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Uday (2025)
Organic Chemistry- Some Basic Principles and Techniques
Practice Sheet

Single Correct Type Questions: (1 to 9) 8. The correct order of electron density in aromatic
1. Heterolysis of propane gives? ring of following compound is.
(1) Methyl and ethyl free radicals
(2) Methyl carbocation and ethyl free radicals
(3) Methyl anion and ethyl carbocation
(4) Methyl free radicals and ethyl carbocation
2. Which of the following is an electrophilic reagent? (1) IV > III > II > I (2) I > II > III > IV
(1) H2O (2) OH– (3) IV > II > I > III (4) IV > II > III > I
(3) NO2 (4) All of these 9. Arrange the following in decreasing order of
3. Which hybridised state of carbon exerts strongest –l stability.
effect having how much percentage of ‘s’ character?
(1) 25% (2) 33%
(3) 50% (4) Equal in all
4. Find correct order of stability of carbocations
(1) i > ii > iii (2) iii > ii > i
(3) ii > iii > i (4) iii > i > ii
(1) IV > III > II > I
(2) IV > I > II > III Assertion and Reason type question (10 to 11)
(3) IV > III > I > II 10. Assertion: Anisole undergoes electrophilic
(4) IV > II > I > III substitution at ortho and para positions.
5. Give correct order of increasing acidity of following Reason: Anisole is an aromatic compound
compounds (1) Both Assertion and Reason are true and the
Reason is a correct explanation of the
Assertion.
(2) Both Assertion and Reason are True, but
Reason is not a correct explanation of the
(1) I > III > II > IV Assertion.
(2) I > II > III > IV (3) Assertion is True, but the Reason is False.
(3) I > III > IV > II (4) Assertion is false, but the Reason is True.
(4) IV > I > II > III
6. Which of the following has most negative heat of 11. Assertion: In heterolytic cleavage, the bond breaks
hydrogenation? in such a way that both the electrons of the shared
pair are carried away by one of the atoms.
(1) (2) Reason: Heterolytic fission occurs readily in polar
covalent bonds.
(1) Both Assertion and Reason are True, and the
(3) (4) Reason is a correct explanation of the
7. The correct orientation of dipoles in pyrrole & Assertion.
pyridine is? (2) Both Assertion and Reason are True, but
Reason is not a correct explanation of the
(1) (2) Assertion.
(3) Assertion is True, but the Reason is False.
(3) (4) None of these (4) Assertion is false, but the Reason is True.
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Match the Column Type Questions: (12 to 13) (a) CH3OH

12. Match the terms mentioned in Column-I with the (b) RCONH2
terms in Column-II: (c) H3CCH=CHCH2NH2
Column I Column II
(A) Carbocation (p) Cyclohexane and 1- Case Based Study type: (17 to 20)
hexene Resonance and hyperconjugation are two fundamental
(B) Nucleophilic (q) Conjugation of concepts in organic chemistry that help us understand the
electrons of C–H σ electronic behavior of molecules. Resonance occurs
bond with empty p-
orbital present at
when multiple resonance structures can be drawn for a
adjacent positively molecule, indicating the delocalization of electrons. It
charged carbon leads to the stabilization of molecules and is often
(C) Hyperconjugation (r) sp2 hybridised carbon observed in compounds with pi bonds or lone pairs. On
with empty p-orbital the other hand, hyperconjugation involves the interaction
(D) Isomers (s) Ethyne
between a sigma bond and an adjacent pi bond or lone
(E) sp hybridisation (t) Species that can receive pair, resulting in the distribution of electron density. This
a pair of electrons phenomenon can stabilize carbocations by spreading the
(F) Electrophile (u) Species that can supply
positive charge over neighboring atoms.
a pair of electrons
(1) A-(p); B-(r); C-(q); D-(t); E-(u); F-(s)
17. What is the primary outcome of resonance in a
(2) A-(s); B-(p); C-(r); D-(t); E-(q); F-(u)
molecule?
(3) A-(r); B-(u); C-(q); D-(p); E-(s); F-(t)
(4) A-(t); B-(u); C-(p); D-(s); E-(r); F-(q) (1) Increase in molecular weight.
(2) Stabilization of the molecule
(3) Decrease in the number of pi bonds
13. Match the ions given in Column-I with their nature
(4) Formation of a new compound
given in Column-II:
Column I Column II
18. In hyperconjugation, which type of bonds interact to
(A) (p) Stable due to
stabilize a molecule or ion?
resonance
(B)  (q) Destabilised due (1) Pi bond only
F3C – C to inductive effect (2) Sigma bonds only
(C) (r) Stabilised by (3) Pi bonds and sigma bonds
hyperconjugation (4) Lone pairs only

(D)  (s) A secondary 19. When multiple resonance structures are possible for
CH3 – CH – CH3 carbocation a molecule, what does it indicate about the electron
(1) A–(r): B–(p); C–(q); D–(s) distribution?
(2) A–(p, q, r); B–(q); C–(q); D–(r, s) (1) Electrons are localized on specific atoms
(3) A–(r); B–(q); C–(s); D–(p) (2) Electrons are evenly distributed
(4) A–(s); B–(p); C–(r); D–(q) (3) Electrons are delocalized or spread out
(4) Electrons are completely removed from the
Short Answer type questions: (14 to 16) molecule
14. What causes SO3 to function as an electrophile?
20. How does hyperconjugation contribute to the
15. Among the provided carbocation species, which one stability of carbocations?
is the most stable, and why? (1) By increasing the positive charge on the
1. Primary carbocation carbocation.
2. Secondary carbocation (2) By decreasing the positive charge on the
3. Tertiary carbocation carbocation
(3) By spreading the positive charge over
16. Identify which of the listed compounds cannot form neighboring atoms
a resonance hybrid and provide a rationale for your (4) By forming new sigma bonds
choice among the given options (a), (b), and (c)
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Answer Key
1. (3) 11. (2)
2. (3) 12. (3)
3. (3) 13. (2)
4. (3) 14. (Conceptual)
5. (2) 15. (Conceptual)
6. (1) 16. (a, c)
7. (1) 17. (2)
8. (4) 18. (3)
9. (4) 19. (3)
10. (2) 20. (3)
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Hints & Solutions

1. (3) 6. (1)
Magnitude of heat of hydrogenation ∝
1
Stability of alkene
stability of alkene:
2. (3) 2  3  4  1
(1) H2O lone pairs → Nucleophile (Less

(More

– magnitude) magnitude)
(2) O H (–) charge → Nucleophile
(3) O=N+=O Polarisable π bond (or π*) →
(electrophile)

7. (1)
Delocalised lone pair hence, e– density is going
3. (3) towards the ring due to resonance.
sp > sp2 > sp3 (–I effect order) ∴ bond dipole will be shown towards the ring.
(50%) (33%) (25%)

4. (3)

Localized lone pair; & X N  XC hence, bond

sp2

dipole will be away from ring.

(2 ∝ H) (1 ∝ H) (2 ∝ H) (2 ∝ H)
(–I of Cl) (–I of Cl) (–I of Cl)
–I is distance dependent & Hyperconjugation >
Inductive
IV > III > I > II (– I destabilizes carbocation)
8. (4)
5. (2)

IV  II  III  I
(  H) (– M;
X N  XO Electron Electron
donation Withdrawing)

9. (4)

Hence, –COOH is more acidic than –OH group.

∴ I > II > III > IV
(– M stabilizes – negative charge) (+M, 3 ∝ H) (6 ∝ H) (6 ∝ H)
(– I stabilizes – negative charge) +M
In II, Due to 2 bulky –Me groups on ring, SIR effect
comes into role. Hence no + M.
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∴ iii > i > ii.

10. (2) 13. (2)
A→
→P

(σ C–H hyperconjugation)
A→R
Due to resonance, – charge is focused on ortho & (Destabilised by –I effect)
para position. Due to which, it shows electrophilic A → Q. (∴ A → P, Q, R)
substitution on O & P positions. 
B → F3C C → Destabilized due to (–I) → Q

(4n + 2) πe– = 6πe– ∴ Aromatic compound C → H3C → Destabilized due to (–I) → Q

n=3 
D → H3C– C H –CH3 → (S) 2o carbocation
11. (2)
Heterolytic fission → It generally takes place in a (σ C–H conjugation)
polar covalent bond. More electronegative atom
takes away the shared pair of electrons and anion is
∴ Stabilized by hyperconjugation.
generated and the other part becomes e– deficient.
D→R
and becomes a cation. Hence, it is due to
electronegativity difference or resultant stability of
14. (Conceptual)
cation or anion formed.

12. (3)
⇒ Neutral electrophile,
A → C Eg → ⇒ sp2 & empty P– S is multiply bonded with three electronegative.
Oxygen atoms, & hence, it can accept e– in π*
orbitals A → R. orbital & behave as electrophile.
B → Nu → (U) species that can supply a pair of
electrons.
C → Hyperconjugation → (Q) Eg: .
Conjugation of e– of σ C – H bond with empty
p – orbital present at adjacent  charged
carbon

D → Isomers → (P) C6H12

15. (Conceptual)
(same) molecular formula; different structural
formula)
E → sp → (S) H–C ≡ C – H ⇒ 2 σ ⇒ sp
F → Electrophile → (T) species that can receive a
pair of electrons
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18. (3)
16. (a, c) σ & π bond
(A) No resonance

(B)
(Resonance)
19. (3)
(C) H3C – CH = CH – CH2 – NH2 (No alternate π Electrons are delocalized or spread out.
bonds for resonance)
For resonance, we need alternate positions of 20. (3)
the molecule having π-bond with + / – / odd e– / By dispersing the (+) charge on neighbouring atoms.
lone pair / π bond. 

17. (2) H2 C– CH3  H2 C  CH2  H

Stabilization of molecules.

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