Narayana IIT Academy 21-02-21_ Jr.

IIT_*CO-SC _JEE-ADV_WAT-37_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. Consider the given reaction sequence

Among the following [X] can be

22. Consider all possible isomeric ketones including stereoisomers of MW = 100, All
these isomers are independently reacted with CH3MgBr (NOTE: stereoisomers are
also reacted separately and also consider no racemization of alpha carbon of the
carbonyl group during the reaction). The total number of ketones that give a racemic
product is/are

23. Consider the given reaction sequence

Number of secondary hydroxyl group(s) presents in [Q] is

24.
H+/H2O
[X] Major

BH3·THF
[Y] Major
H2O2, -OH

Hg(OAc)2, H2O
[Z] Major
NaBH4

Jr.IIT_*CO SC Page 11
Narayana IIT Academy 21-02-21_ Jr.IIT_*CO-SC _JEE-ADV_WAT-37_Q’P
How many of the following statements are correct with respect above scheme of

reactions?

I) ‘Z’ is primary alcohol

II) ‘Y’ forms immediately turbidity with Lucas reagent

III) ‘X’ is 2º alcohol

IV) Both ‘Y’ and ‘Z’ are 2º alcohol

V) All (X, Y & Z) change the orange colour of acidified potassium dichromate to green

under normal conditions.

25. Position of the Br (as per IUPAC system) in major organic product P

26. How many of the following are more reactive than p-nitro fluorobenzene with NaOH?

F F
F F
NO2 O2 N NO2
NO2

NO2
NO2 NO2

27. How many alkenes give 2-methylbutan-2-ol as a major product upon reaction with dil

H2SO4?

28. One mole of acidified K2Cr2O7 oxidizes how many moles of butan-2-ol to butan-2-one

Jr.IIT_*CO SC Page 12
Narayana IIT Academy 21-02-21_ Jr.IIT_*CO-SC _JEE-ADV_WAT-37_Q’P
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. Terpinen-4-ol is an active ingredient in tea tree oil has the following structure

The correct observation for the terpinen-4-ol is/are

A) It can rotates the plane of plane polarized light
B) It reacts with Bayer’s reagent can form triol

C) On reaction with excess of NaBr and H2SO4, it can form a dibromo compound

D) On ozonolysis (with O3; Zn/H2O) it gives a compound with molecular formula

C10H18O3

30. In the following reaction three products [P], [Q], [R] are obtained

The approximate experimental yields of the three compounds were 64%, 33% and 3%
respectively. Choose the correct option(s) among the following

A) B)

C) D)

31. Which among the following new C-C bond formed in the product is/are?

A) B)

CH3MgCl
Ethylene oxide
C) D) NH4Cl

Jr.IIT_*CO SC Page 13
Narayana IIT Academy 21-02-21_ Jr.IIT_*CO-SC _JEE-ADV_WAT-37_Q’P
32. Choose the correct statement regarding major organic product obtained in the given

reaction

A) Tertiery alcoholic group present in [P]

B) There is a one chiral centre present in [P]

C) [P]is an isomer of reactant.

D) During this reaction mechanism hydroxyl group is the one which protonated first

33. An alkyl halide(X) on reaction with ethanolic sodium hydroxide forms an alkene(Y)

which on further reaction with HBr gives the same alkyl halide. The alkene(Y) on

reaction with HBr/peroxide followed by reaction with Mg metal followed by reaction

with HCN produces an aldehyde (Z) (here consider the reaction between RMgX and

HCN is nucleophilic addition not the acid base reaction). Among the following Z can

be

CHO
A) B) C) D)

34. Which of the following gives pair of diastereomer on reaction with NaBD4?

A) B) C) D)

Jr.IIT_*CO SC Page 14
Narayana IIT Academy 21-02-21_ Jr.IIT_*CO-SC _JEE-ADV_WAT-37_Q’P
35. Possible products in the given reaction

C4H8O2 1. CH3MgBr (excess)

possible esters
2. NH4Cl

H3C C2H5
OH H3C OH

A) H3C B) C2H5

C2H5 C2H5

H OH H3C OH

C) H D) H3C

36. Select the correct statement(s) regarding the given molecules?

A) The rate difference between III and IV is more compare to I and II with NaOH

B) The rate difference between III and IV is less compare to I and III with NaOH
C) I and III react with same rate with NaOH
D) Resonance effect is more in I than II
37.

Which of the following reagents can bring the above transformation in good yield?

A) NaBH4 / H+ B) LiAlH4 / H+ C) H2; Pd/C D) CH3MgBr/H+

38. Which among the following has/have lower boiling point than butan-1-ol

A) pentan-1-ol B) butan-2-ol C) propan-1-ol D) ethanol

Jr.IIT_*CO SC Page 15
Narayana IIT Academy 21-02-21_ Jr.IIT_*CO-SC _JEE-ADV_WAT-37_Q’P
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, R
and 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. Match the given reaction in column–I with appropriate statement(s) of column-II
Column-I Column-II
One of the product shows optical
A) P)
isomerism
H 3C
H2SO4 / 
Major product contains even
dehydration number of α-hydrogens
B) Q)
Ph (hydrogens which can involve in
hyperconjugation)
OH

One of the product shows

C) R)
geometrical isomerism

Reactant can turns acidified

D) S)
dichromate to green

T) Will not undergo dehydration

40. Match the conversion in Column-I with appropriate reagent(s) of column-II
Column-I Column-II

PCC (pyridinium
A) P)
clorochromate)

B) Q) Cu/573K

K2Cr2O7 + dil H2SO4 /293

C) R)
K

D) S) KMnO4/H+ / 293 K

T) H3PO4/358K

Jr.IIT_*CO SC Page 16