Test (04-10-2007)

SECTION : I
OBJECTIVE QUESTIONS HAVING ONLY ONE CORRECT OPTION.

O O
a c
1. H3C – C – O – H H3C – C – O–
b d

a,b,c and d are C – O bond lengths in acetic acid and acetate ion respectively. What is the correct
order among the following ?
(a) a = c < b = d (b) a < c < b < d (c*) a < c = d < b (d) None of these

2. Which of the following is the strongest base ?

NH2 H3C CH3 H3C CH3
N NH2
N
(a) (b) (c) H3C CH3 (d*) H3C CH3
H3C CH3 H3C CH3

3. Which of the following molecules is paramagnetic during hemolytic fission ?

..
(a) N (b*) (c) .. (d)
H 
4. Among the following compounds which one is having highest C – Br heterolytic bond dissociation
energy ?

CH2–Br
(1) CH2 = CH – CH2Br (II)
(III) (IV) Br
Br

(a) I (b) II (c*) III (d) IV

5. Which compound will have highest dipole moment ?

(a) (b*)

(c) (d)

6. Identify most acidic H in ascorbic acid (Vitamin C)

H O O H
B A

H
D O O
HC
H
C
O
HO
(a) HA (b*) HB (c) HC (d) HD

H3C CH2
7.
Hb Hc Hd
Ha

All the hydrogen’s marked (Ha, Hb, Hc and Hd) are attached with a sp3 hybridised carbon. Which
among these is most acidic ?

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 Test (04-10-2007)
(a) Ha (b*) Hb (c) Hc (d) Hd

8. Match List – I with List – II and select the correct answer using the codes given below the lists.
List – I (carbanions) List – II (Half lives)
CH3
HC

(a) 1. 4.3 × 10–8s

H5C2 C2H5
CH3
HC
(b) 2. 2.5 × 10–5 s

NO2
CH3
HC

(c) 3. 8.7 × 10–7 s

O
CH3
CH2

(d) 4. 1.4 × 10–4 s

N
H5C2 C2H5
(A) (B) (C) (D)
(a) 3 1 2 4
(b*) 3 4 2 1
(c) 4 3 2 1
(d) 3 4 1 2

9. Arrange the following compounds in increasing rate of electrophilic aromatic substitution reactions
N
N
..
N O N N
.. H ..
(I) (II) (III) (IV) (V)
(a) IV < I < V < III < II (b*) I < IV < V < II < III
(c) I < III < IV < V < II (d) V < IV < III < II < I

10. Match List – I with List – II and select the correct answer using the codes given below the lists.
List – I (Compounds) List – II (pKa value)

(A) CH 3  CH 2  O H 2 1. 15.9

(B) CH 3  CH 2  N H 3 2. –6.1
CH3 – C – OH
(C) 3. 11
OH
+

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 Test (04-10-2007)
(D) CH3 – CH2 – OH 4. –2.4

(A) (B) (C) (D)

(a) 2 3 4 1
(b) 4 1 2 3
(c) 3 2 1 4
(d*) 4 3 2 1

11. CH3O – CH = CH – NO2 I

CH2 = CH – NO2 II
CH2 = CH – Cl III
CH2 = CH2 IV
Which of the following is the correct order of C-C bond lengths among these compounds.
(a*) I > II > III > IV (b) IV > III > II > I (c) I > III > II > IV (d) II > III > I > IV

12. In which of the following molecules all the effects namely inductive, mesomeric and
hyper conjugation operate:

COCH3 CH3
(a) Cl (b*) (c) (d)
CH3 CH3

13. In PhSO3H which of the following statement is correct ?

(a*) m position is relatively highly electron dense w.r.t. o & p positon.
(b) ring becomes electron dense due to +R effect of SO3H group
(c) ring becomes less reactive towards nucleophile
(d) none
+ +
14. Ph N 2 is more stable than R N 2 because
+
(a*) in Ph N 2 , +ve charge undergoing delocalization in the ring
(b) Ph having –I effect whereas R having +I effect
(c) in Ph group is more electron deficient w.r.t. carbon in R group.
(d) all are correct
SECTION : II
MULTIPLE CHOICE QUESTIONS MAY HAVE ONE OR MORE THAN ONE CORRECT OPTION.

15. Which of the following is the correct representation of canonical forms ?

. 14 .
(a*) C H 2  CH  CH 2   H 2 C  CH  C H 2
14
. .
(b) CH 2  CH  CH  CH 2 
 H 2 C CH  CH  C H 2
O– O

(c*)
N+ N+
–
O O— O O—

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 Test (04-10-2007)
  ..  

(d*) CH 2  N  N 
 H 2C  N  N :

16. The incorrect order of increasing basic nature of the following compound is :
NH2 CH3 CN

N N N N
(I) (II) (III) (IV)
(a) IV < I < III < II (b*) I < II < III < IV (c*) IV < III < II < I (d*) II < IV < I < III
17. In which of the following pair first compound has less resonance energy with respect to second one?
OH
(a*) & (b) &
*
O O
(c*) CH2 = CH – OH & CH2 = CH – CH = CH – OH (*d) &

H+ H+
..  .. 
18. N NH2 N NH
H
I II III IV

Which of the following statement is false regarding the aromatic character of the four species ?
(*a) All the four are aromatic (b*) I and III are aromatic
(c) I, III and IV are aromatic (d*) I, II and III are aromatic

19. Which of the following groups can participate in resonance with other suitable groups?
 CH2
(a) –CH2 – (b) (c*) – BH2 (d*)  P+ Ph
C H2 3

20. Which of the following is the incorrect order of acidity of the following compound ?
(*a) CH3 –C  N > CH3CH2NH2 > CH3 – NH2 > CH3CH = NH
(*b) HN3 > NH2OH > N2H4 > NH3
(c*) FCH2CO2H > HCO2H > CH3CO2H > ICH2CO2H > CHMe2CO2H
(d*) H2O > CH3OH > Me2CHOH > Me3COH > EtOH > OH–

21. Which of the following reactions is highly favoured to the reactant-side and goes nearly to
completion ?
(a*) PhOH + NaHCO3 
 PhONa + CO2 + H2O

(b*) HC  CH + NaOH 
 HC  CNa + H2O
ONa
(c*)
CH3COCH3 + NaOH 
 CH3C = CH2 + H2O

(d) [(CH3)2CH]2NH + CH3CH2CH2Li 

 [(CH3)2CH]2NLi + CH3CH2CH3
22. Which of the following statement is correct ?
(a*) Maleic acid is a stronger acid than fumaric acid.
(b*) cyclopentadiene is more acidic than 1, 3-pentadiene

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 Test (04-10-2007)
(c*) Amides are protonated on oxygen rather than on nitrogen
(d) Trimethyl borate, (CH3O)3B, is a stronger Lewis acid than BF3.

SECTION – III
COMPREHENSION BASED QUESTIONS HAVING ONLY ONE CORRECT OPTION.
COMPREHENSION – I :
Bond length is the average distance between the nuclei of the two atoms held by a bond. This
represents the internuclear distance corresponding to minimum potential energy for the system.
Main factors which affect the bond length are given below :–
i) Multiple bonds are shorter than corresponding single bonds.
ii) Sometimes single bond distances are some what large than double of their respective
covalent radii(e.g. F2). It is due to strong repulsive interaction between the lone-pair
electrons on adjacent atoms.
iii) Some times single bond distances are some what shorter than double of their respective
covalent radii because bonds acquire some partial double bond character. This normally
happens when one atom having vacant orbital and another atom containing lone pair. It is
also possible that it becomes shorter due to high ionic character in the covalent bond.

23. Which is correct about two C – N bond lengths (marked as ‘a’ and ‘b’) ?
NO2
O2N b I
a NO
2

(a) a = b (b) b > a

(c*) a > b (d) Can’t be predicted
24. Which is not true about the N – N bond length among the following species ?

I. H2N – NH2 II. N2 III. H N  NH 2 IV. N2O
(a) N – N bond length is shortest in II.
(b) N – N bond length in I is shorter than that of in III
(c*) N – N bond length in III is shorter than that of in I
(d) N – N bond length IV is intermediate between I and III

25. The C – Cl bond in vinyl chloride is ………. and ………. compared to C – Cl bond in ethyl chloride.
(a) longer, weaker (b) shorter,weaker (c*) shorter, stronger (d) longer, stronger
COMPREHENSION – II :

Pyridine is allowing to react with different para substituted Benzyl bromide.

CH2Br

G
G Rate
–Me x
–Et y
–Isopr z
–tBu w
–O– p

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 Test (04-10-2007)
–OH q
–Cl r
–CN s

26. The correct order is

(a) r>y>z>w (b) q>p>r>s (c) y > r > z > s (d*) x > y > z > w
–
27. Here O  shows
(a) +I effect (b) +R effect (c*) +I, +R effect (d) +H effect
28. Which of the following option is correct :
(a) for Cl group –I > –R (b) for –OH group +R > +I
(c*) for –Me group +H > +I (d) for tBu group +I > +H
29. CN groups shows
(a) +I, –R (b*) –I, –R (c) +I, +R (d) –I, +R
COMPREHENSION – III :

Electronegativity of C in CF 3 group is much more with respect to eletronegativity of C in CH 3

group because of electron withdrawing tendency of 3F atoms, carbon in CF 3 groups develops
more  + charge.

30. What would be the product when CF3 – I undergo basic hydrolysis
(a) CF3 – OH, I– (b*) HCF3 + IO– (c) H3C – I + HOF (d)CO2  + I2 + F2

31. The organic products when CH3 – I undergo basic hydrolysis is

(a) Ether (b) Alkane
(c*) Alcohol (d) All 3 formed in equal amount
COMPREHENSION – IV :

b c
H H
2 3 4 d
H3C – C – CH – CH2 – H
CH2 – H
1 a

undergoes homolytic bond fission.

The bond energies are given below
1 a
C H  x kJ mole 1
2 b
C H  y kJ mole 1
3 c
C H  z kJ mole 1
4 d
C H  w kJ mole 1

32. The correct order of bond energy is

(a) x>y>z>w (b) z>w>x>y (c) y > z > w > x (d*) x > w > z > y

33. What is the most stable free radical is

   
(a) C1 (b*) C2 (c) C3 (d) C4

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 Test (04-10-2007)
34. The stability of free radical is explained by
(a) +I effect (b) +H effect (c*) +I, +H effect (d) None of these

SECTION – IV
CONSISTS OF FOUR NUMERICAL QUESTIONS WHOSE ANSWERS ARE POSITIVE INTEGERS RANGING
FROM 0 TO 9999. IF ANSWER IS LIKE 216.6 THEN YOU HAVE TO MENTION ONLY 217 EX : IF THE
ANSWER OF A QUESTION IS 5 THAN MARK AS
0 0 0 0 0 0 0 0
1 1 1 1 1 1 1 1
2 2 2 2 2 2 2 2
3 3 3 3 3 3 3 3
4 4 4 04 4 4 04
4
5 5 5 5 5 5 5 5
6 6 6 6 6 6 6 6
7 7 7 7 7 7 7 7
8 8 8 8 8 8 8 8
9 9 9 9 9 9 9 9
Correct Method Wrong Method

35 Consider the following reaction

15
C6 H 6    O 2  g  
 6CO 2  g   3H 2 O   . H = –3301 kJ mole–1
2
heat of vaporisation of benzene = 30.5 kJ mole–1
heat of vaporisation of H2O = 43.9 kJ mole–1
C – C = 347.3 kJ mole–1
C = C = 606.7 kJ mole–1
C – H = 414.2 kJ mole–1
O = O = 497.9 kJ mole–1
C = O = 803.3 kJ mole–1
H – O  464.4 kJ mole–1
What is the resonance energy of benzene in kJ mole –1. Ans : 0145

36 The summation of C–O bond order in formate ion & Dianion of Squaric acid is Ans : 0003

37 Heat of hydrogenation of cyclohexene to cyclohexane is –28.6 Kcals/mole. The observed heat of

hydrogenation of benzene to cydohexane is – 49.8 Kcals/mole. What is the resonance energy of
benzene in Kcals/mole. Ans : 0036

SECTION –V :
CONSISTS OF MATCH THE COLUMN MAY HAVE MORE THAN ONE MATCH.
Ex : If the answers is A  P, Q ; B  R, S ; C  P ; D  S, T than mark as
A: P Q R S T
B: P Q R S T
C: P Q R S T
D: P Q R S T

38 Match the following

Note : In column I any option can be related to more than one option of coloum II.
Column I
(A) – I effect
(B) + I effect

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(C) Resonance effect
(D) The distance of electron withdrawing substituent increases from –OH group

Column II
(P) Benzyl carbonium ion is more stable than ethyl carbonium ion
(Q) Trichloro acetic acid is stronger than acetic acid
  
(R) CH 3CH 2 C H 2  CH 3 C HCH3  CH 2  CH C H 2
(S) o–bromophenol > m–bromophenol > p–bromophenol (increasing order of acidity)
Ans : A : Q, B : R, C : P,R D : S

39 Match the following

Note : In column I any option can be related to more than one option of coloum II.
Column – I Column – II
H2N – C – NH2
(A) Guanidine is example of (P) Resonance stabilization of conjugate Acid
NH
strong base.
(B) Carbanions stability CCl3 > CF3 (Q) s character of the central atoms.
(C) Alkyne is more acidic than alkene which (R) d orbital resonance
is more acidic than alkane
(D) Acidity order HClO4 > HClO3 > HClO2 > HOCl (S) The oxidation state of central atom
(T) Stability of conjugate base due to more
number of identical R.S.
A  P ; B  R ; C  Q ; D  S, T

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