Narayana IIT Academy 24-07-22_INC.SR.

IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-55_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. Which of the following molecule has highest rate of decarboxylation on treating with
soda lime
COOH COOH COOH

COOH

SEC: InC.SR_*CO-SC Date: 24-07-22

Time: 3 Hrs Max. Marks: 183
CH 3 OCH3 NO 2 NO 2
24-07-22_INC.SR.IIT_STAR CO-SC (MODEL-A)_JEE ADV_WAT-55_SYLLABUS A) B) C) D)
PHYSICS: PRESENT WEEK
EEK (80%): AC : Alternating currents, peak and RMS 20. The best reagent for converting 2–phenylpropanamide into 2-phenylpropanamine is
____.
A) excess H 2
current. AC generator and transformer.
PREV
PREVIOUS WEEK EEK (20%): Self and mutual induction,on, L-R circuits, B) Br2 in aqueous NaOH
L-
L-C Oscillations with D--C source and eddy currents
C) iodine in the presence of red phosphorus
CHEMISTRY: PRESENT WPRESENT
WEEK
EEK (80%): WEEK (80%):
Amines: Amines: from
Preparation Preparation from nitro compounds,Preparation from nitro compounds,
nitro compounds,
nitriles and amides; Hoffmann bromamide degradation, Gabriel D) LiAlH 4 in ether
phthalimide synthesis, Physical properties, reaction with nitrous acid, 21. How many of the below listed compounds on treatment with HNO 2 can go for ring
alkylation, acylation, carbylamine reaction, hinsberg test, Hoffman
expansion ?
mustard oil reaction, EAS of aniline, nitration, sulphonation,
bromination, diazotisation, Azo coupling reaction of diazonium salts
of aromatic amines; Sandmeyer and related reactions of diazonium
salts;
PREVIOUS WEEK (20%): Carboxylic Acids & Derivatives:
Preparation methods of carboxylic acids from alcohols, aldehydes,
alkylbenzenes, nitriles and amides, Grignard reagents,acyl halides,
esters and anhydrides, Formation of anhydride, heating effect,
Esterification Reactions with PCl5, PCl3 and SOCl2, Reaction with
ammonia and reduction, decarboxylation, HVZ reaction EAS of
benzoic acid, Preparation and properties of acid derivatives, reaction
with water, alcohol, ammonia, amines, claisen condensation,
Dieckmann condesation (Exclude: acylion condensation)
MATHEMATICS: PRESENT WEEK EEK (80%): Cube roots of unity, De-Moivre's
-Moivre's theorem, A) 2 B) 3 C) 4 D) 5
nth roots of unity
PREV
PREVIOUS WEEK EEK (20%): Rotation - Coni's Theorem,
T Rotation form,
Geometrical interpretation INC.Sr.IIT_*CO SC Page No: 11

Narayana IIT Academy 24-07-22_INC.SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-55_Q’P Narayana IIT Academy 24-07-22_INC.SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-55_Q’P

22. Gabriel-Pthalimide synthesis is suitable for preparation of SECTION-II
(ONE OR MORE OPTIONS CORRECT TYPE)
CH 3 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.
CH 3 C NH 2 Marking scheme: +4 for all correct options, 0 if not attempted and -2 in all wrong cases.
A) CH 3CH 2 NHCH 2CH 3 B) 26. Isocyanate is the intermediate in case of which of the following reactions?
CH 3
A) Hoffmann’s mustard oil reaction
NH 2
B) Schmidt’s rearrangement of carboxylic acids

C) D) CH 3 CH 2 NH 2 C) HVZ reaction
D) Lossen rearrangement
23. The Hinsberg test of a C5H14 N 2 compound produces a solid that is insoluble in 10% 27. Which of the following statement (s) is / are correct
O
aq. NaOH. This solid derivative dissolves in 10% aq. sulfuric acid. Which of the
following would best fit these facts? CH3  C  Cl  CH3CO2 O  CH3COOEt  CH3CONH 2
A)
A) NH 2CH 2CH 2CH 2 N CH 3 2 B) CH 3 2 NCH 2CH 2 NHCH 3 Rateof hydrolysis
CH3  CH 2COOH  CH3  CH  COOH  CH3 3 C  COOH
C) NH 2CH 2CCH 3 2 CH 2 NH 2 D) CH 3 2 NCH 2 N CH 3 2 B) Rateof esterification
CH 3
24. IUPAC name of the following compound is C)
CONH 2 CONH 2 CONH 2
O
CH 3
C N
CH 3
  Rateof Hoffimann bromamidereaction
A) N,N – Dimethyl cyclopropanamide

B) N-methyl cyclopropanamide
NO 2 Cl CH 3
C) N,N-Dimethyl cyclopropane carboxamide
CHO CHO CHO
D) N,N-Dimethyl cyclopropolonamide

25. How many isomeric mono bromo tricarboxylic acids are formed
CH 2  COOH   Rateof cannizaro's reaction 
CH  COOH    
Br / red phosphorus
2


D)
CH 2  COOH
NO 2 Cl CH 3
A) 4 B) 5 C) 3 D) 2
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Narayana IIT Academy 24-07-22_INC.SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-55_Q’P Narayana IIT Academy 24-07-22_INC.SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-55_Q’P
28. p-Aminobenzoic acid (PABA) is the active ingredient of sunscreen lotions. Which of 29. Which of the following reaction(s) is (are) correct as per major product formation ?
the following synthetic method(s) would give PABA as the major product ?
H H
NH 2 Cl  2NH3 
 NH 2  NH 4Cl

A) H H
 2 iNaNO2 / Con.HCl i NaOHaq,
    
i Ac O
  
Sn / Con.HCl
iiHNO3 / Ac2O iiCuCN iiH O
3

A) Cl 
aq.KOH


NO 2
B)

Cl 
alc.KOH


   
i KCN Sn / Con.HCl
iiH O ,
3 C)

O C
NH 2  HNO2    OH
B) F
D)
COOH
30. Primary amine group is formed in

NO 2

con.HNO3
con.H 2SO4
 
Sn / Con.HCl

O
C)
 
NH 4 HS
NH 2  
Br2 / KOH
NH 2

NO 2
A) B)
K 2Cr2O7 / H

 

1.CHCl3 / NaOH
2.con.H2SO4
Cl N 2Cl
D)

CH3 NH 2
 
Zn / HCl

Cu 2O / 

C) D)

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Narayana IIT Academy 24-07-22_INC.SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-55_Q’P Narayana IIT Academy 24-07-22_INC.SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-55_Q’P

31. Which of following molecules undergo dehydration in presence of P2O5 ( use suitable 33. The compound ‘D’ is
conformations) OCH3 CH 2OH COOH OH
COOH
CHO
COOH

A) COOH B) COOH
CHO CHO CH 3 CH 3
A) B) C) D)
COOH
34. The mixture of compounds (A) and (B) are respectively

NH 2 OCH3 NHCH 3 CH 2OH

C) COOH D) Fumeric acid

32. Which of the following true about carbylamines test

& &
A) only aliphatic primary amines give positive test

B) Dichlorocarbene is the electrophile involved in the test. A) B)

C) one mole of methylamine requires three moles of potassium hydroxide to form one CH 3 CH 3

mole of isocyanide.
NHCH 3 OH NH 2 OH
D) It is used to distinguish between primary, secondary and tertiary amines

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. C) D)
Marking scheme: +3 for correct answer, 0 if not attempted and 0 in all other cases.
Paragraph for Questions 33 and 34: CH 3 CH 3 CH 3
A mixture of two aromatic compounds (A) and (B) was separated by dissolving in
chloroform followed by extraction with aqueous KOH solution. The organic layer
containing (A) when heated with alkali KOH produced compound (C) with M.F.
C8H 7 N associated with unpleasant odour. The alkaline aqueous layer on the other
hand when heated with chloroform and then acidification gave a compound (D) with
M.F. C8H8O 2 .

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Narayana IIT Academy 24-07-22_INC.SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-55_Q’P
Paragraph for Questions 35 and 36:
 yellow precipitate 

NaOI

A 
HCl,H 2O

 B 
OH

 C 
O3
BD
C5H8O3   C3H6O 
Zn,H 2O

 Pleasant smell 
1.CH3O Na 
2.CH3  Br 1eq.

  2 3
OH excess ,I  CHI CH3 OH
E 
HCl,H2O

 F 
2.H
 G 
SOCl2
 H   I 
1.CH3ONa
2.HCl
J
– hybrid orbital, electron pair can’t enter into resonance, hence only inductive effect
35. Compound C is

A) B)
amines, doesn’t not dissolve in aq 10 % NaOH

C) D)

36. Compound J is

A) B)

C) D)

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Narayana IIT Academy 20-06-21_INC.SR.IIT_*CO-SC_JEE-ADV_WAT-47_Q’P

CHEMISTRY Max Marks: 60
SECTION – I
(SINGLE 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 ONLY ONE option can be correct.
Marking scheme: +3 for correct answer, 0 if not attempted and -1 in all other cases.
 i  LiAlH 4
21. PhNH 2  CHCl3
KOH / 
  ii  H 2O
?

A) PhCH 2CH 3 B) PhNHCH 3 C) Ph  CHO D) PhCH 2  OH

22.

The product formed is

A) B) C) D) None of these
23.

A) B)

C) D)

24. Compound ‘D’ is

A) B) C) D)

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Narayana IIT Academy 20-06-21_INC.SR.IIT_*CO-SC_JEE-ADV_WAT-47_Q’P Narayana IIT Academy 20-06-21_INC.SR.IIT_*CO-SC_JEE-ADV_WAT-47_Q’P
25. Predict the product of the following reaction: 29. A basic volatile nitrogen compound (M.wt-59) gave a foul smelling gas when treated
with chloroform and alcoholic potash. A sample of the substance dissolved in
aqueous HCl and treated with HCl and NaNO2 solution at 0 C liberated a colourless
gas. After the solution of gas was complete the aqueous solution was distilled to give
an organic compound which does not contain nitrogen and which on warming with
alkali and Iodine gave a yellow precipitate. Identify the original substance. Assume
A) B) C) D) that it contains one N atom per molecule.
26. The Incorrect order of basicity among the following is/are

A) B) CH 3CH 2  CH 2  NH 2
I) II) III) IV)

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

27. The product formed in the reaction is: 30.

Hydrocarbon ‘B’ is:

A) B) A) CH 4 B) CH 2  CH 2 C) CH 2  CH  CH 3 D) CH 3.  CD  CH 2

SECTION - II
C) D) (PARAGRAPH TYPE)
28. The major product (X) of the reaction is: This section contains 3 Paragraph of questions. Each paragraph 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 -1 in all other cases.
Paragraph for Question Nos. 31 & 32:
Amides with no substituent on the nitrogen react with solution of Bromine in sodium
hydroxide to yield amines.

A) B) O||
R  C  NH 2  Br2  4 NaOH 
H 2O
 R  NH 2  2 NaBr  Na2CO3  2 H 2O

If the mechanism of the rearrangement shown in the scheme

C) D)

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Narayana IIT Academy 20-06-21_INC.SR.IIT_*CO-SC_JEE-ADV_WAT-47_Q’P Narayana IIT Academy 20-06-21_INC.SR.IIT_*CO-SC_JEE-ADV_WAT-47_Q’P

(R) The rearrangement is accelerated by incorporation of electron with drawing group
is

(S) The rearrangement is accelerated by incorporation of electron donating groups.

A) P, R are true B) Q, S are true C) Q, R are true D) P, S are true

Paragraph for Question Nos. 33 & 34:

31. Based on the above mechanism the following statement/statements are correct
(K) No change in oxidation number through out all the steps w.r.t “N”
(L) No change in oxidation number through out all the steps w.r.t carbon in 33. Which of the following amines cannot be prepared by path-I?

group
(M) If R is CH3 , the carbon in alkyl group can’t oxidized in Isocyanate form
A) B) C) D)
(N) ‘N’ gets reduced in the amine form
A) K, L, M are correct B) L, M, N, O are correct 34. Consider path II, choose the major product for 1 and 2:

C) K, M, O are correct D) L, M, O are correct

32. The correct reaction Products or/ statements

(P)

A) 1  Y , 2  X B) 1  X , 2  Y C) 1  X , 2  X D) 1  Y , 2  Y
(Q)

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Narayana IIT Academy 20-06-21_INC.SR.IIT_*CO-SC_JEE-ADV_WAT-47_Q’P Narayana IIT Academy 20-06-21_INC.SR.IIT_*CO-SC_JEE-ADV_WAT-47_Q’P
Paragraph for Question Nos. 35 & 36: SECTION - III
When an primary aromatic amine is treated with NaNO2  HCl at 00  50 C , a (Matching List Type)
This section contains four questions, each having two matching lists (List-1 & List-II). The options for
diazonium salt is formed and the reaction is called diazo reaction. In this reaction the correct match are provided as (A), (B),(C) and (D) out of which ONLY ONE is correct.
Marking scheme: +3 for correct answer, 0 if not attempted and -1 in all other cases.
mineral acid must be added to prevent the coupling reaction of diazonium salt with 37. Match the following options
excess of aryl amine. Diazonium salt is highly useful in the synthesis of number of List I Amines List II pK b values
coloured dyes.
P) 1) 3.0
35. For the following diazonium ion the decreasing order of reactivity of these ion in

azo-coupling reaction:
Q) 2) 8.8

R) CH 3CH 2 NHCH 3 3) 3.35

S) CH 3 NH 2 4) 9.4

Codes: P Q R S P Q R S
A) Q  S  R  P B) Q  S  P  R C) P  Q  R  S D) S  R  Q  P A) 3 1 4 2 B) 3 2 4 1
C) 2 4 3 1 D) 2 4 1 3
36. In the given reaction:
38. Match the following options
List I Compound List II Prepared by
P) CH 3CH 2CH 2  NH 2 1) Gabriel phthalimide synthesis
Q)  C2 H 5 3 CNH 2 2) Hoffmann bromamide synthesis
The final product is R) C2 H 5 NHCH 2CH 2COCH 3 3) Ritter reaction
S) Ph  NH2 4) Mannich reaction

A) B) Codes: P Q R S P Q R S
A) 1,2 2,3 2 4 B) 2,3 1,2 2 4
C) 1,2 2,3 4 2 D) 1,2 2 2,3 4

C) D)

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Narayana IIT Academy 20-06-21_INC.SR.IIT_*CO-SC_JEE-ADV_WAT-47_Q’P Narayana IIT Academy 20-06-21_INC.SR.IIT_*CO-SC_JEE-ADV_WAT-47_KEY&SOL

39. Match the following options
List I Compound List II Reaction
CHEMISTRY
Ph  NH 2 
CHCl3 / KOH

 Ph  NC 
LiAlH 4
 Ph  NH  CH 3
P) 1) Evolution of N 2 with HNO2 21.
22. Conceptual

Q) 2) Azo dye test

R) CH 3CH 2  NH 2 3) N-Nitroso compound with HNO2

S) 4) C- Nitroso compound with HNO2 23. Reaction proceeds via diazonium salt with neighbouring group participation.

Codes: P Q R S P Q R S
A) 1,2 2,3 1 2,4 B) 1,2 2,3 4 2
C) 1,2 2,4 1 2,3 D) 2,4 2,3 2,4 1

24.
40. Match the following
List I (Amines) List II (Distinguished by)
P) C2 H 5 NH 2 and C6 H 5 NH 2 1) Carbylamine test
Q)  C2 H 5 3 N and  C2 H 5 2 NH 2) Azo dye test

R) C2 H 5 NH 2 and  C2 H 5 3 N 3) Hinsberg reagents 25. Conceptual

26. Conceptual
S)  C2 H 5 3 N and C6 H 5 NH 2 4) Liebermann nitroso reaction 27. Conceptual
28.

Codes: P Q R S P Q R S
A) 2,3 3,4 1,2,3 1,3 B) 2 3,4 1,3 1,2,3
C) 1,3 2,3 3,4 1,2,3 D) 2 1,3,4 3,4 1,2,3

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Narayana IIT Academy 20-06-21_INC.SR.IIT_*CO-SC_JEE-ADV_WAT-47_KEY&SOL Narayana IIT Academy 26-04-20_Incoming.Sr.IIT_*CO SC_JEE-Adv_WAT-41_Q’P
CHEMISTRY MAX.MARKS: 60
SECTION- I
(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.
19. Reaction of RCONH 2 with a mixture of Br2 and KOH gives RNH 2 . The intermediates
involved in this reaction are

A) RCONHBr B) RNHBr C) RN = C = O D) RCONBr2

20. Which of the following statements are correct

A) Hinsberg test involves the reagent benzene sulphonyl chloride in the presence of
29. Conceptual aqueous KOH to distinguish primary, secondary and tertiary amines
30. Hoffman elimation
B) Libermann reaction is shown by only primary amines
35. EWG in Diazonium salt increase the rate of Azocorupling
C) Primary amines gives solid with diethyl oxalate
D) Benzene diazonium salt reacts with water to yield phenol
CHEMISTRY
21. Example of Gatterman’s reaction is
21 B 22 C 23 C 24 C 25 B
26 A 27 B 28 C 29 A 30 B
A) C6 H 5 N 2 HSO4 
CuBr
 C6 H 5 Br B) C6 H 5 N 2 HSO4 
Cu
HBr
 C6 H 5 Br

31 C 32 D 33 C 34 A 35 B C) C6 H 5 N 2Cl 
Cu
 C6 H 5Cl D) C6 H 5 N 2Cl 
HF
 C6 H 5 F
HCl BF , 
3

36 A 37 D 38 C 39 A 40 B
22. Diazocoupling is correctly represented with major product in case of
 A)

S.NO SUB QNO GIVEN.KEY FINAL.KEY REMARKS
5 CHEM 28 C A or C KEY CHANGE

6 CHEM 30 B Delete Ambiguity

7 CHEM 31 C DELETE statement O not given

No answer(IPSO attack possible
8 CHEM 36 A DELETE
and will -COOH is replaced)
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Narayana IIT Academy 26-04-20_Incoming.Sr.IIT_*CO SC_JEE-Adv_WAT-41_Q’P Narayana IIT Academy 26-04-20_Incoming.Sr.IIT_*CO SC_JEE-Adv_WAT-41_Q’P
B)
SECTION - II
(Maximum Marks : 24)
This section contains EIGHT (08) questions. The answer to each question is a NUMERICAL VALUE
For each question, enter the correct numerical value (in decimal notation, truncated/rounded off to the second
decimal place; e.g. 6.25, 7.00, -0.33, -.30, 30.27, -127.30) designated to enter the answer.
Answer to each question will be evaluated according to the following marking scheme:
Full Marks: +3 If ONLY the correct numerical value is entered as answer.
Zero Marks: 0 In all other cases.
25.
C)

To get given product from substrate mentioned through suitable path with specified
reagents. The minimum number of moles of CH3I needed for 0.01 mole of substrate is
D)
26.

23. An organic compound “A” on reduction with LiAlH 4 gave compound ‘B’. Compound B The position of principal functional group in IUPAC name of x is

with HNO2 gave ethyl alcohol, and ‘B’ on treatment with CHCl3 , alcoholic KOH formed an 27.

offensive smelling compound “ C ”. The correct combinations are

A) A is CH 3CN B) B is CH 3CH 2 NH 2 C) C is CH 3 NC D) C is CH 3CH 2 NC

24. Which of the following group on benzene ring acts as activating group for aromatic
electrophilic substitution

A) CH  B)  NHCOCH3 C) -Oph D) CH3

2 NMe3

x
A, B, C are organic compounds. If x is sum of degree of unsaturation in A, B, C then is
10

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Narayana IIT Academy 26-04-20_Incoming.Sr.IIT_*CO SC_JEE-Adv_WAT-41_Q’P Narayana IIT Academy 26-04-20_Incoming.Sr.IIT_*CO SC_JEE-Adv_WAT-41_Q’P
28. 30. Number of amines those can be synthesized from Gabriel phthalimide reaction
*  
NH 2
CH 3 MgBr  C O2 
 A 
H
B 
SOCl2
 C 
NH 3
 E  BrO
G |

| CH 3CH 2 NH 2 CH 3CH 2 NHCH 3  CH 3CH 2 3 N CH 3  C  CH 3

 H2
Pd  BaSO4
 D NaOI
 F  ppt   H |
CH3

The number of correct statements related to this sequential reactions is C6 H 5 NH 2 C6 H 5CH 2 NH 2

I) B is an acid can release CO2 from NaHCO3 31. How many of the following molecules with Hisberg’s reagent form sulphonamide, which
*
II) Both E and F have isotopic carbon as specified in initial C O2 is soluble in aqueous KOH.

III) F by reaction with silver powder release a gaseous product which form white i )C6 H 5 NH 2 ii )CH 3CH 2 NH 2 iii )  CH 3CH 2 2 NH iv )  CH 3CH 2 2 N v ) C6 H 5CH 2 NH 2
precipitate with tollen’s reagent
IV) Calcium salt of H by drydistillation gives acetone as one of the products
V) G gives yellow colour oily liquid with HNO2
VI) C by reaction with  CH 3 2 Cd form a compound which gives yellow precipitate (ppt)
32. The number of reactions given below proceed through free radical intermediate
with NaOI
I. C6 H 5 N 2Cl 
H PO
3
H O
 C6 H 6
2
2
II. C6 H 5 N 2Cl 
HBF

 C6 H 5 F
4

29. How many of the following are correct statements

III. Ar N 2 
PhSNa
 ArSph IV. C6 H 5 N 2Cl 
Cu
HBr
 C6 H 5 Br
A) Aliphatic amides are weaker bases than aliphatic amines
V. C6 H 5 N 2Cl 
CuCl
HCl
 C6 H 5Cl
B) PhCONH 2 is stronger base than CH 3CONH 2

C) SECTION – III
(COMPREHENSIN TYPE)
This section contains 2Paragraphs. Based on each paragraph, there are 2 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.
Paragraph for Question Nos. 33 to 34
An organic acid P  C11H12O2  can easily be oxidized to a dibasicacid which reacts with
ethylene glycol to produce a polymer Dacron. The isomer of same dibasicacid with
NH 3 on heating form an imide, which on further treatment with KOH and primary alkyl
D) Pyrrole is soluble in dil HCl
halide gives primary amine finally with N 2 H 4 . Up on ozonolysis “P” gives an aliphatic
E) Pyridine is more basic than pyrrole
ketone as one of the products. “P” undergoes the following reaction sequence to furnish R
F) N-phenyl hydroxyl amine reduces tollen’s reagent via Q. The compound P also undergoes another set of reactions to produce S.
G) Basic strength of Para  CH 3C6 H 4 NH 2  C6 H 5 NH 2  Ortho  CH 3C6 H 4 NH 2

H) Tertiary aromatic amines react with nitrous acid to yield P – nitroso derivatives

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Paragraph for Question Nos. 35 to 36
Internal elimination is observed in case of esters, alkyl xanthates, 3 - amine oxides.
Thermal elimination of these compounds is syn – periplanar in general. But thermal
elimination of quaternary ammonium hydroxides is similar to bimolecular
elimination  E2  , means proceed for anti – periplanar elimination. Thermal eliminations
prefer Hoffman’s products as major.

35.

33. True about compound R is

I. R can undergoes substitution at   carbon of principal functional group with Red P +

Br2

II. R has one chiral carbon

III. R when heated with NH 3 form a compound which gives secondary amine by warming
with alcoholic KOH  Br2

IV) Functional group in R can reduce to primary alcohol by HCHO / ConC OH  , 

A) I, II only B) I, II, IV, only C) I, II, III only D) I, II, III, IV

34. The compound “ S ” is

36.

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Narayana IIT Academy 26-04-20_Incoming.Sr.IIT_*CO SC_JEE-Adv_WAT-41_KEY&SOL Narayana IIT Academy 26-04-20_Incoming.Sr.IIT_*CO SC_JEE-Adv_WAT-41_KEY&SOL
CHEMISTRY
25.

Sec: Incoming.SR_*COSC WTA-42 Date: 03-05-20

Time: 3hrs 2018-P1 Max.Marks: 180
KEY SHEET
26.

27.

CHEMISTRY
19 AC 20 ACD 21 BC 22 ACD 23 ABD

24 BCD 25 0.03 26 4.00 27 1.60 28 3.00

28. I, II, VI are correct statements
29 7.00 30 2.00 31 5.00 32 4.00 33 A

34 B 35 A 36 B

29. Pyrrole is insoluble in HCl

30. CH 3CH 2 NH 2 , C6 H 5CH 2 NH 2 can be synthesize
31.

32. I, III, IV, V are proceeding through free radical intermediates

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Narayana IIT Academy 26-04-20_Incoming.Sr.IIT_*CO SC_JEE-Adv_WAT-41_KEY&SOL Narayana IIT Academy 18-06-23_SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-43_Q’P

33. CHEMISTRY MAX.MARKS: 60
SECTION- I
(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.
19. Among the following, the reaction(s) that yield a dicarboxylic acid is(are):
Me
O Cl
34.
(i) KMnO 4, KOH, 
(i) H2/Pd-BaSO 4, Qunoline
+
(ii) H 3O
(ii) Ammonical AgNO 3
CHO +
(iii) H 3O
A) Me O B)
CONH 2 CH 2Cl

CN Cl
+
H3O ,  (i) KCN
+
(ii) H 3O , 
C) D)
20. Among the following, the correct order(s) is (are):

A) Basic strength: (CH 3)3N < CH3NH2 < (CH3)2NH

B) boiling point - (CH 3)2NH < CH 3CH2OH < CH3CH2NH2

36. C) solubility in water - C 6H5NH2< (C2H5)2NH < C2H5NH2

basic strength - C 6H5NH 2 < pyridine < C 6H5CH 2NH 2
D)
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Narayana IIT Academy 18-06-23_SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-43_Q’P Narayana IIT Academy 18-06-23_SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-43_Q’P
21. Which of the following reaction(s) produces a compound which gives foul smelling 23. Choose the correct statement(s) regarding the following compounds:
NH2 NHMe NMe2
compound with CHCl3 in ethanolic KOH?
O
1. AgCN 1. SOCl 2, 
CH 3CH 2Cl Me NH2 2. Na - Hg/EtOH
2. LiAlH 4
A) B) (I) (II) (III)
O OH A) Basic strength of the compounds follows the order (III) >(II) > (I)
N2Cl
B)(III)on reaction with NaNO2 and HCl at 0o C gives para- nitroso derivative as the
1. CuCN/KCN 1. NH3, 
major product
2. H2, Pd - C 2. Br2, NaOH
C) (II)on reaction with CH3Cl in presence of AlCl3 forms para- methylated derivative
C) D)
as the major product.
22. Consider the following reaction sequence: D) (I)on reaction with CHCl3 in presence of ethanolic KOH forms phenyl isocyanide.
Me O
1. LiAlH 4
24. The product [P] formed in the following reaction has generic name ‘Acetaminophen’
(CH3CO) 2O
[W] [Z] can act as analgesic (pain reliever) and antipyretic (reduce fever) drug. The correct
O 2. H 2O Excess
Me option(s) for [P] is (are):
+
CrO 3/H
NH2


[X] [Y] (CH3CO)2O (1 eq)
[P]
pyridine
The correct statement(s)about [W], [X], [Y] and [Z] is (are): (major)
OH
A) [W]has two asymmetric carbons. NH2 O

B) [X] gives effervescence of CO 2 with aq.NaHCO 3 Me

C) [Y] can show iodoform test

A) Its structure is OH
D) Molecular formula of [Z] is C 7 H14O 3
B) Its IUPAC name is 4-aminophenylethanoate
C) It gives positive carbylamine test
D) Its IUPAC name is N-(4-hydoxyphenyl)ethanamide

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Narayana IIT Academy 18-06-23_SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-43_Q’P Narayana IIT Academy 18-06-23_SR.IIT_*CO-SC(MODEL-A)_JEE-ADV_WAT-43_Q’P

SECTION - II 28. The molecular formula the major product [V] of the following reaction is CxHyOz.
(Maximum Marks : 24)
This section contains EIGHT (08) questions. The answer to each question is a NUMERICAL VALUE The sum (x+y+z) is______.
For each question, enter the correct numerical value (in decimal notation, truncated/rounded off to the second O O
decimal place; e.g. 6.25, 7.00, -0.33, -.30, 30.27, -127.30) designated to enter the answer. O
Answer to each question will be evaluated according to the following marking scheme:
Full Marks: +3 If ONLY the correct numerical value is entered as answer. (i) O 3, H2O 2
O [V]
Zero Marks: 0 In all other cases. +
(ii) H 3O , 
25. The total number of carbon atoms and hetero atoms present in the major product [Q] of
O
the following reaction sequence is____. O O

NH2 29. The molecular weight (g/mol) of the major product[P] of the following reaction is ___
+ NO 2
NaNO 2 - HCl 1Naphthylamine, H
[P] [Q] (i) Br 2(excess), CH3COOH
273 K
[red azo dye] (ii) Sn/HCl
o
[P]
SO 3H (iii) NaNO 2/ HCl (excess), 0 C
(iv) HBF 4 (excess)
[Sulphanilc acid] NH2
(v) Heat
[Atoms other than C and H are considered as hetero atoms]
[Use: molar mass H=1, C=12, N=14, O=16, F=19, Br = 80 ]
26. The total number of isomeric amines with molecular formula C4H11N which on
30. The degree of unsaturation of the major product [U] of the following reaction sequence
reaction with Hinsberg reagent forms sulphonamides which are insoluble in aqueous is____.
KOH is____. NH2 OH
0
(i) NaNO 2/HCl, 0 C
27. Aniline reacts with mixed acid (conc. HNO3 and conc. H2SO4) at 288 K to give [P] (51 [U]
(ii) aq. NaOH
%), [Q] (47%) and [R] (2%).
1. Ac 2O, Pyridine 1. Sn/HCl
31. The weight (g) of major product[Q] formed in the following reaction sequence is ____.
2. Br2/ CH3COOH 2. Br2/ H2O (excess) O
[R] [S] [T](Major)
+ HCN/ KCN 95% H2SO 4
3. H3O 3. NaNO 2, HCl/273 K Me [P] [Q]
Me Heat
75% yield
4. NaNO 2, HCl/273 K 4. H3PO 2
(0.2 mol) (80% yield)
5. EtOH, 
[Use: molar mass H=1, C=12, N=14, O=16, S=32 ]
Sum of locant numbers of bromine in [T] according to IUPAC nomenclature is ____.

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32. Consider the following reaction sequence. Paragraph for Question Nos. 35 to 36:
HNO 3 NH 4SH An organic acid P (C11H12O2) can easily be oxidized to terephthalic acid. Upon
Nitrobenzene [Q]
H2SO 4
[R] ozonolysis, P gives an aliphatic ketone as one of the products. P undergoes the
[P]
following reaction sequences to furnish R viaQ. The compound P also undergoes
(mononitration)
another set of reactions to produce S.
The number of moles of electrons involved in conversion of 1 mole of [P] into [Q] and
x
[Q] into [R] are, x and y, respectively. The value of is_____.
y
SECTION – III
(COMPREHENSIN TYPE)
This section contains 2Paragraphs. Based on each paragraph, there are 2 questions. Each question has 4
options (A), (B), (C) and (D) for its answer, out of which ONLY ONE option can be correct. 35. The compound [R] is:
Marking scheme: +3 for correct answer, 0 if not attempted and -1 in all other cases. HO 2C
Me
Paragraph for Question Nos. 33 to 34:
COOH
2 NH3,  Strong Heat (i) KOH aq NaOH Me Me CO 2H
[P] [R] [S] [T]
(ii) PhCH 2Cl 
COOH
(i) (CH3CO)2O, pyridine
Br 2/NaOH A) Me B) Me
(ii) LiAlH 4
Me Me
[Q]
Me
[U]
33. The compound [Q] is:
O O CO 2H
O
CO 2H
Br NHBr Me
NH2
N Br C) Me D) Me
Br NHBr

NH2
36. The compound [S] is:
A) O B) O C) O D)
Me
34. The compound [U] is:
O OH Me
Me Me Me

NH Me NH Me Me
Me Me

A) B) NH
NH2 Me
NH Me NH2 NH
Me H2N
A) B) C) D)
C) D)
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CHEMISTRY
19 ABC 20 ACD 21 BCD 22 ABC 23 ABD

24 D 25 23 26 3 27 11 28 26

29 272 30 10 31 12 32 0.33 33 D

34 C 35 B 36 A

Narayana IIT Academy 18-06-23_SR.IIT_*COSC(MODEL-A)_WAT-43_Key&Sol’s Narayana IIT Academy 18-06-23_SR.IIT_*COSC(MODEL-A)_WAT-43_Key&Sol’s

CHEMISTRY 22.
19. OH
Me O OCOMe
Me COOH 1. LiAlH 4 CH 2OH (CH3CO) 2O
Me CH 2OCOMe
O 2. H 2O Me
Me Me
(i) KMnO 4, KOH,  Me
+
+ CrO 3/H
(ii) H 3O
O

Me O HO O CO 2H Me
Me Me

Me O
O Cl 23
CHO COOH NC
NH2

(i) H2/Pd-BaSO 4, Qunoline (ii) Ammonical AgNO 3 CHCl 3/KOH

+
(iii) H 3O
CHO CHO COOH
(I)
CONH 2 COOH NHMe
CN COOH
+
H3O ,  MeCl/AlCl 3
No reaction

CH 2Cl COOH (II)

Cl NMe2 NMe2
Cl
(i) KCN
+ NaNO 2/HCl
(ii) H 3O , 
0 0 0
20. Solubility of 3 -amine< 2 - amine< 1 -amine
Aniline is slightly soluble but ethylamine is very soluble (III) NO
Boiling point- Alcohol> 10 -amine> 20 -amine > 30 -amine (comparable molar mass) 24.
1. AgCN NHCOCH 3
CH 3CH 2Cl MeCH2NHCH 3 NH2
2. LiAlH 4
21.
O (CH3CO)2O (1 eq)
SOCl 2,  Na-Hg/EtOH
Me-CN MeCH 2NH 2 pyridine
Me NH2
N2Cl CH 2NH 2 OH
OH
(major)
1. CuCN/KCN 25.
NH2
2. H2, Pd - C

O OH N
NH2 N2Cl
NH2 N
1. NH3, 
+
NaNO 2 - HCl 1Naphthylamine, H
2. Br2, NaOH 273 K

SO 3H SO 3H SO 3H
[Sulphanilc acid] [red azo dye]

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Narayana IIT Academy 18-06-23_SR.IIT_*COSC(MODEL-A)_WAT-43_Key&Sol’s Narayana IIT Academy 18-06-23_SR.IIT_*COSC(MODEL-A)_WAT-43_Key&Sol’s
26. 33 and 34.
Me O
O
NH Me NH NH
Me Me Me CONH 2 NH2
N
Me NH
Me Ph
27. CONH 2 NH2
O
Br O
NH2 Q
P R S
1. Ac2O, Pyridine 1. Sn/HCl
NO2 NO2
2. Br2/ CH3COOH 2. Br2/ H 2O (excess)
+
3. H3O 3. NaNO2, HCl/273 K Br Br NH2
NH Me
4. NaNO2, HCl/273 K 4. H3PO 2 Br
Br
5. EtOH, 
T
U
28. 35.
O O COCl
O CO 2H CO 2H
O O Me Me SOCl 2
Me
H2/Pd-C

Me Me
Me Me
(i) O 3, H2O 2
O + Me
(ii) H 3O ,  MeMgBr-CdCl 2
MgCl OH
O O O COMe
O O Me Me 1. HCl Me
Me Me NaBH 4
29. 2. Mg-Et2O
F Me Me
NO 2 Me
(i) Br 2(excess), CH3COOH
CO 2
(ii) Sn/HCl Me
o
(iii) NaNO 2/ HCl (excess), 0 C
Br Br Me CO 2H
(iv) HBF 4 excess
NH2 F
(v) Heat Me

30. 36.
NH2
NH2 OH N N CO 2H CONH 2 Me
-
Me 1. H2/Pd C Me Br 2, NaOH
0
(i) NaNO 2/HCl, 0 C 2. NH3, Heat Me
Me Me
(ii) aq. NaOH
CHCl 3/KOH
OH
31. NC
OH COOH NHMe
O Me H2/Pd-C
Me
HCN/ KCN Me 95% H2SO 4 Me
Me
Me Me Heat Me Me Me
75% yield CN
(80% yield)
32.
NO 2 NH2

HNO 3 NH 4SH
Nitrobenzene
H2SO 4
[P] NO 2
NO 2
(mononitration)

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