IITJEE201429

Note: For the benefit of the students, specially the aspiring ones, the question of IITJEE 2014 are also given in this booklet.
Keeping the interest of students studying in class XI, the questions based on the topics from class XI have been marked with ‘*’,
which can be attempted as a test. For this test the time allocated in Physics, Chemistry and Mathematics are 33 minutes, 15 minutes
and 12 minutes respectively.

IITJEE, 2014
PAPER 2
PART II: CHEMISTRY
SECTION – 1: (Single option correct type)
This section contains 10 multiple choice questions. Each question has four choices (A), (B), (C) and (D)
out of which ONE Option is correct.

21. Which of the following has/have greater pKa than benzoic acid
COOH COOH
COOH COOH
CH3 NO2
(A) (B) (C) (D)

NO 2 CH3
21. D

22. Ethylbromide can not be obtained by

LAH HBr CCl4
(A) CH3COOC2H5     (B) CH3 CH2COOAg  Br2  
P Soda lim e LAH NBS
(C) CH3 CH2COOH  Br2 

   (D) CH3COOH    
22. D

23. O

P4 O10 CH3MgBr , H3O Ca( OH)2 ,I2 
  A      B    C  D. D is
NH2
O

(A) (B) COOH

CH3
O

(C) (D)

23. C

FIITJEE (Hyderabad Classes) Limited. 5-9-14/B, Saifabad, (Opp. Secretariat) Hyderabad. 500 063. Phone: 040-66777000 – 03 Fax: 040-66777004
 IITJEE201430

24. When a mixed vapours of butanoic acid and cyclopentane carboxylic acid is passed over
hot manganous oxide (MnO), the organic product(s) is/are obtained
O
C C
All
O
O

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

24. D

25. Which of the following gives HVZ reaction?

(A) HCOOH (B) C6H5COOH (C) Cl3C–COOH (D) Cl2CH–COOH
25. D

26. Which of the following reaction, reactants and products are incorrectly matched?
(A) O OH
OH LiAlH 4
OH

(B) O O
HOCH2CH2OH LiAlH4 H3O+
OH OH

(C) O
O
OH LiAlH4 PCC H

O
O

(D) O
H+ NaBH4 H3 O+
+ HOCH2CH2OH (1.0 equiv)
H
H2 O
O
O

HO
O
26. D

FIITJEE (Hyderabad Classes) Limited. 5-9-14/B, Saifabad, (Opp. Secretariat) Hyderabad. 500 063. Phone: 040-66777000 – 03 Fax: 040-66777004
 IITJEE201431

27. A compound (A) has molecular formula C7 H 8O. It reacts with Na, NaOH and gives violet
colour with FeCl3 , but doesnot decompose NaHCO3 . On oxidation ‘A’ gives B. B reacts
with Na, NaOH , NaHCO3 and gives violet colour with FeCl3 . A on nitration gives mono
nitroderivative. Then the compound A can not be
OH (B) OH

(A)
CH3
CH3
OH (D) H2C OH
CH3
(C)

27. D

28. How many of the following respond to  Ag NH3 2  .
NH OH

O
H C OH
HCHO C H Fructose
O
O
CH3
(i) (ii) (iii) (iv) (v)
(A) 4 (B) 5 (C) 3 (D) 2
28. B

29. HCOOH and CH3COOH cannot be distinguished by

(A) NaHCO3 (B) Benedict solution (C) Tollen’s reagent (D) Fehling solutions
29. A

O CH3
+
CH3 H2O/H
30. C
H3C O A (acid) B(alcohol); A & B are respective
18 CH3
18 18
(A) CH3 COOH;Me3COH (B) CH3  COOH ; Me3COH
18 18 18
(C) CH3COOH ; Me3 C  OH (D) CH3 COOH ; Me3 C  OH
30. A

FIITJEE (Hyderabad Classes) Limited. 5-9-14/B, Saifabad, (Opp. Secretariat) Hyderabad. 500 063. Phone: 040-66777000 – 03 Fax: 040-66777004
 IITJEE201432

SECTION – 2: Paragraph Type

This section contains 3 paragraphs each describing theory, experiment, data etc., Eight questions relate to
three paragraphs with two question on each paragraph. Each question of a paragraph has only one correct
answer among the four choices (A), (B), (C) and (D).

Paragraph for questions 31 and 32

Hofmann rearrangement
In the Hofmann rearrangement an unsubstituted amide is treated with sodium hydroxide and
bromine to give a primary amine that has one carbon lesser than starting amide.

If the migrating group is chiral then its configuration is retained. Electron releasing effecs in the
migrating group increases reactivity of Hofmann rearrangement.

31. Which of the following compounds(s) cannot give Hofmann rearrangement:

(A) (B)

(C) (D)

31. B

32. Arrange the following amides according to their relative reactivity when reacted with Br2 in
excess of strong base

(I) (II)

(III) (IV)

(A) IV > I > II > III (B) II > I > III > IV (C) II > IV > III > I (D) II > I > IV > III
32. D

FIITJEE (Hyderabad Classes) Limited. 5-9-14/B, Saifabad, (Opp. Secretariat) Hyderabad. 500 063. Phone: 040-66777000 – 03 Fax: 040-66777004
 IITJEE201433

Paragraph for questions 33 and 34

Most of the chemical reactions of alcohols and phenols are due to the –OH group. Chemical
reactions of phenols (and alcohols) can be divided into three categories.
(i). Those reactions involving the cleavage of the oxygen – hydrogen bond C  O  H with
substitution of hydrogen as a proton.
(ii). Those reactions in which the cleavage of carbon – oxygen bond [C-OH] bond with
substitution or removal of the –OH group.
Phenols do not undergo reactions involving the cleavage of C-OH bond or substitution of the
–OH group. It is so because phends are more acidic than alcohols and thus do not undergo
protonation easily.
(iii). Electrophilic substitution reactions of the benzene ring.

OH

CHCl3 i ) NaOH
33. 
OH 
 A 
ii ) CH 2 I 2
B
OH
Identify the final product B in the above reaction
CH2 I OCH2I
OH

(A) (B)
OHC OH
OHC OH
OH O

(C) (D) CH 2

OHC OCH2I OHC O

33. D

34. O

O C CH3 AlCl3
  X (major compound )

OH H3 COC OH
(A) (B)

COCH 3

OH
(C) (D) O OH

COCH 3
34. A

FIITJEE (Hyderabad Classes) Limited. 5-9-14/B, Saifabad, (Opp. Secretariat) Hyderabad. 500 063. Phone: 040-66777000 – 03 Fax: 040-66777004
 IITJEE201434

Paragraph for questions 35 and 36

Esters are much more stable than acid chlorides and anhydrides. For example, most esters do not
react with water under neutral conditions. They hydrolyze under acidic or basic conditions,
however and an amine can displace the alkoxyl group to form an amide.

35. Examine the structure formulas of following compounds and find out how many compounds
can show Claisen condensation reaction.
O O
OC2H 5
, H C OC 2H5 C OC 2H5
,
O

O
OC2H5 O OC2H5
, , CH2 C OC2H 5
O O OC2H5
(A) 3 (B) 1 (C) 5 (D) 4
35. A

36. The order of reactivity of the following esters

O Cl O
O O
H3C
Cl OMe Cl OMe
OMe OCH3
I II III IV
towards hydrolysis is:
(A) I  II  III  IV (B) II  I  III IV
(C) IV  III  II  I (D) IV  III  I  II
36. C

SECTION – 3: (Matching List Type)

This section contains 4 questions, each having two matching lists. Choices for the correct combination of
elements from List–I and List–II are given as option (A), (B), (C) and (D) out of which ONLY ONE is correct.

37. Match List – I (name of reaction) and List – II (Product) and select the correct answer from
the code given below the list.
List – I List – II
a) Perkin reaction 1. CH3 – CH2 – COOC2H5
O O
|| ||
b) Claissen condensation 2. CH3 – C – CH2 – C – OCH3
c) Aldol condensation 3. C6H5 – CH = CH – CHO
d) Tischenko reaction 4. C6H5 – CH = CH – COOH
Codes
a b c d
(A) 4 2 3 1
(B) 4 2 1 3
(C) 2 4 3 1
(D) 2 4 1 3
37. A

FIITJEE (Hyderabad Classes) Limited. 5-9-14/B, Saifabad, (Opp. Secretariat) Hyderabad. 500 063. Phone: 040-66777000 – 03 Fax: 040-66777004
 IITJEE201435

38. Match the following

Column – I Column – II
(1) RCONH2 (p) Most reactive towards acyl substitution
(2) RCOOR| (q) Reduces HgCl2
Undergoes Hoffmann bromamide
(3) HCOOH (r)
reaction
(4) RCOCl (s) Fruity odour
Codes:
1 2 3 4
(A) p q s r
(B) r p q s
(C) q s p r
(D) r s q p
38. D

39. Match the following

Column – I Column – II
Characteristic colour with neutral FeCl3
(1) Salicylic acid (p)
solution
(2) P–hydroxy acetophenone (q) Product of Fries rearrangement
(3) Quinol (r) Elbs persulphate oxidation
(4) Picric acid (s) Decomposes NaHCO3 solution.
Codes:
1 2 3 4
(A) p,q q,s s r,s
(B) r,s p,q q,s s
(C) q,s s p,q r,s
(D) p,s p,q p,r p,s
39. D

40. Match the example given in Column I with the name of the reaction in Column II.
Column I (Example) Column II (Reaction)
O O
(A) || || (p) Tischenko reaction
Pd  C / BaSO 4
CH3  C Cl  H2  CH3  C H
CHO CH2OH COO Na

(B) NaOH (q) Stephen’s reaction

 i SnCl / HCl
(C) CH3  CN  2

ii H O / H
 CH3CHO (r) Cannizaro’s reaction
2

O
(D) ||
A OEt  (s) HVZ reaction
2CH3 CHO 
3
 CH3  C  OC2H5

(t) Rosenmund’s reduction
(A) A  r; B  t; C  q; D  p (B) A  t; B  q; C  r; D  p
(C) A  t; B  r; C  q; D  p (D) A  t; B  r; C  p; D  q
40. C

FIITJEE (Hyderabad Classes) Limited. 5-9-14/B, Saifabad, (Opp. Secretariat) Hyderabad. 500 063. Phone: 040-66777000 – 03 Fax: 040-66777004