CHEMISTRY

JEE ADVANCED SAMPLE PAPER

Chapter 16. General Organic Chemistry

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 JEE Advanced Sample Paper – 16. General Organic Chemistry

1. Among the following, the least stable resonance structure is

+ O
+
– N
(a) O–

– O
+
+ N
(b) O–
– O
+
+ N
(c) O–

+ O–
N
(d) + O–

2. The hyperconjugative stabilities of tert-butyl cation and 2-butene, respectively, are due to
(a)  -p (empty) and  -  electron delocalisations
(b)  -  and  -  electron delocalisation
(c)  -p (filled) and  -  electron delocalisations
(d) p (filled) →  and  -  electron delocalisations

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 JEE Advanced Sample Paper – 16. General Organic Chemistry

3. The order of decreasing ease of abstraction of hydrogen atoms in the following molecule is
Ha Me
Hb

Hc
(a) Ha > Hb > Hc
(b) Ha > Hc > Hb
(c) Hb > Ha > Hc
(d) Hc > Hb > Ha

4. Most stable radical is

(a)

(b)

(c)

(d)

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 JEE Advanced Sample Paper – 16. General Organic Chemistry

(Q. 5-7)Passage/Comprehension Type

An organic reaction occurs through making and breaking of bonds. The breaking of bonds may
occur either homolytically leading to the formation of radicals or heterolytically generating positively
and negatively charged species. The neutral species (free radicals, carbenes, nitrenes, etc) and
positively charged species being electron deficient are collectively called electrophiles while neutral
and negatively charged species are electron rich are called nucleophiles. An organic reaction usually
involves the attack of a reagent (radicals, positively and negatively charged species) on the substrate
molecule.
The substrate molecule, although as a whole electrically neutral, has centres of low and high
electron density due to displacement of bonding electrons. These electron displacements occur
through inductive, electromeric, resonance and hyperconjugation effects. Whereas inductive effects
involve displacement of - electrons, resonance effects involve transfer of n-and - electrons along
a conjugated system. Hyperconjugation effects, on the other hand, involve  -  -conjugation. Both
inductive and hyperconjugation effects can be used to explain the stability of carbocations and free
radicals which follow the stability order: 3o > 2o > 1o. The stability of carbanions, however, follows
opposite order. The stability of a molecule can be judged on the basis of contribution of its
resonance structures. Resonance structures have same position of nuclei and have same number of
unpaired electrons. Among resonance structures, the one which has greater number of covalent
bonds, has less separation of opposite charges, a negative charge on more electronegative and a
positive charge on a more electropositive atom are more stable than others.

5. Out of the following, the one containing only nucleophiles is

(a) NH3, CN–, CH3OH
(b) AlCl3, BF3, NH3
(c) AlCl3, NH–2, H2O
(d) RNH2, :CX2, H–

6. What is decreasing order of stability of the ions?

I.

II.

III.
(a) I > II > III
(b) II > III > I
(c) III > I > II
(d) II > I > III

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 JEE Advanced Sample Paper – 16. General Organic Chemistry

7. The most stable carbanion among the following is

(a)

(b)

(c)

(d)

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 JEE Advanced Sample Paper – 16. General Organic Chemistry

Q.8 Match the column

8.
Column-I Column-II
(A) (p) Condensation reaction
(B) (q) Isomerization reaction
(C) (r) Rearrangement reaction
(D)
(s) Elimination reaction

(E) (t) Substitution reaction

(a) A-t; B-p; C-r; D-s; E-q
(b) A-p; B-r; C-q; D-s; E-t
(c) A-r; B-s; C-t; D-p; E-q
(d) A-q; B-t; C-s; D-p; E-r

Q.9 Integer Type

Directions : The answer to each of the following questions is a single digit integer, ranging from 0
to 9. If the correct answer to the question number A, B, C and D (say) are 4, 0, 9 and 2
respectively, then the correct darkening of bubbles should be as shown on the side:

9. The total number of contributing structures showing hyperconjugation (involving) C—H bonds)
for the carbocation given on R.H.S. is
H3C ⊕ CH2CH
3

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 JEE Advanced Sample Paper – 16. General Organic Chemistry

Assertion-Reason Type I
Directions : The question given below contain Statement-1 (Assertion) and statement-2 (Reason).
Each question has four choices (a), (b), (c), (d) out of which ONLY ONE is correct. Choose the
correct option as under.
(a) Statement-1 is True, Statement-2 is True; Statement-2 a correct explanation for Statement-1.
(b) Statement-1 is True, Statement-2 is True; Statement-2 is not a correct explanation for
Statement-1.
(c) Statement-1 is True, Statement-2 is False.
(d) Statement-1 is False, Statement-2 is True.

10. Statement-1. Free radicals are always planar.

Statement-2. They can achieve sp2 as well as sp3-hybridisation.

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 JEE Advanced Sample Paper – 16. General Organic Chemistry

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 JEE Advanced Sample Paper – 16. General Organic Chemistry

Answer Keys

Q1 Q2 Q3 Q4 Q5
(a) (a) (b) (a) (a)

Q6 Q7 Q8 Q9 Q10
(d) (d) (c) 6 (d)

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