ORGANIC CHEMISTRY – SOME BASIC PRINCIPLES AND TECHNIQUES

Organic chemistry is the branch of chemistry that deals with carbon compounds. But all carbon
compounds are not considered as organic compounds. (E.g. CO2, CO, metal carbonates, bicarbonates
etc.). So organic chemistry can be defined as the branch of chemistry that deals with hydrocarbons and
their derivatives. Hydrocarbons are the major class of organic compounds and they contain only
carbon and hydrogen atoms. All other organic compounds are formed by replacing one or more
hydrogen atoms of hydrocarbons by other atoms or groups (They are called hydrocarbon
derivatives).
All carbon compounds present in plants and animals are organic compounds. E.g.
carbohydrates, proteins, vitamins, nucleic acids, amino acids, fats and oils, natural polymers etc.
Petroleum and coal are the major source of organic compounds (hydrocarbons).
In ancient times, it was believed that a vital force (living body) is necessary for the production
of an organic compound. But in 1828, Frederic Wohler prepared urea in the laboratory, by heating
ammonium cyanate (NH4CNO). It was the first organic compound prepared in the laboratory.
Heat
NH4CNO →−−−→ NH2CONH2
Ammonium cyanate Urea
Another scientist Kolbe synthesized acetic acid and Berthelot synthesized methane in the
laboratory. Nowadays about 95% of the organic compounds are synthesized in the laboratory.

Chemistry behind the existence of large number Carbon compounds

Carbon is a unique element and it can form large number of compounds due to the following reasons:
i) Tetravalency of carbon: In all of its compounds, the valency of carbon is four. Carbon has 4 electrons
in its valency shell and requires 4 more electrons to complete the octet. So it attains the octet configuration by
forming 4 covalent bonds.
ii) Ability to form single bond and multiple bonds: C can form single bond and multiple bond (double or
triple bond) with itself and also with other elements like oxygen, nitrogen etc. This is possible by sp3,
sp2 or sp hybridization.
iii) Catenation: Carbon shows catenation. It is the self-linking property of an element to form long chains
and rings.
iv) Isomerism: Carbon compounds can show isomerism. It is the phenomenon in which compounds
having same molecular formula but different structural formula or spatial arrangement of atoms.

How many σ and π bonds are present in each of the following molecules?
(a) HC≡CCH=CHCH3 → σC–C: 4; σC–H : 6; πC=C :1; π C≡C:2
(b) CH2=C=CHCH3 → σC – C: 3; σC–H: 6; πC=C:2

What is the type of hybridization of each carbon in the following compounds?

(a) CH3Cl → sp3
(b) (CH3) 2CO → sp3, sp2
(c) CH3CN → sp3, sp
(d) HCONH2 → sp2
(e) CH3CH=CHCN → sp3, sp2sp2, sp

Write the state of hybridization of carbon in the following compounds and shapes of each of the
molecules.
(a) H2C=O → sp2 hybridized carbon, trigonal planar
(b) CH3 → sp3 hybridized carbon, tetrahedral
(c) HC≡N → sp hybridized carbon, linear.
Structural representation of organic compounds
An organic compound can be represented by the following ways:
1. Complete structural formula: Here all the bonds between atoms are denoted by dashes (--). A
single dash represents a single bond, a double dash represents a double bond and a triple dash
represents a triple bond. E.g.

2. Condensed stuctural formula: Here the carbon-hydrogen bonds or all the bonds are omitted except
the multiple bonds. It is a simplified representation of an organic compound.
E.g. ethane - CH3CH3, propane - CH3CH2CH3, butane - CH3CH2CH2CH3, ethene - CH2CH2 etc. The
condensed formula can again simplify as follows: Butane – CH3(CH2)2CH3, Hexane- CH3(CH2)4CH3,
Decane – CH3(CH2)8CH3 etc.

3. Bond line representation: It is the simplest form of representation of an organic compound.

Here carbon and hydrogen atoms are not shown and the lines representing carbon-carbon bonds are
drawn in a zig-zag fashion. The only atoms specifically written are oxygen, chlorine, nitrogen etc. The
free terminals denote methyl (–CH3) groups.

4. Three-Dimensional Representation (Wedge Representation): Here the structure of an organic

molecule can be represented by using solid ( ) and dashed ( ) wedges. The solid- wedge
is used to indicate a bond projecting out of the plane of paper, towards the observer. The dashed-
wedge indicates the bond projecting out of the plane of the paper and away from the observer. The
broad end of the wedge is always towards the observer. The bonds lying in plane of the paper are
depicted by using a normal line (—).
E.g. methane
 Classification of Organic compounds
Organic compounds can be broadly classified into two – Acyclic or open chain compounds and
cyclic or ring compounds.

1. Acyclic or open chain or aliphatic compounds: In these compounds, the carbon atoms are joined
together to form long chains which may be straight chain or branched chain. They are further
classified as saturated compounds and unsaturated compounds.
Saturated compounds contain only carbon – carbon single bonds.
But unsaturated compounds contain at least one carbon – carbon multiple bond (double or triple
bond).
Saturated hydrocarbons are called alkanes and unsaturated hydrocarbons are of two types – alkenes
and alkynes.

2. Cyclic or closed chain or ring compounds: In these compounds, the carbon atoms are joined
together to form rings. These rings may be homocyclic or heterocyclic. If the ring contains only
carbon atoms, it is called homocyclic compound and if it contains atoms other than carbon (like O, N,
S etc), it is called heterocyclic compound.
Homocyclic compounds are further classified into two – Alicyclic compounds and Aromatic
compounds. Alicyclic compounds contain atleast one carbo-cyclic ring. Alicyclic hydrocarbons are of
three types – cycloalkanes, cycloalkenes and cycloalkynes.

Aromatic compounds are some special type of compounds. These are of two types. Aromatic
compounds containing benzene ring are called benzenoid compounds and those which do not
contain benzene ring are called non-benzenoid compounds. E.g. for a non-benzenoid aromatic
compound is tropolone.
 Heterocyclic compounds may be alicyclic heterocyclic compounds or aromatic heterocyclic
compounds. The classification of organic compounds can be diagrammatically represented as
follows:

Functional groups: Atoms or group of atoms (except hydrogen) which are bonded to carbon atoms
are called functional groups. These groups are responsible for the characteristic chemical properties
of the organic compounds. Some important functional groups, their names and name of the
compounds are listed below:
Functional group Name of the group Name of compound
-OH Hydroxyl group Alcohol
-NH2 Amino group Amine
-X Halo group Halo compound
-CHO Aldehydric (formyl) group Aldehyde
-CO- or >CO Carbonyl (keto) group Ketone
-COOH Carboxyl group Carboxylic acid
-O- Oxy group Ether
-CN Cyano group Nitrile
-NO2 Nitro group Nitro compound

Homologous series: A series or group of organic compounds in which adjacent members are
differed by a –CH2 group is called a homologous series. The members of a homologous series are
called homologues. They contain same functional groups. So they have similar chemical properties
and show gradation in physical properties. They can be prepared by some general methods of
preparation. E.g. for homologous series are alkanes, alkenes, alkynes, alcohols, ethers, carboxylic
acids, aldehydes, ketones, amines, halo compounds etc

Nomenclature of organic compounds

An organic compound has two types of names – Common name and IUPAC name. The
common name is based on the source or some properties. For e.g. citric acid is named so because it
is found in citrus fruits and the acid found in red ant is named formic acid since the Latin word for
ant is formica.

IUPAC Nomenclature of organic compounds

A systematic name of an organic compound is generally derived by identifying the parent
hydrocarbon and the functional group(s) attached to it. This name is called IUPAC name. It contains
two parts – word root and suffix or prefix. The word root indicates the number of carbon atoms in
the compound. The word roots for compounds containing 1 -12 carbon atoms are as follows:
 No. of C atoms Word root No. of C atoms Word root
C1 Meth- C7 Hept-
C2 Eth- C8 Oct-
C3 Prop- C9 Non-
C4 But- C10 Dec-
C5 Pent- C11 Undec-
C6 Hex- C12 Dodec-
There are two types of suffixes – primary suffix and secondary suffix. Primary suffix indicates
saturation or unsaturation [for alkane the primary suffix is –ane, alkene –ene and for alkyne –yne].
Secondary suffix indicates the type of functional group. Some functional groups are also indicated as
prefixes.

Nomenclature of branched chain alkanes:

A branch (side chain or substituent) is obtained by removing a hydrogen atom from an
alkane. The resulting group is called an alkyl group [alkane – H = alkyl (i.e. word root + yl)]. The
names of some common branches are as follows:
Branch Name
-CH3 Methyl
-CH2-CH3 Ethyl
-CH2-CH2-CH3 n-propyl (normal propyl)
(CH3)2CH- Isopropyl
-CH2-CH2-CH2-CH3 n-butyl
CH3-CH-CH2-CH3 sec-butyl (secondary butyl)

(CH3)2CH-CH2- Isobutyl
(CH3)3C- tert-butyl (tertiary butyl)
(CH3)3C-CH2- Neopentyl

Rules for naming branched chain alkanes:

IUPAC recommenced the following rules for naming a branched chain alkane.

1. Select the longest continuous chain of carbon atoms. This chain is called parent chain or root chain.
If there is more than one such chain, the chain that contains maximum number of branches is selected
as the parent chain. Also identify all the branches or substituents.
2. Number the carbon atoms of the parent chain in such a way that the branched carbon atoms get the
lowest possible numbers.

3. The names of alkyl groups attached as branches are then prefixed to the name of the parent alkane
and position of the substituents is indicated by the appropriate numbers.

4. If different alkyl groups are present, they are listed in alphabetical order. In alphabetical order, the
prefixes iso- and neo- are considered to be the part of the fundamental name of alkyl group. The
prefixes sec- and tert- are not considered to be the part of the fundamental name.
 If two or more identical substituent groups are present then their numbers are indicated by
prefixes like di (for 2), tri (for 3), tetra (for 4), penta (for 5) etc and the numbers are separated by
commas. The number and word are separated by a hyphen. (The IUPAC name is written as a single
word). For example: 3-Ethyl-4,4-dimethylheptane

5. If the two substituents are found in equivalent positions, the lower number is given to the one
coming first in the alphabetical listing. For example:

The above compound is 3-ethyl-6-methyloctane and not 6-ethyl-3-methyloctane.

6. While naming the branched alkyl groups, the carbon atom of the branch that attaches to the root
alkane is numbered 1. For example:

1,3-dimethyl butyl-

IUPAC nomenclature of compounds containing functional groups

For naming organic compounds containing functional group, the following rules are used:

1. Select the longest continuous chain containing the functional group.

2. Number the carbon atoms in such a way that the carbon to which the functional group is attached
should get the lowest possible number. In the case of functional groups containing carbon atom like
–CHO, -CN, -COOH, -CONH2, -COX. -COOR etc. the numbering should start from the carbon atom of
the functional group. (i.e. carbon atom of these groups should be numbered as 1). (But for ketones,
the functional group –CO- should get the lowest possible number).

3. The name of the functional group is indicated by the following suffix or prefix
In the case of suffixes, the ending –e of the corresponding alkane is replaced. E.g. IUPAC name of
the alcohol CH3-OH is methanol (methane + ol). But for nitriles, the –e of the corresponding
alkane is retained. E.g. IUPAC name of CH3-CH2-CN is propanenitrile.
In the case of alkenes and alkynes, the suffix –ane of the alkane is replaced by –ene and –yne
respectively. (i.e. word root + ene or yne). For naming alkenes or alkynes, the numbering is done in
such a way that the double or triple bond should get the lowest possible number.
Some examples are:
Compound IUPAC Name
Compounds IUPAC Names
CH3-CH2-CH=CH2 But-1-ene OR 1-Butene
CH3-CH=CH-CH3 But-2-ene OR 2-Butene
CH3-CH2-C≡C-CH3 Pent-2-yne OR 2-Pentyne
CH3-CH2-CH2-CH2-CH2-C≡CH Hept-1-yne OR 1-Heptyne
CH3-CH2-OH Ethanol
CH3 -CH2-CHOH-CH2-CH2-CH3 Hexan-3-ol OR 3-Hexanol
CH3-CO-CH2-CH2-CH3 Pentan-2-one OR 2-Pentanone
HCHO Methanal
CH3-CO-CH3 Propanone
CH3-COOH Ethanoic acid
CH3-CH2-CH2-CO-CH2-CH2-CH2-CH3 Octan-4-one OR 4-Octanone
HCOOH Methanoic acid

Nomenclature of organic compounds containing more than one functional groups (Poly
functional compounds)
Here one of the functional groups is chosen as the principal functional group and the
compound is named on that basis. The remaining functional groups (called subordinate functional
groups) are
named as substituents using the appropriate prefixes. The choice of principal functional group is
made on the basis of order of preference. The decreasing order of priority for some functional
groups is
-COOH, –SO3H, -COOR, -COCl, -CONH2, -CN,-CHO, >CO, -OH, -NH2, >C=C<, -C≡C-
The groups like alkyl (–R), phenyl (C6H5-), halogens (F, Cl, Br, I), nitro (–NO), alkoxy (–OR) etc. are
always prefix substituents.
For example if a compound contains both alcoholic and aldehydic groups, it is named as
hydroxy alkanal, since here aldehydic group is the principal functional group and –OH group is the
subordinate functional group.
The prefix names of some functional groups are as follows:

While numbering the carbon chain, the principal functional group should get the lowest possible
number. Some examples are:
Compound IUPAC Name
CH3-CHOH-CH2-CO-CH3 4-Hydroxy-2-pentanone
CH2Cl-CH2-CHBr- CH2-CH2OH 3-Bromo-5-chloropentan-1-ol or, 3-Bromo-5-chloro-1-pentanol
CH3-CH2-CO-CH2-CH2-CHO 4-Oxohexanal
CH3-CHNH2-CH2-COOH 3-Aminobutanoic acid
CH3-CH2-CHCl-CH2-CO-CH2-COOH 5-Chloro-3-oxo-heptanoic acid
 If a compound contains more than one same functional group, their number is indicated by
adding the numeral prefixes di, tri, etc. before the suffix. In such cases the full name of the parent alkane
is written before the suffix. However, the ending – ne of the parent alkane is dropped in the case of
compounds having more than one double or triple bonds.
When both double and triple bonds are present, the double bonds are given the lowest numbers.
Here first give the suffix of the double bond (-ene) and then that of the triple bond (-yne) [the ending –e
of the suffix –ene is avoided].
Examples:
Compound IUPAC Name
CH2OH-CH2OH Ethane-1,2-diol (Ethylene glycol)
CH2OH-CHOH-CH2OH Propane-1,2,3-triol (Glycerol)
CHO-CHO Ethane-1,2-dial (Glyoxal)
COOH-COOH Ethane-1,2-dioic acid (Oxalic acid)
CH3-CO-CH2-CO-CH3 Pentane-2,4-dione
CH2=CH-CH=CH2 1,3-Butadiene or Buta-1,3-diene
CH≡C-CH2-C≡CH 1,4-Pentadiene or Penta-1,4-diene
CH2=CH-CH2-C≡ CH Pent-1-en-4-yne
CH≡C-CH=CH-C=CH2 Hexa-1,3-dien-5-yne
(The names given in the bracket are the common names)

Nomenclature of Substituted Benzene Compounds

For IUPAC nomenclature of substituted benzene compounds, the substituent is placed as prefix to
the word benzene. But common names of some compounds are accepted by IUPAC

Nomenclatrue of di or polysubstituted benzene

If benzene ring is disubstituted, the position of substituents is indicated by numbering the
carbon atoms of the ring such that the substituents get the lowest possible numbers.
Example – Dibromobenzene
 In the common system of nomenclature the terms ortho (o), meta (m) and para (p) are used as
prefixes to indicate the relative positions 1,2- 1,3- and 1,4- respectively. So 1,2-dibromobenzene is
named as ortho-dibromobenzene (o-dibromobenzene), 1,3-dibromobenzene as meta-
dibromobenzene (m-dibromobenzene) and 1,4-dibromobenzene as para-dibromobenzene (p-
dibromobenzene).
For tri - or higher substituted benzene derivatives, these prefixes cannot be used and the
compounds are named by identifying substituent positions on the ring by following the lowest locant
rule. In some cases, common name of benzene derivatives is taken as the base compound. Substituent
of the base compound is assigned number1 and then the direction of numbering is chosen such that
the next substituent gets the lowest number. The substituents are named in alphabetical order.
Some examples are:

When a benzene ring is attached to an alkane with a functional group, it is considered as

substituent, instead of a parent. The name for benzene as substituent is phenyl (C6H5-, also
abbreviated as Ph).
Example:

• Write the structural formula of: (a) o-Ethylanisole, (b) p-Nitroaniline, (c) 2,3-Dibromo-1-
phenylpentane, (d) 4-Ethyl-1-fluoro-2-nitrobenzene.
• Derive the structure of (i) 2-Chlorohexane, (ii) Pent-4-en-2-ol, (iii) 3- Nitrocyclohexene, (iv)
Cyclohex-2-en-1-ol, (v) 6-Hydroxyheptanal.

Isomerism
The phenomenon of existence of two or more compounds having the same molecular formula but
different structural formula or spatial arrangement of atoms is known as
isomerism. Such compounds are called as isomers. Isomers have different physical and chemical
properties. Isomerism can be broadly classified into two –structural isomerism and stereo
isomerism.
Structural isomerism
Compounds having same molecular formula but different structural formula (arrangement of
atoms) are called structural isomers and the phenomenon is called structural isomerism. There are
mainly four types of structural isomerism:

Chain Isomerism: Isomers differ in carbon chain or skeleton are called chain isomers and the
phenomenon is called chain isomerism.
E.g.:

Position isomerism: Isomers which differ in the position of the substituent or side chain are called
position isomers and the phenomenon is called position isomerism.
E.g. : Alcohol with molecular formula C4H10 O may be 1-butanol or 2-butanol
CH3-CH2-CH2-CH2-OH CH3-CHOH-CH2-CH3
1-Butanol 2-Butanol

Functional group isomerism: Isomers which differ in the functional group are called functional
group isomers and the phenomenon is called functional group isomerism. This isomerism is shown
by alcohols and ethers and aldehydes and ketones.
E.g. compound with the molecular formula C2H6O may be an alcohol ethanol (CH3-CH2OH) or an ether
methoxy methane (CH3-O-CH3).

Metamerism: Isomers which differ in the carbon chain (alkyl groups) around the functional group
are called metamers and the phenomenon is called metamerism. It is commonly shown by
ethers.
E.g.: Ether with molecular formula C5H12O may be methoxybutane (CH3-O-CH2-CH2-CH2-CH3) or
ethoxypropane (CH3-CH2-O-CH2-CH2-CH3).

Tautomerism: It is a type of structural isomerism where a single chemical compound exists in two
or more readily interconvertible forms.

Ring chain isomerism:

Stereo isomerism
Compounds having same molecular formula but different spatial arrangement of atoms are
called stereoisomers and the phenomenon is called stereoisomerism. They have same atom to atom
bond. There are two types of stereo isomerism – Geometrical isomerism and Optical isomerism.
 Geometrical Isomerism Optical isomerism

Compounds that share the same molecular and

structural formulas but exhibit different optical
activities are called optical isomers. differ in their
ability to rotate the plane of polarized light

Geometrical isomers are stereoisomers

that have a different arrangement of groups
or atoms around double bonds.

ORGANIC REACTION MECHANISM - Fundamental Concepts

In an organic reaction, the organic molecule (called substrate) reacts with an attacking reagent
to form one or more intermediates and finally the products.

A sequential account of different steps in which the reactants are converted to products is called
reaction mechanism.
Fission of a covalent bond
A covalent bond can be broken either by homolysis or by heterolysis.

Homolysis:
It is a type of bond fission in which each of the bonded atoms gets one of the electrons of the shared
pair. Here the movement of a single electron takes place. The single electron movement is shown by
half – headed arrow or fish hook arrow ( ).

The species formed as a result of homolysis is called free radical. These are species which contain
an odd electron or an unpaired electron.
0 0 0
There are three types of free radicals – primary (1 ), secondary (2 ) and tertiary (3 ). Their stability

0 0 0
increases in the order 1 < 2 < 3 .
Organic reactions, which take place by homolytic fission are called free radical or homopolar or
nonpolar reactions.
Heterolysis:
It is a type of bond fission in which the shared pair of electrons remains with one of the
fragments. After heterolysis, one atom has a sextet of electron and a positive charge and the other
atom has an octet of electron with at least one lone pair and a negative charge.

For example, the bond cleavage in methyl bromide takes place in the following manner.
A species having a carbon atom possessing sextet of electrons and a positive charge is called a
carbocation (carbonium ion). They are of three types – primary, secondary and tertiary.
Carbocations are highly unstable and reactive species. Their stability increases in the
order 10 < 20 < 30. The high stability of tertiary carbocations is due to inductive effect and hyper
conjugation. In carbocations, carbon atom is in sp2 hybridisation and hence they have trigonal planar
(planar triangular) shape.
If the group attached to the carbon atom is less electronegative than C, due to heterolytic
cleavage, a species with C atom containing a shared pair of electrons and negative charge is formed.

Such a species carrying a negative charge on carbon atom is called carbanion. They are also
unstable and reactive. Their stability increases in the order : 30 < 20 < 10.
The organic reactions which proceed through heterolytic bond cleavage are called ionic or
heteropolar or polar reactions.

Differences between Homolysis and Heterolysis

Homolytic bond cleavage (Homolysis) Heterolytic bond cleavage (Heterolysis)
It is a type of bond fission in which each of Here, the bond breaks in such a manner that
the bonded atoms gets one of the electrons the shared pair of electrons remains with one
of the shared pair. of the fragments.
Movement of a single electron occurs. Movement of a pair of electrons occurs.
The species formed as a result of homolysis The species formed as a result of heterolysis,
is called free radical. may be carbocations or
carbanions.

Substrate and Reagent

A molecule whose carbon is involved in new bond formation is called substrate and the other
molecule or species is called reagent. When both of the reactants contain carbon atoms, the molecule
under observation is the substrate.
CH2 = CH2 + Br2 CH2Br – CH2Br
Substrate Reagent Product

Nucleophiles and Electrophiles

A reagent that brings an electron pair is called a nucleophile (:Nu –) and the reaction is called
nucleophilic reaction. Or, nucleophiles are electron rich species attack at electron deficient centre.
(The word nucleophile means nucleus seeking).
Examples for nucleophiles are OH-, CN-, NO2-, Cl-, Br-, I-, H2O, NH3, R-NH2 etc.
A reagent that takes away an electron pair is called an electrophile (E+) and the reaction is
called electrophilic reaction. Or, electrophiles are electron deficient species attack at electron rich
centre. (The word electrophile means electron seeking).
Examples for electrophiles are carbocations (R+), -CHO, >CO, X+ (halonium ion), NO2+ (nitronium
ion), SO2 etc.
Electron displacement effects in covalent bonds
In an organic molecule, the electron displacement may take place either under the influence of
an atom or in the presence of an attacking reagent. The important types of electron displacement
effects are inductive effect, electromeric effect, resonance effect and hyper conjugation.

Inductive effect (I effect):

It is a permanent effect arising due to the shifting of sigma electrons through a carbon chain
in presence of an atom or group of atom (having different electronegativity) attached to a carbon
chain. This effect propagates only through C – C σ bonds. This effect decreases rapidly as the number
of C atoms increases.
E.g. 1-chlorobutane CH3 – CH2 – CH2 – CH2 –Cl
Here Cl is more electronegative than C. So the electron pair in the C – Cl bond is shifted towards
Cl and it gets a slight –ve charge (δ-) and C gets a slight +ve charge (δ+). This carbon attracts the
electron density from the second carbon and so the 2nd carbon gets a relatively smaller positive
charge (δδ+).

The inductive effect is related to the ability of substituents to either withdraw or donate electron
density to the attached carbon atom. Based on this ability, the substituents can be classified as
electron- withdrawing group (-I effect group) or electron donating groups (+I effect group) relative
to hydrogen.
Groups that withdraw (attract) electrons from the carbon chain are said to have -I effect.
Example for such groups are –X (F, Cl, Br, I), nitro (-NO2), cyano (CN-), carboxy (-COOH),
ester (-COOR), aryloxy (-OAr) etc.
Groups which donate (release) electron pairs towards the carbon chain are said to have +I
effect. Example for such groups are alkyl groups like methyl (-CH3), ethyl (-CH2-CH3) etc.

Electromeric effect (E effect):

It is defined as the complete transfer of a shared pair of π-electrons to one of the atoms joined
by a multiple bond in presence of an attacking reagent. It is a temporary effect. It is possible only in
compounds containing multiple bonds( alkene or alkyne). This effect cancels when the attacking
reagent is removed from the reaction site. The shifting of the electrons is shown by a curved arrow
(↷). There are two types of E effects:
Positive Electromeric effect (+E effect): Here the pi electrons are transferred to that atom to which
the attacking reagent gets attached.

Negative Electromeric effect (-E effect): Here the pi electrons of the multiple bonds are transferred
to that atom to which the attacking reagent does not get attached.

When inductive and electromeric effects operate in opposite directions, the electromeric effect
predominates.
Differentiate between Inductive effect and Electromeric effect
Inductive Effect Electromeric Effect
It is the shifting of sigma electrons It is the complete transfer of the shared pair of
through a carbon chain in presence of an π- electrons to one of the atoms joined by a
atom or group of atom attached to a multiple bond in presence of an attacking
carbon chain. reagent.
It is a permanent effect. It is a temporary effect.
It propagates only through C – C sigma It is possible only in compounds containing
bonds. multiple bonds.
Partial polarity is developed. Complete polarity is developed.
No attacking reagent is required Takes place only in presence of attacking
reagent.

Resonance Effect (R effect) or Mesomeric effect (M effect):

It is defined as ‘the polarity (charge) produced in the molecule by the interaction of two π-bonds
or between a π-bond and lone pair of electrons present on an adjacent atom’. The effect is
transmitted through the chain.
There are two types of resonance effect (R effect):
Positive Resonance effect (+R effect): Here the transfer of electrons is away from an atom or
substituent group attached to the conjugated system. E.g. + R effect in phenol:

Negative Resonance Effect (- R effect): Here the transfer of electrons is towards the atom or
substituent group attached to the conjugated system. E.g. – R effect in nitrobenzene:

The presence of alternate single and double bonds in an open chain or cyclic system is termed
as a conjugated system.
E.g. for +R effect groups: –X (halogen), –OH, –OR, –OCOR, –NH2, –NHR, –NR2, –NHCOR etc.
E.g. for – R effect groups: – COOH, –CHO, >C=O, – CN, –NO2 etc.

Hyper conjugation:
It is a permanent effect. In this effect the σ electrons of C—H bond of the alkyl group enter
into partial conjugation with the unsaturated system or with the unshared p orbital. i.e. the σ
electrons of C –H bonds get delocalised.
E.g. Ethyl cation (CH3-CH2+)

Hyper conjugation stabilizes the carbocation because electron density from the adjacent σ
bond helps in dispersing the positive charge. In general, the greater the number of alkyl groups
attached to a positively charged carbon atom, the greater is the hyper conjugation interaction and
stabilization of the cation.
Thus, the relative stability of carbocations is in the order: (CH3)3C+ > (CH3)2CH+ > CH3-CH2+ > CH3+
 Here tertiary carbocation has 9, isopropyl has 6, ethyl carbocation has 3 and methyl
carbocation has zero hyper conjugative structures.
Hyper conjugation is also called no-bond resonance and it is also possible in alkenes and alkyl arenes.

Types of Organic reactions

Organic reactions can be classified into the following categories:
i. Substitution reactions iii. Elimination reactions
ii. Addition reactions iv. Rearrangement reactions

PURIFICATION OF ORGANIC COMPOUNDS

An organic compound may contain impurities and is essential to purify it. Various methods
used for the purification of organic compounds are based on the nature of the compound and the
impurity present in it. The common techniques used for purification are as follows:
i. Sublimation v. Differential extraction and
ii. Crystallization vi. Chromatography
iii. Distillation
iv. filtration

Sublimation
It is the process of conversion of a solid substance directly to vapour by heating. It is used to
separate sublimable compounds from non-sublimable impurities.

In this method, the substance is placed in a sublimation apparatus and heated under vacuum.
Under this reduced pressure, the solid sublimes and condenses as a purified compound on a cooled
surface. The impurities left behind on the apparatus. This method is used for the purification of
naphthalene, iodine, camphor etc.

Crystallization
This is one of the most commonly used techniques for the purification of solid organic
compounds. It is based on the difference in the solubilities of the compound and the impurities in a
suitable solvent. The impure compound is dissolved in a solvent in which it is sparingly soluble at
room temperature but appreciably soluble at higher temperature. The solution is concentrated to
get a nearly saturated solution. On cooling the solution, pure compound crystallizes out and is
removed by filtration. If the compound is highly soluble in one solvent and very little soluble in
another solvent, crystallization can be satisfactorily carried out in a mixture of these solvents.
 Filtration :
The process of filtration is used to separate
insoluble solid component of a mixture from the
soluble components in a given solvent.
It is used to separate a mixture of
naphthalene and urea using water as solvent.
Urea dissolves in water while naphthalene
remains insoluble. Upon filtration, naphthalene
remains on the filter paper while urea is
recovered from the filtrate by evaporating water.

Distillation
This method is used to separate (i) volatile
liquids from non-volatile impurities and (ii) the
liquids having sufficient difference in their boiling
points. The principle of this method is that liquids
having different boiling points vapourise at
different temperatures. The vapours are cooled
and the liquids so formed are collected
separately.
In this method, the liquid mixture is taken in a
round bottom flask and heated carefully. On
boiling, the vapours of lower boiling liquid are
formed first. The vapours are condensed by using
a condenser and the liquid is collected in a
receiver. The vapours of higher boiling liquid
form later and it can be collected separately.
Chloroform (b.p 334 K) and aniline (b.p. 457 K)
are separated by this technique. There are
different types of distillation methods. They are:

Fractional distillation:

Fractional distillation is used to separate two or more liquids that are miscible. It is a special
type of distillation designed to separate a mixture of two or more liquids that have different boiling
points. The process involves heating the mixture and partial condensation of the vapours along a
fractionating column. The column is set up such that components with lower boiling points pass
through the column and are collected earlier than components with higher boiling points.
Repeated vaporization and condensation result in the separation of the components of the
mixture. The efficiency of fractional distillation depends on the use of the fractionating column. The
fractionating column is packed with glass beads. It provides a large surface area for vaporization and
condensation of the liquid mixture. Ethanol and water mixture, crude oil, toluene and cyclohexane
etc. are separated by this method.
 Distillation under reduced pressure:
This method is used to purify liquids having
very high boiling points and those, which
decompose at or below their boiling points. Such
liquids are made to boil at a temperature lower
than their normal boiling points by reducing the
pressure on their surface. The pressure is
reduced with the help of a water pump or
vacuum pump. Glycerol can be separated from
spent-lye in soap industry by using this technique.

Steam Distillation:
This technique is applied to separate
substances which are steam volatile and are
immiscible with water. In steam distillation, steam
from a steam generator is passed through a heated
flask containing the liquid to be distilled. The
mixture of steam and the volatile organic
compound is condensed and collected. The
compound is later separated from water using a
separating funnel. Aniline – water mixture is
separated by this method.

Differential Extraction
When an organic compound is present in an aqueous medium, it is separated by shaking it with
an organic solvent in which it is more soluble than in water. The organic solvent and the aqueous
solution should be immiscible with each other. So they form two distinct layers which can be
separated by separating funnel. The organic solvent is later removed by distillation or by
evaporation to get back the compound.
Chromatography
This method is used to separate mixtures into their components, to purify compounds and to
test the purity of compounds. Here the mixture to be separated is passed through a stationary phase,
which may be a solid or a liquid. A pure solvent (sometimes a mixture of solvents or a gas) is allowed
to move slowly over the stationary phase. The moving phase is called the mobile phase. The
components of the mixture get gradually separated from one another.

Based on the principle involved, there are mainly two types of chromatography
I. Adsorption chromatography
II. Partition chromatography

Adsorption Chromatography: Ad sorption chromatography is based on the fact that different

compounds are adsorbed on an adsorbent in different degrees. Commonly used adsorbents are silica
gel and alumina. Here a mobile phase is allowed to move over a stationary phase (adsorbent).

Based on the adsorbing power, the components of the mixture are adsorbed at different places over
the stationary phase. Following is two main types of chromatographic techniques based on the
principle of differential adsorption.
i. Column chromatography ii. Thin layer chromatography.

Column Chromatography:
It involves the separation of a mixture over a column of adsorbent (stationary phase) packed in
a glass tube. The column is fitted with a stopcock at its lower end. The mixture to be separated is
passed through the column. Based on the adsorbing power, the components are adsorbed at
different places over the column. The most readily adsorbed substances are retained near the top
and others come down to various distances in the column. Then an appropriate eluant (mobile
phase) is allowed to flow down the column slowly. [Eluant is a solvent or a mixture of solvents used
to move the compounds through the column]. Thus the different components can be collected
separately.
Thin Layer Chromatography (TLC):
It is another type of adsorption chromatography. It involves the separation of substances of a
mixture over a thin layer of an adsorbent coated on a glass plate. A thin layer of an adsorbent like
silica gel or alumina is coated over a glass plate of suitable size. The plate is known as thin layer
chromatography plate or chromaplate.
The solution of the mixture to be separated is applied as a small spot, 2 cm above one end of the
TLC plate. The glass plate is then placed in a closed jar containing the eluant. As the eluant rises up
the plate, the components of the mixture move up along with the eluant to different distances
depending on their degree of adsorption and separation takes place. The relative adsorption of each
component of the mixture is expressed in terms of its retardation factor (Rf value).
Rf = Distance moved by the substance from base line (x)
Distance moved by the solvent from base line (y)
The spots of colored compounds are visible on TLC plate due to their original colour. The spots
of colorless compounds can be detected by putting the plate under ultraviolet light.

Partition Chromatography:
It is based on continuous differential partitioning of components of a mixture between stationary
and mobile phases. Paper chromatography is a type of partition chromatography.
In paper chromatography, a special quality paper known as chromatography paper is used.
Chromatography paper contains water trapped in it, which acts as the stationary phase. A strip of
chromatography paper, spotted at the base with the solution of the mixture, is suspended in a
suitable solvent or a mixture of solvents. This solvent acts as the mobile phase. The solvent rises up
the paper by capillary action and flows over the spot. The paper selectively retains different
components according to their differing partition in the two phases. The paper strip is known as a
chromatogram. The spots of the separated coloured compounds are visible at different heights from
the position of initial spot on the chromatogram. These spots can be visible by u.v. light or by
 QUALITATIVE ANALYSIS OF ORGANIC COMPOUNDS
An organic compound mainly contains carbon and hydrogen. Some compounds may also
contain oxygen, nitrogen, sulphur, halogens and phosphorus.

Detection of Carbon and Hydrogen

Organic compound is heated with copper (II) oxide [CuO]. Carbon present in the compound is
oxidised to carbon dioxide and hydrogen to water. CO2 can be tested by passing through lime-
water, which turns milky and water can be tested with anhydrous copper sulphate, which turns
blue.
C + 2CuO −−Δ → 2Cu + CO2 2H + CuO −−Δ → Cu + H2O
CO2 + Ca(OH)2 −→ CaCO3↓ + H2O

Detection of Nitrogen, Sulphur and Halogens – Lassaigne’s Test

Nitrogen, sulphur and halogens present in an organic compound are detected by “Lassaigne’s
test”. Here the organic compound is fused with metallic sodium in a fusion tube. It is then plunged
into distilled water taken in a china dish. The solution is boiled and filtered. The filtrate is known as
sodium fusion extract.

Principle: In an organic compound, nitrogen, sulphur and halogen atoms are present in covalent
form. By heating with metallic sodium, these elements are converted to ionic form as follows:
Na + C + N −−Δ → NaCN 2Na + S −−Δ → Na2S
Na + X −−Δ → Na X (X = Cl, Br or I)
For the detection of the elements, the following tests are done:

Detection of Nitrogen
After preparing the Lassaigne extract, the presence of nitrogen is tested by adding freshly
prepared ferrous sulfate solution followed by the addition of ferric chloride and heating. After
cooling, concentrated sulfuric acid is added.
 The reaction produces Prussian blue (ferric ferrocyanide), which confirms the presence of
nitrogen.
Reaction:

The formation of a blue or green color indicates that nitrogen is present in the organic compound.

Detection of Sulfur
Sulfur in the Lassaigne’s extract is detected by two common methods:
a) Lead Acetate Test
To a portion of the extract, add sodium nitroprusside or lead acetate solution. If sulfur is
present, black precipitates of lead sulfide (PbS) will form.
Reaction:

b) Sodium Nitroprusside Test

To another portion of the Lassaigne’s extract, add sodium nitroprusside solution. The
appearance of a violet color indicates the presence of sulfur.

Detection of Halogens (Chlorine, Bromine, and Iodine)

For the detection of halogens, Lassaigne’s extract is acidified with dilute nitric acid to remove
any sulfides or cyanides, which can interfere with the test. Then, silver nitrate solution is added
to the acidified extract.
• Chlorine: A white precipitate of silver chloride (AgCl) forms, soluble in ammonia solution.
• Bromine: A pale-yellow precipitate of silver bromide (AgBr) forms, sparingly soluble in
ammonia.
• Iodine: A yellow silver iodide (AgI) precipitate forms, insoluble in ammonia solution.
Reactions:

These color changes and solubility patterns help identify which halogen is present in the
compound.

Test for Phosphorus

The organic compound is heated with an oxidising agent like sodium peroxide. The phosphorus
present in the compound is oxidised to phosphate. The solution is boiled with nitric acid and then
treated with ammonium molybdate. A yellow colouration or precipitate indicates the presence of
phosphorus.
 QUANTITATIVE ANALYSIS OF ORGANIC COMPOUNDS

The percentage composition of elements present in an organic compound is determined by the

following methods:
Estimation of Carbon and Hydrogen
Carbon and hydrogen are estimated by Liebig’s combustion method. In this method, a known
mass of an organic compound is burnt in the presence of excess of oxygen and copper(II) oxide. Then
carbon is oxidised to CO2 and hydrogen is oxidised to H2O.
CxHy + (x + y/4) O2 −→ x CO2 + (y/2) H2O

The water so produced is absorbed in a weighed U-tube containing anhydrous calcium chloride
and carbon dioxide is absorbed in another U-tube containing concentrated solution of potassium
hydroxide. These tubes are connected in series. The increase in masses of calcium chloride and
potassium hydroxide gives the amounts of water and carbon dioxide from which the percentages of
carbon and hydrogen are calculated.
Calculations:
Let the mass of organic compound be w g, mass of water and carbon dioxide produced be m1 and
m2 g respectively.
2 x 𝑚1 x 100
Percentage of hydrogen = %
18 x w
12 x 𝑚2 x 100
Percentage of carbon = %
44 x w

Estimation of Nitrogen
There are two methods for estimation of nitrogen: (i) Dumas method and (ii) Kjeldahl’s method.

Dumas method:
Here the organic compound is heated with copper oxide in an atmosphere of carbon dioxide so that
free nitrogen, carbon dioxide and water are produced.
CxHyNz + (2x + y/2) CuO −→ x CO2 + y/2 H2O + z/2 N2 + (2x + y/2) Cu
This mixture of gases is collected over an aqueous solution of potassium hydroxide which absorbs
carbon dioxide. Nitrogen is collected in the upper part of the graduated tube.
Calculations:
Let the mass of organic compound = w g Volume of nitrogen collected = V1 mL
Room temperature = T1 K
Volume of nitrogen at STP = P1V1 x 273 = V mL
760 × T1
Where P1 and V1 are the pressure and volume of nitrogen gas.
P1= Atmospheric pressure – Aqueous tension
We know that 22400 mL N2 at STP weighs 28 g. Therefore, V mL N2 at STP weighs = 28 x V g
22400
Percentage of nitrogen = 28 x V x 100 %
22400 x w

Kjeldahl’s method:
Here the organic compound containing nitrogen is heated with concentrated sulphuric acid.
Nitrogen in the compound gets converted to ammonium sulphate. The resulting acidic mixture is
then heated with excess of sodium hydroxide. The liberated ammonia gas is absorbed in an excess
of standard solution of sulphuric acid. The amount of ammonia produced is determined by
estimating the amount of sulphuric acid consumed in the reaction. It is done by estimating unreacted
sulphuric acid left after the absorption of ammonia by titrating it with standard alkali solution. The
difference between the initial amount of acid taken and that left after the reaction gives the amount
of acid reacted with ammonia.

Let the mass of organic compound taken = m g

Volume of H2SO4 of molarity, M,
taken = V mL
Volume of NaOH of molarity, M, used for titration of excess of H2SO4 = V1 mL
V1mL of NaOH of molarity M = V1 /2 mL of H2SO4 of molarity M
Volume of H2SO4 of molarity M unused = (V - V1/2) mL
(V- V1/2) mL of H2SO4 of molarity M = 2(V-V1/2) mL of NH3 solution of molarity M.
1000 mL of 1 M NH3 solution contains 17g NH3 or 14 g of N
2(V-V1/2) mL of NH3 solution of molarity M contains:

Note: Kjeldahl’s method is not applicable to compounds containing nitrogen in nitro and azo
groups and nitrogen present in the ring (e.g. pyridine) as nitrogen of these compounds does not
change to ammonium sulphate under these conditions.

Estimation of halogens (Carius method):

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

Calculations:

Estimation of Sulphur (Carius method):

A known mass of an organic compound is heated in a Carius tube with sodium peroxide or fuming
nitric acid. Sulphur present in the compound is oxidised to sulphuric acid. It is precipitated as
barium sulphate by adding excess of barium chloride solution. The precipitate is filtered, washed,
dried and weighed. The percentage of sulphur can be calculated from the mass of barium sulphate
(BaSO4).
Calculations:
Let the mass of organic compound taken = ‘w’ g and the mass of barium sulphate formed = ‘x’ g
1 mol of BaSO4 = 233 g → contains 32 g sulphur
Estimation of Phosphorus
A known mass of an organic compound is heated with fuming nitric acid. Phosphorus present in
the compound is oxidised to phosphoric acid. It is precipitated as ammonium phosphomolybdate
[(NH4)3PO4.12MoO3] by adding ammonia and ammonium molybdate.
Calculations:
Weight of ammonium phosphomolybdate = x g
Weight of magnesium pyrophosphate = y g
Mole mass of (NH4)3PO4.12MoO3 is =1877g
[3 x(14 + 4) + 31 +4(16)] + 12 (96+3x16)
1877g of (NH4)3PO4.12MoO3 contains 31g of P

Estimation of Oxygen
The percentage of oxygen in an organic compound is usually found by difference between the total
percentage composition (100) and the sum of the percentages of all other elements.
i.e. percentage of oxygen = 100 – sum of the percentage of all the other elements.

Multiple Choice Questions (MCQs)

1. What is the valency of carbon? a) geometric isomerism b) chain isomerism
a) Pentavalent b) Divalent c) metamerism d) tautomerism
c) Trivalent d) Tetravalent 10. Optical isomerism is a type of ____________
2. Identify the condensed formula of ethane from a) metamerism b) stereoisomerism
the following. c) geometrical isomerism d) tautomerism
a) CH3 – CH3 b) HC – H2 – C – H3 11. Acetaldehyde and ethenol show ____________
c) CH2 = CH2 d) CH3CH3 a) stereoisomerism b) metamerism
3. Which is not a heteroatom? c) positional isomerism d) tautomerism
a) Oxygen b) Nitrogen 12. A compound with the same molecular
c) Carbon d) Sulfur formula exists in two forms one is alcohol and
4. What is the other name for acyclic compounds? the other is Ether, what type of isomerism does
a) Aliphatic b) Aromatic it show?
c) Heterocyclic d) Alicyclic a) positional isomerism b) metamerism
5. The successive members of a homologous c) functional isomerism d) chain isomerism
series differ by an unit of which of the following? 13. Nucleophilic reagents behave as
a) – CH3 b) – CH c) – CH2 d) – CH2CH3 ______________
6. Which of these is not an aliphatic compound? a) water b) lewis base c) lewis acid d) salt
a) Acetic acid b) Acetaldehyde 14. Carbocations bear a ______________ charge.
c) Ethane d) Tetrahydrofuran a) no b) negative c) positive d) 0
7. Pick out the option that is not a functional 15. Which of the following is false regarding
group from the following. inductive effect?
a) Hydroxyl group b) Benzene group a) temporary effect b) permanent effect
c) Aldehyde group d) Carboxylic acid group c) propagates through a carbon chain
8. 2-chloropropane and 1-chloropropane exhibit d) groups having high electron affinity than
____________isomerism. hydrogen show the negative inductive effect
a) chain b) position 16. In a molecule, when displacement of electron
c) functional d) metamerism pair is away from the group it is ______________
9. Which of the following is not a type of electromeric effect.
structural isomerism? a) zero b) negative c) positive d) no
17. Resonating structures are also known as c) Packed column d) Electric motor
______________ forms. 24. Which is not used as an absorbent in
a) canonical b) inductor adsorption chromatography?
c) electromeric d) nucleophilic a) Silica gel b) Alumina
18. What is obtained by thermolysis of c) Potassium permanganate d) Starch
haloalkane? 25. In column chromatography, identify the
a) free radicals b) carbocation mobile and stationary phase from the following.
c) arene d) nitrene a) Solid, Liquid b) Liquid, Solid
19. The purification method where solid c) Gas, Liquid d) Solid, Solid
substances change from solid to vapor state 26. Paper chromatography is a type of which
without passing through the liquid state is called chromatography?
as which of the following? a) Column chromatography
a) Sublimation b) Crystallization b) Thin layer chromatography
c) Distillation d) Differential extraction c) Adsorption chromatography
20. In crystallization, the compound dissolved in d) Partition chromatography
a solvent is more soluble in what temperature? 27. The mobile phase in chromatography can
a) Room temperature b) Lower temperature comprise of which of the following?
c) Higher temperature d) Very low temperature a) Gas or liquid b) Liquid or solid
21. What is the basis for the process of c) Solid or gas d) Liquid only
distillation? 28. Carbon and hydrogen are detected by
a) Difference in melting point heating the compound with which of the
b) Difference in temperature following?
c) Difference in pressure a) Copper (II)oxide b) Iron(II)oxide
d) Difference in boiling point c) Iron(III)oxide d) Copper(I)oxide
22. Identify the example of compounds separated 29. Identify the element that cannot be detected
by steam distillation method. by Lassaigne’s test.
a) Glycerol-spent lye mixture in soap industry a) Nitrogen b) Fluorine
b) Aniline-water mixture c) Sulfur d) Phosphorous
c) Chloroform and aniline mixture 30. The amounts of water can be detected by the
d) Different fractions of crude oil in petroleum increase in the mass of __________ during
industry quantitative analysis of hydrogen.
23. Which of the following is the apparatus a) potassium hydroxide b) sodium hydroxide
for differential extraction? c) sodium chloride d) calcium chloride
a) Separatory funnel b) Porous sheet
Fill in the blanks by choosing the appropriate word from those given in the brackets:
SET-1
(electronegativity, same plane, towards, sp3, sp2, urea)
1. F. Wohler synthesised an organic compound, _________ from an inorganic compound, ammonium
cyanate.
2. The hybridisation of carbon in methane is _________ .
3. The greater the s character of the hybrid orbitals, the greater is the ___________.
4. In ethene molecule all the atoms must be in the ___________.
5. In three-dimensional representation of organic molecules, solid-wedge is used to indicate a bond
projecting out of the plane of paper, ________ the observer.
SET-2
(Alicyclic, Tropone, functional group, aliphatic, away, towards)
1. In three-dimensional representation of organic molecules, dashed-wedge is used to indicate a
bond projecting out of the plane of paper, ________ from the observer.
2. The acycliccompounds are also called as ________.
3. ________ compounds contain carbon atoms joined in the form of a ring.
4. ________ is the example of non-benzenoid compound.
5. The ________ is an atom or a group of atoms joined to the carbon chain which is responsible for the
characteristic chemical properties of the organic compounds.
SET-3
(homologues, chain isomers, position isomers, isomerism, –CH2, homologous series)
1. A group or a series of organic compounds each containing a characteristic functional group forms
a ________.
2. The members of homologous series are called _________ .
3. The members of a homologous series can be represented by general molecular formula and the
successive members differ from each other in molecular formula by a _______ unit.
4. The phenomenon of existence of two or more compounds possessing the same molecular formula
but different properties are known as ____________.
5. Pentane and Isopentanes are _________.
SET-4
(carbocation, Carbanions, stereoisomers, homolytic cleavage, heterolytic cleavage, substrate)
1. The compounds that have the same constitution and sequence of covalent bonds but differ in
relative positions of their atoms or groups in space are called __________ .
2. In _________ the bond breaks in such a fashion that the shared pair of electrons remains with one of
the fragments.
3. A species having a carbon atom possessing sextext of electrons and a positive charge is called a
_______.
4. In ________one of the electrons of the shared pair in a covalent bond goes with each of the bonded
atoms.
5. In an organic reaction, the organic molecule is also referred as a ________.
SET-5
(nucleophile, free radical, lassaigne’s test, sublimation, crystallization, electrophile)
1. Organic reactions, which proceed by homolytic fission are called _________ reactions.
2. A reagent that brings an electron pair to the reactive site is called a ___________.
3. A reagent that takes away an electron pair from reactive site is called _________.
4. Nitrogen, sulphur, halogens and phosphorus present in an organic compound are detected by
________.
5. Conversion of a substance from the solid to the gaseous state without its becoming liquid is called
_____.
Two-mark questions:
1. Write the structures of the following compounds. (i) Cyclopropane (ii) chlorocyclohexane
2. Represent the methane in Three-Dimensional structure.
3. Give one example for each benzenoid aromatic compounds and non-benzenoid compounds.
4. What are acyclic compounds? Give an example.
5. What is functional group? Write the functional group for ketone.
6. Write a short note on homologous series.
7. Expand IUPAC. Before the IUPAC system of nomenclature, how organic compounds were assigned
names?
8. Write the structures of isopropyl and neopentyl groups.
9. Write the IUPAC names for HOCH2(CH2)3CH2COCH3 and BrCH2CH=CH2.
10. Write the IUPAC names for toluene and anisole.
11. Write the structures of 1-Chloro-2,4-dinitrobenzene and 2-Chloro-1-methyl-4-nitrobenzene.
12. Explain structural isomerism with suitable example.
13. Illustrate the position isomerism taking appropriate example.
14. Explain functional group isomerism with suitable example.
15. Write a short note on metamerism.
16. Write any two differences between heterolytic bond cleavage and homolytic bond cleavage.
17. What are nucleophiles? Give an example.
18. What are electrophiles? Give an example.
19. Explain hyperconjugation effect with suitable example.
20. Write a short note on sublimation.
Three-mark questions:
1. Mention any three types of organic reactions.
2. Mention any three types of separating techniques.
3. Write any three differences between inductive effect and electromeric effect.
4. Give the brief classification of organic compounds.
5. Give the general formula for the following classes of organic compounds
(a) Aliphatic monohydric alcohol (b) Aliphatic ketones. (c) Aliphatic amines.
6. Write the molecular formula of the first three members of homologous series of alcohols.
7. Define Rf value. Write a short note on paper chromatography.
8. How will you prepare Lassaigne’s extract? How will you detect presence of halogen atom in a
organic compound?
9. Explain the principle and calculations involved in the estimation of carbon in the organic
compound.
10. How is the nitrogen determined quantitatively by Kjeldahl’s method?
11. How is the nitrogen determined quantitatively by Dumas method?
12. How is the halogen determined quantitatively by Carius method?
13. During estimation of nitrogen present in an organic compound by Kjeldahl’s method, the
ammonia evolved from 0.5 g of the compound in Kjeldahl’s estimation of nitrogen, neutralized 10
mL of 1 M H2SO4. Find out the percentage of nitrogen in the compound.
14. In Carius method of estimation of halogen, 0.15 g of an organic compound gave 0.12 g of AgBr.
Find out the percentage of bromine in the compound.
15. In Dumas’ method for estimation of nitrogen, 0.3g of an organic compound gave 50mL of
nitrogen collected at 300K temperature and 715mm pressure. Calculate the percentage composition
of nitrogen in the compound. (Aqueous tension at 300K=15 mm)
16. 0.26 g of an organic compound gave 0.039 g of water and 0.245 g of carbondioxide on
combustion. Calculate percentage of Carbon and Hydrogen.