ORGANIC CHEMISTRY

TARGET : JEE (ADVANCED)

  INFORM ATIO


E E ST
DPP DAILY PRACTICE PROBLEMS

Course : JP, JF, JR

NO. 3

DPP Syllabus : Organic Nomenclature, Structural Isomerism, Structure Identification, POC, Stereoisomerism, GOC-I & GOC-II

DPP No. # 3
Total Marks: 160 Max. Time: 106 min.
Single correct Objective ('–1' negative marking) Q.1 to Q.8 (3 marks, 2 min.) [24, 16]
One or more correct objective ('–2' negative & partical marking) Q.9 to Q.23 (4 marks, 2 min.) [60, 30]
Comprehension SCQ ('–1' negative marking) Q.24 to Q.35 (3 marks, 2 min.) [36, 24]
Integer type ('1' negative marking) Q.36 to Q.43 (3 marks, 3 min.) [24, 24]
Match the Following (each row '(2, -1)' negative marking) Q.44 to Q.45 (8 marks, 6 min.) [16, 12]

* Marked Questions may have more than one correct option.

1. Which of the following compounds might be useful to the chemist trying to increase the optical purity of
the (d) sample ?
HO2C
CO2H
(A) (B)
HO CO2H
HO
HO2C
CO2H
(C) (D)
CO2H
2. An organic compound A containing C = 70 % and H = 11.6 % gave the following results:
(i) 0.384 gm of the compound A displaced 100 ml of air at 1atm & 273 K.
(ii) On treatment with PCl5 A gave another compound, which contained 33.97% (34 %) chlorine.
IUPAC name of the compound A is:
(A) Pentanal (B) 2-pentanone (C) Cyclopentanol (D) 1,3-epoxypentane
3. What is the correct stereochemical assignment for each of the following alkenes?

Cl Cl
(I) (II) (III) (IV)
(A) I = E; II = Z; III = E; IV = Z (B) I = Z; II = E; III = E; IV = E
(C) I = E; II = E; III = Z; IV = Z (D) I = E; II = E; III = Z; IV = E

4. Order of enolic content

P: Q: R: S:

(A) P > Q > R > S (B) P > S > R > Q (C) R > S > P > Q (D) S > R > P > Q

Reg. & Corp. Office : CG Tower, A-46 & 52, IPIA, Near City Mall, Jhalawar Road, Kota (Raj.) - 324005
Website : www.resonance.ac.in | E-mail : contact@resonance.ac.in
Toll Free : 1800 258 5555 | CIN: U80302RJ2007PLC024029
Page No. - 1
5. Write the total number of benzenoid structural isomers of molecular formula C 8H8O, which can give
Fehling test.
(A) 2 (B) 3 (C) 4 (D) 1

6. Which of the following has lowest pKa value?

(A) CH (B) CH

(C) (D)

CH3

7. IUPAC name of the compound is

Br

(A) 3-(2-bromo cyclopentyl)-6-methyl-cyclohex-1-ene

(B) 3-methyl-6-(2-bromo cyclopentyl)-cyclohex-1-ene
(C) 1-methyl,4-(2-bromo cyclopentyl)-cyclohex-2-ene
(D) 4-methyl-1-(2-bromo cyclopentyl)-cyclohex-2-ene

8. Among the following, the most stable isomer is :

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

9.* Which statement about the following equilibrium is False ?

(A) The equilibrium favours the products

(B) t-Butoxide is the dominant anionic species in the equilibrium
(C) Water is the weaker acid than t-butyl alcohol
(D) t-Butoxide is stabilized by resonance
10.* Which of the following encircled carbon represent a stereogenic center.
COOH COOH COOH Cl
H OH H OH H OH
Br Br
(A) H OH (B) HO H (C) HO H (D)
H OH H OH HO H
COOH COOH COOH
Br CH3

11.*
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.
Reg. & Corp. Office : CG Tower, A-46 & 52, IPIA, Near City Mall, Jhalawar Road, Kota (Raj.) - 324005
Website : www.resonance.ac.in | E-mail : contact@resonance.ac.in
Toll Free : 1800 258 5555 | CIN: U80302RJ2007PLC024029
Page No. - 2
12. * Which of the following statement(s) is/are correct :
(A) sum of total number of chiral centres and total number of pairs of enantiomers for following structure is 3

(B) Possible isomeric alkenes that can give 2,3-Dimethylpentane on catalytic hydrogenation are 8.
(C) Total monochloro product possible for 1,2,3-trimethylcyclopropane are (8) and out of them total
meso compound possible (4)
Br Br
C
C
(D) Meso isomer of the given compound is 1.

Br Br
13.* Which of the following compound is/are resolvable.
Cl Br Br Cl Br H3C OH Br CH3 Br

(A) (B) H3C CH3

HOOC Br Br COOH H3C Br HO CH3

Br H3C OH Br CH3 HO3S SO3H

(C) H3C CH3 (D)

H3C Br HO CH3 Br H H
14.* Select the correct options:

(A) < (pKa order) (B) < (% enol content)

(C) > (Kb order) (D) Both the C – O bond lengths in HCOOK are equal

15.* 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.
16.* Which of the following structure has correct IUPAC name :

(A) 2-Bromo-5,5-dimethylcyclopent-3-en-1-one

Reg. & Corp. Office : CG Tower, A-46 & 52, IPIA, Near City Mall, Jhalawar Road, Kota (Raj.) - 324005
Website : www.resonance.ac.in | E-mail : contact@resonance.ac.in
Toll Free : 1800 258 5555 | CIN: U80302RJ2007PLC024029
Page No. - 3
 (B) 6-Methoxy-1-nitrocyclohex-1-ene

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

(D) 2-Bromo-6-nitrosobenzenecarboxamide

17.* Different conformational situation is encountered in molecule of type X–CH2–CH2–Y such as butane
(X = Y = CH3) find the correct statement/s regarding conformers of butane.
(A) Butane has two chiral forms (gauche)
(B) Anti form of butane is achiral due to plane of symmetry and center of symmetry.
(C) Two gauche forms of butane are achiral
(D) Two gauche forms of butane are enantiomeric.
18.* Which of the given statement(s) about N, O, P and Q with respect to M is (are) correct ?

(A) M and N are non-mirror image stereoisomers (B) M and O are identical
(C) M and P are enantiomers (D) M and Q are identical
O O O O
O3
19.* X 
 H–C–CH2CH2–C–C–CH2–CH2–CH as one of the product. X can be :
Me 2S

(A) (B)

(C) (D)

20.* Which of the following is / are correct order for acidic strength.
COOH COOH COOH OH OH OH
CH3 CH3
(A) (B)
CH3 CH3
CH3 CH3
COOH OH CH2–H COOH OH OH

(C) (D)
CH3
Cl NO2
21.* Analyse the following pairs of compounds.

(A) , are Geometrical isomers.

Reg. & Corp. Office : CG Tower, A-46 & 52, IPIA, Near City Mall, Jhalawar Road, Kota (Raj.) - 324005
Website : www.resonance.ac.in | E-mail : contact@resonance.ac.in
Toll Free : 1800 258 5555 | CIN: U80302RJ2007PLC024029
Page No. - 4
 (B) , are Position isomers
O O

(C) , are Chain isomers.

CHO
CHO

(D) , are Chain isomers.

22.* Find the correct statement/s for conformation of ethane.

(A) Most of the conformations are unstable like the extreme or intermediate position in the swing of a
pendulum.
(B) Stable conformations which are at energy minima are called conformational isomers, so ethane has
three conformational isomers.
(C) Ethane has infinite number of conformation by virtue of rotation about C–C bond.
(D) All three conformational isomers of ethane are indistinguishable so they are degenerate.
23.* The correct statement about the following compound is :

(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 configuuration about the two double bonds.
Comprehension # 1
Observe the following sequence of reactions,
Cl / h H Ni O
T 2 S 2 P 
3
 Q  R
Zn,H2O optically optically
activ e inactiv e
in this reaction P is the lowest molecular weight alkene which can show optical isomerism as well as
geometrical isomerism.
24. In the above reaction which of the following is Q.
CH2CHO

(A) C2H5 CH3 (B) CH3–CHO

H
CHO CHO

(C) C2H5 CH3 (D) C3H7 CH3

H H
25. Which of the following is true about Q
(A) Q gives only one product with NH2OH (B) Q gives two products with NH2OH
(C) Q gives three products with NH2OH (D) Q gives four product with NH2OH
26. How many structurally isomeric monochloro derivatives for T are possible?
(A) 6 (B) 7 (C) 8 (D) 9
Comprehension # 2
The compound shows below in the diagram, on treatment with acid catalyst isomerizes and equilibrium
is established among the stereoisomers where X  H or CH3

Reg. & Corp. Office : CG Tower, A-46 & 52, IPIA, Near City Mall, Jhalawar Road, Kota (Raj.) - 324005
Website : www.resonance.ac.in | E-mail : contact@resonance.ac.in
Toll Free : 1800 258 5555 | CIN: U80302RJ2007PLC024029
Page No. - 5
 The equilibrium mixture contains all the three stereoisomers of this compound. Specific rotation of pure
dextro isomer is +62° while the specific rotation of the equilibrium mixture is + 22°. Also the equilibrium
mixture contains 20% of the meso isomers. Answer the following three qeustions based on the above
information.
27. The percentage purity of the equilibrium mixture is :
(A) 28% (B) 35% (C) 46% (D) 54%
28. The percentage of racemic mixture present in the equilibrium mixture is :
(A) 35% (B) 45% (C) 65% (D) 80%
29. Composition of equilibrium mixture is :
(A) 20% meso, 58% dextro and 22% laevo (B) 20% meso, 60% dextro and 20% laevo
(C) 20% meso, 54% dextro and 26% laevo (D) 20% meso, 30% dextro and 50% laevo
Comprehension # 3
A research scholar synthesised the compound A in the laboratory
CH3

A is O O
CH3
CH2–COOH
He wanted to study this compound in acidic medium and kept for some time with heating. After an hour,
when isolated the compound, to this surprise, he got the mixture of two compounds B, C. He studied
their properties and compound 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
H O / 
[Hint : A 
3
B + C]
30. Compound B is :
O O
O
O O O
(A) (B) CH3 (C) (D) None
OH CH2–OH
31. Compound C is :
O
(A) CH3–C–CH3 (B) CH3–CH2–CH=O (C) H–C–H (D) CH3–CH=O
O
32. 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
Comprehension # 4
An optical inactive compound (A), which gives (+) iodoform test and gives coloured compound with
braddy's reagent. When it is treated with hydroxyl amine in mild acidic medium. It produces two
different compounds (B) & (C). Each when further heated with conc.H 2SO4 produces (D) & (E)
respectively. Further hydrolysis of (D) & (E) both produces mixture of a carboxylic acid and an amine.
Acid produce by hydrolysis of (D) is most acidic among its isomers and the amine produce by
hydrolysis of (E) is least basic among its positional isomers.
33. Select incorrect statement.
(A) Acid produced by hydrolysis of D will give effervescence of CO 2 with NaHCO3 faster than the acid
produced by hydrolysis of E
(B) Base produced by hydrolysis of D will be more basic than the base produced by hydrolysis of E
(C) Reaction involves formation B & C can also be carried out with NH 2NH2.
(D) Reaction involves formation D & E can also be carried out with PCl5.

Reg. & Corp. Office : CG Tower, A-46 & 52, IPIA, Near City Mall, Jhalawar Road, Kota (Raj.) - 324005
Website : www.resonance.ac.in | E-mail : contact@resonance.ac.in
Toll Free : 1800 258 5555 | CIN: U80302RJ2007PLC024029
Page No. - 6
34. Identify (A) among the following.
O OH O OH
C–CH3 CH–CH3 C–CH3 CH–CH3

CH3 CH3
(A) (B) (C) (D)

CH 3 CH3
35. Compound D & E are related with each other as
(A) Positional isomers (B) Functional isomers (C) Metamers (D) Geometrical isomers

36. Total dibromo isomers possible for prismane (an isomer of benzene)

14
D
37. 
 ?


Number of product having five membered ring are:

38. How many ozonides are possible during ozonolysis of propene?

39. Total number of stereoisomers of the following compound.

CH3–CH=CH CH=CH–CH3
C=C
CH3–CH=CH CH=CH–CH3

40. How many optically active compounds are possible in the following reaction?
CH3

Cl /h

2
product (S)
monochlorination

CH3

41. 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?

42. 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

(i) (ii) (iii)

(iv) (v) (vi)

Reg. & Corp. Office : CG Tower, A-46 & 52, IPIA, Near City Mall, Jhalawar Road, Kota (Raj.) - 324005
Website : www.resonance.ac.in | E-mail : contact@resonance.ac.in
Toll Free : 1800 258 5555 | CIN: U80302RJ2007PLC024029
Page No. - 7
43. Cyclohexane-1, 4-dione is a polar compound, having dipole moment value of 1.2 D. If mol fraction of its
chair form is 0.80, what will be the dipole moment of twisted boat form?

44. Different possible thermal decomposition pathways for peroxyesters are shown below. Match each
pathway from List I with an appropriate structure from List II and select the correct answer using the
code given below the lists.

List-I List-II

(A) Pathway P (P)

(B) Pathway Q (Q)

(C) Pathway R (R)

(D) Pathway S (S)

45. Match the column (I) and (II)

Column-I (Molecule) Column-II (Property)

(A) (p) Chiral atom is present

(B) (q) Molecule is chiral

(C) (r) Plane of symmetry is present

(D) (s) Centre of symmetry is present

Reg. & Corp. Office : CG Tower, A-46 & 52, IPIA, Near City Mall, Jhalawar Road, Kota (Raj.) - 324005
Website : www.resonance.ac.in | E-mail : contact@resonance.ac.in
Toll Free : 1800 258 5555 | CIN: U80302RJ2007PLC024029
Page No. - 8