Sec: ISR.

IIT _*CO-SC(MODEL-A) Date: 21-04-24

Time: 3 Hrs Max. Marks: 198

CHEMISTRY: PRESENT WEEK(80%): Aldehydes and Ketones: Preparation of:

aldehydes and ketones from acid chlorides and nitriles; aldehydes from
esters; benzaldehyde from toluene and benzene, Physical properties,
mechanism of nucleophilic addition reactions- addition of H2O, ROH,
addition of RMgX, HCN, NaHSO3,addition of NH3 and derovatives,
beckmann rearrangement (Exclude: beckmann fragmentation)
PREVIOUS WEEK(20%): Phenols : Preparation & Properties of Phenol
from haloarenes, benzene sulphonic acid, benzene daizonium salts, and
cumene, Physical properties, reactions: halogenation, sulphonation,
nitration, ipso substitution, kolbes reactions, Reimer-Tiemann reaction,
esterification, etherification, reduction and oxidation of phenols, Neutral
FeCl3 test, Pthalein dye test, azo dye test, Libermann nitroso test
(Exclude: Reaction of phenol with daizonium salts-to be covered in amines)
Ethers: Preparation by williamson synthesis, using alcohols, Reactions
involving C-O bond cleavage and EAS of anisole
Narayana IIT Academy 21-04-24_ISR.STAR CO-SC(MODEL-A)_JEE-ADV_WAT-42_QP
CHEMISTRY MAX.MARKS: 66
SECTION – 1 (Maximum Marks: 18)
This section contains SIX (06) questions.
Each question has FOUR options for correct answer(s). ONLY ONE of these four option is the correct answer.
For each question, choose the correct option corresponding to the correct answer.
Answer to each question will be evaluated according to the following marking scheme:
Full Marks : +3 If only the correct option is chosen.
Zero Marks: 0 If none of the option is chosen.(i.e the question is un answered)
Negative Marks: -1 In all other cases.
37. Predict the product when given compound reacts with LiAlH 4 :

A) B)

C) D)

38. Choose the best synthesis of phenyl n-propyl ether.

A) B)

C) D)

ISR.IIT_*CO-SC Page. No. 11

Narayana IIT Academy 21-04-24_ISR.STAR CO-SC(MODEL-A)_JEE-ADV_WAT-42_QP

39.

Product (A) of the above reaction is:

A) B) C) D)

40. The major product of the following reaction is

41. The correct order of boiling point of the following is

I. Propanal II.Propan-1-ol III. Acetone IV. n-butane
V. Methoxyethane
A) IV<V<I<III<II B) IV<V<III<I<II
C) V<IV<I<II<III D) V<IV<II<I<III

42. The reaction of

with HBr gives mainly

A) B)

C) D)

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Narayana IIT Academy 21-04-24_ISR.STAR CO-SC(MODEL-A)_JEE-ADV_WAT-42_QP
SECTION - 2 (Maximum Marks : 24)
This section contains SIX (06) questions.
Each question has FOUR options for correct answer(s). ONE OR MORE THAN ONE of these four option(s) is
(are) correct option(s).
For each question, choose the correct option(s) to answer the question.
Answer to each question will be evaluated according to the following marking scheme:
Full Marks : +4 If only (all) the correct option(s) is (are) chosen.
Partial Marks: +3 If all the four options are correct but ONLY three options are chosen.
Partial Marks: +2 If three or more options are correct but ONLY two options are chosen, both of which are
correct options.
Partial Marks : +1 If two or more options are correct but ONLY one option is chosen and it is a correct
option.
Zero Marks : 0 If none of the options is chosen (i.e. the question is unanswered).
Negative Marks: -2 In all other cases.
43. A new carbon–carbon bond formation is possible in

A) Williamson synthesis B) Friedel-Crafts’ reaction

C) Clemmensen’s reduction D) Reimer-Tiemann reaction

44. Which of the following compounds will react with ethanolic KCN?

A) Ethyl chloride B) Acetone C) Chlorobenzene D) Benzaldehyde

.
+
18 H 3O
O. A+B

45.

The products A&B are

18
A) OH B) OH

. .

18
C) OH. D) OH.

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Narayana IIT Academy 21-04-24_ISR.STAR CO-SC(MODEL-A)_JEE-ADV_WAT-42_QP
46. Which of the following reactions will result in a product with retention of configuration
as compared to the initial substrate?

OH
B) . i) SOCl2 / Ether
ii)NaCN
.

47. Acetaldehyde is obtained from which of the following reactions?

0
1.DIBAL-H/-78 C
C C2 H5
CH 3-C-O
A) 2.H2 O

B) CH 3CH  CH  CH 3  1.O3

2. Zn , H 2O


C)  CH 3COO 2 Ca   HCOO 2 Ca 



D) CH 3  C  N 
1. SnCl , HCl
2
2. H O
3


48. Which of the following procedures would be suitable for preparing 3-methyl-1-phenyl-
1-butanone, C6 H 5COCH 2CH  CH 3 2 ?

A) i)C6 H 5COCH  CHCH 3   CH 3 2 CuLi in ether; ii ) H 3O workup

B) i) benzene   CH 3 2 CHCH 2COCl & AlCl3

C) i)C6 H 5 MgBr   CH 3 2 CHCH 2CHO in ether ; ii) H 3O workup; iii) PCC in CH 2Cl2

D)  CH 3 2 CHMgBr  C6 H 5COCH 3 in ether; ii) H 3O  workup; iii) PCC in CH 2Cl2 .

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Narayana IIT Academy 21-04-24_ISR.STAR CO-SC(MODEL-A)_JEE-ADV_WAT-42_QP
SECTION - 3 (Maximum Marks : 24)
This section contains SIX (06) questions. The answer to each question is a NUMERICAL VALUE
For each question, enter the correct numerical value of the answer using the mouse and the on-screen virtual
numeric keypad in the place designated to enter answer. If the numerical value has more than two decimal
places truncate/round- off the value to TWO decimal places.
Answer to each question will be evaluated according to the following marking scheme:
Full Marks: +4 If ONLY the correct numerical value is entered as answer.
Zero Marks: 0 In all other cases.
49.

Sum of number of alcoholic groups in product (P) and (Q) is:

50. How many of the following are more reactive than benzaldehyde towards nucleophilic
addition?

p-methylbenzaldehyde, p-nitrobenzaldehyde, p-anisaldehyde, methylphenylketone,

p-salcylaldehyde.

51. How many of the following given stable hydrates?

formaldehyde, cyclopropanone, ninhydrin, acetone, hexafluoro acetone.

52. Among the following the number of reaction(s) that produce(s) benzaldehyde is

A) B)

C) D)

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Narayana IIT Academy 21-04-24_ISR.STAR CO-SC(MODEL-A)_JEE-ADV_WAT-42_QP
53. In how many of the following the equilibrium lies towards forward direction?

54. Consider all possible isomeric ketones, including stereoisomers, of MW=100. All these
isomers are independently reacted with NaBH 4 (Note: stereoisomers are also reacted
separately). The total number of ketones that give a racemic product(s) is/are

CHEMISTRY
37 C 38 A 39 A 40 D 41 A

42 B 43 BD 44 ABD 45 BC 46 AD

47 ABCD 48 ABC 49 5 50 1 51 3/4

52 4 53 4 54 5

ISR.IIT_*CO-SC Page. No. 16

Narayana IIT Academy 21-04-24_ISR.IIT_*CO SC(MODEL-A)_JEE-ADV_WAT-42_KEY&SOL

CHEMISTRY
37.
O O
OH

H O CH3 OH
LiA/H4

O OH
OH ONa

O
Br .
Na .

38.
OH OH OH

NO2

HNO3/H2SO4 +

(B)
(A)
NO 2
39.
.
.
. O
. O
t-BuOK
.
Cl
+
H
.
.

O
O
.
.
Intra

+
40.
41. n-butane(iv)<Methoxy ethane(v)<Propanal(i)<Acetone(iii)<Propan-1-o1
+
H
CH3-CH=CH . OH

42.
Br
.
Br CH 3CH 2-CH.
.
CH 3-CH2-CH OH OH

ISR.*CO SC Pg.No: 15
Narayana IIT Academy 21-04-24_ISR.IIT_*CO SC(MODEL-A)_JEE-ADV_WAT-42_KEY&SOL
43. B (Friedal-Crafts) and
D (Reimer-Tieman)
44. A,B,D
KCN
CH 3CH 2Cl CH 3CH 3CN
OH
O
KCN
H3C CH3
H3 C CH3
CN
HO
O

H3 C H CN
KCN

H2 C
45. B,C
OH

+
18 H 18
O. . +
H2 O OH

46. AD
47. A)
O O

A) DIBAL-H
+C2H5OH

H3C OC 2H5 H3C H

O

O3
B) CH3-CH=CH-CH3
Zn/H2O H3 C2 H
O O
O

+
C) +
(CH3COO)2Ca+(HCOO)2Ca H H H 3C CH3
H3C H
O

Stephen
D) CH3- C N
H3C H
48.
O .
O

.
1) (CH3)2CuLi
.
A) +
2) H3 O

ISR.*CO SC Pg.No: 16
Narayana IIT Academy 21-04-24_ISR.IIT_*CO SC(MODEL-A)_JEE-ADV_WAT-42_KEY&SOL
O .

O
CH3
.
AlCl3
B) Cl
+ H C
3

HO
. O
O .
PCC
C) C 6H5MgBr + Ph
+ . Ph .
. H H3O
O OH
.
+ PCC
D) H3O No Reaction
(CH3)2CH MgBr + Ph CH3 Ph .
.
49.
O
OH

CH3
O HO
OH
P
Q)
OH

OH
5
P=2, ; Q=3
50. P-nitro benzaldehyde,
51. Formaldehyde, cyclopropanone
Ninhydrin, hexathroacetone
52. 4
53.
OH
OH ;
;
; .
Ph OH

OH
; OH
. .

54.
Cn H 2 n O  12n  2n  16  100
14n  84
n6
O
.
.
.
. . . .
.

O
O OH

. .
.

.
.

ISR.*CO SC Pg.No: 17
Narayana IIT Academy 28-05-23_ISR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-40_Q’P
CHEMISTRY Max. Marks: 61
SECTION – I
(SINGLE CORRECT CHOICE TYPE)
This section contains 7 multiple choice questions. Each question has 4 choices (A), (B), (C) and (D) for its
answer, out of which ONLY ONE is correct.
Marking scheme +3 for correct answer , 0 if not attempted and -1 in all other cases.
19. Among the following, the number of reaction (s) that product(s) benzaldehyde is

COCl
CO,HCl H2
P) Q)
Anhydrous AlCl3 / CuCl
Pd  BaSO 4

CO2 Me CHCl2

R) DIBAL  H S) H2O
Toluene,  78 C, H 2 O
0
1000 C

A) 4 B) 3 C) 2 D) 1

20.
CH 3

CrO2 Cl2 H2O

A  B

The functional group present in (B) and name of the reaction would be
A) –CHO, gattermann aldehyde synthesis
B) –CHO, Etard reaction
C) COCH3 , Fridel Crafts reaction
D) –CHO, Oxo reaction
21. The possible number of stereoisomers of the product of following reaction would be :

Ph  CH  CH  CH  CHO
NH 2 OH
CH 3

A) 2 B) 4 C) 6 D) 8

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Narayana IIT Academy 28-05-23_ISR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-40_Q’P

22.


conc.H3PO4

'A ' 
O3 /Zn
H 2O
 P1  P2
(Ketone)  Aldehyde 

Which one of the following reagent is best suitable for distinction between P1 & P2 ?

A) Brady`s reagent (2, 4 DNPH) B) NaHSO 3

C) NaHCO3 D) Na

23.

 i  NH 2 OH
H3C O
 ii  H 2SO4
Which of the following is correct about the product?

A) A single achiral compound is formed

B) A pair of diastereomers is formed

C) A pair of enantiomers is formed

D) A single optically active compound is formed

24. Give the decreasing order of reactivity towards nucleophilic addition of the following.

I) HCHO II) PhCHO III) CH 3 CHO IV) Acetone

A) III > I > II > IV B) IV > II > I > III C) I > III > II > IV D) IV > II > III > I

25. Identify X in the sequence.

 i  CH3MgCl
X 
(ii) H O/H 
 C5 H12 O 
Cu
575 K
 C5 H10
2

A) CH3  C  CH 2  CH3 B) CH 3 CH 2 CH 2 CH 2 CHO

||
O
C)  CH 3 2 CHCHO D) CH 3 CH 2 CH 2 CH 2 OH

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Narayana IIT Academy 28-05-23_ISR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-40_Q’P
SECTION-II
(ONE OR MORE OPTIONS CORRECT TYPE)
This section contains 7 multiple choice equations. Each question has four choices (A) (B),(C) and (D) out of which
ONE or MORE THAN ONE are correct.
Marking scheme: +4 for all correct options, 0 if not attempted and -2 in all wrong cases.
26. Which of the following oxidation reactions correctly matched? (w.r.t. final organic
product)
 
A) CH3  CH 2 OH   CH3CHO
Cr VI
H O 3

B) CH 3   CH 2 2 C  C  CH  CH 3 
CrO3 .H 2SO 4
Pr opanone
CH 3  CH 2 2 C  C  C  CH 3
| ||
OH O
CHO
CH 2  OH
CH 3
CH 3

PCC/CH 2Cl2

CH 3 CH 3
C)


MnO2
CHCl , 250 C

3

D) HO O

27. Which of the following reactions form cyclobutane carbaldehyde?

CH  N  OH
CN SnCl2  HCl
dil.H 
H3O
A) B)
COOH MeLi
CH 2 OH PCC
H3O
C) D)
28. Check the sequence and pick the correct statement :
CH 2 NH 2
HCN LiAlH 4 NaNO 2
A C
HCl
OH
A) [A] and [C] are homologes
B) [A] and [C] are not homologes
C) Rate of reaction with HCN is more for PhCOPh than [C]
D) Number of acyclic isomers of [A] retaining the same functional group are 5

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Narayana IIT Academy 28-05-23_ISR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-40_Q’P
29. Which of the following are correct regarding below reaction

O K 

i) CO 2 /  A  B
  major   minor 
ii) H3O

A) ‘A’ is stream volatile B) ‘B’ is stream volatile

C) ‘A’ is more acidic than ‘B’ D) ‘A’ is less acidic than ‘B’
30. With reference to the scheme given below, which of the following statement(s) is/are
true about compounds (A) to (E)?
O

LiAlH4 Al2O3 SOCl2 (i) HBr/ROOR

O
(B) (C) (D) (E)
 (ii) Na/dry ether

(A) CH3

A) Compound (B) releases a gas on treatment with sodium metal.

B) Compound (C) gives a resolvable mixture on reaction with Hg(OAC)2 followed by

reduction with NaBH4

C) Compound (D) does not exhibit geometrical isomerism.

D) (E) is a mixture containing achiral molecules.

31. Which of the following reagent can be used to differentiate between A and B?

A) Victor-Mayer test B) Sodium metal

C) Lucas reagent D) K 2 Cr2 O7 / H 

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Narayana IIT Academy 28-05-23_ISR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-40_Q’P
32. Consider the following reaction
OH

NaOH  aq. H3O

 CHBr3

The correct statement regarding above reaction is/are


A) Phenol undergo electrophilic attack by C Br2
B) Electrophile in the above reaction is produced by  - elimination
C) Meta-hydroxy benzaldehyde is the major product
D) Ortho-hydroxy benzaldehyde is the major product
SECTION – III
(PARAGRAPH TYPE)
This section contains 2 groups of questions. Each group has 2 multiple choice questions based on a paragraph.
Each question has 4 choices A), B), C) and D) for its answer, out of which ONLY ONE is correct.
Marking scheme: +3 for correct answer, 0 if not attempted and 0 in all other cases.
Paragraph For Questions 33 and 34:
An acyclic hydocarbon P, having molecular formula C6 H10 , gave acetone as the only
organic product through the following sequence of reaction, in which Q is an
intermediate organic compound.
O
 i  conc. H2SO4
P  i  dil. H 2SO4 / HgSO4  catalytic amount 
 C6 H10   ii  NaBH4 / ethanol Q
 ii  O3
2 C

 iii  Zn / H2 O H3C CH 3

33. The structure of compound P is

A) CH 3 CH 2 CH 2 CH 2  C  C  H B) H 3 CCH 2  C  C  CH 2 CH 3

H3C
H3C

H C C C CH 3
H3C C C C H

H3C H3C
C) D)

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Narayana IIT Academy 28-05-23_ISR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-40_Q’P
34. The structure of compound Q is
H3C OH H3C OH

H C C CH 2 CH 3 H3C C C CH 3

H3C H H3C H
A) B)
H3C OH

H C CH 2 CHCH3 OH

H3C CH3CH 2 CH 2 CHCH 2 CH3

C) D)
Paragraph For Questions 35 and 36:
An organic compound X  C9 H12 O  gives the following reactions:
i) Na-Slow gas bubble formation
ii) Acetic anhydride – Pleasant smelling liquid
iii) CrO3  H 2SO 4  Blue  green solution
iv) Hot KMnO 4 - Benzoic acid
v) Br2  CCl 4  No decoloration
vi) Can give blue colour in Victor Meyer`s test
vii) X rotates the plane polarized light
35. The structure of X is

A) B) C) D)

36. If X is treated with HCl in the presence of ZnCl2 , the major product would be

A) B) C) D)

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Narayana IIT Academy 28-05-23_ISR.IIT_*COSC(MODEL-A)_WAT-40_Key&Sol’s
CHEMISTRY
19. The reaction is pH sensitive, rate of reaction decreases with increase or decrease in pH.
20. Conceptual
21.
Product  Ph  CH  CH  CH  CH  NOH

CH 3
Total number of stereoisomers = 2 n  23  8
22.

23. Conceptual
24. More the e – withdrawing group, more is the NA reactivity
Cl3 C  CHO  HCHO  PhCHO  MeCOMe
25. Must be a tertiary alcohol as it gives alkene on treatment with Cu. Thus, C 4 H 8 O is a ketone.

CH  NOH dil.H3O CHO

26.

Aldoximes on treatment with dilute acid give aldehydes

CN SnCl2  HCl
Stephens reaction
H3O
28.

29.

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Narayana IIT Academy 28-05-23_ISR.IIT_*COSC(MODEL-A)_WAT-40_Key&Sol’s
30.
OH Cl
O OH

O
CH2 CH2
OH
(B) (D)
(A) CH3 (C) CH3 CH3
CH3

Cl

Na/dry ether

Br
CH3 CH3
(E)

32. CHBr3  OH  

  Elimination
 : CBr2  H 2 O  Br 
: CBr2 act as electrophile, attack at ortho-position of phenol give finally salicyldehyde,
Reimer-tiemann reaction.
35. Conceptual

36.

ISR.IIT_*CO SC Page No: 6

 NARAYANA EDUCATIONAL SOCIETY
SUPER CHAINA CAMPUS
ISR'S_WAT-40(MODEL-A)_28.05.23_FINAL KEY
S.NO SUB Q.NO GIVEN KEY FINAL KEY REMARKS

4 CHEM 27 ABC ABC or BC KEY CHANGE

5 CHEM 30 ABC AC KEY CHANGE

6 CHEM 32 ABD ABD or BD or B KEY CHANGE

CHEMISTRY
19 A 20 B 21 D 22 B 23 C

24 C 25 A 26 BCD 27 ABC 28 AD

29 BD 30 ABC 31 ACD 32 ABD 33 D

34 B 35 B 36 C
Narayana IIT Academy 01-02-20_Jr.IIT_SC-60_JEE-Adv_WAT-38_Q’P
CHEMISTRY Max Marks: 62
SECTION – I
(SINGLE CORRECT ANSWER TYPE)
This section contains 5 multiple choice questions. Each question has 4 options (A), (B), (C) and (D) for its
answer, out of which ONLY ONE option can be correct.
Marking scheme: +3 for correct answer, 0 if not attempted and –1 in all other cases.
O

NH 2OH +
H LiAlH 4
X Y Z will be
Beckmann
rearrangement
19.
O O
O H
N
NH
NH
A) B) C) D)
20. Product (B) of the given reaction is :
O

dry HCl Gas (CH3)2SO4

HO OH (A) (B)
+ base
OH

Me OMe SO 2OMe SO 2OMe

O O O O O O O O

A) B) C) D)
21. The general order of reactivity of carbonyl compounds for nucleophilic addition reaction
is-
A) H 2C  O  R 2C  O  Ar2C  O  RCHO  ArCHO
B) ArCHO  Ar2C  O  RCHO  R 2C  O  H 2C  O
C) Ar2C  O  R 2C  O  ArCHO  RCHO  H 2C  O
D) H 2C  O  RCHO  ArCHO  R 2C  O  Ar2C  O

Sec: Jr-IIT_SC-60 Page 8

Narayana IIT Academy 01-02-20_Jr.IIT_SC-60_JEE-Adv_WAT-38_Q’P
O
H
N
pH = 4.5 - 6
+ X
22. Heat

Hence the product X is ?

N
N N N

A) B) C) D)
23. The incorrect statement(s) about the following reaction sequence is
i) O 2 CHCl 3, NaOH
Cumene (C9H12) P Q (major) + R (minor)
+
ii) H3O

NaOH
Q S
PhCH 2Br

A) Q is steam volatile
B) Q gives dark violet coloration with 1% aqueous FeCl3 solution
C) S gives colored precipitate with 2,4 - dinitrophenylhydrazine
D) S gives dark violet coloration with 1% aqueous FeCl3 solution
SECTION – II
(MULTIPLE CORRECT ANSWER TYPE)
This section contains 8 multiple choice questions. Each question has 4 options (A), (B), (C) and (D) for its answer,
out of which ONE OR MORE than ONE option can be correct.
Marking scheme: +4 for all correct options & +1 partial marks, 0 if not attempted and -2 in all wrong cases
24. Correct statement regarding above reaction sequences :
Cl O
CH3
NO 2
NH 2-NH 2 (2 eq) H3C
[R] [S]+[T]
+ - pH=4-5
- NH 2-NH 3.Cl
NO 2

[Q]
A) [R] is 2,4-DNP
B) [Q] to [R] formation is SN Ar reaction
C) [S] & [T] are Non-superimposable, non-mirror images
D)  R  S involve nucleophilic addition followed by elimination

Sec: Jr-IIT_SC-60 Page 9

Narayana IIT Academy 01-02-20_Jr.IIT_SC-60_JEE-Adv_WAT-38_Q’P
25. The compounds A and B in the following reaction are respectively.

HCHO+HCl AgCN
A B

A) A = Benzyl chloride B) B = benzyl isocyanide

C) A = benzyl alcohol D) B = benzyl cyanide
26. Which of the following reactions form cyclo-butane carbaldehyde.
CN
CH=NOH 1) SnCl 2+HCl
+
H ,H2O
+
2) H 3O
A) B)
CH 2OH COOH
1) CH 3Li (2 eq)
PCC
+
CH 2Cl 2 2) H 3O
C) D)
27. Which of the following reagents can perform this conversion successfully ?
O

SH , BF3 followe d by H2/Ni

A) HS B) Zn  Hg / HCl

C) Mg.THF / H 2O D) N2H4/KOH/ethylene glycol, 

28. Which of the following combination can give following product ?

CH3
OH

CH3

1. EtMgBr, Et 2O
CH3
+
2. H3O
A)
O
CH3 1. CH 3MgBr, Et 2O
+
2. H3O
B)

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Narayana IIT Academy 01-02-20_Jr.IIT_SC-60_JEE-Adv_WAT-38_Q’P
CH 2MgBr
O
1. , Et 2O
CH3
H3C +
2. H3O
C)
MgBr
O
1. , Et 2O
CH3
H3C +
2. H3O
D)
29. Which of the following products can be obtained by S N 1 reaction?
CH 3OH
Products
1
SN
CH 2-Cl
O
OCH 3

CH 2-OCH 3 CH3
A) O B) O
H3CO

H CO CH CH3
C) 3 O 3
D) O
30. In which of the following reaction K eq. > 1 :
O

H2O
O O

H2O
A) B) O
O

CH3 H2O
H2O
CF3CHO
C) D)
31. In which of the reaction, final product is an aldehyde ?
H2
C6H5COCl
Pd-BaSO4
A)
i) SnCl 2+HCl
RCN +
ii) H3O
B)
-
i) AlH(i Bu) 2
CH 3-CH=CH-CH 2CH 2CN
ii) H2O
C)
i) DIBAL-H
CH 3COOEt
ii) H2O
D)

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Narayana IIT Academy 01-02-20_Jr.IIT_SC-60_JEE-Adv_WAT-38_Q’P
SECTION – III
(INTEGER ANSWER TYPE)
This section contains 5 questions. The answer is a single digit integer ranging from 0 to 9 (both inclusive).
Marking scheme +3 for correct answer , 0 if not attempted and 0 in all other cases
32. If glycerol is allowed to react with formaldehyde in presence of dry HCl. What are the
number of products (formal = analogous to acetal) formed ?
33. If ethane dial (glyoxal) is treated with excess of KCN followed by complete acidic
hydrolysis. How many dicarboxylic acids would be formed ?
34. How many stereo centres are present in product
O O
OH
(I) (1 eq)
EtO CH3 OH
A
(II) LiAlH 4
+
(III) H ,H2O
CHO

35. Examine the structural formulas of following compounds and find out number of

compounds which show higher rate of nucleophilic addition than

H3C C H

O H O H O H O H O H
O H

, , , , ,
,

Cl NO 2 :N(CH 3)2 C N
:OCH 3 :OH

36. How many carbonyl isomers of C5H10O which reacts with MeMgBr to give racemic
mixture?

CHEMISTRY
19 C 20 B 21 D 22 C 23 D

24 ABCD 25 AB 26 ABC 27 ABD 28 ABD

29 ABC 30 ABD 31 ABCD 32 3 33 3

34 1 35 3 36 3

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Narayana IIT Academy 02-07-22_INC.SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-52_Q’P
CHEMISTRY Max Marks: 88
SECTION – I
(SINGLE INTEGER ANSWER TYPE)
This section contains 8 questions. The answer is a single digit integer ranging from 0 to 9 (both inclusive).
Marking scheme +4 for correct answer, 0 if not attempted and 0 in all other cases.
21. An organic compound (A)  m. f . C10 H 20  on reductive ozonolysis gives 2-methyl
butanal. Then total no. of steroisomers possible for A is
22. Benzaldehyde, on reaction with aniline forms Schiff’s base. The number of  bonds in
Schiff’s base is
23. Number stereoisomers possible in reaction of NH 2OH with
CH 3CH  CH  CH 2  C  CH 3 (only oximes)

24. Examine the structural formulas of following compounds and find out number of
compounds which show higher rate of nucleophilic addition than
O

H 3C C H

O CH 3 O H
C C CHO CHO CHO CHO

OCH 3 Cl NO2 N  CH 3 2 OH CN

O O

25. C12 H16 

hot KMnO4
 H 3C  C  CH 3  HO  C  C  C  OH
O O
 A
1mole   2mole   2mole 
Number of  bonds present in A
26. 1 mole SBH (sodium boro hydride) reduces ‘y’ moles acetaldehyde to ethyl alcohol.
The value of ‘y’ is
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Narayana IIT Academy 02-07-22_INC.SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-52_Q’P
27. How many of the following compound will not show enolisation?
O O OH

O O
 A  B C   DO OH
Me
Ph
O O O OH O O
Me Ph
COOH

E F 

O O

28. Alkaline hydrolysis of chloral hydrate produces a compound (A) which is used as
solvent and preservative for anatomical specimens and also has anesthetic properties.
(A) is prone to aerial oxidation in presence of sunlight to give a poisonous compound
(B) which may be made non poisonous by adding dilute solution of ethanol which
converts it into a non poisonous compound (C). How many moles of CH 3 MgBr will be
added to (C) followed by acidic hydrolysis to give alcohol?

SECTION – II
(ONE OR MORE CORRECT ANSWER TYPE)
This section contains 10 multiple choice questions. Each question has 4 options (A), (B), (C) and (D) for its
answer, out of which ONE OR MORE than ONE option can be correct.
Marking scheme: +4 for correct answer, 0 if not attempted and -2 in all other cases.
29. Which of the following is reactive intermediate for the following reaction?

O O
O

 HO  CH 2  CH 2  OH 
H 2 SO4


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Narayana IIT Academy 02-07-22_INC.SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-52_Q’P
O
N  NH 2

30. 
NH 2 NH 2


The correct statements regarding this conversion is

A) The rate of the reaction is very low at pH = 1
B) Elimination of water become rds when pH of the reaction mixture is approximately
7
C) Addition of nucleophile become rds when pH of the reaction is = 4
D) Hydrazine is more nucleophilic than a regular amine in nucleophilic addition
reaction of carbonyl compounds
O

 2
1 NH  NH
31. 
 2 OH  / 
2
A

The correct statement of the following related to given equation are

A) Product "A" is Ph CH 3
N
NH 2
B ) One of the intermediates of reaction is Ph

C) The same reagents can also reduces ketones to alkanes

D) Hydrolysis can also carried out with ter – butoxide instead of hydroxide ion
32. Which of the following compound have larger C  O bond length than C  O bond
length of
O

H 3C  C  CH 3 ?

O O
O O

A) B) C) D)

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Narayana IIT Academy 02-07-22_INC.SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-52_Q’P
33. In the following reaction

Which of these either intermediate or final product of reaction

34. The possible products obtained by the following reaction is/are

O


1.LDA
CH 3 Br

O O O OCH 3

A) B) C) D)

35. Chlorination of Toluene with an excess of Cl2 in the presence of light and heat gives
product (X). The compound (X) is heated with aqueous NaOH and finally acidified to
give a compound (Y). Y can be
CH 3 CH 3 CH 3

OH COOH

A) B) C) D)

OH

OH

36. Reducing agent(s) which can be used to carry out following conversion is/are
O O OH


Reducing agent

OR OH

A) NaBH 4 B) LiAlH 4
C) H 2 / Ni D) B2Cl6 / THF

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Narayana IIT Academy 02-07-22_INC.SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-52_Q’P
37. An ether reacts with H 2 SO4 to form
A) Alcohol if boiled with dilute sulphuric acid
B) Alcohol and alkyl hydrogen sulphate
C) An oxonium ion
D) An oxy anion
38. Which of these carbony compounds on reduction winth Zn – Hg / HCl will give the
same compound as product
O O

A) H  C CH 2CH  CH 3 2 B) H 3  C C  CH  CH 3 2

O H C  O O

C) H3  C CH 2  C  CH 3 D) H3  C C  C  CH 3 2

SECTION - III
(MATRIX MATCHINGANSWER TYPE)
This section contains 2 questions. Each question has four statements (A, B, C and D) given in Column I and four
statements (P, Q, Rand S) in Column II. Any given statement in Column I can have correct matching with ONE
or MORE statement(s) given in Column II.
For example, if for a given question, statement B matches with the statements given in Q and R, then for the
particular question darken the bubbles corresponding to Q and R in the OMR sheet. For each correct
matching will be awarded +2 marks ONLY and 0 if not attempted and -1 in all other cases.
39.
COLUMN – I COLUMN – II
O
A 
1. LiAlH 4
2. H 2O
 P Racemic mixture

O
B 
1. KCN / HCN
 Q Diastereomers
2. H  / H O
2

C PhCH 2Cl 

1. KOH / alcohol
2. PCl3
 R Nucleophilic addition
O

D S Nucleophilic substitution

1.CH 3 MgBr
2. H O 

3

T Final product is alcohol

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Narayana IIT Academy 02-07-22_INC.SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-52_Q’P
40.
COLUMN – I COLUMN – II

OH OH
OH OH

A 
CHCl3
KOH , alc , 
 P Rosenmund’s reduction

CHO

O
O Beckman’s
B  HC  CH 2  CH 2  CH  CH 2 Q
rearrangement

COCl CHO

C 
R Claisen rerrangement


D O 
1. NH 2OH / H
2. PCl5
 S Clemmonsen reduction

Reimer – Tiemann’s
T
reaction

CHEMISTRY

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Narayana IIT Academy 02-07-22_INC.SR.IIT_*COSC(MODEL-A)_WAT-52_Key&Sol’s
19:

21 6 22 7 23 4 24 3 25 4

26 4 27 4 28 3 29 C 30 ABCD

31 ABCD 32 BC 33 BC 34 ABCD 35 D
A-PRT A-T
B-R B-R
36 BC 37 ABC 38 ABC 39 40
C-S C-P
D-PRT D-Q

20. REFER THE THEORY OF SOLENOID

LENOID
CHEMISTRY
21.

22. Benzalidine aniline

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Narayana IIT Academy 02-07-22_INC.SR.IIT_*COSC(MODEL-A)_WAT-52_Key&Sol’s
23.
CH 3
CH 3 CH 2  C  CH 3 H
CH  C C C CH 3
H CH 2 C
N
OH
N
CH 3
OH
H
C C
CH 3 CH 2
H CH 2 CH 3
CH 3 C C C
C H H
N
N HO
HO
24.

25.

28.

29.

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Narayana IIT Academy 02-07-22_INC.SR.IIT_*COSC(MODEL-A)_WAT-52_Key&Sol’s
31.

32.

33.

34.
O O O O O


LDA
 

annotate ion
OCH 3

MATHS
20
f x
41. I  g  x  dx
20

f  x 
20 20
f  x   f  x 
using King's rule, we have I=  dx   dx
20
g   x  20
g  x 
f  x   1  f   x   20
f  x   1  f   x  
Addition the two, we get 2I   dx  
gx 20
gx
 I  1010

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Narayana IIT Academy 04-04-21_Jr.IIT_*CO-SC _JEE-ADV_WAT-43_Q’P
CHEMISTRY Max.Marks: 62
SECTION-I
(Single Correct Answer Type)
This section contains 6 multiple choice questions. Each question has 4 options (A), (B), (C) and (D) out of which
ONLY ONE option can be correct.
Marking scheme: +3 for correct answer, 0 if not attempted and -1 in all other cases.
19. The degree of unsaturation of the major product (X) of the following reaction is:
O CH3
NH2 +
H
+ X
NH2 H3C O

A) 5 B) 6 C) 7 D) 8

20. The decreasing order of rate of the following compounds towards cyanohydrin
formation is:
O CH3
CHO
O O
H3C H3C
H
H3C
(II) (III) (IV)
(I)

A) IV>III>I>II B) I>IV>III>II C) IV>I>III>II D) IV>III>II>I

21. The decreasing order of boiling points of the following compounds is:
H3C O O
H3C O H3C
H3C
CH3 H CH3
OH
(I) (II) (III) (IV)

A) II>III>IV>I B) II>IV>III>I

C) II>I>III>IV D) III>II>IV>I

22. 0.2 moles Benzo nitrile is reacted with excess methyl magnesium bromide and the
mixture is treated with aq. acid. If the percentage yield of the reaction is 50%, the
weight of organic product formed is:

A) 24 g B) 12 g C) 27.2 g D) 13.6 g

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Narayana IIT Academy 04-04-21_Jr.IIT_*CO-SC _JEE-ADV_WAT-43_Q’P
23. The product formed in the following reaction is:
O
+
OC2H5 1) ethylene glycol/H

2) LiAlH4
O
+
3) H3O

OH
O O
OH OC 2H5

O
A) B)
O OH
OH OH

C) D)

24. The major product (R) in the following reaction sequence is:
H3C CH3 O3
Ca dry distillation
P Q R
H2O 2 (aq) 
H H

A) (CH3COO)2Ca B) CH3COCH3 C) CH3CHO D) CH3CH2COCH2CH3

SECTION-II
(Multiple Correct Answer Type)
This section contains 8 multiple choice questions. Each question has 4 options (A), (B), (C) and (D) for its
answer, out of which ONE OR MORE than ONE option can be correct.
Marking scheme: +4 for all correct options & +1 partial marks, 0 if not attempted and -2 in all wrong cases.
25. Which of the following reaction(s) produces benzaldehyde?

1) CH3Cl/AlCl 3
CN
1) SnCl 2/HCl
2) CrO2Cl2 +
+ 2) H3O
A) 3) H3O B)
CO2Me
COCl
H2/Pd - BaSO 4 DIBAL - H
0
Toulene, -78 C
C) D) H2O

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Narayana IIT Academy 04-04-21_Jr.IIT_*CO-SC _JEE-ADV_WAT-43_Q’P
26. Choose the option(s) in which same product(s) is (are) formed:

(At least one product should be same)

CH3 CH3

HO O
H3C aq. NaOH
H3C +
H3O
O O
A) CH3 B)

CH3
O
H3C 1) 2 eq CH3SH/H+

H 2) PhLi H3C
3) n - C3H7Cl aq. NaOH
O O
C) 4) H2O , HgCl 2 D)

27. Choose the option(s) in which the equilibrium lies towards forward direction:
O +
O OH H2O/H HO OH
+ H
H2O/H HO H
H H
A) B)
O + O +
H2O/H HO OH H2O/H HO OH
H3C H3C F 3C F 3C
CH3 CH3 CF3 CF3
C) D)

28. Consider the following reaction sequence:

Cl

HNO3 (2 eq)/H2SO4 NH2NH2 CH3CHO

P Q R + S
I II III

Choose the correct option(s):

A) Q is 2,4- DNP
B) R and S are diastereomers.
C) 2 moles of hydrazine is required in step II
D) Acid catalyzes the step III

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Narayana IIT Academy 04-04-21_Jr.IIT_*CO-SC _JEE-ADV_WAT-43_Q’P
29. The IUPAC name(s) of the following compound is(are):
CHO

NO 2

A) 4- formylnitrobenzene B) 4- nitrobenzaldehyde

C) 4- nitrobenzenecarbaldehyde D) 4-oxonitrobenzene

30. Which of the following reaction(s) lead to formation of Schiff’s base?

CHO

+
H
+ H3C NH2
A)
H3C O

+
H
+ H3C NH

B) CH3

NH2
O
+
H3C + H
CH3
C)
O
H
N +
H
+
D)
31. Colloidal solution of Arsenic sulphide sol is subjected to electroosmosis, then:

A) Colloidal particles move towards cathode

B) Colloidal particles move towards anode

C) Dispersion medium moves towards cathode

D) Dispersion medium moves towards anode

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Narayana IIT Academy 04-04-21_Jr.IIT_*CO-SC _JEE-ADV_WAT-43_Q’P
32. The correct statement(s) about surface properties is(are):
A) Adsorption is accompanied by decrease in enthalpy and decrease in entropy of the
system
B) The critical temperatures of ethane and nitrogen are 563 K and 126 K, respectively.
The adsorption of ethane will be more than that of nitrogen on same amount of
activated charcoal at a given temperature
C) Cloud is an emulsion type of colloid in which liquid is dispersed phase and gas is
dispersion medium
D) Brownian motion of colloidal particles does not depend on the size of the particles
but depends on viscosity of the solution

SECTION-III
(Paragraph Type)
This section contains 2 groups of question. Each group has 2 multiple choice questions based on a paragraph.
Each question has 4 choice (A), (B),(C) AND (D) for its answer, out of which ONLY ONE is correct.
Marking scheme: +3 for correct answer, 0 if not attempted and 0 in all other cases.
Paragraph For Questions 33 and 34:
Precipitation of colloidal solution by addition of electrolyte is termed as coagulation.
According to Hardy-Schulze rule, generally, the greater the valence of the flocculating
ion added, the greater is its power to cause precipitation. Greater the coagulation
value, less is coagulation power.
Stability of a lyophobic sol can be increased by adding a lyophilic sol. Hence lyophilic
sol is also known as protective colloid. The ability of lyophilic colloid to stabilize
lyophobic colloid is measured in terms of gold number. Gold number is defined as the
milli grams of protective colloid required for 10 mL of gold sol to prevent its
coagulation by 1mL of 10% NaCl solution.
33. As per Hardy-Schulze formulation, the flocculation values of the following for ferric
hydroxide sol are in the order:
A) AlCl3  K3 Fe(CN)6   K 2CrO4  KBr  KNO3

B) K3 Fe(CN)6   K 2CrO4  KBr  KNO3  AlCl3

C) K3 Fe(CN)6   K 2CrO4  AlCl3  KBr  KNO3

D) K3 Fe(CN)6   AlCl3  K 2CrO4  KBr  KNO3

34. The coagulation of 100 mL of a gold sol is completely prevented by adding 0.25 g of
starch to it before adding 10 mL of 10% NaCl solution. The gold number of starch is:
A) 0.25 B) 0.025 C) 25 D) 250

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Narayana IIT Academy 04-04-21_Jr.IIT_*CO-SC _JEE-ADV_WAT-43_Q’P
Paragraph For Questions 35 and 36:

Consider the following reaction sequence:

Cl Cl
0 +
H2O, 100 C NH2OH/H PCl5
X Y Z

Answer the following questions.

35. The major product Y is:
OH OH
N
+
N

A) B)
HO
N HO NH OH

C) D)

36. The major product Z is:

O
N

OH
OH NH2
A) B)
O
H O
NH N

C) D)

CHEMISTRY

19 C 20 C 21 B 22 B 23 C
24 B 25 ABCD 26 ABC 27 ABD 28 ABCD
29 BC 30 AC 31 C 32 AB 33 B
34 C 35 B 36 D

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Narayana IIT Academy 04-04-21_ JR.IIT_*COSC_JEE-ADV_WTA-43_Key&Sol’s
CHEMISTRY
19.
O CH3
NH2 + N CH3
H
+
NH2 H3C O N CH3

20. Based on steric and electronic effects.

21. Based on hydrogen bonding and polarity effects
1 ) CH3MgBr
PhCN  2) H
 PhCOCH3
22.
0.2mol 0.1mol  12g
23.
O
O
+ OH
OC2H5 1) ethylene glycol/H

2) LiAlH4
O
+
3) H3O

24.

H3C CH3 O3
Ca dry distillation
CH3COOH (CH3COO) 2Ca CH3COCH3
H2O 2 (aq) 
H H

25.
CHO

1) CH3Cl/AlCl 3

2) CrO2Cl 2
+
3) H3O

CHO

CN
1) SnCl2/HCl
+
2) H3O

CHO
COCl
H2/Pd - BaSO4

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Narayana IIT Academy 04-04-21_ JR.IIT_*COSC_JEE-ADV_WTA-43_Key&Sol’s
CHO
CO2Me
DIBAL - H
0
Toulene, -78 C
H2O

26. Hemiacetal and acetalhydrolyse in acidic medium.

Hemiacetal hydrolyse in alkaline medium but acetal is stable in alkaline medium
O H3CS SCH3 H3CS SCH3
2) PhLi 3) n - C3H7Cl
H3C 1) 2 eq CH3SH/H+ - CH3COCH2CH2CH3
H3C H3C C
4) H2O , HgCl 2
H H
NH2 N=CHCH3
Cl HN HN
NO2 NO2 NO 2

28. P= NO2 Q= NO2 R, S= NO 2

29. NCERT
30. Substitutedimineis Schiff’s base. (NCERT)
31. During electroosmosis dispersion medium moves towards respective electrode.
Arsenic sulphide sol is negatively charged hence DM moves towards cathode.
32. Emulsion is liq in liq colloid.
Brownian motion of colloidal particles depends on the size of the particles
33. More charge less coagulation value. Same charge same coagulation value.
34. 10mL of 10% NaCl solution is added to 100mL of solution of gold.
Thus, 1mL of 10% NaCl solution has been added to 10mL solution of gold.
Since, 100mL gold solution required =0.25g starch=0.25×103mg
So, 10mL gold solution required =0.025g starch
Thus, by definition, the gold number of starch is 25.
35 and 36.
OH
Cl Cl O N H O
0
N
+
H2O, 100 C NH2OH/H PCl 5

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