is determined by applying the equation,

%N= 1.4 x Molarity of the acid x Basicity of the acid x Vol of the acid used / Mass of the substance taken

Halogens Carius method:

A known mass of an organic compound is heated with fuming nitric acid in the presence of silver nitrate contained in a hard glass test tube known as carius tube in a furnace. Carbon and hydrogen present in the compound are oxidized to carbon dioxide and water. The halogen present forms the corresponding silver halide. It is filtered, dried, and weighed.

Let the mass of the organic compound taken = m g Mass of AgX formed = m₁ g

1 mol of AgX contains 1 mol of of X

Mass of halogen in m₁ g of AgX = at mass of X xm₁ g / Molecular mass of AgX

% of halogen=  at mass of X xm₁ g x 100 / The molecular mass of AgX x m

Sulphur

Let the mass of the organic compound taken = m g

Mass of BaSO₄ formed = m₁ g

% of sulphur = 32 x m₁ x 100 / 233 x m

Phosphorous

Let the mass of the organic compound taken = m g

Mass of ammonium phosphomolydate = m₁ g

% of phosphorous = 31 x m₁ x 100 / 1877 x m

Oxygen

Let the mass of the organic compound taken = m g

Mass of CO₂= m₁ g

% of oxygen =   32 x m₁ x 100 / 44 x m