Chemistry: NO CHO

JEE (Main + Advanced) 2021 DPP - 03 Chemistry
CHEMISTRY
Course : JEE (Main + Advanced) 2021
DPP
DAILY PRACTICE PROBLEM
Target : JEE (Main + Advanced) DPP NO. # 03

Multiple choice Question with one option correct Q.1 to Q.10
Multiple choice Question with one or more than one may be correct Q.11 to Q.30
Numerical Based Question (no negative marking) Q.31 to Q. 50
DPP Syllabus : IUPAC Nomenclature, GOC-1, 2 & 3, Structural & stereoisomerism and POC
1. Which of the following structure represent incorrect IUPAC name ?

NO2
(A) CH3O 6-Methoxy-1-nitrocyclohex-1-ene
(B) 6-(Cyclobut-2-enyl) hex-2-ene
CONH2
(C) Br N=O 2-Bromo-6-nitrosobenzenecarboxamide
Me Me
(D) O 2-Bromo-5,5-dimethylcyclopent-3-en-1-one
Br
2. How many possible isomeric alkenes give 2, 3-Dimethylpentane on catalytic hydrogenation ?
(A) 4 (B) 6 (C) 8 (D) 5
3. Column - I Column - II
(Orbital overlaps)
+ +
(1) (P) p(filled) - *(vacant)
–
O O
(2) – (Q) (filled) - p(vacant)

H+
– C—H
(3) H (R) (filled) - p(vacant)
+
(4) H (S) p(filled) - (vacant)
C
+ H
H
(T) (filled) - *(vacant)
(A) (1)R ; (2)P ; (3)T ; (4)Q (B) (1)P ; (2)R ; (3)Q ; (4)T
(C) (1)R ; (2)Q ; (3)T ; (4)P (D) (1)S ; (2)R ; (3)P ; (4)Q
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4. List-I List-II
(Compound) (Statements)
H O
C
(P) (1) It can show tautomerism, optical isomerism but not
Ph
geometrical isomerism.
H3C CHO
(Q) (2) It can show tautomerism, geometrical isomerism but
Ph
not optical isomerism.
CHO
(R) (3) It can show geometrical isomerism, optical isomerism but not
Ph
tautomerism.
O
(S) (4) It can show tautomerism, geometrical isomerism &
Ph
also optical isomerism.
Code :
P Q R S
(A) 2 1 3 4
(B) 2 3 4 1
(C) 3 2 4 1
(D) 2 3 1 4
5. Racemic mixture of tartaric acid can be resolved by addition of -
H OH CH3
OH
(A) (B)
Me (C) H (D)
Me H
H H D D
6. Give the correct order of initials T or F for following statements. Use T if statement is true and
F if it is false.
I. Me–CH=C=C=CH–Br is optically active.
II. All optically active compounds are chiral.
III. All chiral pyramidal molecules are optically inactive.
IV. CH3–CH2–CH2–COOH and CH3–CH–CH3 are positional isomers.
COOH
(A) FTFF (B) FTFT (C) TFTF (D) FTTF
7. Sum of total number of chiral centres (x) and total number of pairs of enantiomers (y) for following
structure is :-
Cl
Cl
(A) 2 (B) 3 (C) 4 (D) 5
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Comprehension
A research scholar synthesised the compound A in the laboratory.
CH3
O O CH
A is 3
CH2–COOH
He wanted to study this compound in acidic medium and kept for some time with heating. After an hour,
he surprised because he got the mixture of two different compounds B and C. He studied their properties
and compared them with A.
A B C
Reaction with NaHCO3 CO2 No reaction No reaction
Blue litmus red No No
NaOI No No Yellow ppt
[Ag(NH3)2]+ No No Silver mirror

H3O / 
[H int : A   B  C]
On the basic of above information answer following question 8, 9 and 10
8. Compound B is :-
O
O O
O O
(A) (B) O (C) (D) None
CH3
OH CH2–OH
9. Compound C is :-
O
(A) CH3–C–CH3 (B) CH3–CH2–CH=O (C) H–C–H (D) CH3–CH=O
O
10. B is formed due to :-
(A) Cleavage of C–O bond followed by esterification between –COOH & –OH present.
(B) Decarboxylation of –COOH group
(C) Oxidation of –CH2COOH into –COOH
(D) None
11. Correctly matched option(s) for following compound is/are :

x
O
C CH2–CH3
CH3–CH2 O
y z
(A) x > y > z (Bond order)
(B) Ethyl ethnoate (IUPAC name)
(C) x > y > z (Bond energy)
(D) z > y > x (Bond length)
12. In which of the following compounds inductive effect, mesomeric effect and hyperconjugation all three are
present ?
:
CH3 O–CH3 OCH3 NH2
(A) (B) (C) (D)

O H3C
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13. Identify the compound(s) in which electron density is more than benzene?
CH3
+
N CH3–N–CH3
:
C= N O
(A) (B) (C) (D)
14. Match the column :-

Column - I Column - II
(1) (P) Group attached with benzene ring is + M group
(2) (Q) Group attached with benzene ring is – M group
(3) (R) Group attached with benzene ring is –I
(4) (S) Group attached with benzene ring is +I
Choose the correct options :

(A) (1) P (2) Q (3) P (4) Q (B) (1) R (2) R (3) R (4) R
(C) (1) P (2) Q (3) R (4) Q (D) (1) P (2) Q (3) R (4) S
15. Select the order which is correct among following :
(A) > > > (Stability of alkene)

–
(B) > + > – + (Stability order of resonating structure)
N N N
H H H
< <
(C) – O– (Stability order)
N N
–
CH3
N N
(D) < < (Basic strength order)
N O N
H H
16. Correct statement is/are regarding carboxylic acids having molecular formula (C8H8O2) containing
aromatic ring.
(A) The total number of carboxylic acids (with one benzene ring) is 4.
(B) Out the three Toluic acids, the ortho isomer is the strongest acid.
(C) All these Toluic acids are weaker acids than benzoic acid.
(D) All these are weaker acids than H2CO3.
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17. Select the correct statement(s) about the following reaction :-

O traces of H+ or OH O
H
N N
OCH3 OCH3
O H O
O O
(I) (R) Thalidomide derivative (II)
(A) It is an isomerisation reaction.
(B) It is a racemisation reaction.
(C) The reaction is passing through the process of enolisation.
(D) I and II are tautomers.
18. Which of the compounds will show G.I. ?
(A) D–C C–C–C C–D (B) O S S O

C
HC
HC=
D
(C) (D) 2-chloro pent-1-ene
19. Which enamine of molecular formula C5H11N can exhibit geometrical isomerism ?
NH2
(A) (B) NH (C) N (D)
NH2
20. Which of the following compound(s) have R configuration ?
Br CHO
Br H D H H
T D + –
(A) Cl (B) (C) (D) N Cl
H Me H OH D CH3
H
CH3 D T
21. Identify compounds having plane of symmetry ?
O H
Br
(A) H–P O Me (B)
H
O Me
O
O
(C) (D)
Me
Me O
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22. Select the correct statements :-
(A) A racemic mixture can be distinguished from a meso or an achiral compound by optical resolution.
(B) d and  stereoisomer of the same compound are enantiomers of each other.
(C) A chiral compound may or may not have assymetric carbon.

(D) There is no obvious correlation that exists between the configurations (R or S) of enantiomers and the
direction [(+) or (–)] in which they rotate plane polarised light.
23. The element(s) of symmetry present in the following molecule is/are :-
(A) Alternating axis of symmetry (B) Plane of symmetry

(C) Axis of symmetry (D) Centre of symmetry
24. Mark the compound given below which have atleast one meso stereoisomers :-
(A) Cyclopentane-1, 3-dicarbaldehyde (B) Hexane-1,2,3,4,5,6-hexaol
(C) 2,3,4,5,6-pentahydroxyhexanal (D) 2,3-Dihydroxybutanedioic acid
Br CH3
25.
CH3 Br
Choose the correct option/s according to the given compound.
(A) Total stereoisomers are five.
(B) All stereoisomers are optically active.
(C) All stereoisomers are optically inactive.
(D) Four stereoisomers have plane of symmetry & one has centre of symmetry.
26. Match the column (I) and (II) :-

Column-I Column-II
Molecule Property
CH3
(1) Cl (p) Chiral atom is present
Br H
(2) O (q) Molecule is chiral
O
CH3
(3) CH3 (r) Plane of symmetry is present
(4) Cl Cl (s) Centre of symmetry is present
(A)(1)  p ; (2)  q ; (3)  p ; (4)  r (B) (1)  q ; (2)  q ; (3)  r ; (4)  s

(C) (1)  r ; (2)  q ; (3)  p ; (4)  s (D) (1)  q ; (2)  p ; (3)  r ; (4)  s
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27. The correct statement about the following compound is :-
HO OH
(A) It has four enantiomeric pairs.
(B) It has six diastereomers.
(C) It has two optically inactive stereoisomers.
(D) It has only one enantiomeric pair with cis and trans configuration about the two double bonds.
28. Identify compounds correctly matched with number of stereoisomers :

CH3
CH
Cl
CH
Cl
(A) CH3–CH=CH–C–CH=CH–CH3 = 4 (B) Cl = 5
H Cl
Cl Cl
(C) = 7 (D) CH3–(CH=CH—

)3 CH3 = 6
Cl Cl
Cl Cl Cl
29. CH3–CH–CH–CH–Br
(A)
H
H Y
For the above compound (A) the given newmann projection can be represented
Cl X
Cl
X & Y are respectively :
(A) CH3 and CHClBr (B) CH3 & CH3
(C) –CH–CH3 & Br (D) –CH–Cl & –CH3
Cl CH3
30. Identify compounds or reactions correctly matched with Keq. ?
O Keq. > 1
(A) (B)
O
OH
OH
Et Me OH OH
OH
Keq. > 1 Keq. < 1
(C) Me Et (D) OH
31. What is the number of all the structural isomers of octane with five carbons in their principal chain ?
32. Number of structural isomers possible from the molecular formula C2H2FCl BrI is :
33. Total number of ether structure possible for molecular formula C5H12O = N1 :
Total number of structural isomers possible for molecular formula C4H9Cl = N2 :

value of (N1 + N2) is
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O O
O3/H2O
34. C12H16 CH3–C–CH3 + HOOC–C–COOH
(A) (2 mole) (2 mole)
(1 mole)
How many  bonds are present in compound A ?
35. How many 1,2-shifts are involved in the following rearrangement of carbocaiton ?
+
+
36. How many of the following orders are correctly matched ?
(i) > > (Heat of combustion)
CH+2 CH+2 +
(ii) (Carbocation stability)
> >
(iii) > > (Stability of free radical)
+
(iv) + (Number of resonating structure involving monocation)
<
COOH COOH COOH

CH3
(v) > > (Acidic strength)
CH3
CH3
(vi) > (Stability of alkene )
>
N N
(vii) > > (Basic strength)
:
N N
H H
+
(viii) + + (Stability of carbocation)
OMe > OMe >
37. + NaH (P) + (Q)
If X = Number of resonating structure of (P) involving monoanion &

Y = Molecular weight of gas (Q).
Then find out the value of (X + Y) :
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38. If Number of Aromatic compounds are X.
Number of Non Aromatic compounds are Y.
and number of Anti aromatic compounds are Z.
Then value of (X + 2Y – Z) is :
:
O H NH2
B N
:
:
: :
O N
(a) (b) (c) H
(d)
O
– + H –
:
:N N
H
(e) (f) (g) (h)

39. How many of the following orders are correctly matched ?
(i) (Heat of hydrogenation)
> >
O O
(ii) (Solubility in water)
>
H3C CH3 H3C H
(iii) C=C < C=C (Melting point)
H H H CH3
+ +
(iv) (Carbocation stability)
+ > >
NH2 NH2
H3C CH3
(v) (Basic strength)
>
–
O
(vi) > (Number of resonating structure involving monoanion)

–
(vii) –NO2 > –CN > –F > –I (–I effect) –I
H3C NO2 H3C H
(viii) C=C C=C (Dipole moment)
<
H H H NO2
+
40. How many of the following carbocation is more stable than CH3–CH–CH3 :
+
+
+ Me
(a) CH3–CH+2 (b) (c) N (d)
Me
+ +
(e) (f) + (g) Ph–CH2 (h)
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41. How many of the following are less basic than Et–NH2

(i) NH2–Cl (ii) CH3–CH2–OH (iii) CH3–CH2–NH (iv) O2N–CH2–NH2
(v) F3C–CH2–NH2 (vi) Et–NH–CH3 (vii) Et–NH–Et (viii) CH3–NH2
42. How many stereoisomers are possible for the following :

Me CH=CH–CH=CH2
Me CH=C=C=CH–Me
43. How many compounds are there which can show geometrical isomerism ?
H H O
Cl N
(i) (ii) HN NH (iii) (iv)
N
H
O O O
(v) (vi) O O (vii) (viii)
O O
Br Br
(ix)
44. Allegra, a common prescription drug with the structure shown below, is given for the treatment of seasonal
allergies. How many stereogenic carbon does Allegra possess?
CH3
COOH
CH3
H N
OH
HO
45.
The total number of isomeric organic products (Y) formed is :-

46. How many optically active compounds are possible in the following reaction ?
CH3
Cl2/h Cl2/h
Product (S)
monochlorination eksuksDyksjhuhdj.k
mRikn product (S)
CH3
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47. A smallest, optically active, acyclic alkane can obtained by catalytic hydrogenation of any of the five
structural isomers of an alkene. How many of these alkenes are chiral ?
48. Calculate sum of X and Y in the given molecules.

X = Number of molecule having plane of symmetry
Y = Number of molecule having centre of symmetry
Cl
H OH Br Br
(i) (ii) (iii)
Br Br
Cl
CH3
D OH
(iv) (v) (vi)
H3C CH3 HO D
49.
X : Write the number of that compound which show geometrical isomerism.

Y : Write number of that compound which show optical isomerism.
Write the sum of X + Y = ?
50. Identify total number of compounds having “D” configuration :

O
CHO OH OH
C–H
H OH
(ii) HOCH2 (iii) HOCH2 OH
(i)
HO CH2OH C–H
H OH O H OH
H
CH2OH
O
HO H
C–H H HO H
H OH HOCH2 OH
(iv) (v) (vi) H OH
H OH H OH
H O
H OH C–H
C–H
CH2OH O
O
O
C–H
(vii) H OH
HO H
CH2OH
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ANSWER KEY OF DPP-03

1. (D) 2. (C) 3. (A) 4. (B) 5. (D) 6. (A) 7. (B)
8. (A) 9. (D) 10. (A) 11. (ACD) 12. (CD) 13. (BC) 14. (ABC)
15. (ACD) 16. (AB) 17. (ABC) 18. (ABC) 19. (ABC) 20. (ABC) 21. (ABC)
22. (ABCD) 23. (ABC) 24. (ABD) 25. (ACD) 26. (AB) 27. (ABC) 28. (ABCD)
29. (AC) 30. (ABCD) 31. 6.00 32. 7.00 33. 10.00 34. 4.00 35. 4.00
36. 3.00 37. 7.00 38. 7.00 39. 5.00 40. 5.00 41. 5.00 42. 16.00
43. 6.00 44. 1.00 45. 1.00 46. 4.00 47. 2.00 48. 6.00 49. 4.00
50. 6.00
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Chemistry: NO CHO

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JEE (Main + Advanced) 2021 DPP - 03 Chemistry

Target : JEE (Main + Advanced) DPP NO. # 03

1. Which of the following structure represent incorrect IUPAC name ?

(B) 6-(Cyclobut-2-enyl) hex-2-ene

(2) – (Q) (filled) - p(vacant)

(P) (1) It can show tautomerism, optical isomerism but not

11. Correctly matched option(s) for following compound is/are :

CH3 O–CH3 OCH3 NH2

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

14. Match the column :-

(1) (P) Group attached with benzene ring is + M group

(2) (Q) Group attached with benzene ring is – M group

(3) (R) Group attached with benzene ring is –I

(4) (S) Group attached with benzene ring is +I

Choose the correct options :

(A) > > > (Stability of alkene)

17. Select the correct statement(s) about the following reaction :-

18. Which of the compounds will show G.I. ?

(A) D–C C–C–C C–D (B) O S S O

(C) (D) 2-chloro pent-1-ene

(C) A chiral compound may or may not have assymetric carbon.

23. The element(s) of symmetry present in the following molecule is/are :-

(A) Alternating axis of symmetry (B) Plane of symmetry

26. Match the column (I) and (II) :-

(3) CH3 (r) Plane of symmetry is present

(4) Cl Cl (s) Centre of symmetry is present

(A)(1)  p ; (2)  q ; (3)  p ; (4)  r (B) (1)  q ; (2)  q ; (3)  r ; (4)  s

28. Identify compounds correctly matched with number of stereoisomers :

(C) = 7 (D) CH3–(CH=CH—

Total number of structural isomers possible for molecular formula C4H9Cl = N2 :

36. How many of the following orders are correctly matched ?

(i) > > (Heat of combustion)

(iii) > > (Stability of free radical)

COOH COOH COOH

37. + NaH (P) + (Q)

If X = Number of resonating structure of (P) involving monoanion &

(e) (f) (g) (h)

(vi) > (Number of resonating structure involving monoanion)

42. How many stereoisomers are possible for the following :

The total number of isomeric organic products (Y) formed is :-

48. Calculate sum of X and Y in the given molecules.

X : Write the number of that compound which show geometrical isomerism.

50. Identify total number of compounds having “D” configuration :

ANSWER KEY OF DPP-03

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