Updated on 5th March, 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 B)
(previous years Solved questions and related questions with answers)

Q: Taking hybridisation into consideration, explain the shape

of the followings.
3) 4)
(i) CH3+ (ii) :CH2
A: Alkene 1 has shortest C=C bond. In other molecules,
A: (i) The structure of methyl carbocation is trigonal planner.
electronegative chlorine atoms are present which
Since the C-atom is sp2 hybridised. The unhybridised p-
withdraw the π electrons towards itself. Consequently, the
orbital remains perpendicular to the trigonal plane.
double bond character reduces to single bond and hence
the bond length increases.
Q: Which of the following is better nucleophile and why?
Cl- or Br- ion
A: The nucleophilicity of Cl- and Br- depend on the solvent
used. In case of polar protic solvent, Br- is more
nucleophilic than Cl-. Since, in protic solvent, Cl- ions
(ii) Carbene has a bent shape. The C-atom is sp2 form stronger H-bonding with the solvent in comparison
hybridised where two hybrid orbitals involve in bond to Br- ions. As a result, the negative charge on the ion is
formation. There are two possibilities. In one case, the unavailable for interaction with electrophile. In presence
remaining two electrons occupy vacant p orbital and of polar aprotic solvents, due to the absence of H-bonding,
nonbonding sp2 hybrid orbital each. This form of carben Cl- is more nucleophilic than Br-.
is called triplet carbene. In another case, remaining two
electrons occupy nonbonding sp2 orbital and the form is
called singlet carbene.

Q: Which of the following carbon atom is most

electronegative and why? 2 Q: Which of the following statement is correct for
electromeric effect?
(i) It is a temporary effect
(ii) It is the property of π bond
A: C-I & C-II are more electronegative than the other two (iii) It takes place in presence of reagents i.e.
since those C-atoms are sp hybridised. Between I & II, C- electrophile or nucleophile
I is more electronegative than C-II. Because, C-I is (iv) All correct.
terminal carbon and attached to only H atom. While C-II A: (iv) All correct
is attached to alkyl group which reduces the
electronegativity of that carbon atom by pushing the Q: Which of the following has only one type of hybridised
shared electrons towards it (+ I-effect of alkyl group). carbon?

Q: In which of the following compounds, carbon-carbon 1) 2)

double bond length is minimum?
1
3)
1) 2)
A: 3) All the C-atoms are SP2 hybridised.
Q: Arrange the following compounds in the order of
increasing dipole moment with explanation.
HF, HCl, HBr, HI
A: The order is HI< HBr< HCl< HF. Dipole moment depends
on the electronegativity difference between two
covalently bonded atoms. In HF, the electronegativity
difference is higher since F is the most electronegative
element.
Q: Arrange the following compounds in decreasing order of
C-Cl bond length.
2 2) (CH3)3- < (CH3)2CH-. In t-Butyl carbanion, due to +I-
1) 2) 3)
A: 3<2<1. Due to resonance & aromaticity, C-Cl bond in
Benzene is shortest. Partial resonance is also present in
vinyl chloride (2) because of –I effect of Cl.
Q: Acyl cation has resonating structure (I) & (II).
Which structure is more stable and why?
A: Structure I is more stable than II. In structure II, the
positive charge is on the electronegative Cl atom which
makes the ion a little bit unstable.
Q: Compare the stability of the following pairs of
carbocations and give reasons.
1)
A B
2)
C D
A: 1) The stability order is A>B. In carbocation A, the central
C-atom is surrounded by three CH3 groups. Consequently,
the C-atom realizes more concentration of charges due to
+I-effect of three CH3 groups. In carbocation B, the central
carbon is surrounded by only one alkyl group which shows
lesser +I-effect. Thus, the positive charge of carbocation A
is more stabilized than that of B.
(2) The stability order is D>C. Carbocation D is resonance
stabilised. No resonance is possible in carbocation C.
Q: Arrange the following carbanions in the order of
increasing stability and provide explanation for such
arrangement: 3 Mesomeric effect.
A: 1) CH3—CH2- < CH2═CH-< HC≡C-.
The negative charge is on most electronegative C hence,
HC≡C- is most the stable carbanion.
effect of three methyl groups, the negative charge is
unstable in comparison to that of isopropyl carbanion
where there are two methyl groups.
3) C5H4- > C3H5- > C3H7-. Cyclopenta dienyl anion is most
stable due to the presence of aromaticity.
Q: Explain Huckel rule for aromaticity with example. 2
A: Huckel rule states that
1) The molecule must be cyclic & planar.
2) The molecule must have alternative π bonds or
conjugation.
3) The molecule should have 4n+2 π electrons.
For example: Benzene fulfils all the criteria of
aromaticity hence it is aromatic.
Q: What is ambient nucleophile? Explain with examples. 2
A: The nucleophile contains two nucleophilic sites. At a time,
one site acts as nucleophile. Such nucleophiles are called
ambient nucleophile. For example: CN- ion.
R-X + KCN  R-CN + K-X
R-X + AgCN R-NC + K-X
Q: Give examples of an organic compound that behaves as
both electrophile as well as nucleophile. 1
A: Acetone can act as both electrophile and nucleophile. In
C=O bond of acetone, the C-atom acquires partial positive
charge and O-atom acquires partial negative charge. As a
result, C can act as electrophile and O can act as
nucleophilic site.
Q: “The boiling point of water (100oC) is higher than the
boiling point of HF (19oC) and ethanol (78oC). Explain. 2
A: The boiling point depends on the existence of H-bonding
in a molecule. All the three molecules mentioned above
contain H-bonding. But the extend of H-bonding is
highest in water in comparison to HF and ethanol. As a
result, the density is high and hence the boiling point.
Q: Bring out the difference between Inductive effect and
2
A: The differences are as follows.
Inductive Effect Mesomeric Effect
 Operates in both saturated Operates in Unsaturated Q: Select the compounds from the following which have sp3,
& Unsaturated system. and Conjugated system. sp2 and sp hybridisation.
Electrons of σ bond Lone pair and Electrons NH3, H2O, HC≡CH, C6H6
involves of π bonds involve
Permanent polarization Temporary polarization A: NH3, H2O  sp3
C6H6  sp2
Q: “Acidity of alkane, alkene and alkyne depends on the HC≡CH  sp
hybridization of carbon.” Explain. 2
Q: Write the product of the following reactions.
A: The hybridisation of C-atom in alkane, alkene and alkyne
CH3CH2Cl + AlCl3 
are sp3, sp2 and sp respectively. As the s-character
A: The product of the reaction is ethyl carbocation.
increases in the hybrid orbital, the proximity from nucleus
decreases making the hybrid orbital electronegative.
Thus, sp is the most electronegative and sp3 is the least
electronegative orbital. Hence, the C-atom (sp hybridised)
of alkyne can easily lose the proton in comparison to
Q: Which one between OH- (aq) and OH- (alc) is better
others and it is most acidic.
nucleophile? Justify your answer.
Q: Ethanol is miscible with water. Explain. 2
A: OH- in aqueous medium acts as better nucleophile than it
A: Ethanol is miscible in water because there is inter-
is in alcohol medium. OH- converts to water due to the
molecular H-bonding between ethanol and water
presence of acidic proton in alcohol. The RO- ion thus
molecules.
generated acts as base and leads the reaction to
Q: Why the hydrogen of ethyne is acidic? elimination instead of substitution reaction.
A: As the s-character increases in the hybrid orbital, the
ROH + OH-  RO- + H2O
proximity from nucleus decreases making the hybrid
orbital electronegative. Thus, sp is most electronegative Q: What do the following symbols mean in the organic
and sp3 is the least electronegative. Hence, the C-atom (sp reaction mechanism?
hybridised) of alkyne can easily lose the proton in
comparison to others and is acidic in nature. (i) (ii)
Q: Explain whether cyclooctatetraene is aromatic or not. A: (i) This symbol means a pair of electron or a negative
A: Cycloocatetraene is not aromatic since it doesn’t obey charge has been shifted from one to another position.
Huckel rule. The molecule is not planar and it does not
contain 4n+2 π electrons. (ii) This symbol signifies the shifting of a single electron.

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Q: Distinguish between Electrophile and Nucleophile. 2

A: The differences between electrophile and nucleophile are

given below.
Electrophile Nucleophile
Good Lewis acids Good Lewis bases
Accepts electron pair Donate electron pair
Always electron deficient Always electron rich

Q: Compare the nucleophilicity of the following species with

proper reasoning.
(i) HOH and OH- (ii) CH3- and NH2-
-
A: (i) OH > H2O. Negative charge on the atom makes it more
nucleophilic than the neutral atom. Since, it has the
tendency to release the extra negative charge to
electrophile.

(ii) CH3- > NH2-. As the electronegativity increases,

nucleophilicity decreases. More electronegative atoms
have lesser tendency to lose the electron pair.