Updated on 20th Feb, 2019 rdschemistry@gmail.com Prepared By Dr.

Rupa Dey
(Mob No-8638155244/9854813489)

CBCS: B.Sc. CHEMISTRY (Honors)

(2nd SEMESTER)
COURSE NO. C-201
ORGANIC CHEMISTRY-I
Unit 1: Basic of Organic Chemistry (PART A)

(previous years Solved questions and related questions with answers)

Q: What is hydrogen bonding? Give examples. 2

A: Electrostatic force of attraction between H-atom of one molecule and a small highly electronegative atom (such as N, O,
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F) present within the same or another molecule is known as Hydrogen bonding. For example: Hydrogen bonding is
present in HF and Salicylic acid as shown below.

H-Bonding
H F H F H
O O

C
H- Bonding
OH

Q: Write the difference between H-bonding and Covalent Bonding.

A: Covalent bond is a chemical bond while H-bonding is the electrostatic force of attraction between H-atom and small
electronegative atom like O, N, F.

Q: What is hybridization? In ethane, C-C bond length is 1.54 Å but in ethene C-C bond length is 1.34 Å. Explain why? 2+2 =4
A: According to VBT, the intermixing of orbitals of equivalent energy of an atom to give equal numbers of orbitals of same
energy, identical shape and symmetrical orientation in space is known as Hybridization. In case of C atom, hybridization
is of three types: sp3, sp2 and sp.
The bond length of C-C bond depends on hybridization and the extend of overlapping of hybrid orbitals. Longer the
C-C bond means weaker is the overlapping between orbitals and vice versa. The extend of overlapping between two sp3
hybrid orbitals are lesser than that of sp2 hybridised orbital due to the presence of more p-character in those orbitals. In
ethane, both the C atoms are in sp3 hybridization and in ethene, they are in sp2 hybridization. Hence, the bond length of C-
C bond present in ethane is longer than that of ethene.
H3C CH3 H2C CH2
Longer Bond Shorter Bond

Q: How s and p character can be used to generally predict the bond lengths in ethane, ethene and ethyne?
A: The order of C-C bond length in ethane, ethene and ethyne: C—C > C=C > C≡C. Higher the value of p character, longer the
C-C bond. In ethane, the sp3 hybridised c-atom has 25% s character and 75% p character. In ethene, the c atom is sp2
hybridised having ~33% s character and ~67% p character, whereas in ethyne, sp hybridised orbital has 50% s character
and 50% p character.

Q: What is resonance? Heat of hydrogenation of cyclohexene to cyclohexane is -28 Kcal/mol. The observed heat of
hydrogenation of benzene to cyclohexane is -49.8 Kcal/mol. Find out the resonance energy of benzene. 2+3=5
A: Some covalent molecules can be represented by more than one Lewis structure. But none of them individually can explain
all the properties of that molecule. The actual structure is in between of all these contributing structures and is known as
the resonance hybrid. The phenomenon is called resonance. For example: Ozone (O 3) can be represented by two
resonating structure.
O O O

O O O O O O

Heat of hydrogenation of cyclohexene to cyclohexane = -28 kcal/mol

 So, calculated heat of hydrogenation of benzene to cyclohexane = 3 X (-28) kcal/mol = -84 kcal/mol
The observed value of heat of hydrogenation of benzene to cyclohexane = -49.8 kcal/mol
Thus, the resonance energy of benzene = (Actual – Observed) value of heat of hydrogenation = [-84 – (-49.8)] kcal/mol
= -34.2 kcal/mol

Q: Write notes on: (i) Hyper-conjugation (ii) Dipole moment 1½X2=3

A: Hyper-conjugation: The electronic interaction between shared electrons of C-H σ-bond with the adjacent C-C π-bond to
extend the conjugation of the system is known as hyper-conjugation. The displacement of the C-H bond electrons causes
a partial positive charge on the H-atom without the actual release of proton.
Hyper-conjugation enhances the stability the molecule. As the number of α-H atom increases, hyperconjugation
increases and thereby increasing the stability.
H H
H
H C C CH2 H C C CH2 HC C CH2

H H H H H H
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Dipole Moment: Dipole moment of a molecule is the product of its net positive or negative charge on the atom and the
distance between those charges. Mathematically, it can be represented as
Dipole Moment (µ) = Charge (q) X Distant (d)
The SI unit of dipole moment is Debye. Diatomic molecules with polar covalent bond possess definite amount of
dipole moment. For example: H-Cl, H-F, -O-H etc. In case of polyatomic molecules, the shape of the molecule determines
the polarity. For example: CO2 has two polar bond but its net dipole moment is zero and hence non polar whereas SO2 is
a polar molecule. Due to the linear structure of CO2, the vectors of dipole moment cancel each other. The bent structure
of SO2 does not cancel out dipole moments. So it is a polar molecule.

>

>
> O O
I I >
O C O >
Q: What is the difference between Hyper-conjugation and resonance?
A: The difference between hyperconjugation and resonance are that –
In hyperconjugation, the electrons delocalize between σ and neighbouring π bond. While resonance means the
delocalization of only π electrons.
Q: What are carbocation? How are they formed? Discuss the stability of carbocation. 1+2+2=5
A: The carbocation is an ion where the C atom present in that molecule bears a positive charge and forms three covalent
bond with sextet electron in its valence shell.
Carbocation are formed when unsaturated compounds reacts with acid. For example:

C O + H+ C OH Carbocation

H
C C + H+ C C Carbocation

In carbocation, the c atom is sp2 hybridised which involve in bond formation. The un-hybridised vacant p orbital
remains perpendicular to the sp2 hybrid orbital. The format of structure pertains maximum stability to the system.
Vacant p orbital

H Plane of sp2 hybrid orbital

Q: Distinguish between homolytic and heterolytic bond cleavage. 2

A: In homolytic fission, the bond breaks in such a way that the atom takes away one shared electron. In heterolytic fission,
both the shared electrons are taken away by one of the bonded atom.
Homolytic fission generates free radical and heterolytic fission gives rise to a pair of ion-cation and anion.
Q: What are free radicals? Discuss the structure of free radical. 1+3=4
 A: Free radicals are an atom or some molecular species with one nonbonding unpaired electron present in the valence shell
of one of its atom. For example:

CH3 Cl

Chlorine Free Radical

Methyl Free Radical

Free radicals generate due to the homolytic fission. In methyl free radical, the C atom undergoes sp2 hybridisation.
Hence the free radical assumes the trigonal planar shape. However, the unpaired electron occupies the vacant un-hybridised
p orbital which remains perpendicular to the sp2 hybrid plane.
Unpaired Electron
H
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H sp2 hybridised plane

H

Q: Distinguish between activation energy and transition state. 3

A: According to Transition State Theory, every molecule possesses some amount of energy in the form of kinetic or potential
energy. But to convert into product, those reactant molecules must achieve a minimum amount of energy called Activation
Energy.
As the molecule attains activation energy, its structure slightly deforms from the original structure so that it can
easily transform to the shape of product molecule. This distorted structure of the molecule is called transition state. The
transition state is highly unstable. The difference between activation energy and transition state is further described by
the following diagram.

Q: Why o-nitrophenol is stream volatile but p-nitrophenol is not?

A: In o-nitrophenol, intramolecular H-bonding is present while in p-nitrophenol, the H-bonding is intermolecular. The
molecules having intermolecular H-bonding contains more number molecules per unit volume in comparison to those
having intramolecular H-bonding. Consequently, those molecules containing inter molecular H-bonding require more
energy to get boiled. They have higher melting point than the o-isomer. Thus, at 100oC temperature, o-nitrophenol is volatile
and p-nitrophenol is not.
Intramolecular H-bonding Intermolecular H-bonding

H H O
O O O
N OH
N
O
O

o-Nitrophenol N
O O

p-Nitrophenol

Q: Which of the following species is more stable and why?

O O

H3C C H H3C C O
A: In between acetaldehyde and acetate ion, acetate ion is more stable due to the presence of resonance which is not
observed in acetaldehyde.

O O

H3C C O H3C C O

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Part B will be uploaded soon
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