CPP 20220411175711706233

CHEMISTRY
RANK BOOSTING COURSE-2022

CPP
CLASSROOM PRACTICE PROBLEMS
ST
IUPAC NOMENCLATURE NO. 01
Type : 1 (Hybridization)
1 2 3 4
1. In CH2  C  CH  CH3 molecule, the hybridization of carbon 1,2,3 and 4 respectively are :
(1) sp3, sp, sp3, sp3 (2) sp2, sp2, sp2, sp3 (3) sp2, sp, sp2, sp3 (4) sp2, sp3, sp2, sp3
[JEE Main 2021]
2. In the following molecules,

a
H3C b

C C—O
c
H H
Hybridisation of carbon a, b and c respectively are :

(1) sp3, sp, sp (2) sp3, sp2, sp (3) sp3, sp2, sp2 (4) sp3, sp, sp2
Type-2 (Alkane, alkene, alkyne and cyclic compounds)
3. The IUPAC name for the following compound is

[JEE Main 2019]
CH3
H3C CH
CH3
CH2
(1) 3-methyl-4-(3-methylprop-1-enyl)-1-heptyne
(2) 3,5-dimethyl-4-propylhept-6-en-1-yne
(3) 3-methyl-4-(1-methylprop-2-ynyl)-1-heptene
(4) 3,5-dimethyl-4-propylhept-1-en-6-yne
: 353, Rajeev Gandhi Nagar, Instrumentation Limited Colony, Kota, Rajasthan 324005
DOWNLOAD OUR APP & GET
UNLIMITED PRACTICE FOR FREE : www.atpstar.com PAGE NO.-1
4. What is the IUPAC name of the following compound ?
CH3 CH3
H
H Br
CH3
(1) 3-bromo-3-methyl-1,2-dimethylprop-1-ene
(2) 3-bromo-1,2-dimethylbut-1-ene
(3) 2-bromo-3-methylpent-3-ene
(4) 4-bromo-3-methylpent-2-ene
5. The IUPAC name of the following compound is

O
CH3
C—OH
(1) 3-bromo-5-methylcyclopentane carboxylic acid

(2) 3-bromo-5-methylcyclopentanoic acid
(3) 5-bromo-3-methylcyclopentanoic acid
(4) 4-bromo-2-methylcyclopentane carboxylic acid
6. The IUPAC name of the compound shown below is

Cl
Br
(1) 2-bromo-6-chlorocyclohex-1-ene (2) 6-bromo-2-chlorocyclohexene

(3) 3-bromo-1-chlorocyclohexene (4) 1-bromo-3-chlorocyclohexene
Type-3 (Monofunctional and Polyfunctional compounds)

7. The IUPAC name for the following compounds is
[JEE Main 2020]
CHO
CH3
H 3C
COOH
(1) 6-formyl-2-methyl-hex-3-enoic acid
(2) 2, 5-diamethyl-6-oxo-hex-3-enoic acid
(3) 2, 5-dimethyl-6-carboxy-hex-3-enal
(4) 2, 5-dimethyl-5-carboxy-hex-3-enal
8. The IUPAC name of the following compound is
CH3 OH
H3C—CH—CH—CH2—COOH
(1) 4, 4-dimethyl-3-hydroxybutanoic acid (2) 2-methyl-3-hydroxypentan-5-oic acid
(3) 3-hydroxy-4-methylpentanoic acid (4) 4-methyl-3-hydroxypentanoic acid
9. Which of the following compounds has incorrect IUPAC nomenclature?

O
(1) CH3CH2CH2COC2H5 (2) CH3CHCH2CHO
ethyl butanoate
CH3
3-methylbutanal
(3) CH3CHCCH2CH3 (4) CH3CH–CH–CH3

CH3 H3C OH
2-methyl-3-pentanone 2-methyl-3-butanol
Type-4 (Aromatic compound)
10. The IUPAC name of the following compounds is

[JEE Main 2020]
OH
NH2
O2N
CHO
(1) 2-nitro-4-hydroxymethyl-5-amino benzaldehyde
(2) 3-amino-4-hydroxymethyl-1-5-nitrobenzaldehyde
(3) 5-amino-4-hydroxymethyl 1-2-nitrobenzaldehyde
(4) 4-amino-2-formyl-5-hydroxymethyl-nitrobenzene
11. The correct IUPAC name of the following compounds is

NO2
Cl
CH3
(1) 2-methyl-5-nitro-1-chlorobenzene
(2) 3-chloro-1-methyl-1-nirobenzene
(3) 2-chloro-1-methyl 1-4-nitrobenzene
(4) 5-chloro-4-methyl 1-1nitrobenzene
12. The IUPAC name(s) of the following compound is
H3C Cl
(1) 4-methylchlorobenzene (2) Methylchloro benzene
(3) 1-chloro-4-methylbenzene (4) 1-methyl-4-chlorobenzene
Type-5 (Common name)
13. Mesityl oxide is a common name of :
(1) 2,4-Dimethyl pentan-3-one
(2) 3-Methyl cyclohexane carbaldehyde
(3) 2-Methyl cyclohexanone
(4) 4-Methyl pent-3-en-2-one
[IUPAC, JEE Main 2021]
ANSWER KEY
1. (3) 2. (3) 3. (4) 4. (4) 5. (4)
6. (3) 7. (2) 8. (3) 9. (4) 10. (3)
11. (3) 12. (3) 13. (4)
SOLUTIONS
1 2 3 4
1. [ CH2  C  CH  CH3 ]
H
2 2 3
H sp sp sp sp
C=C=C—C—H
H
H H
3
a(sp )
H3C b(sp ) (sp )
2 2
2. 
C C—O c
H H
3. The IUPAC name for the given compound is 3, 5-dimethyl-4-propylhept-1-en-6-yne.

CH3
7
H3C 5
CH Longest possible
4 6 chain containing
2 3
double and triple
1 CH3 bond
CH2
If both double and triple bonds are present in the compound, the endings like-en-yne, a
(numeral)dien-(numeral)-yne etc. are used. Numbers as low as possible are given to double
and triple bonds as a set.
4. While naming the compound, alkene gets priority over functional group (—Br) and numbering
starts from alkene side. Hence, IUPAC name :
4-bromo-3-methylpent-2-ene
1
CH3 CH3
2 H
3
H 4Br
5
CH3
5. The IUPAC name of the given compound.
CH3 O
2
C—OH
3
1
4 5
Br
4-bromo-2-methylcyclopentane carboxylic acid.
6
CHO
3
7. 2 CH3
5
H3C 4 Principal chain
1COOH
IUPAC name is 2, 5-dimetyl-6-oxo-3-enoic acid.
8. The IUPAC name of the given compound is 3-hydroxy-4-mehylpentanoic acid.

CH3 OH
5 4
H3C—CH—CH—CH2—COOH
Principal chain
While naming the compound, the longest chain than have principal function group —COOH is
chosen and numbered in such a manner that the principal functional group gets the lowest
possible number. —OH act as substituent and used as prefix in nomenclature.
OH
4
3
NH2
10. 5
6
O2N 2
1
CHO  Main functional group
Substituent
5-amino-4-hydroxymethyl-1-2-nitrobenzaldehyde
11. The IUPAC name of the given compounds is
NO2
Incorrect way
Correct way
4
3
2
1 Cl
CH3
2-chloro-1-methyl l-4-nirobenzene
Here, the given compound contains two or more functional groups, So, the numbering is done
in such a way that the sum of the locants is the lowest.
O
4
13. 1 2 3 5
Mesityloxide
IUPAC [4-Methylpent-3-en-2-one]
C HE M IS T R Y

CPP
ST
GENERAL ORGANIC CHEMISTRY NO. 02
Type : 1 (RHI)
1. Given below are two statements :

Statement I : Hyperconjugation is a permanent effect.

 
Statement II : Hyperconjugation in ethyl cation  CH3 – CH2  involves the Overlapping of
 
Csp2  H1s bond with empty 2p orbital of other carbon.
Choose the correct option :

(1) Both statement I and statement II are false
(2) Statement I is incorrect but statement II is true
(3) Statement I is correct but statement II is false
(4) Both Statement I and statement II are true. [JEE Main, 2020]
2. Which of the following compounds does not exhibit resonance?

CH2OH
(1) CH3CH2OCH=CH2 (2)
(3) CH3CH2CH2CONH2 (4) CH3CH2CH=CHCH2NH2
3. Which one among the following resonating structures is not correct?
 
 O  O
(1)  N (2)  N
O O
   
 O  O
(3)   N (4)  N
O O

CH2  
CH2 CH2 
CH2
4. H
O
(A) (B) (C) (D)
Among the given species the Resonance stabilised carbocations are:
(1) (C) and (D) only (2) (A), (B) and (D) only
(3) (A) and (B) only (4) (A), (B) and (C) only
5. Which of the following has the shortest C—Cl bond ?

(1) Cl–CH=CH–CH3 (2) Cl–CH=CH–NO2
(3) Cl–CH=CH–OCH3 (4) Cl–CH=CH2
Type-2 (Stability of intermediates)


CH2
  
6. CH2= C H CH3– C H2 HC C
A B C D
The correct order of stability of given carbocation is :
(1) A > C > B > D (2) D >B > C > A (3) D > B > A > C (4) C > A > D > B
[JEE Main, 2021]
7. Arrange the carbanions, (CH3 )3 C,CCl3,(CH3 )2 CH,C6H5CH2 in order of their decreasing stability-
(1) (CH3 )3 CH  CCl3  C6H5CH2  (CH3 )3 C (2) CCl3  C6H5CH2  (CH3 )2 CH  (CH3 )3 C
(3) (CH3 )3 C  (CH3 )2 CH  C6H5CH2  CCl3 (4) C6H5CH2  CCl3  (CH3 )3 C  (CH3 )2 CH
8. The order of stability of the following carbocations:


CH2
 
CH2=CH–CH2 ; CH3–CH2–CH2 ;
(I) (II) (III)

is
(1) II > III > I (2) I > II > III (3) III > I > II (4) III > II > I
9. The increasing order of stability of the following free radicals is
   
(1) (C6H5 )CH < (C6H5 )C < (CH3 )3 C < (CH3 )2 CH
   
(2) (CH3 )2 CH < (CH3 )3 C < (C6H5 )2 CH < (C6H5 )3 C
   
(3) (CH3 )2 CH < (CH3 )3 C < (C6H5 )2 CH < (C6H5 )3 C
   
(4) (C6H5 )3 C < (C6H5 )2 CH < (CH3 )3 C < (CH3 )2 CH
Type-3 (Aromaticity)
10. Which of the following is an aromatic compound ?
Θ 
(1) Θ (2) (3) (4)
Θ
[JEE Main, 2021]
11. Which one of the following compounds is nonaromatic ?


(1) (2) (3) (4)
O 
12. Among the following, the aromatic compounds are :
(A) CH2 (B) (C) (D)

Θ 
Choose the correct answer from the following options :
(1) (A) and (B) only (2) (B) and (C) only
(3) (B), (C) and (D) only (4) (A), (B) and (C) only
13. Which of the following compounds will produce a precipitate with AgNO3 ?
Br Br Br
Br
(1) (2) (3) (4)

N
Type-4 (Acidic Strength)

14. Which amongst the following is the strongest acid?
(1) CHBr3 (2) CHl3 (3) CHCl3 (4) CH(CN)3

[JEE Main, 2020]
15. The correct order for acid strength of compounds
CHCH,CH3—CCH and CH2CH2 is as follows :
(1) CH3—CCH > CH2CH2 > HCCH (2) CH3—CCH > CHCH > CH2CH2
(3) HCC > CH3—CCH > CH2CH2 (4) CHCH > CH2CH2 > CH3—CCH
16. Which among the following is the strongest acid ?
(1) CHCH2CH2CH3 (2) (3) (4)
17. The correct order of acid character of the following compounds is :

OH COOH COOH COOH
I II III IV
NO2 CH3
Options :
(1) III > II > I > IV (2) IV > III > II > I (3) I > II > III > IV (4) II > III > IV > I
Type-5 (Basic Strength)

Statement I : Aniline is less basic than acetamide.
Statement II : In aniline, the lone pair of electrons on nitrogen atom is delocalised over
benzene ring due to resonance and hence less available to a proton.
Choose the most appropriate option ;
(1) Statement I is true but statement II is false.
(2) Statement I is false but statement II is true.
(3) Both statement I and statement II are true.
(4) Both statement I and statement II are false. [JEE Main, 2021]
19. A. Phenyl methanamine B. N,N-Dimethylaniline

C. N-Methyl aniline D. Benzenamine
Choose the correct order of basic nature of the above amines.
(1) A > C > B > D (2) D > C > B > A
(3) D > B > C > A (4) A > B > C > D
20. Which of the following is least basic ?
•• ••
(1) (CH3CO)NHC2H5 (2) (C2H5 )3 N
•• ••
(3) (CH3CO)2 NH (4) (C2H5 )2 NH
21. The increasing order of pKb values of the following compounds is

N(CH3)2 N(CH3)2 NHCH3 NHCH3
CN OH
OCH3
(I) (II) (III) (IV)
(1) II < IV < III < I (2) I < II < IV < III (3) II < I < III < IV (4) I < II < III < IV
22. The decreasing order of basicity of the following amines is

NH2
N NH2 N
|
H
(I) (II) (III) (IV)
(1) (III) > (I) > (II) > (IV) (2) (III) > (II) > (I) > (IV)
(3) (I) > (III) > (IV) > (II) (4) (II) > (III) > (IV) > (I)
23. The increasing order of basicity of the following compounds is

NH2
NH2 NH
I. II. III. NH IV. NHCH3
(1) (I) < (II) < (III) < (IV) (2) (II) < (I) < (III) < (IV)
(3) (II) < (I) < (IV) < (III) (4) (IV) < (II) < (I) < (III)
24. The increasing order of basicity for the following intermediates is (from weak o stronger)
CH3
Θ   
H3C—CΘ H2C=CH—CH2 HC  C CH3 CN
(ii)
CH3 (iii) (iv) (v)
(i)
(1) (v) < (iii) < (ii) < (iv) < (i) (2) (iii) < (i) < (ii) < (iv) < (v)
(3) (v) < (i) < (iv) < (ii) < (iii) (4) (iii) < (iv) < (ii) < (i) < (v)
Type-6 (Miscellaneous)
25. Which one of the following compounds will liberate CO2, when treated with NaHCO3?
O
   
(1) (CH3 )3NHCl (2) (CH3 )4NOH (3) CH3–C–NH2 (4) CH3NH2
[JEE Main, 2021]
26. Compound(s) which will liberate carbon dioxide with sodium bicarbonate solution is/are:
NH2 COOH NH2

O2N NO2
A= B= C=
H2N NH2
OH NO2
(1) B only (2) C only (3) B and C only (4) A and B only
27. The correct order of heat of combustion for following alkakdienes is
(I) (II) (III)
(1) (II) < (III) < (I) (2) (I) < (II) < (III) (3) (I) < (III) < (II) (4) (III) < (II) < (I)
ANSWER KEY
1. (3) 2. (4) 3. (1) 4. (3) 5. (2)
6. (1) 7. (2) 8. (3) 9. (2) 10. (1)
11. (1) 12. (2) 13. (1) 14. (4) 15. (3)
16. (4) 17. (4) 18. (2) 19. (4) 20. (3)
21. (2) 22. (2) 23. (4) 24. (1) 25. (1)
26. (3) 27. (2)
Type-1 (Structural Isomerism)
1. Which one of the following pairs of isomers is an example of metamerism ?
(1) CH3CH2CH2CH2CH3 and (2) and
(2) and (4) and
2. The number of acyclic structural isomers (including geometrical isomers) for pentene are ____
3. Which of the following compound will show the maximum 'enol' content ?
(1) CH3COCH3 (2) CH3COCH2COCH3
(2) CH3COCH2COOC2H5 (4) CH3COCH2CONH2
4. Assertion A : Enol form of acetone [CH3COCH3] exists in < 0.1% quantity. However, the enol
form of acetyl acetone [CH3COCH2OCCH3] exists in approximately 15% quantity.
Reason R : enol form of acetyl acetone is stabilized by intramolecular hydrogen bonding,
which is not possible in enol form of acetone.
Choose the correct statement :
(1) A is false but R is true
(2) Both A and R are true and R is the correct explanation of A
(3) Both A and R are true but R is not the correct explanation of A
(4) A is true but R is false
5. Compound with molecular formula C3H6O can show :

(1) Positional isomerism (2) Both positional isomerism and metamerism
(2) Metamerism (4) Functional group isomerism
DOWNLOAD OUR APP & GET : 353, Rajeev Gandhi Nagar, Instrumentation Limited Colony, Kota, Rajasthan 324005

6. Identify the compound that exhibits tautomerism.
(1) 2-butene (2) lactic acid (3) 2-pentanone (4) phenol
Type-2 (Geometrical Isomerism)
7. Among the following compounds, geometrical isomerisation is exhibited by

CHCl
O CHCl CHCl
(1) (2) (2) H3C CH3 (4)

CH3
Cl
8. Which of the following compounds shows geometrical isomerism ?
(1) 2-methylpen-2-ene (2) 4-methylpen-2-ene
(2) 4-methylpent-1-ene (4) 2-methylpent-1-ene
9. Which of the following molecules does not show stereo isomerism ?
(1) 3,4-Dimethylhex-3-ene (2) 3-Methylhex-1-ene
(2) 3-Ethylhex-3-ene (4) 4-Methylhex-1-ene
10. Which of the following compound will exhibit geometrical isomerism?
(1) 1-phenyl-2-butene (2) 3-phenyl-1-butene
(3) 2-phenyl-1-butene (4) 1,1-diphenyl-1-propane
Type-3 (Optical Isomerism)

11. Which of the following compounds produces an optically inactive compound on
hydrogenation?
H CH3
H CH3
(1) (2)
H CH3
H CH3
(3) (4)

12. The number of chiral centres present in threonine is ..............
13. Which of the following molecules is expected to rotate the plane of polarised light?
CHO
(1) HO H (2)
CH2OH SH
COOH
H2N NH2
(3) H H (4) H2N H
Ph Ph H
14. Which of the following compounds is not chiral ?
(1) 1-chloropentane (2) 2-chloropentane
(3) 1-chloro-2-methylpentane (4) 3-chloro-2-methylpentane
CO2H
H OH
15. The absolute configuration of H Cl is
CH3
(1) (2S, 3R) (2) (2S, 3S) (3) (2R, 3R) (4) (2S, 3S)
Type-4 (Conformational Isomerism)
16. Staggered and eclipsed conformers of ethane are :
(1) Polymers (2) Rotamers
(2) Enantiomers (4) Mirror images
17. The dihedral angle in staggered form of Newman projection of 1, 1, 1-Trichloro ethane is ........
degree. (Round off to the nearest integer)
18. Increasing order of stability among the three main conformations (i.e., Eclipse, Anti, Gauche)
of 2-fluoroethanol is
(1) Eclipse, Gauche, Anti (2) Gauche, Eclipse, Anti
(3) Eclipse, Anti, Gauche (4) Anti, Gauche, Eclipse

ANSWER KEY
1. (4) 2. 6 3. (2) 4. (2) 5. (4)
6. (3) 7. (2) 8. (2) 9. (2) 10. (1)
11. (4) 12. 2 13. (1) 14. (1) 15. (1)
16. (2) 17. 60 18. (2)

CHEMISTRY

CPP
ST
HYDROCARBON NO. 04
Type-1 (Chemical Reaction of alkanes)

1. Presence of which reagent will affect the reversibility of the following reaction, and change it to
a irreversible reaction :
hv
CH4 + I2 Reversible
CH3 – I + HI [JEE Main 2021]
(1) HOCl (2) dilute HNO2 (3) Liquid NH3 (4) Concentrated HIO3
2. Excess of isobutane on reaction with Br2 in presence of light at 125°C gives which one of the
following, as the major product?
Br CH3
(1) CH3–C–CH2–Br (2) CH3–CH–CH2Br (3) CH3–CH–CH2Br (4) CH3–C–Br
CH3 CH2Br CH3 CH3
Type-2 (Chemical Reaction of alkenes)

3. The major product in the following reaction is [JEE Main 2020]
CHCH2 H3O+

CH3
CH3
H3C CH3
CH3 H3C CH3
CH3
(1) (2) (3) (4)
CH3 CH3
4. The major product formed in the following reaction is
CH3CH  CHCH(CH3 )2 

HBr

(1) CH3CH(Br)CH2CH(CH3)2 (2) CH3CH2CH(Br)CH(CH3)2

(3) Br(C2)3CH(CH3)2 (4) CH3CH2CH2C(Br)(CH3)2
5. The increasing order of the boiling points of the major products A, B and C of the following
reactions will be I.
O
(C6H5CO)2
+ HBr A
II. + HBr B
III. + HBr C
(1) II < III < I (2) III < I < III (3) I < II < III (4) I < III < II
6. The major product of the given addition reaction is

H3C — CH  CH2 
Cl2 /H2O

(1) CH3 — CH— CH2 (2) CH3 — CH— CH2

| | | |
Cl OH OH Cl
O
O
(3) H3C (4)
H3C CH3
7. Which one of the following alkenes when treated with HCl yields majorly an anti Markovnikov
product ?
(1) Cl—CHCH2 (2) H2N—CHCH2
(3) CH3O—CHCH2 (4) F3C—CHCH2
8. The major product of the following reaction is

(i) Br2
(ii) EtOH
Br OEt OEt OEt

OEt OEt Br
(1) (2) (3) (4)
9. The major product in the following conversion is

HBr (excess)
CH3O CHCH—CH3 Heat
?
(1) CH3O CH—CH2—CH3 (2) HO CH2—CH—CH3

Br Br
(3) CH3O CH2—CH—CH3 (4) HO CH—CH2—CH3

Br Br
Type-3 (Sequential Reaction of Alkenes)
10. The major product [B] in the following sequence of reaction is
(i) B2H6 Dil. H2SO4
CH2—CCH—CH2CH3 Θ
[A] 
[B]
(ii) H2O2, OH
CH(CH3)2 [JEE Main 2020]
(1) CH2—C—CHCH—CH3 (2) CH3—CCH—CH2CH3
CH(CH3)2 CH(CH3)2
(3) CH3—C—CH2CH2CH3 (4) CH2C—CH2CH2CH3
C CH(CH3)2
H3C CH3
Cl
(i) HBr
(ii) alc. KOH
OH Cl Cl
(1) (2) (3) (4)
O O O O
CH3O
(i) Cl3/CCl4
(ii) AlCl3 (anhyd.)
Cl
CH3O CH3O
(1) (2)
Cl
Cl
CH3O
CH3O
(3) (4)
Cl
13. Identify A and B in the chemical reaction.
OCH3
HCl NaI
[A] [B]
(major) dry acetone (major)
NO2
OCH3 OCH3 OCH3 I

Cl
(1) A = B= (2) A = B=
Cl Cl Cl
NO2 NO2 NO2 NO2
OCH3 I OCH3 OCH3

Cl Cl Cl I
(3) A = B= (4) A = B=
NO2 NO2 NO2 NO2
14. (i) (C6H5CO)2O2,HBr

(ii) CoF2 P
(major product)
Br
Major product P of above reaction, is :
F
(1) (2)
Br F
F
(3) (4)
F
Br Br
OH
15. H3PO4 (BH3)2
120oC
A P
H2O2/OH, H2O
Major Product Major Product
Consider the above reaction and identify the Product P :
OH OH CH3
CH3 OH
OH OH
(1) (2) (3) (4)
Type-4 (Chemical Reaction of Dienes)
16. The major product formed in the following reaction is :
HBr
Major product [JEE Main 2020]
(excess)
Br Br
(1) (2) (3) (4) Br
Br Br
Br
Type-5 (Chemical Reaction of Alkynes)

CH3C  CH 
(i) DCl(1equiv.)
(ii) D
 [JEE Main 2019]
(1) CH3CD(Cl)CHD(I) (2) CH3CD2CH(Cl)(I)

(3) CH3CD(I)CHD(Cl) (4) CH3C(I)(Cl)CHD2
18. Which one of the following carbonyl compounds cannot be prepared by addition of water on
an alkyne in the presence of HgSO4 and H2SO4 ?
O O O O
(1) CH3–C–H (2) C–CH2 (3) CH3–CH2–C–H (4) CH3–C–CH2–CH3
H2
(A)
Pd-BaSO4
19. CH3–CC–CH3
Na
(B)
liq. NH3
A & B are related as :

(1) Structural isomer (2) Idential
(3) Geometrical isomers (4) Optical isomers
Type-6 (Sequential Reaction of Alkynes)
20. The major product [R] in the following sequence of reaction is

HC  CH 
(i) LiNH2 /ether
(ii)CH3  CHBr
(i) HgSO4 /H2SO4
[P] (ii) NaBH4
Conc. H2SO4
[Q]  
[R] [JEE Main 2020]
l
CH(CH3 )2
H 3C H3C
(1) CCH—CH3 (2) CH—CHCH2
(CH3)2CH (CH3)2CH
H3C H2C
CC(CH3)2
(3) (4) C—CH2—CH3
H3CCH2 (CH3)2CH
21. The major product (Y) in the following reaction is
CH3
|
CH3 — CH — C  CH 
HgSO4 ,H2SO4
H O
(i) C2H5MgBr,H
X 
(ii) Conc.H SO / 
2
Y 2 4
CH3 CH3
(1) CH3—CC—CH3 (2) CH3—CH—CCH—CH3
CH2CH32 CH3
CH2 CH3
(3) H3C—C—CH—CH3 (4) CH3—CH—CCH2

C2H5 CH2CH3
Type-7 (Ozonolysis)
22. The major product(s) obtained in the following reaction is/are
t
(i) KO Bu
(ii) O3/Me2S
Br [JEE Main 2019]

CHO and OHC—CHO
(1) OHC (2) OHC
CHO
t
O Bu
(3) OHC CHO (4) OHC
CHO
23. The number of optically active products obtained from the complete ozonolysis of the given
compound is
CH3 H
CH3–CH=CH–C–CH=CH–C–CH=CH–CH3
H CH3
(A) 4 (B) 2 (C) 0 (D) 1
24. What is the major product formed on reaction of but-2-yne with O3 followed by Zn/H2O?
OH
(A) (B) CH3COOH (C) CH3CHO (D)

OH
25. An unsaturated hydrocarbon X on ozonolysis gives A. Compound A when warmed with

ammonical silver nitrate form a bright silver mirror along the sides of the test tube. The
unsaturated hydrocarbon X is :
(1) CH3 — C
|

C — CH3
|
(2) CH3—C 
CH3 CH3

(3) HC C—CH2—CH3 (4) CH3—C C—CH3
ANSWER KEY
1. (4) 2. (4) 3. (4) 4. (4) 5. (1)
6. (2) 7. (4) 8. (4) 9. (4) 10. (3)
11. (3) 12. (3) 13. (4) 14. (4) 15. (4)
16. (1) 17. (4) 18. (3) 19. (3) 20. (3)
21. (1) 22. (1) 23. (3) 24. (1) 25. (3)
SOLUTIONS
1. lodination of alkane is reversible reaction.
It can be irreversible in the presence of strong oxidising agent like conc. HNO3 or conc. HIO3
CH3 CH3
2 Br
2. CH3–CH–CH3 hv/ CH3–C–CH3
(excess isobutane)
Br
3. Complete mechanism is as follows :

CHCH2 H CHCH2
4 3
(H3O+) 5 6
2
CH3 Electrophilic addition CH3
3 CH3 ••
Ring expansion H2O
••
4 1
+
(Rearrangement of 5 2 r (H3O )
6
carbonation CH3 –H
intermediate
5 membered  6 membered
ring (Thermodynamically
more stable
Saytzeff centre
CH3
CH3 CH3
–H2O
H 
OH
CH3 CH3
Hofmann (Major)
H
centre
The major product obtained in the given reaction is 1, 2-dimethyl cyclohexene.
H
HBr 
4. CH3—CHCH—CH—CH3 CH3—CH2—CH—C—CH3
CH3
1, 2–H shift (for more
stable carbon cation

CH3—CH2—CH2—C—CH3
Θ
Br CH3
Br
CH3—CH2—CH2—C—CH3
CH3
Major
5. Complete reaction of I, II and II are as follow :

O
(C6H5CO)2
I. + HBr (A)
Br
II. + HBr Br (B)
Br
III.
+ HBr (C)
RX are polar, therefore intermolecular forces of attraction (e.g., dipole-dipole and van der
Waals') are stronger in RX.
Hence, the boiling point of RX is greater than those of hydrocarbons of comparable molecular
masses. Branching decreases the surface area as in alkane because the branched C chains
are more spherical-like, which results in lower boiling point.
1
B.P 
Branching
Hence, the boiling point of isomeric RX decreases with increase in branching, hence the order
will be B < C < A
6. The major product of the given addition reaction is CH3 — CH— CH2 . In this reaction,
| |
OH Cl
H2O is used as a solvent and the major product of the reaction will be a vicinal halohydrin. A
halohydrin is an organic molecule that contains both OH group and a halogen. In a vicinal
halohydrin, the OH and halogen are bond to adjacent carbons.
Cl2/H2O
H3C—CHCH2 H3C—CH—CH2 +
OH Cl
A chlorohydrins (major product)
CH3—CH—CH2 + HBr
Cl Cl
(major product)
The reaction proceeds through following mechanism :

+
Cl
••
•• •• Slow H2••
O
CH3—CHCH2 + Cl—Cl CH3—CH—CH2
••
••
•• •• Fast
Chloronium ••Θ
••
••
ion + Cl
••
•• H2••
O •• +
CH3—CHCH2—Cl CH3CH—CH2—Cl + H3O
••
•• Fast ••
+
••
OH OH
••
••
Chlorohydrin
OH
7. Attachment of electron donating group (+ R or +l) with sp2-carbon of an unsymmetrical alkene

supports Markownikov's addition rule through electrophilic-addition-pathway.
But, attachment of electron-withdrawing group (—R or —l) for the same will follow anti-
markownikov's pathway (even in absence of organic peroxide which favours free radical
addition) through electrophilic addition pathway.
The product formed by given alkenes when treated with HCl.
+R Cl
+ –
•• H—Cl  Cl–
Cl—CHCH2 Cl CH—CH3 fast
••
••
Slow
Cl—CH—CH3
•• ••
Similarly,
Cl
+ –
+ –
Cl
H2N—CHCH2
H—Cl
NH2—CH—CH3 Fast
NH2—CH—CH3
(+R)
+ –
H—Cl + –
Cl
CH3O—CHCH2 CH3O—CH—CH3 Fast
CH3O—CH—CH3
(+R)
Cl
– –
Cl—H
HCl  ClΘ
F3C—CHCH2 Slow F3C—CH2—CH2 Slow F3C—CH2CH2Cl
(–l)
8. The road map of the given reaction is :
Br
Isolated CC *
Br
Br2/CCl4 *
Anti-addition (electrophilic)
of Br2 with the isolated
(non-aromatic C C  EtOH (Polar protic
– medium as well as
SN1, –Br
nucleophilic)
OEt 2º-benzyl
* Br carbocation
* (Stable)
•• 
EtOH Br
•• *
Recemised ± as well as –H
inverted (+ and –)
9.
Key Idea The excess of HBr and high temperature in given reaction serves for dual purpose :
(i) Hydrolysis of ether via SN2 mechanism, i.e. Zeisel's method.
(ii) Markownikoff addition at double bond of the branch
The road map of complete reaction is as follows :
CH3—O CHCH—CH3
+
H HBr excess/Heat
+
CH3—O CH—CH2—CH3
–
Br
••
CH3—O CH—CH2—CH3
••
Br
– +
Br H
–
 + –
BF  BB 
Br------C------O CH—CH2—CH3
BF
H H H+ Br
Transition state
SN2 Reaction
(Zeisel's Method)
CH3Br + HO CH—CH2—CH3
Br
Product
Here, BB = Bond breakage
BF = Bonf formation
OH
(i) B2H6
10. CH3—CCH—CH2—CH3 (ii) H2O2/OH–
CH3—CH—CH—CH2—CH3
Anti-Markownikoff hydration
C CH
CH3 CH3 CH3 CH3
(A)
+
(+H )  +
(A) + dil. H2SO4 –H2O
CH3—CH—CH—CH2—CH3
(2º carbocation
(Protonation of OH
CH
group and removal of H2O)
CH3 CH3
Carbocation
rearrangement
2º to 3º
by H– shift
 + 
CH3—C—CH2—CH2—CH3 –H
+ CH3—C—CH2—CH2—CH3
C From -position with CH
least number of H-atoms
CH3 CH3 forms major product CH3 CH3
(Saytzeff's rule
[B]
11. In presence of HBr, reactant containing CC undergoes electrophilic addition reaction and
give substituted alkyl halide. On further reaction with alc. KOH, -elimination takes place
that give corresponding diene. The diene undergoes enolisation to give stable product
(phenol).
Cl -l effect at -position to CC Cl H

HBr Acidic
Br
-H
Carbocation formation in the H
O electrophilic addition of HBr
O
-l effect at -position to CC –HCl Alc. KOH

–HCl (, -elimination)
Enolisation to H
[Conjugated diene, stable]
attain aromaticity H
OH O
[Very stable, phenol]
12. The given reactant in presence of Cl2/CCl4, given vicinal dihalide. Chlorine adds up to alkene
via electrophilic addition eaction involving cyclic chlorinium ion formation.
Cl
H3CO H3CO
Cl2/CCl4
Cl
The vicinal dihalide in presence of anhyd. AlCl3 results in the formation of carbocation that
rearranges itself to form a cyclic compound.
Cl Cl
H3CO H3CO +–
+ AlCl3  + AlCl4
Cl (Anhyd.)
CH3O CH3O
–H+
Cl Cl
H
OMe OMe OCH3

Cl Cl I
HCl NaI
13. Marcovnikov’s dry acetone
Addition
NO2 NO2 NO2
st
 I reaction marcovnikov's addition of HCl on double bond while 2nd reaction is halide
substitution by finkelstein reaction.
(C6H5CO2)2 O2, HBr

14.
AMKR Product
Br
Br
Br CoF2 (Swart reaction)

F
Br
OH
OH
15. H3PO H.B.O

dehedration of H-attached at more hindard

alcohol by E1 site while OH attached at
Rxn less hidndard in H.BO.
Reaction
2 4 HBr
16. 1
3 Br
(excess) 1,4addition product
(major product)
17. The major product obtained in the given reaction is CH3C (l) (Cl) CHD2.
CH3C  CH 
(i) DCl(1 equiv.)
(ii) D
 CH3C(l)(Cl)CHD2
Addition in unsymmetrical alkynes takes place according to Markovnikov's rule.
Reaction proceed as follows :
DCl Cl Cl
(1 equiv.) Dl
CH3CCH CH3 C=CHD CH3—C—CHD2
Prop-1-yne l
Product
18. Reaction of HgSO4/dil.H2SO4 with alkyne gives addition of water as per markonikoff’s rule.
O O
HgSO4
(1) HCCH H2SO4
CH2–CH CH3–CH
OH
O
HgSO4
(2) C–CH H SO C–CH C–CH
2 4
OH
O
HgSO4
(3) CH3–CCH CH3–C=CH2 CH3–C–CH3
H2SO4
OH
Hence, CH3–CH2–CHO cannot be form
HgSO4
(4) CH3–CC–CH3 H2SO4 CH3–C=CH–CH3 CH3–C–CH2–CH3
OH O
20.

LiNH2/ether Θ
H—CC¾H It abstract H+ H—CC Li+
Acetylene from alkine and (P)
act as a base
H—CCΘ Li+ + CH3—CH—Br

CH(CH3)2
CH3
CH—CC—H 2+
H3C—HC Hg (HgSO4)
HO—H Hydration
H3C
OH
CH3
Tautomerism CH—CCH2
H3C—CH
H3C
O
CH3
CH—CCH3
H3C—CH
CH3 OH
CH3
CH—CHCH3
NaBH4 CH3—CH
Reduction (Q)
O CH3
conc. H2SO4

of —C— group
H
CH3 
C—CH—CH3
H3C—CH
(1, 2 shift)
H3C Rearrangement
undergoes for more
stable carbocation
CH3 
C—CH2—CH3
CH3—CH
(According to
H3C Markownifoff rule
Hydrogen aliminate from
highly substitute carbon
CH3
C—CH2—CH3
CH3—C
CH3 (R)
Major product
So, correct options is (3).
CH2 CH3 O
HgSO4, H2SO4 C2H=MgBr, H2O
21. H3C—CH—C CH H2O
CH3—CH—C—CH3
(X)
(Hydration of alkynes)
(Ketone)
CH2 OH
CH3—CH—C—CH3
Conc. H2SO4
 C2H5
(3º alcohol)
CH3 CH3
CC (acid catalysed
CH3 CH2—CH3 dehydration of alcohol
2, 3-dimethyl pent-2-ene give alkene, major
(Y) product is Saytzeff's
Step II
Step I
CHO
O3/Me2S
22. t OHC
KO Bu Ozonolysis
Br Cyclohex-1, and OHC—CHO

3-diene
In step-1 dehydrohalogenation reaction takes place. Here, hydrogen is eliminated from -
carbon and the halogen is lost from -carbon atom. As a result diene is formed.
H –
OtBu
Br Cyclohex-1,
3-diene
Cyclohex-1, 3-diene on ozonolysis gives butane-1, 4-dial and ethane-1,2-dial.
CHO
O3 CHO
Me2S + (CH2)2
CHO
CHO
Ozonolysis Ammonical
25. (X)  (A) 
AgNO3
 Ag 
Unsaturated (Tollne’s silver
Hydrocarbon regent) mirror
As (1) compound given positive tollen’s test hence it may consist—CHO (aldehyde group).
or it can be HCOOH
So for the given option :
(3) CH3—CH2—C CH    CH3CH2COOH + HCOOH (1) +ve tollen’s test and for
Ozonolysis
other compounds (options) :

CH3 CH3 Ozonolysis CH3
(1) C=C C=O (Does not
CH3 CH3 CH3 show tollen’s
Test
CH3 Ozonolysis CH3
(2) C= C=O + O
CH3 CH3
(Both do not show
tollen’s test)
 Ozonolysis
(3) CH3—C C–CH3  2CH3–COOH
(Does not show
tollen’s test)
Type-1 (Nucleophilic Substitution Bimolecular (SN2))
1. Which of the following compounds will show retention in configuration on nucleophilic
substitution by OH– ion ? [JEE Main 2020]
(1) (2)
(3) (4)
2. The decreasing order of reactivity of the following compounds toward nuleophilic substitution
(SN2) is
(I) (II) (III) (IV)
(1) (II) > (III) > (IV) > (I) (2) (IV) > (II) > (III) > (I)
(3) (III) > (II) > (IV) > (I) (4) (II) > (III) > (I) > (IV)
3. In a substitution reaction of the type

R – Br + ClΘ which one of the following has the highest relative rate.
(1) (2)
(3) CH3–CH2Br (4) CH3–CH2–CH2Br
4.
(1) (2) (3) (4)

5.
(IV) Cl
2
Write decreasing order of SN reaction ?
(1) I > II > III > IV (2) II > I > III > IV (3) IV > III > II > I (4) IV > III > I > II
CH3
6. What are the suitable reactant for the following ether synthesis CH3—C—O—CH2–Ph
CH3
CH3 O Na
(1) CH3—C—O Na + Ph–CH2–Cl (2) Ph — CH— CH2—CH3 + CH3—CH—CH3

Cl
CH3
CH3 CH3
(3) CH3—C—Cl + PhCH2ONa (4) CH3 — C — ONa + CH3 – Cl
CH3 CH3
Type-2 (Nucleophilic Substitution Unimolecular (SN1))

7. What is the final product (Major) 'A' in the given reaction ?
CH OH
3
CH
CH3 
HCl
→ 'A'
(major product )
CH3 CH3 CH3 Cl

CH3
Cl CH Cl CH
(1) CH3 (3) CH3
CH2–CH3 (2) CH2–CH3 (4)
[JEE Main 2021]
8. The mechanism of SN1 reaction is given as :

R—X → R⊕XΘ → R⊕||XΘ
Ion pair Solvent
Separated
ion pair
Θ
Y
R—Y + XΘ
A student writes general characteristics based on the given mechanism as :
(1) The reaction is favoured by weak nucleophiles.
(2) R⊕ would be easily formed if the substituents are bulky.
(3) The reaction is accompanied by recemisation
(4) The reaction is favoured by non-olar solvents.
Which observation are correct ?
(1) (1) and (2) (2) (1) and (3) (3) (1), (2) and (3) (4) (2) and (4)

9. The decreasing order of reactivity of the following organic molecules towards AgNO3 solution
is
Cl Cl
(A) (B) (C) CH CH CH (D) CH CH CH NO

3 3 3 2 2
| |
OMe Cl Cl
(1) (A) > (B) > (C) > (D) (2) (C) > (D) > (A) > (B)
(3) (B) > (A) > (C) > (D) (4) (A) > (B) > (D) > (C)
10. Which of the following compounds will form the precipitate with aq. AgNO3 solution most
readiliy ?
Br
Br N N Br
N
(1) (2) (3) O Br (4)
OCH3
11. Increasing order of reactivity of the following compounds for SN1 substitution is
CH3
Cl Cl
CH2—Cl Cl
H3C H3CO
CH3
(A) (B) (C) (D)
(1) (A) < (B) < (D) < (C) (2) (B) < (C) < (D) < (A)
(3) (B) < (A) < (D) < (C) (4) (B) < (C) < (A) < (D)
12. Increasing rate of SN1 reaction in the following compounds is
Ι Ι Ι
MeO Ι
(A) (B) (C) (D)
H3C H3CO
(1) (A) < (B) < (C) < (D) (2) (B) < (A) < (C) < (D)
(3) (A) < (B) < (D) < (C) (4) (B) < (A) < (D) < (C)
CH3
CH3OH
CH3—C—CHCH3
H Br
CH3 CH3 CH3
CH3
(1) CH —C=CHCH (2) CH3—C—CH=CH2 (3) CH3—C—CHCH3 (4) CH3—C—CHCH3
3 3
H OCH3 H OCH3
14. Which of the following compounds will produce a precipitate with AgNO3 ?
Br Br Br
Br
(1) (2) (3) (4)
N

15. The correct increasing order of the reactivity of halides for SN reaction is - 1
(1) CH3 – CH2 – X < (CH3)2 CH – X < CH2 = CH – CH2 – X < PhCH2 – X
(2) (CH3)2CH – X < CH3 – CH2 – X < CH2 = CH – CH2X < PhCH2 – X
(3) PhCH2 – X < (CH3)2 CH – X < CH3 – CH2 – X < CH2 = CH – CH2 – X
(4) CH2 = CH – CH2 – X < Ph – CH2 – X < (CH3)2 CH – X < CH2 – CH2 – X
16. Which one is most reactive towards SN reaction? 1
(1) C6H5CH2Br (2)C6H5CH(C6H5)Br (3) C6H5CH(CH3)Br (4) C6H5C(CH3)(C6H5)Br
17. In an SN1 reaction on chiral centres, there is :

(1) 100% retention
(2) 100% inversion
(3) 100% racemization
(4) inversion more than retention leading to partial recemization
18. Correct order of reactivity towards SN1 is
(i) (ii) CH3 – CH2 – Br (iii) (iv)
(1) i > ii > iv > iii (2) iii > iv > ii > i (3) iv > ii > i > iii (4) ii > iv > iii > i
19. Arrange the following compounds in order of reactivity towards SN reaction. 1
(a) CH2 – CH2 – CH2 – CH3 (b) H3C – CH – CH2 – CH3 (c) OHC – CH – CH2 – CH3
| | |
Br Br Br
(1) a > b > c (2) b > a > c (3) c > b > a (4) a > c > b
20. Reactivity order for SN1
(i) (ii) (iii) (iv) CH3–CH2–CH2–Cl
(1) i > ii > iii > iv (2) iii > i > ii > iv (3) iii > ii > i > i v (4) iv > iii > ii > i
Type-3 (Nucleophilic Aromatic Substitution (SNAr))

21. The correct order of the following compounds showing increasing tendency towards nucleophilic
substitution reaction is :
Cl Cl Cl Cl
NO2 O2N NO2
(i) (ii) (iii) (iv)
NO2 NO2 NO2

(1) (iv) < (iii) < (ii) < (i) (2) (iv) < (i) < (ii) < (iii)
(3) (iv) < (i) < (iii) < (ii) (4) (i) < (ii) < (iii) < (iv)
[JEE Main 2021]

ANSWER KEY
1. (2) 2. (1) 3. (3) 4. (2) 5. (2)
6. (1) 7. (1) 8. (3) 9. (3) 10. (2)
11. (3) 12. (2) 13. (3) 14. (1) 15. (1)
16. (4) 17. (4) 18. (1) 19. (2) 20. (2)
21. (4)
SOLUTIONS
1. In (1) and (4), carbon atom bearing the leaving group (Br atom) are chiral. So, their
configurational change will take place with OH– ion by SN2 or SN1 pathway.
Me Me
* Br * Br
Ph C6H13
In (3), (CH3)2CH—Br does not have any chiral entra. So, no comment on configuration will
arise with (3). In option (2), the α-carbon (with respect to —CH2Br with which SN2 reaction will
take place) is only chiral. This α-carbon remains unaffected in SN2 pathway. So, it will show
retention in configuration.
1 1
2. Rate of SN2 reaction ∝ Stability of carbocation ∝ (effective
Stability of carbocation −I / −M
group)
δ+ δ+
CH2—Cl CH2Cl
NO2
NO2
–l-effect –M-effect
(I) –l-effect
(II)
(Distance dominating)
δ+ δ+
CH2—Cl CH2Cl
NO2 NO2 NO2

–M-effect –l-effect
–l-effect (IV)
(III)
S, the decreasing order of reactivity of the given compound toward SN2 reaction is
(II) > (III) > (IV) > (I)

+
OH OH2
+
H–Cl H–Cl
7.
1,2-shift
of H–
+
Cl–
Cl
⊕ ⊕ y~
R—X → RXΘ → R||XΘ R—Y + XΘ
8.
It indicates R⊕ (carbocation) formation takes place and R⊕ got stabilized by electronic factors
and polar solvent molecules because solvent separation of R⊕ is possible.
So, statement (4) is not correct.
Here, XΘ (leaving group) of R—X is substituted by YΘ, (nucleophile) via the formation of
carbocation (R⊕) intermediate, So, it is an SN1 reaction.
SN1 reaction is accompanied by inversion and retention in configuration, i.e. racemisation
provided 'R' of R—X is chiral. So statement (3) is correct.
Attachment of bulkier substituents or 3º-nature of the carbon atom of C—X bond of R—X will
favour formation of R⊕ (carbocation). So, statement (2) is also correct.
9. General reaction :
AgNO3 + X(Halogen) → AgX + NO32–
It follows SN1 reaction
In SN1 reaction,
Rate of reaction ∝ stability of carbocation
Cl
⊕
–
–Cl
(1)
AgNO3 NO3Θ+AgCl
(A) Aromatic
(i)
Cl ⊕
–
–Cl
AgNO3
(2) ••
(B) OCH3 OCH3
Aromatic and +M effect
(ii)

−
⊕
− Cl
(3) CH3 — CH— CH3 
AgNO3
→ CH3 — CH— CH3
| (2º)
Cl (iii)
(C)
−
⊕
− Cl
(4) CH3 — CH— CH2NO2 
AgNO3
→ CH3 — CH— CH2 — NO2 NO2 shows –M effect
| (iv )
Cl
Stability of carbocation is (ii) > (i) > (iii) > (iv)
So, the reactivity order towards AgNO3 solution is (2) > (1) > (3) > (4)
10. All given species in the question are alkyl halide. They react with aqueous AgNO3 solution
with different rate. Reaction undergoes as follows :
R — X + AgNO(aq) 
RDS
→ R + + AgX
Pr ecipitate
Hence, rate precipitate formation of AgX depends on stability of carbocation (R+).

In the given question all formed carbocation will be
⊕
⊕
N ⊕ N
N ⊕
O
(c)
(a) (d)
OCH3
(b)
Among the above given option(s) carbocation (1) is most stable due to stronger +M effect, s
give precipitate with aqueous AgNO3 solution most readily.
⊕
11. Reactivity of substitution nucleophilic unimolecular (SN1) reaction depends on the formation of
carbocation. Greater the stability of carbocation, greater will be its ease of formation of alkyl
halide and faster will be the rate of reaction. So, the correct order of (SN1) reactivity is
CH2Cl CH2—Cl
> > > CH3CH2Cl

Cl
OCH3
(+R)
(C) (D) (A) (B)

In compound C, the carbocation formed is stabilized by activating group (—OCH3). Compound
D forms benzyl carbocation (C6H5—CH2+) that is stabilised by resonance. Compound A
produces a primary carbocation that further rearranges itself o secondary carbocation.
NuΘ Rearrangement
⊕ ⊕
Cl
1º carbocation 2º carbocation
Compound B produces primary carbocation which is least stable among all the given options.
12. More stable the carbocation intermediate, higher will be the rate of SN1 reaction.
The reaction involving carbocation intermediate formation for the given compounds are as
follows :
Ι CH3 Three positive
hyperconjugation
Θ ⊕
–Ι 2º-benzyl carbocation
rds
⇒ Stable
(A)
+R
(A')
CH3
Ι
MeO ⊕ ⇒ Less stable
MeO Θ
–Ι
rds
–l effect
(B) from m-position
(B')
Ι CH3
Θ ⊕ ⇒ More stable
–Ι
rds
H3C H3C
(C)
Additional three
hyperconjugation
(C')
Ι CH3
Θ ⊕ ⇒ Highly stable
–Ι
rds
CH3O ••
(D) CH3—O
••
Additional +R effect from
p-position (D')
Stability of intermediates will follow the order
B' < A' < C' < D'
( −Ι ) ( −HPC =3) ( + HPC =
6)
(
+ HPC =
+R =1
3
)
So, the rate of SN1 reaction with the given compounds will be, B < A < C < D

13. In the given question, the substrate is a 2º-halide (bromide) and the medium, CH3OH (as well
as a poor nucleophile) is protic in nature, So, the reaction will follow mainly SN1 pathways via
the formation of a carbocation intermediate (l).
Me Me Me Me •• Me
–Br⊕ ⊕ CH3OH
rds
C—CH –H⊕ Fast
CH—CH—Me
Me H Me (2º) Me
H (I) OCH3
(Minor)
The intermediate, I can be rearranged into the more stable form l' (3º) by α-hydride shift.
l' will give the major product.
Me Θ Me ⊕
C—CHMe α-H shift C—CH2—Me
Me Me ••
H I' CH3OH –H⊕
••
I (3º carbocation)
(2º carbocation) Me
C—CH2Me
Me
OCH3
(Major)
14. Only ionic halides (X–) give precipitate of AgX with AgNO3 solution. So, an organic bromide
able to produce R⊕ (stable carbocation) and Br– in aqueous solution will give precipitate of
AgBr with AgNO3.
••(+ R-effect)
(1) Br ⊕ + BrΘ
••
••
(Bond energy also Unstable
increases (Aromatic, 6π system)
Θ
(2) Br ⊕ + Br
Stable carbocation
(Aromatic, 6π system
(3) Br ⊕ + BrΘ
Unstable
(Aryl carbocation
••(+ R-effect)
Br ⊕ + BrΘ
••
(4)
N •• N
Unstable
(Aryl carbocation
Br
So, only produces a precipitate of AgBr with AgNO3 solution.

21. For nucleophile substitution in aromatic halides
Cl Cl Cl Cl
NO2 O2N NO2
(i) (ii) (iii) (iv)
NO2 NO2 NO2

Correct order is :
(i) < (ii) < (iii) < (iv)
More No. of NO2 substituted aromatic halide, increase the rate of nucleophile substitution
reaction in aromatic halides.

C HE M IS T R Y

CPP
ST
ALCOHOL & ETHERS NO. 06
Type-1 (Elimination Unimolecular (E1))

1. The major product in the following reaction is [JEE Main 2020]

t-BuOH
heat
Ot–Bu
(1) (2) (3) (4)
2. When neopentyl alcohol is heated with an acid, it slowly converted into an 85 : 15 mixture of
alkenes A and B, respectively. What are these alkenes ?
H3C CH3 CH3
H3C CH2 H3C CH2
and H3C
(1) (2) and
H3C H C
CH 2
3 HC 2
H3C CH3 H3C CH2 CH3

H3C CH2
(3) and (4) H3C and
H3C H3C CH2 H3C
3. The decreasing order of reactivity towards dehydrohalogenation (E1) reaction of the following
compounds is :
(A) Cl (B) Cl (C) (D)

Cl Cl
(1) B > A > D > C (2) B > D > A > C (3) D > B > C > A (4) B > D > C > A
Type-2 (Elimination Bimolecular (E2))

4. For the given reaction :
1.NaNH2
HC CHBr A
2.Red hot iron tube, 873 K
(major product)
CH3
H3C CH3
(1) CH3CH2CH2NH2 (2) CH=CH–NH2 (3) (4)
CH3
CH3
[JEE Main 2021]
5. The major product obtained from E2-elimination of 3-bromo-2-fluoropentane is
Br
|
(1) CH3CH2 — CH— CH2  CH2 (2) CH3 CH2CH  C — F
|
CH3
F Br
| |
(3) CH3 — CH  CH — CH— CH3 (4) CH3 — CH2 — C  CH — CH3

CH2CH3
NaOEt
H3C C Cl D
COOCH2CH3
CO2CH2CH3
(1) CH3CH2CCH2 (2)
CH3CCHCH3
CO2CH2CH3
CH2CH3 OCH2CH3
(3) H3C C OCH2CH3 (4) H3CH2C C CO2CH2CH3
COOCH2CH3 CH3
Type-3 (Mixed Reaction of Alkene)

7. The major product of the following reaction is [JEE Main 2019]
1. KOH (alc.)
Cl 2. Free radical
Cl polymerisation
CH3 CH3
n n n
n
(1) (2) (3) (4)
Cl
Cl OH OH
8. The major product Y in the following reaction is

Cl EtONa HBr
Heat
X Y
Br
Cl HO
(1) (2) (3) (4)
Br
9. The major product(s) obtained in the following reaction is/are
t
(i) KO Bu
(ii) O3/Me2S
Br
CHO and OHC—CHO
(1) OHC (2) OHC
CHO
t
O Bu
(3) OHC CHO (4) OHC
CHO
Br
KOH alc. (excess)

Ph
Br
(1) (2)
Ph Ph
(3) (4)
Ph Ph
Type-4 (Consecutive E2)

11. The major product of the following reaction is [JEE Main 2019]
(i) KOH alc.
CH3 CH2 CH— CH2  (ii)NaNH2

| | in liq. NH3
Br Br
(1) CH3CH2 CH — CH2 (2) CH3CHCHCH2NH2
| |
NH2 NH2
(3) CH3CHCCH2 (4) CH3CH2CCH
Type-5 (Substitution v/s Elimination)

12. For the following reactions :
CH3CH2CH2Z+BrΘ
CH3
Θ |
CH3CH2CH2Br+Z where, Z  CH3CH2O (A) or H3C — C — O (B)
|
CH3CH2CH2+HZ+BrΘ CH3
ks and ke, are respectively the rate constants for substitution and elimination, and
CH3
|
µ = Z  CH3 CH2O (A) orH3C — C — O (B) , correct option is …….. [JEE Main 2020]
  
|
CH3
(1) µB > µA and ke (2) > ke (1) (2) µB > µA and ke (2) > ke (2)
(3) µA > µB and ke (2) > ke (2) (4) µA > µB and ke (2) > ke (1)
13. Consider the reaction sequence given below :
Θ
OH
Br OH + BrΘ ...(1)
rate = k [t-BuBr]
CH3
OHΘ + HOH + BrΘ ...(2)
C2H5OH
H2C CH3
rate = k [t-BuBr] [OH]Θ
Which of the following statements is true ?
(1) Changing the base from OHΘ to ΘOR will have no effect on reaction (2)
(2) Changing the concentration of base will have no effect on reaction (1)
(3) Doubling the concentration of base will double the rate of both the reactions
(4) Changing the concentration of base wil have no effect on reaction (2)
Type-6 (Ether based reactions)
14. The major product [B] in the following reactions is [JEE Main 2020]
CH3
|
HI H2 SO 4
CH3 — CH2 — CH — CH2 — OCH2 — CH3 
Heat
[A]alcohol 
[B]
CH3
|
(1) CH3 — CH  C — CH3 (2) CH2CH2
CH3
|
(3) CH3 — CH2 — C  CH2 (4) CH3—CH2—CHCH—CH3
15. 1-methyl ethylene oxide when treated with an excess of HBr produces :
Br Br CH3 Br
(1) Br (2) (3) Br (4)
Br CH3
CH3
16. Main Products formed during a reaction of 1-methoxy naphthalene with hydroiodic acid are :
I OH
(1) and CH3OH (2) and CH3I
OH I
(3) and CH3OH (4) and CH3I
ANSWER KEY
1. (2) 2. (1) 3. (3) 4. (4) 5. (2)

6. (2) 7. (2) 8. (2) 9. (1) 10. (4)
11. (4) 12. (4) 13. (2) 14. (1) 15. (1)
16. (2)
SOLUTION
1. Complete reaction is as follows :
 (Polar protic bond) 
t-BuOH 1, 2H
 Shift
H
 
1, 2H
Shift

H
More substituted
Alkene (major)
The alkene formed is stable according to Saytzeff's rule. It states that alkenes with less
number of hydrogen on the double bonded carbon atoms are proffered product.
2. Reaction is as follows :
CH3 CH3
•• H2SO4(acid)
H3C—C—CH2 OH H3C—C—CH2 OH2
••
CH3
H2SO4 is sulphuric acid, that contain H and alcohol f contain lone pair.

Lone pair of oxygen accept H ion and form OH2 but oxygen is electronegativity element and
here O contain positive charge means it is unstable. Then H2O will remove from here.
(1º carbocation)
CH3 CH3
–H2O 
H3C—C—CH2 OH2 H3C—C—CH2
(3ºcarbocation) CH3
Stability of carbocation
is 3º > 1º.
CH3
H3C—C—CH2—CH3

3º carbocation
On heating 3º carbocation, 2 possible products are possible.
These are as follows :

CH3
 
H3C—C—CH2—CH3

Left Right
(–H+)
CH3 CH3
H2CC—CH2—CH3 CCH2—CH3
CH3
2-substituted 3-substituted
(Minor product (B) (Major product (A)
(15%) (85%)
So, correct option is (1).
3. E1 reaction proceeds via carbocation formation, therefore greater the stability of carbocation
faster is the reaction. Carbocation formed by D,  (2º, resonance stabilised and the
product is diene) is most stable followed by B,  (1º and the product formed is diene).
Further among C and A, he carbocation formed is diene). Further among C and A, the
carbocation formed by C is more stable  (2º) than A,  (1º). Thus the

reactivity towards dehydrohalogenation follows the order : D > B > C > A
NaNH2
4. CH CHBr CCH
–HBr
CH3 CH3
Red hot iron

tube 873 K
H3C CH3
CH3
5. Br atom is large than F atom, So, C—Br is weaker than C—F bond. In elimination (E2), C—Br
bond will be cleared.
Br F(–l)
' 

CH3—CH—CH—C—CH
2 3
5 4 3 1
H More
H acidic ,-elimination
Hofmann Saytzeff (E2)
centre for centre for –HBr
E2 E2 F
CH3—CH2—CH
5 4 3
C—CH
2 1
3
(2-fluoro-pent-2-ene)
(Major)
–l-effect of F atom makes the -hydrogen more acidic for its elimination by a strong base used
in E2.
6. Presence of strong base (EtO–) and heat indicates elimination.

Thus, the compound undergo dehydrohaloganation and alkene is produced. As per the
position of Cl in substrate, following 2 alkenes are formed as product.
(i) CH3CH2CCH2
COOCH2CH3
(ii) CH3CHC—CH3
COOCH2CH3
In accordance with Saytzeff rule
CH3CHC—CH3
COOCH2CH3
Will be the major product.
7. In presence of alc. KOH, the given halide undergoes elimination reaction.
1. KOH (alc.)
Cl Cl Cl
The alkene produced undergoes polymerization via free radical mechanism. This process
involve three steps, i.e. initiation, propagation and termination.
Polymerisation n
Cl Cl
Polymerisation
8. The given reaction takes place as follows :
Cl
EtONa/
H
-H for -elimination
Saytzeff elimination –HCl
CH2
H -H for
Hoffmann elimination
Markownikov's
centre for BrΘ +
3-methyl but-2-ene 3-methyl but-1-ene
major (X) minor
(Saytzeff product) (Hoffmann product)
HBr Electrophilic addition

(Markownikov's rule)
Br
Br +
2-bromo-3-methyl 2-bromo-2-methyl
butane (minor) butane (major) (Y)
9.
Step II
Step I
CHO
O3/Me2S
t
KO Bu Ozonolysis OHC
Br Cyclohex-1, and OHC—CHO

3-diene
In step-1 dehydrohalogenation reaction takes place. Here, hydrogen is eliminated from -

carbon and the halogen is lost from -carbon atom. As a result diene is formed.
H –
OtBu
Br Cyclohex-1,
3-diene
Cyclohex-1, 3-diene on ozonolysis gives butane-1, 4-dial and ethane-1,2-dial.
CHO
O3 CHO
Me2S
+ (CH2)2
CHO
CHO
10. The reaction follows , -elimination mechanism to give a more substituted stable alkene as a
major product. As the substrate is a , -dibromo (1, 3-) compound it gives a conjugated
diene.
HOΘ Br Alc. KOH

H

Ph H –2HBr
(It is very stable because
Θ
Br OH the conjugated diene
system present. It is
further conjugated with
the benzene ring.
11. The reaction proceeds as :

Alc. KOH
CH3CH2—CH—CH2 CH3—CH2—CHCH2
Br Br Br
NaNH2/liquid NH3
–
CH2—CH2—CCH + CH3CH2CCNa+
H
Thus, option (4) is the correct answer.
12.
CH3—CH2—CH2—OCH2—CH3
ks(Rate constant of
–
CH3—CH2—CH2—Br
Z =(A) substitution)
–
–Br ke (Rate constant of
elimination)
CH3—CHCH2+CH3CH2OH
CH3
CH3
+CH3—C—O–
CH3 CH3—CH2—CH2—O—C—CH3
ks
Z–=(B) CH3
–
–Br k CH
e 3
CH3—CHCH2 + CH3—C—OH
CH3
When alkyl halides react with nucleophiles (Z–), both substitution and elimination reactions
can be expected. 1º alkyl halides generally favour substitution, but stronger bases favour
elimination. So, in the above reaction in which (CH3—CH2—CH2—Br is 1º alkyl halide,
CH3CH2—O– is a strong base), reasonable amounts of substitution and elimination products
can form between A = CH3CH2O– and alkyl halide.
(1) is an unhindered nucleophile, so it can give substitution better than (2) which is hindered
(more crowded or sterically hindered). But (B tends to give elimination better than (1) due to
the same reason also.
ks
 µ is in the order A > B and ke is in the order B > A.
ke
13. Reaction (1)

Rate k[t-BuBr], it is a first order nucleophilic substitution reaction (SN1), so, rate of this reaction
will depend only on the concentration of the substrate, i.e. t-BuBr.
So, option (2) is correct, but option (3) is not correct.
Θ
RDS OH
Br –Br  fast
OH
3º
(t-Br) Carbocation
intermediate
Reaction (2)
Rate = k [t-ByBr] [OH–], it is a second order
(base)
, -elimination reaction (E2), because t-BuBr undergoes dehydrohalogenation (—HBr) with a
strong base (alcoholic or ethanolic OH–) to give an alkene.
So, rate of the reaction depends on concentrations of substrate (t-ByBr) and base (OH/alc.).
So, option (1) is not correct.
  
O R is a stronger base than OH , So, use of OR will make the E2 reaction faster. Hence,
option (1) is also not correct.
14.
CH3
CH3—CH2—CH—CH2—O—CH2—CH3
via I (Iodine attahced to
HI (SN2) less hindered alkyl
reaction group)
CH3
CH3
CH3—CH2—CH—CH2—OH + CH3—CH2—l
[A] H2SO4/D
E1 reaction
CH3
CH3—CH2—CH—CH2r
CH3
Rearrangement
1, 2-H-shift
CH3—CH2—C—CH
r 3
For more stable According to

carbonation  Markownikoffs rule (more
subtituted alkene formed
CH3 CH3
CH3—CH3—C + CH3—CHC
CH3 CH3
(Minor product (Major product
(B)
15. The given reaction is completed as follows :

+
H
CH3—CH—CH2
(From HBr)
O CH3—CH—CH2
1-methylethyleneoxide +
O
Br Br H
–
HBr Br
CH3—CH—CH2Br CH3—CH—CH2
(Product)
OH
16.
O—CH3 OH
HI
+ CH3–I
Mechanism H

O—CH3 O—CH3 OH
H I
+ CH3–I
(SN2)
C HE M IS T R Y

CPP
ST
ALDEHYDE, KETONE & CARBOXYLIC ACID NO. 07
Type-1 (Nucleophilic Addition)

1. The increasing order of the following compounds towards HCN addition is
H3CO CHO CHO
CHO
(i) (ii) O2N CHO
NO2 (iii) (iv)
OCH3
(1) (i) < (iii) < (iv) < (ii) (2) (iii) < (iv) < (i) < (ii)
(3) (iii) < (iv) < (ii) < (i) (4) (iii) < (i) < (iv) < (ii) [JEE Main 2020]
2. The increasing order of the reactivity of the following compounds in nucleophilic addition
reaction is : Propanal, Benzaldehyde, Propanone, Butanone
(1) Benzaldehyde < Butanone < Propanone < Propanal
(2) Butanone < Propanone < Benzaldehyde < Propanal
(3) Propanal < Propanone < Butanone < Benzaldehyde
(4) Benzaldehyde < Propanal < Propanone < Butanone
3. The increasing order of the rate of HCN addition to compounds a-d is

(a) HCHO (b) CH3COCH3 (c) PhCOCH3 (d) PhCOPh
(1) a < b < c < d (2) d < b < c < a (3) d < c < b < a (4) c < d < b < a
4. In the following reaction,

HCl
Aldehyde + Alcohol   Acetal
t
HCHO BuOH
CH3CHO MeOH
The best combination is
(1) CH3CHO and MeOH (2) CH3CHO and tBuOH
(3) HCHO and MeOH (4) HCHO and tBuOH
O O
Ethylene Glycol A
5. +
OC2H5 H (Major Product)
The product "A" in the above reaction is :
OH O
O O O O
OC2H5
(1) OH (2) O O (3) (4) O O
OC2H5 OC2H5 OH
OH

Type-2 (Grignard Reagent)
6. The product formed in the first step of the reaction of [JEE Main 2021]
Br
CH3–CH2–CH–CH2–CH–CH3 with excess Mg/Et2O(Et = C2H5) is:
Br
(1) CH3–CH2–CH–CH2–CH–CH3 (2) CH3–CH2–CH–CH2–CH–CH3
CH3–CH–CH2–CH–CH2–CH3 CH3–CH2–CH–CH2–CH–CH3
MgBr
CH2
(3) CH3–CH (4) CH3CH2–CH–CH2–CH–CH3
CH–CH3
MgBr
CN
(i) C6H5MgBr Ether (1.0 equivalent ), dry
7.  (ii) H3O
 X Major Product
OCH3
The structure of X is :
O O
C6H5 C6H5
(1) NH2 (2) NH2 (3) (4)
C6H5
C6H5 OCH3 C6H5 OCH3
8. Reaction of Grignard reagent, C2H5MgBrwith C8H8O followed by hydrolysis gives compound

"A" which reacts instantly with Lucas reagent to give compound B, C10H13Cl. The Compound
B is :
Cl
CH3 Cl CH3
CH3
Cl
(1) CH3 (2) (3) CH3 (4) CH3
Cl
OH
9. CH3CH2—C—CH3 cannot be prepared by
Ph
(1) CH3CH2COCH3 + PhMgX (2) PhCOCH3 + CH3CH2MgX
(3) PhCOCH2CH3 + CH3MgX (4) HCHO + PhCH(CH3)CH2MgX
10. The aldehydes which will not form Grignard product with one equivalent Grignard reagents
are
CHO CHO
(A) (B)
HO2C
CHO CHO
(C) (D)
HO3CO HOH2C
(1) (C), (D) (2) (B), (D) (3) (B), (C), (D) (4) (B), (C)

11. Phenyl magnesium bromide reacts with methanol to give
(1) a mixture of anisol and Mg(OH)Br (2) a mixture of benzene and Mg(OMe)Br
(3) a mixture of toluene and Mg(OH)Br (4) a mixture of phenol and Mg(Me)Br
Type-3 (Oxidizing Reagent Based)
12. Which of the following reagent is used for the following reaction ?
?
CH3CH2CH3   CH3CH2CHO [JEE Main 2021]
(1) Manganese acetate
(2) Copper at high temperature and pressure
(3) Molybdenum oxide
(4) Potassium permanganate
13. The major product of the following reaction is:

H /CO
CH3CH2CH = CH2 2
Rh catalyst

(1) CH3CH2CH=CH–CHO (2) CH3CH2C=CH2

CHO
(3) CH3CH2CH2CH2CHO (4) CH3CH2CH2CHO]

Statement-I : 2-methylbutane on oxidation with KMnO4 gives 2-methylbutan-2-ol.
Statement-II : n-alkanes can be easily oxidised o corresponding alcohol with KMnO4.
Choose the correct option :
(1) Both statement I and statement II are correct
(2) Both statement I and statement II are incorrect
(3) Statement I is correct but Statement II is incorrect
(4) Statement I is incorrect but Statement II is correct
Type-4 (Reducing Agent Based)
15. ?
O
Which of the following reagent is suitable for the preparation of the product in the above
reaction ?
 
(1) NaBH4 (2) NH2–NH2/ C2H5 ONa
(3) Ni/H2 (4) Red P + Cl2 [JEE Main 2021]

O
O
i) DIBAL H, Toluene, 78ºC

16. 
ii) H O 
 "P "
3 (Major Pr oduct )
The product "P" in the above reaction is :

OH
(1) COOH (2) CHO
O–C–H
(3) (4) CHO
17. Which one of the following reactions will not form acetaldehyde?
Cu (i)DIBAL H
(1) CH3CH2OH  573 K
 (2) CH3CN  (ii)H O
 2
Pd(II)/Cu(II) CrO3 H2SO4
(3) CH2 = CH2 + O2 
 H2 O
(4) CH3CH2OH 

Type-5 (Aldol and Intramoleculer Aldol)
18. Identify A in the given chemical reaction,
CH2CH2CHO NaOH
A (Major product)
C2H5OH, H2O, 
CH2CH2CHO
CHO CH2CH2COOH
(1) (2)
CH2CH2CH2OH
O
C–H O
(3) (4) [JEE Main 2021]
O
O
Dil NaOH H+, Heat
19. 2 "X" "Y"
Consider the above reaction, the product 'X' and 'Y' respectively are :
OH O O O
, ,
(1) (2) OH
O
O O O O
(3)
, (4)
,
OH OH

20. The major product formed in the following reaction is
O CH3
O
dil. NaOH
H3C H +
O OH OH O
H3C H3C
(1) (2)
O OH
OH O
H H3C
(3) H C H (4)
3
21. The major product obtained in the following reaction is

CH3 O
NaOH
OHC 
CH3 CH3
CH3 H3C
(1) H (2) H (3) (4)
O CH3 O CH2
O O
22. In the following reactions, products A and B are
O O
Dil. NaOH H3O+
H 3C H [A] 
[B]
H3C CH3
O O
CH3 CH3
(1) A = CH3 ; B= CH3
HO
O O
CH3 CH3
(2) A = CH3 ; B = CH3
HO
O
OH O
C CH3
H3C H H
(3) A = ;B=
H3C H3C
CH3 CH3
O
O
OH C H2C
H3C H H
(4) A = ;B=
H3C H3C
CH3 CH3

Type-6 (Cannizaro Reaction)
23. Identify A in the following chemical reaction
CHO
(i) HCHO,NaOH
A
(ii) CH3CH2,Br,NaH, DMF [JEE Main 2021]
CH3O (iii) HI, 
O
C–OCH2CH3 CH2OH
(1) HO (2) CH3O

CH2I CH2OH
(3) HO (4) HO
24. Major products of the following reaction are

CHO
(i) 50% NaOH
+ HCHO +
(ii) H3O
COOH
(1) CH3OH and HCO2H (2) CH3OH and
CH2OH CH2OH COOH
(3) HCOOH and (4) and
25. Trichloroacetaldehyde was subjected to Cannizzaro's reaction by using NaOH. The mixture of the
products contains sodium trichloroacetate ion and another compound. The other compound is
(1) 2, 2, 2-trichlorethanol (2) trichloromethanol
(3) 2, 2, 2-trichloropropanol (4) chloroform
Type-7 (Acid and it’s derivations)
26. The decreasing order of ease of alkaline hydrolysis for the following esters is
COOC2H5 Cl COOC2H5
I II
O2N COOC2H5 CH3O COOC2H5
III IV
(1) III > II > IV > I (2) III > II > I > IV (3) II > III > I > IV (4) IV > II > III > I

CO2Et
NaOEt/
O
O
O O O O
(1) (2) CO2Et (3) (4) CO2Et
CO2Et CO2Et

ANSWER KEY
1. (4) 2. (2) 3. (3) 4. (3) 5. (2)
6. (4) 7. (4) 8. (3) 9. (4) 10. (2)
11. (2) 12. (3) 13. (3) 14. (3) 15. (2)
16. (2) 17. (4) 18. (3) 19. (3) 20. (3)
21. (3) 22. (2) 23. (3) 24. (3) 25. (1)
26. (2) 27. (2)
SOLUTIONS
O O OH O
5. OH
O O C2H5
OC2H5 H
+ O
Br Br MgBr MgBr
Mg(Excess)
6. 
(dry ether )
Ph
+
CN – + C=N–MgBr
PhMgBr
7. Dry ether
OCH3 OCH3
H3O+
Ph Ph
C=N C=NH Br
+
H3O
+Mg
OH
OCH3 OCH3
MO O
12. CH3–CH2–CH3 
2 3
 CH3–CH2–CH=O
The reagent used will be MO2O3
13. OXO PROCESS (Hydroformylation) :

Rh
CH3–CH2–CH = CH2 + CO + H2 
catalyst
 + CHO
CHO (Major)

14. Alkane are very less reactive, tertiary hydrogen can oxidise to alcohol with KMnO4.
H KMnO4 OH
2-methyl-butane
(i) NH2–NH2
15. – +
(ii) EtO Na /
O
To reduce the carbonyl groups into alkane wolf – kischner reduction is used, without affecting
the double bond.
O H
O OH C=O
(i) DIBAL-H
(ii) H3O
16.
DIBAL cannot reduce double bond It can reduce cyclic ester.
O
CrO3 .H2SO4
17. CH3CH2OH   CH3–C–OH
Strong oxidising agent
(Carboxylic
acid is formed
by complete
oxidation)
O
CH2–CH–C–H –
OH–
18. H
CH2–CH2–C–H
O O
2
CHO 3 1
 H
H
7 H
OH 4 6
5
O
CHO
C2H5OH/
–H2O

O O O
Θ
H OH Θ
19.
–H2O
H2O
O O OH

(X)
(Y)
O
C–H
NaOH 
23. + H–C–H Cannizaro H–C–ONa + H3CO CH2–OH
O O
OCH3
CH3–CH2–Br
H3C – O CH2 – O–CH2–CH3

I–H I–H
HI 
CH2–I
+ CH3–I+CH3–CH2–OH
 HI
OH
CH3–CH2–I

CHEMISTRY

CPP
ST
AMINES NO. 08
Type-1 (Carbylamine Reaction)

1. Carbylamine test is used to detect the presence of primary amino group in an organic
compound. Which of the following compound is formed when this test is performed with
aniline?
NHCH3 CONH2 CN NC
(1) (2) (3) (4)
[JEE Main 2021]

NH2
(i) CHCl3/KOH
(ii) Pd/C/H2
CN O
H H H H
NCH3 NCH3 NCHCl2 NCH3
(1) (2) (3) (4)
CN O CN OH CN OH H2N OH
Type-2 (Gabriel Phthalimide Reaction)
3. The total number of amines among the following which can be synthesized by Gabriel
synthesis is _______.
(1) CH3 CH–CH2–NH2 (2) CH3CH2NH2

CH3
CH2–NH2 NH2
(3) (4)
[JEE Main 2021]

4. Which of the following compounds can be prepared in good yield by Gabriel phthalimide
synthesis ?
CH2NH2
(1) (2) CH3—CH2—NHCH3
O NH2
CH2—C—NH2
(3) (4)
5. Which of the following amines can be prepared by Gabriel phthalimide reaction ?
(1) n-butylamine (2) triethylamine
(3) t-butylamine (4) neo-pentylamine
Type-3 (Hoffman Bromamide Degradation)
6. Which of the following reaction DOES NOT involve Hoffmann Bromamide degradation ?
O
CH2—C—NH2 Br2, NaOH
CH2—NH2
(1)
CN i) KOH, H O NH2
2
(2)
ii) Br2, NaOH
O
i) Br2, NaOH/H+
CH2—C—CH3 ii) NH3/
CH2—NH2
(3)
iii) LiAlH4/H2O
O
i) NH3,NaOH NH2
Cl
(4)
ii) Br2, NaOH
[JEE Main 2021]

7. Hoffman bromomide degradation of benzamide give product A, which upon heating with
CHCl3 and NaOH gives product B. The structure of A and B are :
NH2 NH2
CHO
(1) A - B-
Br Br
NH2 NC
(2) A - B-
NH2 NH2
CHO
(3) A - B-
O O
NH2 NH2
CHO
(4) A - B-
Br Br
O
C O
Cl
8. + C6H5NHC6H5  C6H5—C—N—(C6H6)2
0.140 g 0.388 g 0.210 g
Consider the above reaction. The percentage yield of amide product is ______ .
(Round off to the Nearest Integer).
[Given : Atomic mass : C : 12.0 u, H : 1.0u, N, 14.0 u, O : 16.0 u, Cl : 35.5 u]
9. A compound 'X' on treatment with Br2/NaOH, provided C3H9N, which gives positive
carbylamines test. Compound 'X' is
(1) CH3COCH2NHCH3
(2) CH3CH2CH2CONH2
(3) CH3CON(CH3)2
(4) CH3CH2COCH2NH2

C
NH2 (i) Br2/hv
(ii) KOH(dil.)
CH2CH3
O
NH2
(1) (2) NH
CH3
NH2 NH
(3) (4)
11. In the Hofmann-bromamide degradation reaction, the number of moles of NaOH and Br2 used
per mole of amine produced are
(1) four moles of NaOH and two moles of Br2
(2) two moles of NaOH and two moles of Br2
(3) for moles of NaOH and one mole of Br2
(4) one mole of NaOH and one mole of Br2

ANSWER KEY
1. (4) 2. (4) 3. (3) 4. (1) 5. (1)
6. (3) 7. (2) 8. (77) 9. (2) 10. (1)
11. (3)
SOLUTION
1. CARBYL amine given by 1° amine
NH2 N=C
+ CHCl3 + 3KOH + 3KCl + 2H2O
3. Gabriel phthalimide synthesis is used to prepare 1° aliphatic/alicyclic amine in common.

Hence amine which can synthesised by Gabriel phthalimide synthesis method is :
(A) Me2CH–CH2–NH2 (B) CH3CH2NH2 (C) Ph–CH2–NH2
O O
CH2—C—CH3 CH2—C—OH + CHBr3
i) Br2 + NaOH
6. +
ii) H
NH3/
Haloform Reaction
O
CH2—C—NH2 CH2—CH2—NH2
LiAlH4
 This reaction does no involve haffmann bromanide degradation.

 Rest all options involved haffmann bromamide degradation during the reaction of Br2 +
NaOH with amide.

7. Hoffmann bromamide degradation reaction :
C—NH2+Br2 4NaOH NH2(A)
CHCl3/KOH
NC(B)
Carbylamine reaction :
O O
C C—N(C6H5)2
Cl
8. + C6H5NHC6H5  + HCl
1 mole 1 mole 1 mole

= 140.5 gm = 169 = 273 gm
169
 0.140 gm  0.140
140.5
L.R. = 0.168 gm < 0.388 gm
Excess
 Theoretical amount of given product formed
273
  0.140  0.272 gm
140.5
But is actual amount formed is 0.210 gm. Hence, the percentage yield of product.
0.210
  100  77.20  77
0.272
OR
O O
Ph
C—Cl C—N
0.388 g Ph
(C6H5)2NH
excess
0.140 g 0.210 g
0.140
Mole of Ph—CoCl =  10 3 mol
140
O
||
Mole of Ph — C— N(Ph)2 , that should be obtained by mol-mol analysis = 10–3 mol. Theoritical
mass of product = 10–3 × 273 = 273 × 10–3 g
Observed mass of product = 210 × 10–3 g
210  103
% yield of product =  100  76.9%  77
273  103

C HE M IS T R Y

CPP
ST
AROMATIC CHEMISTRY NO. 9
Type-1 (Oxidation)
CH3
Alkaline KMnO4
H
+ "X"
1. [JEE Main 2021]
CH3
Considering the above chemical reaction, identify the product "X" :

CHO CH2OH COOH CH3
(1) X- (2) X- (3) X- (4) X-
OCH3 OCH3 COOH OH
Type-2 (Electrophilic Substitution Reaction)

2. The major product of the following reaction is:
NO2
H2SO4
NO2 NO2 NO2

NO2
(2) (3) (4)
(1)
[JEE Main 2021]
3. The correct sequence of reagents used in the preparation of 4-bromo-2-nitroethyl benzene

from benzene is :
(1) HNO3/H2SO4, Br2/AlCl3, CH3COCl/AlCl3, Zn-Hg/HCl
(2) Br2/AlBr3, CH3COCl/AlCl3, HNO3/H2SO4, Zn/HCl
(3) CH3COCl/AlCl3, Br2/AlBr3, HNO3/H2SO4, Zn/HCl
(4) CH3COCl/AlCl3, Zn-Hg/HCl, Br2/AlBr3, HNO3/H2SO4

4. Identify the major products A and B respectively in the following reactions of phenol.
OH
(i) CHCl3,NaOH Br2 in CS2

B (ii) H3O+ A
273 K
OH OH OH OH
Br CHO
(1) and (2) and
CHO Br
OH OH OH OH
Br CHO
(3) and (4) and
Br CHO
(1) Zn/HCl
5.
(2) Cr2O3,773K
O 10-20 atm
Considering the above reaction, the major product among the following is :
CH2CH3 CH2CH2CH3 CH3 COCH2CH3
CH3
(1) (2) (3) (4)
NO2
HNO3
6. H2SO4
In the above reaction, 3.9 g of benzene on nitration gives 4.92 g of nitrobenzene. The
percentage yield of nitrobenzene in the above reaction is _______ %. (Round off to the
Nearest Integer). (Given atomic mass : C : 12.0 u, H : 1.0u, O : 16.0 u, N : 14.0 u)
7. In the following reaction sequence the major products A and B are

O
+ O Anhydrous (1)ZnHg / HCl


AlCl3
A 
(2)H3PO4
B
O
O O
(1) A = ;B= (2) A = ;B=

CO2H CO2H
O
O O
(3) A = ;B= (4) A = ;B=

CO2H CO2H
O O

8. The correct match between Item-I (starting material) and Item-II (reagent) for the
preparation of benzaldehyde is
Item-I
(I) Benzene (P) HCl and SnCl2, H3O+
(II) Benzonitrile (Q) H2, Pd-BaSO4, S and quinoline
(III) Benzoyl chloride (R) CO, HCl and AlCl3
(1) (I) - (Q), (II) - (R) and (III) - (P) (2) (I) - (P), (II) – (Q) and (III) - (R)
(3) (I) - (R), (II) - (P) and (III) - (Q) (4) (I) - (R), (II) – (Q) and (III) - (P)

O HO
CH3
O AlCl3
 
+ 
OH OH OH
OH
H3C CH3 CH3
CH3
(1) (2) (3) (4)
O
O O
O

OH
Br2 (excess)
 
SO3H
OH OH OH OH
Br Br Br Br Br
(1) (2) (3) (4)
Br Br
Br SO3H Br SO3H
11. The final major product of the following reaction is

Me
(i) Ac 2O /Pyridine

(ii) Br2 ,FeCl3

(iii)OH / 
NH2
Br
Me Me Br Me Me
(1) (2) (3) (4)
Br Br
NH2 NH2 NH2 NH2

12. What is the correct sequence of reagents used for converting nitrobenzene into m-
dibromobenzene ?
NO2 Br
Br

NaNO2 HCl KBr H
(1)  
     
Br2 /Fe Sn/HCl NaNO 2 /HCl CuBr /HBr
(2)       

Sn/HCl KBr Br2 H
(3)       
Sn/HCl Br2 NaNO2 NaBr
(4)    
    
13. In the following reaction the reason why meta-nitro product also formed is :
NH2 NH2 NH2 NH2
Conc.HNO3 NO2
+ + +
Conc.H2SO4,288K
NO2
[A] [B] [C]
51% 47% 2%
(1) Low temperature

(2) –NH2 group is highly meta-directive
(3) Formation of anilinium ion
(4) –NO2 substitution always takes place at meta-position
NH2 NH2 NH2 NH2

NO2
HNO3, H2SO4
14. + +
288 K
NO2
NO2
(A) (B) (C)
Correct statement about the given chemical reaction is :

(1) group is ortho and para directive, so product (B) is not possible.
(2) Reaction is possible and compound (B) will be the major product.
(3) The reaction will form sulphonated product instead of nitration.
(4) Reaction is possible and compound (A) will be major product.

Statement I : o-Nitrophenol is steam volatile due to intramolecular hydrogen bonding.
Statement II : o-Nitrophenol has high melting due to hydrogen bonding.
In the light of the above statements, choose the most appropriate answer from the options
given below :
(1) Statement I is false but Statement II is true
(2) Both statement I and statement II are true
(3) Both statement I and statement II are false
(4) Statement I is true but statement II is false
Type-3 (Diazotization and Coupling reaction)

NH2 OH
NaNO2, HCl "A"

16. "X"
NaNO2, HCl
In the above chemical reaction, intermediate "X" and reagent/condition "A" are :
N2+Cl– NO2
(1) X - ; A-H2O/NaOH (2) X - ; A-H2O/
N2–Cl– NO2
(3) X - ; A-H2O/ (4) X - ; A-H2O/NaOH
[JEE Main 2021]
17. ‘A’ and ‘B’ in the following reactions are :

NH2
+
NaNO2/HCl SnCl2/HCl/H3O
(A) (B)
KCN
+ +
N2Cl– CHO N2Cl– Cl
(1) (A) : (B) : (2) (A) : (B) :
CN CHO CN Cl
(3) (A) : (B) : (4) (A) : (B) :

18. Which of the following reaction/s will not give p-aminoazobenzene?
NO2 NO2 NH2
(i) Sn/HCl (i) NaBH4 (i) HNO2
(A) (ii) HNO (B) (ii) NaOH (C) (ii) Aniline, HCl
(iii) Aniline (iii) Aniline NaOH
(1) A only (2) B only (3) C only (4) A and B
OCH3
19. C7H7N2OCl+C2H5OH + N2 + "X" + "Y"

(A)
In the above reaction, the structural formula of (A), "X" and "Y" respectively are :
–
N2+Cl– N2+OCH3
O
H H
(1) , CH3—C—H, HCl (2) , H H , HCl
O
OCH3 Cl
–
N2+OCH3 N2+Cl–
O
H H
(3) , CH3—C—H, H2O (4) , H H , H2O
O
Cl OCH3
H3C CH3
N
NH2
NaNO2, HCl 'X' 'Y'

20.
273K-278K (Major Product) (Major Product)
Considering the above reaction, X and Y respectively are :
N+
2Cl
– N+
2Cl
–
N N CH3
(1) N (2) and N N
and CH3
N—CH3
CH3
Cl Cl
N CH3 N
(3) N N (4) and N
and CH3
N
H3C CH3

ANSWER KEY
1. (3) 2. (3) 3. (4) 4. (2) 5. (1)
6. (80) 7. (4) 8. (3) 9. (3) 10. (3)
11. (4) 12. (2) 13. (3) 14. (4) 15. (4)
16. (3) 17. (3) 18. (2) 19. (1) 20. (2)
SOLUTIONS
CH3 CO2H
Alkaline KMnO4
1. H+
CH3 COOH
(X)
NO2 + –
H /HSO4
2. + Products

+
NO2
NO2
O O
NO2
CH3–C–Cl/AlCl3 CH3 Zn–Hg
3. HCl
Br Br
Br2/AlBr3
NO2  More active

HNO3
H
Br Br

OH O OH OH
C–H
(i) CHCl3,NaOH Br2 in CS2
4. B + A
(ii) H3O 273 K
Salicylaldehyde
Br
p-Bromo phenol
Zn–Hg/HCl Cr2O3,773 K 10-20 atm

5.
O
NO2
HNO3
6. H2SO4
1 mole 1 mole
78 gm 123 gm
123
3.9 gm  3.9  6.15 gm
78
But actual amount of nitrobenzene formed is 4.92 gm and hence.
4.92
Percentage yield =  100  80%
6.15
12. Correct sequence of reagents for the following conversion.

NO2 Br
Br
NO2 NO2 NH2
Br2/Fe Sn
 +HCl
Br Br
NaNO2/HCl
+ –
Br N2Cl
CuBr
HBr
Br Br
NH2 NH3
Conc.HNO3
13. (very high –I effect)
+H2SO4
(Anilinium ion)
Aniline on protonation gives anilinium ion which is meta directing. So considerable amount of
meta product is formed.

NH2 NH2 NH2 NH2
NO2
HNO3
14. + +
H2SO4
NO2
NO2
51% 47% 2%
Due to formation of anilinium ion by acid base reaction m-product is form as considerable
amount.
NH2 NH3 NH3
HNO3
+ H2SO4
NO2
H
O O
N
Intramolecular
15. O H-bonding
Thus it is more volatile due to intramolecular H-bonding.

Melting point depends on packing efficiency not on H-bonding thus statement II is false.
NH2 N2Cl OH
NaNO2 + HCl H2O/

16. 273–278K
Diazotisation
Reaction (A) (B)
+
NH2 N2Cl– CN
NaNO2/HCl KCN
17.
KCN
Diazotization
Stephen +
SnCl2/HCl/H3O
reduction
CH=O

18. In basic or neutral medium N–N coupling favourable while in slightly acidic medium C–N
coupling favourable.
NO2 NH2 N2
(i) Sn/HCl (ii) HNO

(A)
Diazonium
1 H
NH2
NH2 N=N
NO2 NH2
NaBH4 NaOH
(B) No reaction
No reaction
Product not
formed
NH2 N2
HNO2
(C)
NH2 HCl
N=N NH2
N2+Cl–
19. + CH3—CH2—OH  + CH3CHO+HCl+N2
OCH3 OCH3
Anisole

NH2 N2+ClΘ
NaNO2, HCl
20. (X) Major product
273-278K
CH3 CH3
N
CH3 CH3
N
N=N
(Y)
Major Product

CHEMISTRY

CPP
ST
BIOMOLECULES NO. 10
Type-1 (Monosaccharides & Reaction of glucose)

1. Consider the following reactions :
Dry HCl x eq. of
(i) Glu cos e  ROH  Acetal 
(CH CO) O
Acetyl derivative
3 2
Ni/H y eq. of
(ii) Glu cos e 
2
 A 
(CH CO) O
Acetyl derivative
3 2
z eq. of
(iii) Glu cos e  Acetyl derivative
(CH3CO) 2 O
x’, y’ and z’ in these reactions are respectively [JEE Main 2020]

(1) 5, 4 and 5 (2) 4, 5 and 5 (3) 5, 6 and 5 (4) 4, 6 and 5
2. Which of the following statements is correct ?

(1) Gluconic acid is obtained by oxidation of glucose with HNO3
(2) Gluconic acid is a dicarboxylic acid
(3) Gluconic acid can form (acetal/hemiacetal) structure
(4) Gluconic acid is a partial oxidation product of glucose
3. Which of the following statement is not true for glucose ?

(1) The pentaacetate of glucose does not react with hydroxylamine to give oxime
(2) Glucose exists in two crystalline forms a and b
(3) Glucose gives Schiff’s test for aldehyde
(4) Glucose reacts with hydroxylamine to form oxime
4. Glucose on prolonged heating with HI gives

(1) n-hexane (2) 1-hexene (3) Hexanoic acid (4) 6-iodohexanal
5. The change in the optical rotation of freshly prepared solution of glucose is known as
(1) tautomerism (2) racemization (3) specific rotation (4) mutarotation
6. The term anomers of glucose refers to

(1) isomers of glucose that differ in configurations at carbons one and four (C-1 and C-4)
(2) a mixture of (D)-glucose and (L)-glucose
(3) enantiomers of glucose
(4) isomers of glucose that differ in configuration at carbon one (C-1)

7. D-(4)-glucose reacts with hydroxyl amine and yields and oxime. The structure of the oxime
would be
CH = NOH CH = NOH CH = NOH CH = NOH
H—C—OH HO—C—H HO—C—H H—C—OH
HO—C—H HO—C—H H—C—OH HO—C—H
(1) (2) (3) (4)
HO—C—H H—C—OH HO—C—H H—C—OH
H—C—OH H—C—OH H—C—OH H—C—OH
CH2OH CH2OH CH2OH CH2OH
8. a-D-(+)-glucose and b-D-(+)-glucose are

(1) anomers (2) epimers (3) enantiomers (4) geometrical isomers
9. Number of stereo-centers present in linear and cyclic structures of glucose are respectively
(1) 4 and 5 (2) 4 and 4 (3) 5 and 4 (4) 5 and 5
Type-2 (Disaccharides)
10. The number of chiral carbons present in sucrose is .........
[JEE Main 2020]
11. What are the functional groups present in the structure of maltose ?
(1) One ketal and one hemiketal (2) One acetal and one ketal
(3) One acetal and one hemiacetal (4) Two acetals
12. Which one of the following statements is not true ?

(1) Lactose contains a-glycosidic linkage between C1of galactose and C4 of glucose
(2) Lactose is a reducing sugar and it gives Fehling’s test.
(3) Lactose (C11H22O11) is a disaccharide and it contains 8 hydroxyl groups.
(4) On acid hydrolysis, lactose gives one molecule of D(+) - glucose and one molecule of D
(+) - galactose
13. Two monomers in maltose are

(1) a-D-glucose and a-D-glucose (2) a-D-glucose and a-D-galactose
(3) a-D-glucose and b-D-glucose (4) a-D-glucose and a-D-fructose
14. Maltose on treatment with dilute HCl gives

(1) D-glucose and D-fructose (2) D-fructose
(3) D-galactose (4) D-glucose

15. Which of the glycosidic linkage between galactose and glucose is present in lactose?
(1) C-1 of galactose and C-4 of glucose (2) C-1 of glucose and C-6 of galactose
(3) C-1 of glucose and C-4 of galactose (4) C-1 of galactose and C-6 of glucose
16. Which of the following is correct structure of -anomer of maltose?

O O O O
H H H H OH H H H OH
H H H
(1) (2)
HO H H O OH H H HO OH H O OH H H
OH OH H OH H OH H OH
O O O O
H H H H H H H H H
H H H
(3) (4)
HO H H O H H OH HO OH H O OH H OH
HO OH HO OH H OH H OH
17. A non-reducing sugar "A" hydrolysis to give two reducing mono saccharides. Sugar A is -
(1) Fructose (2) Galactose (3) Glucose (4) Sucrose
Type-3 (Polysaccharides)
18. Which of the following statement is not true about sucrose ?
(1) It is also named as invert sugar.
(2) The glycosidic linkage is present between C1 of a-glucose and C4 of b-fructose
(3) It is a non-reducing sugar
(4) On hydrolysis, it produces glucose and fructose [JEE Main 2021]
19. Amylopectin is composed of

(1) b-D-glucose, C1-C4 and C2-C6 linkages (2) a-D-glucose, C1-C4 and C2-C6 linkages
(3) b-D-glucose, C1-C4 and C1-C6 linkages (4) a-D-glucose, C1-C4 and C1-C6 linkages
20. Which of the given statements is incorrect about glycogen ?

(1) It is straight chain polymer similar to amylose
(2) Only a-linkage are present in the molecule
(3) It is present in animal cells
(4) It is present in some yeast and fungi
21. The difference between amylose and amylopectin is

(1) Amylopectin have 1  4 a-linkage and 1  6 b-linkage
(2) Amylose have 1  4 a-linkage and 1  6 b-linkage
(3) Amylopectin have 1  4 a-linkage and 1  6 a-linkage
(4) Amylose is made up of glucose and galactose

Type-4 (Reducing sugar)
22. Indicate whether each is a reducing sugar or not
HO
CH2OH CH2OH
HO O O
(1) (2)
OCH2CH2CH3 HO
OH OH
HO OCH3
HO HOCH2
CH2OH O OCH2CH3
O
(3) OH (4) [JEE Main 2021]
HO CH2OH
OH OH OH
23. Which of following compound give positive Tollen’s test ?

OH OH
OH OH
(1) O (2) O
OH OCH3
OH OH
OH OH
OH CH2OH
O
OH H
H H
OH OCH3 O
O OH OH H
(3) (4) H
OCH3 OH
OH OH H H OH
24. Which of the following pairs give positive Tollen's test ?
(1) Glucose, sucrose (2) Glucose, fructose

(3) Hexanal, acetophenone (4) Fructose, sucrose
25. The correct statement(s) about the following sugars X and Y is (are)
CH2OH
O
CH2OH CH2OH H H
H
O O H HO OH
H H HOH2C O H H O
H H
OH H H HO CH2OH HO OH H H OH H
HO O
H OH OH H H OH
(X) (Y)
(1) X is a reducing sugar and Y is a non-reducing sugar

(2) X is a non-reducing sugar and Y is a reducing sugar
(3) The glucosidic linkages in X and Y are a and b, respectively
(4) The glucosidic linkages in X and Y are b and a, respectively

26. Which of the following compounds will behave as a reducing sugar in an aqueous KOH
solution ?
(1) (2)
(3) (4)
Type-5 (Amino Acids)

27. Which of the following is correct structure of tyrosin ?
COOH
H2N H COOH
OH
(1) (2) H2N H
OH
COOH
H2N H COOH
OH
(3) (4) H2N H
OH
[JEE Main 2021]
28. Which of the following is not an essential amino acid ?

(1) Leucine (2) Valine (3) Lysine (4)Tyrosine
39. Among the following compounds, most basic amino acid is

(1) serine (2) asparagine (3)lysine (4) histidine
30. The increasing order of pKa of the following amino acids in aqueous solution is Gly, Asp, Lys,
Arg
(1) Asp < Gly < Arg < Lys (2) Arg < Lys < Gly < Asp
(3) Gly < Asp < arg < Lys (4) Asp < Gly < Lys < Arg
31. The correct sequence of amino acids present in the tripeptide given below is
(1) Thr-Ser-Leu (2) Leu-Ser-Thr (3)Val-Ser-Thr (4) Thr-Ser-Val

32. The correct structure of histidine in a strongly acidic solution (pH = 2) is
(1) (2)
(3) (4)
Type-6 (Nucleic Acid)

33. Which one of the following bases is not present in DNA ?
(1) Quinoline (2) Adenine
(3) Cytosine (4) Thymine [JEE Main 2021]
34. Thiol group is present in

(1) cystine (2) cysteine (3) methionine (4) cytosine
35. The presence or absence of hydroxy group on which carbon atom of sugar differentiates RNA
and DNA ?
(1) 1st (2) 2nd (3) 3rd (4) 4th
36. Which base is present in RNA but not in DNA ?

(1) Uracil (2) Cytosine (3) Guanine (4) Thymine
37. The reason for double helical structure of DNA is operation of

(1) van der Waals’ forces (2) dipole-dipole interactions
(3) hydrogen bonding (4) electrostatic attractions
38. RNA contains

(1) ribose sugar and thymine (2) ribose sugar and uracil
(3) deoxyribose sugar and uracil (4) deoxyribose sugar and thymine

39. Which of the following statement is not true about RNA ?
(1) It controls the synthesis of protein
(2)It has always double stranded a-helix structure
(3) It usually does not replicate
(4) It is present in the nucleus of the cell
40. The secondary structure of protein is stabilised by :

(1) Peptide bond (2) Glycosidic bond
(3) Hydrogen bonding (4) Van der Waals forces

ANSWER KEY
1. (4) 2. (4) 3. (3) 4. (1) 5. (4)
6. (4) 7. (4) 8. (1) 9. (1) 10. 9
11. (3) 12. (1) 13. (1) 14. (4) 15. (1)
16. (4) 17. (4) 18. (2) 19. (4) 20. (1)
21. (3) 22. (3) 23. (1,2,4) 24. (2) 25. (2,3)
26. (1) 27. (4) 28. (4) 39. (3) 30. (4)
31. (3) 32. (4) 33. (1) 34. (2) 35. (2)
36. (1) 37. (3) 38. (2) 39. (2) 40. (3)
SOLUTION
HO 6
5 O OH Lactose
HO 6 4
OH 1
HO 5 O O 2 Glucose
15. 4 OH 3
OH
3 2
OH 1
In lactose linkage is formed between C1 of galactose and C4 of gluocse.
16. -ANOMER OF MALTOSE

maltose is disaccharides of -D-glucopyranose by C1–C4 glycosidic linkage
CH2OH CH2OH
O O
H H H H H
H
HO OH H O OH H OH
H OH H OH
H2O
17. Sucrose   glucose + Fructose
(Non reducing sugar (Reducing sugar) (Reducing sugar)
27. The structure of Tyrosine amino acid is

COOH
H2N H
CH2 OH
40. The secondary structure of protein includes two type :

(1) a-Helix (2) -pleated sheet
In -Helix structure, the poly peptide chain is coil around duet o present of Intramolecular
H-Bonding.

CHEMISTRY

CPP
ST
PRACTICAL ORGANIC CHEMISTRY (POC) NO. 11
Type-1 (Test For Functional Group)

1. Which of the following compound will not give positive iodoform test.
(1) (2)
(3) (4) CH3 – CHO [JEE Main 2021]
2. Match the compounds of column – I with the reagent of column – II which can distinguish the
compounds of column I
Column – I Column – II
(1) (p) Tollen’s reagent
(2) , (q) I2/NaOH
(3) , (r) Lucas reagent
(4) (s) neutral FeCl3
(t) 2,–DNP

3. An organic compound (1) (molecular formula C6H12O2) was hydrolysed with dil. H2SO4 to give
a carboxylic acid (2) and an alcohol (3). ‘C’ gives white turbidity immediately when treated with
anhydrous ZnCl2 and conc. HCl. The organic compound (1) is
(1) (2) (3) (4)
4. An organic compound neither reacts with neutral ferric chloride solution nor with Fehling solution.
It however, reacts with Grignard reagent and gives positive iodoform test. The compound is
(1) (2) (3) (4)
5. Two compounds A and B with same molecular formula (C3H6O) undergo Grignard’s reaction
with methylmagnesium bromide to give products C and D. Products C and D show following
chemical tests.
Test C D
Caric ammonium nitrate test Positive Positive
Lucas test Turbidity obtained Turbidity obtained
after five minutes immediately
Iodoform test Positive Negative
C and D respectively are
(1)
(2)
(3)
(4)

6. Compound A(C9H10O) shows positive iodoform test. Oxidation of A with KMnO4/KOH gives
acid B(C8H6O4). Anhydride of B is used for the preparation of phenolphthalein. Compound A is
(1) (2) (3) (4)
7. Consider the following reactions,
A is
(1) CHCH (2) CH3CCCH3 (3) CH3—CCH (4) CH2CH2
The compound [P] is
(1) (2) (3) (4)

Ozonolysis
(A)  (B)  (C)
(C7H14 )
(1) is
(1) (2) (3) (4)

10. Which of the following compound gives pink colour on reaction with phthalic anhydride in
conc. H2SO4 followed by treatment with NaOH ?
CH3 HO CH3
(1) (2)
OH HO CH3
H3C CH3 CH3
(3) (4)
HO OH HO
11. The diazonium salt of which of the following compounds will form a coloured dye on reaction
with b-Naphthol in NaOH ?
CH3
CH2NH2 N–CH3 NH2 NH–CH3

(1) (2) (3) (4)
Hydrolysis
12. A   B
( C 4H8Cl2 ) 373 K ( C 4H8O )
B reacts with Hydroxyl amine but does not give Tollen's test. Identify A and B
(1) 1,1-Dichlorobutane and 2-Butanone (2) 2,2-Dichlorobutane and Butanal
(3) 1,1-Dichlorobutane and Butanal (4) 2,2-Dichlorobutane and 2-butan-one
13. An amine on reaction with benzenesulphonyl chloride produces a compound insoluble in

alkaline solution. This amine can be prepared by ammonolysis of ethyl chloride. The correct
structure of amine is :
NH–CH2CH2CH3
(1) (2) CH3CH2NH2
H
(3) CH3CH2CH2NHCH3 (4) CH3CH2CH2N–CH2CH3
14. Seliwanoff test and Xanthoproteic test are used for the identification of _______and _____
respectively.
(1) Aldoses, ketoses (2) Proteins, ketoses
(3) Ketoses, proteins (4) Ketoses, aldoses
15. 2,4-DNP test can be used to identify :

(1) Amine (2) Aldehyde (3) Ether (4) Halogens
16. Ceric ammonium nitrate and CHCl3 / alc. KOH are used for the identification of functional
groups present in ______ and ___ respectively.
(1) Alcohol, phenol (2) Amine, alcohol (3) Alcohol, amine (4) Amine, phenol
17. Primary, secondary and tertiary amines can be separated using :-

(1) Para-Toluence sulphonyl chloride (2) Chloroform and KOH
(3) Benzene sulphonic acid (4) Acetyl amide

18. An organic compound "A" on treatment with benzene sulphonyl chloride gives compound B. B
is soluble in di. NaOH solution. Compound A is :
(1) C6H5–N–(CH3)2 (2) C6H5–NHCH2CH3
(3) C6H5–CH2–NHCH3 (4) C6H5  CH  NH2
|
CH3
19. In Tollen’s test for aldehyde, the overall number of electron(s) transferred to the Tollen’s
reagent formula [Ag(NH3)2]+ per aldehyde group to form silver mirror is _______ .
(Round off to the Nearest integer)
20. An organic compound X showing the following solubility profile is

Water
Insoluble
X 5% HCl
Insoluble
10% NaOH
Soluble
10% NaHCO3
Insoluble
(1) o - toluidine (2) oleic acid (3) m-cresol (4) benzamide
21. The correct match between item ‘I’ and item ‘II’ is
Item ‘I’ Item ‘II’
(Compound) (Reagent)
(1) Lysine (P) 1-naphthol
(2) Furfural (Q) Ninhydrin
(3) Benzyl alcohol (R) KMnO4
(4) Styrene (S) Ceric ammonium nitrate
Codes
A B C D A B C D
(1) Q R S P (2) R P Q S
(3) Q P S R (4) Q P R S
Type-2 (Lassaignes Extract)

22. In Lassaigne test thiourea is converted into-
(1) NaCNS (2) Na2S (3) NaCN (4) Na2SO4
[JEE Main 2020]
23. In a Lassaignes’s test for sulphur in the organic compound with sodium nitroprusside solution
the purple colour formed is due to-
(1) Na4 [Fe(CN)5 NOS] (2) Na3 [Fe(CN)5 S]
(3) Na2 [Fe(CN)5 NOS] (4) Na3 [Fe(CN)6 ]
24. Which of the following compound is added to the sodium extract before addition of silver
nitrate for testing of halogens?
(1) Nitric acid (2) Ammonia
(3) Hydrochloric acid (4) Sodium hydroxide

25. Match List-I with List-II
List-I List-II
Test/Reagents/Observation(s) Species detected
(A) Lassaigne’s Test (i) Carbon
(B) Cu(II) oxide (ii) Sulphur
(C) Silver nitrate (iii) N, S, P and halogen
(D) The sodium fusion extract gives black (iv) Halogen Specifically
precipitate with acetic acid and lead acetate
He correct match is :
(1) (A)-(iii), (B)-(i), (C)-(ii), (D)-(iv) (2) (A)-(i), (B)-(iv), (C)-(iii), (D)-(ii)
(3) (A)-(iii), (B)-(i), (C)-(iv), (D)-(ii) (4) (A)-(i), (B)-(ii), (C)-(iv), (D)-(iii)
Type-3 (Purification Methods)

26. A flask contains a mixture of isohexane and 3-methylpentane. One of the liquids boils at 63ºC
while the other boils at 60ºC. What is the best way to separate the two liquids and which one
will be distilled out first ?
(1) Fractional distillation 3-methyllpentane (2) Fractional distillation, isohexane
(3) Simple distillation, 3-methylpentane (4) Simple distillation, isohexane
[JEE Main 2021]
27. In chromatography, which of the following statements is incorrect for Rf ?

(1) Rf value depends on the type of chromatography
(2) Higher Rf value means higher adsorption
(3) Rf value is dependent on the mobile phase
(4) The value of Rf can not be more than one
28. Using the provided information in the following paper chromatogram :
Solvent front
B
5cm 2cm
A
2cm
Base line
Spot
Figure : Paper chromatography for compounds A and B.
the calculate Rf value of A _______ × 10–1.

Statement I : A mixture of chloroform and aniline can be separated by simple distillation.
Statement II : When separating aniline from a mixture of aniline and water by steam
distillation aniline boils below its boiling point.
In the light of the above statements, choose the most appropriate answer from the options
given below.
(1) Statement-I is false but Statement II is true
(2) Both Statement-I and Statement II are false
(3) Statement-I is true but Statement II is false
(4) Both Statement-I and Statement II are true

30. Tin chromatography technique, the purification of compound is independent of :
(1) Mobility of flow of solvent system (2) Solubility of the compound
(3) Length of the column or TLC plate (4) Physical state of the pure compound

Statement-I : Retardation factor (Rf) can be measured in meter/centimeter.
Statement-II : Rf value of a compound remains constant in all solvents.
Choose the most appropriate answer from the options given below :
(1) Statement-I is true but statement-II is false
(2) Both statement-I and statement-II are true
(3) Both statement-I and statement-II are false
(4) Statement-I is false but statement-II is true
Type-4 (Quantitative Analysis)

32. Which of the following is 'a' FALSE statement?
(1) Carius tube is used in the estimation of sulphur in an organic compound
(2) Carius method is used for the estimation of nitrogen in an organic compound
(3) Phosphoric acid produced on oxidation of phosphorus present in an organic compound is
precipitated as Mg2P2O7 by adding magnesia mixture.
(4) Kjeldahl's method is used for the estimation of nitrogen in an organic compound
[JEE Main 2021]
33. In Duma’s method of estimation of nitrogen, 0.1840 g of an organic compound gave 30 mL of

nitrogen collected at 287 K and 758 mm of Hg pressure. The percentage composition of
nitrogen in the compound is _______ . (Round off to the Nearest Integer).
[Given : Aqueous tension at 287 K = 14 mm of Hg]
34. Nitrogen can be estimated by Kjeldahl’s method for which of the following compound ?
(1) (2) (3) (4)

+ N
NNCl– CH2—NH2 NO2
35. The Kjeldahl method of nitrogen estimation fails for which of the following reaction products?
NO2 CN CN
NH2
Sn/HCl LiAlH4 (i) SnCl2+HCl NaNO2
I. II. III. IV.
(ii) H2O HCl
(1) III and IV (2) I and IV (3) I, III and IV (4) II and III

ANSWER KEY
1. (3) 2. (1)  p,q,t ; (2)  s ; (3)  r,t ; (4) q,r,s.
3. (2) 4. (4) 5. (1) 6. (3) 7. (3)
8. (1) 9. (4) 10. (1) 11. (3) 12. (4)
13. (4) 4. (3) 15. (2) 16. (3) 17. (1)
18. (4) 19. (2) 20. (3) 21. (3) 22. (1)
23. (1) 24. (1) 25. (3) 26. (2) 27. (2)
28. (4) 29. (4) 30. (4) 31. (3) 32. (2)
33. (19) 34. (2) 35. (1)
SOLUTION
10.
O O
OH
C C
O + O
C C
O
OH
+ (Pink colour)
(i) H
(ii) –H2O
OH
O
C OH
O + OH
C+
HO
EAS
EAS
O O
C C
H+ +
H
O O –H O
–H2O 2
C C
HO
OH
OH

+
NN –
Cl
NH2
NaNO2
11.
+HCl
1° aromatic
OH –
amine OH
N=N
OH
Organge-Red.dye
Cl OH O
Hydrolysis
12. 373 K H2O
Cl OH
(C4H8Cl2) (C4H8O)
(A) (B)
13. It has to be 2° amine because on reaction with benzene sulphonylchloride it gives water in
soluble product. As it is formed by ammonolysis of ethylchloride, so it has to be R–NH–Et
type.
CH3–CH2–CH2–NH2 + Et–Cl
+
CH3–CH2–CH2–NH2–Et
–H+
CH3–CH2–CH2–NH–Et
14. Seliwanoff test for ketose and Xenthoprotic test for proteins.
15. 2,4-DNP test is useful for the identification of carbonyl compounds.
16. Ceric ammonium nitrate for alcohol and CHCl3/KOH is carbyl amine test for primary amines.
17. Primary amines react with Para Toluene sulfonyl chloride to form a precipitate that is soluble
in NaOH.
Secondary amines reacts with para toluene sulfonly chloride to give a precipitate that is
insoluble in NaOH.
Tertiary amines do not react with para toluene.

18. Hinsberg reagent (benzene sulphonyl chloride) gives reaction product with1º amine and it is
soluble in dil. NaOH.
O O O
•• Dil NaOH Θ
R—NH2+Cl—S R—NH—S R—N—S
O O O
19. AgNO3 + NaOH  AgOH + NaNO3

2AgOH  Ag2O + H2O

Ag2O + 4NH3 + H2O  2Ag(NH3)2+ + 2OH
Oʘ Θ O
–
–e OH HO
R—C—H +
Ag+ Ag R H R H
O
OΘ OH
–e Θ
HO
Ag+ Ag R OH R OH
R—C—OH R—C—OΘ
O O
Total 2e– transfer to Tollen’s reagent
20. M-cresol is the organic compound that shows the following solubility profile.
Water
CH3 Insoluble
5% HCl
Insoluble
10% NaOH
Soluble
m-cresol OH 10% NaHCO3
Insoluble
m-cresol on reaction with 10% NaOH forms 3-methyl sodiumphenoxide ion.

OH O–Na+
10% NaOH
CH3 CH3
It does not react with H2O, 5% HCl and 10% NaHCO3. Oleic acid (C18H34O2) is soluble in 10%
NaOH and 10% NaHCO3 due to the presence of COOH group.
O
Benzamide C6H5CNH2 is insoluble in 5% HCl, 10% NaOH and 10% NaHCO3 due to the
presence —CONH2 group. O-toluidine is soluble in 5%. HCl due to presence of basic group
(–NH2) attached to ring.

21. A (Q) ; B  (P) ; C  (S) ; D  (R)
(1) Lysine (R=-(CH2)4-NH2)
NH2 Ninhyrin test (B)
R—CH Violet colouration
COOH O
OH
(Ninherin), boil
OH
O
OH
CHO +
(2) O
(Furtural)
CH2SO4
 Violet colouration
Molisch Test (P)
(Molisch reagent)
CH2OH Ceric ammonium CHO

Nitrate (s) [CAN]
(3)
50% CH3COOH
(Benzyl alcohol) (Benzaldehydel)
OH
OH
–
Dil. KMnO4/OH /Cold (R)
(4) H H
(Pink) H
2+
(Styrene) +Mn (Colourless)
24. For testing of halogens, Nitric acid is added to the sodium extract because if CN– or S2– are
present then they will be oxidised and removed before the test of halides.
25. Match list :-

(A) Lassaigne’s Test (iii) N, S, P and Halogen
(B) Cu(II) Oxide (i) Carbon
(C) AgNO3 (iv) Halogen specifically.
(D) Sodium fusion extract given black (ii) Sulphur
precipitate with acetic acid and lead
acetate (CH3COOH/(CH3COO)2Pb
Distance travelled by compound

28. Rf =
Distance travelled by solvent
On chromatogram distance travelled by compound is  2cm
Distance travelled by solvent = 5 cm
2
So, Rf  = 4 × 10–1 = 0.4
5

29. Statement 1 : B.P. of chloroform = 334 K
B.P. of aniline = 457 K
thus can be separated of simple distillation.
Statement 2 : Mixture of aniline and water separated by simple distillation.
30. In chromatography technique, the purification of a compound is independent of the physical

state of the pure compound.
31. Rf = retardation factor

Dis tance travelled by the subs tance from reference line(c.m)
Rf 
Dis tance travelled by the solven from reference line(c.m)
Note : Rf value of different compounds are different.
32. Carius method is used in the estimation of halogen in organic compounds.
33. In Dima’s method of estimation of Nitrogen. 0.1840 gm of organic compound gave 30 mL of

nitrogen which is collected at 287 K & 758 mm of Hg.
Give ;
Aqueous tension at 287 K = 14 mm of Hg.
Hence actual pressure = (758 – 14)
= 744 mm of Hg.
273  744  30
Volume of nitrogen at STP =
287  760
V = 27.935 mL
 22400 mL of N2 at STP weighs = 28 gm.
 28 
 27.94 mL of N2 at STP weighs =   27.94  gm
 22400 
= 0.0349 gm
 0.0349 
Hence % of Nitrogen =   100 
 0.1840 
= 18.97%
Rond off. Answer = 19%
34. Kjeldahl method is not applicable o compounds containing nitrogen in nitrogroup, Azo groups
and nitrogen present in the ring (e.g Pyridine) as nitrogen of these compounds does no
change o Ammonium sulphate under these conditions.
35. Complete reactions I, II, III, IV are as follows :

NO2 NH2 ‘N’ of — NH2 can be
(I) Sn/HCl Estimated by
[H] Jjeldahl method
Nitrobenzene Aniline
CN CH2 — NH2 ‘N’ of — NH2 can be

(II) LiAlH4 Estimated by
[H] Jjeldahl method
Benzylamine
CH2CN CH2 – CH = O
(i) SnCl2 + HCl
(III)
(ii) H2O
(Stephen reduction)
(2-phenyl ethanal)
This compound does
Not contain ‘N’. So, Kjeldahl
Method is not applicable.
 Θ
NH2 N = N Cl
(IV) NaNO2
HCl
Kjeldahl method
Diazotisation Benzene is not applicable for
reaction Diazonium chlorid —N=N—or azo group
So, products of reactions (3) and (4) (option-a) fail to give Kjeldahl’s method.
So, option (1) is correct.

CHEMISTRY

CPP
ST
POLYMER NO. 12
1. Adipic acid reacts with hexamethylene diamine to form

(1) Bakelite (2) Nylon-6,6 (3) Terylene (4) Nylon-6, 10
2. Ethylene glycol reacts with dimethyl terephthalate to form
(1) Nylon-6, 6 (2) Teflon (3) Dacron (4) Orlon
3. Select the incorrect statement about Nylon 2-nylon-6.
(1) It is a copolymer.
(2) It is biodegradable.
(3) It is an alternating polyamide.
(4) It is made up of CH 3  CH  COOH and H2N(CH2)5COOH.
|
NH 2
4. Neoprene is a polymer of the following monomer:
(1) Chloroprene (2) Isoprene (3) Isobutene (4) Isopentene
5. Which of the following is an example of a condensation polymer?
(1) Nylon-6, 6 (2) Teflon (3) Polypropylene (4) Orlon
6. Polymers are backbone of which industries
(1) Plastics (2) Elastomers
(3) Fibers and Paints (4) All of these
7. Which of the following is a thermosetting polymer?
(1) Bakelite (2) Nylon-6, 6 (3) Polyethylene (4) Teflon
8. Match the following :
(i) high density polythene (A) Branched chain polymer
(ii) Polyvinyl chloride (B) Linear polymer
(iii) Low density polythene (C) Strong covalent bond
(iv) Bakelite, melamine (D) Cross linked or network polymers
(1) (i)–B, (ii) – A,D (iii) – C (iv) – B (2) (i) – A, D, (ii) – B (iii) – B (iv) – C
(3) (i)–B, (ii) – B (iii) – A (iv) – C, D (4) (i) – A, (ii) – B, D (iii) – C (iv) – B
9. Choose copolymer
(1) Buna–S and Buna–N (2) polythene
(3) polypropene (4) None
10. Which of the following statements about low density polythene is FALSE ?
(1) Its synthesis requires high pressure.
(2) It is a poor conductor of electricity.
(3) Its synthesis requires dioxygen or a peroxide initiator as a catalyst.
(4) It is used in the manufacture of buckets, dust-bins etc.

11. Nylon-66 is made by using
(1) Phenol (2) Benzaldehyde (3) Adipic acid (4) Succinic acid
12. Polymer which has amide linkage is
(1) Nylon-66 (2) Terylene (3) Teflon (4) Bakelite
13. Terylene is a condensation polymer of ethylene glycol and
(1) Benzoic acid (2) Phthalic acid (3) Salicylic acid (4) Terephthalic acid
14. Match the coloum :
(i) Polythene (A) Addition polymer
(ii) Buna–S (B) Condensation polymer
(iii) Nylon 6, 6
(iv) Nylon 6
(v) Dacron (terylene)
(1) (i) – B, (ii) – A, (iii) – A, (iv) – B, (v) – B (2) (i) – B, (ii) – A, (iii) – B, (iv) – A, (v) – A
(3) (i) – A, (ii) – A, (iii) – B, (iv) – B, (v) – B (4) (i) – B, (ii) – B, (iii) – B, (iv) – A, (v) – A
15. Match List I with List II.
List I List II
(Monomer Unit) (Polymer)
(A) Caprolactum (i) Natural rubber
(B) 2-Chloro-1,3-butadiene (ii) Buna-N
(C) Isoperene (iii) Nylon-6
(D) Acrylonitrile (iv) Neoprene
Choose the correct answer from the options given below :
(1) (A)  (iv), (B)  (iii), (C)  (ii), (D)  (i) (2) (A)  (ii), (B)  (i), (C)  (iv), (D)  (iii)
(3) (A)  (iii), (B)  (iv), (C)  (i), (D)  (ii) (4) (A)  (i), (B)  (ii), (C)  (iii), (D)  (iv)
16. In polymer Buna-S: ‘S’ stands for :

(1) Sulphonation (2) Strength (3) Sulphur (4) Styrene
17. Which statement is correct ?

(1) Synthesis of Buna-S needs nascent oxygen.
(2) Neoprene is an addition copolymer used in plastic bucket manufacturing.
(3) Buna-S is a synthetic and linear thermosetting polymer.
(4) Buna-N is a natural polymer.
18. The structure of Neoprene is -

—CH2CH=CH—CH2–CH2–CH— —CH2–CH—
(1) (2)
CN n CN n
—NH N NHCN2—
Cl n
(3) (4) N N
—CH2–C=CH–CH2—
n
NH
19. Which of the following of polymer is used in the manufacture of wood laminates ?
(1) cis-poly isoprene (2) Melamine formaldehyde resin
(3) Urea formaldehyde resin (4) Phenol and formaldehyde resin

ANSWER KEY
1. (2) 2. (3) 3. (4) 4. (4) 5. (1)
6. (1, 4) 7. (1) 8. (3) 9. (1) 10. (4)
11. (3) 12. (1) 13. (4) 14. (3) 15. (3)
16. (4) 17. (1) 18. (3) 19. (3)
SOLUTIONS
O
15. (A) NH Caprolactum is the monomeric unit of polymer Nylon-6 —HN–(CH2)5–C—

O n
(B) 2-Chlorobuta-1, 3-diene is the monomeric unit of polymer neoprene.
(C) 2-Methylbuta-1, 3-diene is the monomeric unit of polymer natural rubber.
(D) CH2=CH–CN (Acrylonitrile) is the one of the monomeric unit of polymer Buna-N
16. BUN-S, ‘S’ stand for styrene.

Polymerisation
+ (Ph–CH=CH2)   Buna-S
Buta
-1,3-diene styrene
Nascent
17. + —CH2 CH2–CH2–CH—
Oxygen
Ph BuNa-S Ph
Polymerization
18. CH2=C–CH=CH2 —CH2–C=CH–CH2—
Cl Cl n
Chloroprene Neoprene
2-Chloro-1, 3-Butadiene
19. Urea-HCHO resin is used in manufacture of wood laminates

CHEMISTRY

CPP
ST
CHEMISTRY IN EVERYDAY LIFE NO. 13
1. Match List-I and List-II.

List-I List-II
(a) Valium (i) Antifertility drug
(b) Morphine (ii) Pernicious anaemia
(c) Norethindrone (iii) Analgesic
(d) Vitamin B12 (iv) Tranquilizer
(1 ) (a)–(iv), (b)–(iii), (c)–(ii), (d)–(i) (2) (a)–(iv), (b)–(iii), (c)–(i), (d)–(ii)
(3) (a)–(ii), (b)–(iv), (c)–(iii), (d)–(i) (4) (a)–(i), (b)–(iii), (c)–(iv), (d)–(ii)
2. The functions of antihistamine are :

(1) Antiallergic and Analgesic (2) Antacid and antiallergic
(3) Analgesic and antacid (4) Antiallergic and antidepressant
3. With respect to drug-enzyme interaction, identify the wrong statement :

(1) Non-Competitive inhibitor binds to the allosteric site
(2) Allosteric inhibitor changes the enzyme’s active site
(3) Allosteric inhibitor competes with the enzyme’s active site
(4) Competitive inhibitor binds to the enzyme’s active site

List-I List-II
Chemical Compound Used as
(a) Sucralose (i) Synthetic detergent
(b) Glyceryl ester (ii) Artificial sweetener
(c) Sodium benzoate (iii) Antiseptic
(d) Bithionol (iv) Food preservative
Choose the correct match :
(1) (a)-(iv), (b)-(iii), (c)-(ii), (d)-(i) (2) (a)-(ii), (b)-(i), (c)-(iv), (d)-(iii)
(3) (a)-(iii), (b)-(ii), (c)-(iv), (d)-(i) (4) (a)-(i), (b)-(ii), (c)-(iv), (d)-(iii)

5. Match the list-I with list-II
List-I List-II
(Class of Drug) (Example)
(a) Antacid (i) Novestrol
(b) Artificial sweetener (ii) Cimetidine
(c) Antifertility (iii) Valium
(d) Tranquilizers (iv) Alitame
(1) (a)-(ii), (b)-(iv), (c)-(i), (d)-(iii) (2) (a)-(iv), (b)-(i), (c)-(ii), (d)-(iii)
(3) (a)-(iv), (b)-(iii), (c)-(i), (d)-(ii) (4) (a)-(ii), (b)-(iv), (c)-(iii), (d)-(i)
6. Match List-I with List-II :

List-I List-II
(Class of Chemicals (Example)
(a) Antifertility drug (i) Meprobamate
(b) Antibiotic (ii) Alitame
(c) Tranquilizer (iii) Norethindrone
(d) Artificial Sweetener (iv) Salvarsan
(1) (a)-(ii), (b)-(iii), (c)-(iv), (d)-(i) (2) (a)-(iv), (b)-(iii), (c)-(ii), (d)-(i)
(3) (a)-(iii), (b)-(iv), (c)-(ii), (d)-(ii) (4) (a)-(ii), (b)-(iv), (c)-(i), (d)-(iii)
7. Match the following drugs with their therapeutic actions :

(i) Ranitidine (a) antidepressant
(ii) Nardil (Phenelzine) (b) Antibiotic
(iii) Chloramphenicol (c) Antihistamine
(iv) Dimetane (Brompheniramine) (d) Antacid
(e) Analgesic
(1) (i) – (a); (ii) – (c); (iii) – (b); (iv) – (e) (2) (i) – (e); (ii) – (a); (iii) – (c); (iv) – (d)
(3) (i) – (d); (ii) – (a); (iii) – (b); (iv) – (c) (4) (i) – (d); (ii) – (c); (iii) – (a); (iv) – (e)
8. The mechanism of action of “Terfenadine” (Seldane) is

(1) Inhibits the secretion of histamine
(2) Inhibits the action of histamine receptor
(3) Helps in the secretion of histamine
(4) Activates the histamine receptor
9. If a person is suffering from the deficiency of nor-adrenaline, what kind of drug can be
suggested?
(1) Antihistamine (2) Analgesic
(3) Antidepressant (4) Anti-inflammatory

10. The following molecule acts as an
N
(CH2)2
N
(Brompheniramine)
Br
(1) antiseptic (2) anti-depressant
(3) anti-bacterial (4) anti-histamine
11. Noradrenaline is a/an

(1) antidepressant (2) antihistamine
(3) neurotransmitter (4) antacid
12. The correct match between Item-I and Item-II is

Item I (Drug) Item II (Test)
A. CHloroxylenol P. Carbylamine test
B. Norethindrone Q. Sodium hydrogen Carbonate test
C. ulphapyridine R.Ferric chloride test
D. Penicillin S. Bayer’s test
(1) A  R ; B  P ; C  S ; D  Q (2) A  R ; B  S ; C  P ; D  Q
(3) A  Q ; B  P ; C  S ; D  R (4) A  Q ; B  S ; C  P ; D  R
13. The correct match between item (I) and item (II) is
Item – I Item – II
(a) orethindrone (P) Antibiotic
(b) Ofloxacin (Q) Antifertility
(c) Equanil (R) ypertension
(S) Analgesics
(1) (a)  (Q); (b)  (R); (c)  (S) (2) (a)  (Q); (b)  (P); (c)  (R)
(3) (a)  (R); (b)  (P); (c)  (S) (4) (a)  (R); (b)  (P); (c)  (R)
14. The drug that relieve or decrease pain is called

(1) Analgesic (2) Antipyretic (3) Tranquillizer (4) Hypnotics

15. Non-narcotic analgesics are use for the treatment of :
(1) Skeletal pain and Heart attacks (2) Antipyretic (reducing fever)
(3) Platelet coagulation (4) All of these
16. Which of the following is Narcotic analgesics

(1) Morphine (2) Asprin (3) paracetamol (4) Equanil
17. Narcotic drugs are use for

(1) relief in postoperative pain
(2) relief in terminal cancer pain
(3) relief in cardiac pain and child birth pain
(4) All of these
18. Which of the following is an analgesic ?

(1) Chloramphenicol (2) Penicillin (3) Paracetamol (4) Streptomycin
19. Use of chemicals for therapeutic effect is called :

(1) Chemotherapy (2) enzymes (3) medicine (4) None
20. What functions are perform by enzymes during catalytic activity

(1) Enzyme hold the substrate for a chemical reaction
(2) Enzyme provide functional groups that will attack the substrate and carry out chemical
reaction
(3) Both (1) and (2)
(4) None
21. Drug (substrate) block the binding site of the enzyme and prevent the binding of substrate.
Such drugs are called :
(1) Protein inhibitors (2) lipid inhibitors
(3) Enzyme inhibitors (4) None
22. Drugs compete with the natural substrate for their attachment on the active sites of enzymes
such drugs are called :
(1) competitive inhibitors (2) Enzyme inhibitors
(3) Both (1) and (2) (4) None
23. Drugs that bind to the receptor site and inhibit its natural function are called :
(1) Receptors (2) Antagonists (3) Enzymes (4) None
24. Which of the following are anatacids :

(1) Histamine (2) Cimetidine (3) Ranitidine (4) All of these

25. Penicillin is an
(1) Antibiotic (2) Antipyretic (3) Hormone (4) Vitamin
26. Which of the following can be used as an analgesic-

(1) Paracetamol (2) Penicillin (3) Chloremphenicol (4) Streptomycin.
27. Morphine is used then as an

(1) Antipyretic (2) Antiseptic (3) Analgesic (4) Insecticide.
28. A substance which can act both as an analgesic and antipyretic is

(1) Quinine (2) Aspirin (3) Penicillin (4) Insulin.
29. Treatment of acidity is done by

(1) Antacids (2) Antihistaines (3) Analgestics (4) None
30. The drug given during hypertension is

(1) Streptomycin (2) Chloroxylenol (3) Equanil (4) Aspirin
31. Tranquilizer are used for treatment of

(i) Pain (ii) Stress
(iii) Mild or mental diseases (iv) Anxiety
(v) use in sleeping pills
(1) (i), (ii), (iii), (v) only (2) (i), (ii), (iv), (v) only
(3) (i), (ii), (v) only (4) (ii), (iii), (iv), (v) only
32. Drug which helps to reduce anxiety and brings calmness is
(1) Tranquilizer (2) Diuretic (3) Analgesic (4) Antihistamine
33. Tranquilizers are/is

(1) chlordiazepoxide (2) meprobamate (3) equanil (4) All of these
34. Match the column :

(i) Chlordiazepoxide (A) Use for tension relieving
(ii) Meprobamate (B) Use for control depression
(iii) equanil
(1) (i) – A, (ii) – B, (iii) – B (2) (i) – B, (ii) – A, (iii) – A
(3) (i) – A, (ii) – A, (iii) – B (4) (i) – B, (ii) – A, (iii) – B

35. Choose Tranquilizers among following:
(1) valium (2) serotonin (3) veronal (4) all of these
36. The correct structure of Aspirin is :
(1) (2)
(3) (4)
37. If Antibiotics effective against a single organism or disease, then they called :
(1) Narrow-spectrum Antibiotics (2) Broad spectrum Antibiotics
(3) Limited spectrum Antibiotics (4) None
38. Penicillin G is :
(1) Limited-Spectrum antibiotics (2) Narrow-spectrum antibiotics
(3) Broad-spectrum antibiotics (4) None
39. Streptomycin is an example of

(1) Antibiotic (2) Analgesic (3) Antipyretic (4) Anaesthetic.
40. Chloroxylenol is an important component of

(1) Soap (2) Antibiotics (3) Dettol (4) Pain killing ointments

ANSWER KEY
1. (2) 2. (2) 3. (3) 4. (2) 5. (1)
6. (3) 7. (3) 8. (2) 9. (3) 10. (4)
11. (3) 12. (2) 13. (2) 14. (1) 15. (4)
16. (1) 17. (4) 18. (3) 19. (1) 20. (3)
21. (3) 22. (3) 23. (2) 24. (2,3) 25. (1)
26. (1) 27. (3) 28. (2) 29. (1) 30. (3)
31. (4) 32. (1) 33. (4) 34. (3) 35. (4)
36. (1) 37. (3) 38. (2) 39. (1) 40. (3)
SOLUTION
1. (a) Valium – Tranquilizer (1)-(iv)
(b) Morphine – Analgesic (2)-(iii)
(c) Norethindrone – Antifertility Drug (3)-(i)
(d) Vitamin B12 – Pernicious anaemia (4)-(ii)
3. Some durg do not bind to the Enzyme’s active site. These bind to a different site of enzyme
which called allosteric site.
This binding of inhibitor at allosteric site changes the shape of the active site in such a way h
substrate can not recognise it.
Such inhibitor is known as Non-competitive inhibitor.
Active site with
Active shape change
site
Enzyme Allosteri Inhibitor

site Occupying allosteric
Inhibitor site
(non-competitive)
4. Arificial sweetner : Sucralose

Antiseptic : Bithional
Preservative : Sodium Benzoate
Glyceryl ester of stearic acid : Sodium steasate
5. (a) Antacid : Cimetidine

(b) Artifical Sweetener : Alitame
(c) Antifertility : Novestrol
(d) Tranquilizers : Valium
6. (a) Antifertility drug  (iii) Nor ethindron

(b) Antibiotic  (iv) Salvarsan
(c) Tranquilizer  (i) Meprobamate

(d) Artificial Sweetener  (ii) Alitame
7. Correct match is
(i)  (d), (ii)  (a), (iii)  (b) and (iv)  (c)
(i) Ranitidine  Antacid
[Ranitidine, in which backward flow of acid occur from stomach.]
(ii) Nardil (Phenelzine)  Antidepressant.
[It is used as an antidepressant and anxiotytic]
(iii) Chloramphenicol  Antibiotic
[It is an antibiotic used for treatment of bacterial infections]
(iv) Dimetane (Brompheniramine)  Antihistamine
[It is used for treatment of the symptoms of common cold and allergic such as runny nose,
itchy eyes etc.]
8. Seldane (Terfenadine) is also an antihistamines drug. Which interfere with the natural action
of histamine by competing with histamine for binding sites of receptors, where histamine acts.
Thus, it do not affect the secretion of acid in stomach but compete with histamine where
histamine exterts its effect.
9. Nor-adrenaline is one of the neurotransmitter that plays an important role in mood changes. If
the level of nor-adrenaline in the body is low for some reason, then the signal-sending activity
becomes low and the person suffers from depression. In such cases, antidepressant drugs
are needed. These drugs ingibit the enzymes which catalyse the degradation of nor-
adrenaline. If the enzyme is inhibited, this important neurotransmitter is slowly metabolized
and can activate its receptor for longer period of time, thus counteracting the effect of
depression. Lproniacid and phenelzine are two such antidepressant drugs.
10. Synthetic Brompheniramine is an antihistamine that is used to treat sneezing, runny nose and
itchy or watery eyes caused by allergies, hay fever and the common cold.
11. Noradrenaline is one of the example of neurotransmitters. It plays a major role in mood
changes. If the level of noradrenaline is low for some reason, then signal-sending activity
becomes low and the person suffers from depression.
Phenolic
OH -OH group
FeCl3
12. (1) (Ferric chloride)
Violet colouration
(R)
H3C CH3
Cl
Chloroxylenol (Dettol)

H3C OH CCH
H H
–
Dil. KMnO4/5°C/OH
(2) H H (Baeyer’s test)
Pink colour of
O (S) KMnO4 gets
Norethindrone discharged
C=C
(Double bond)
O
CHCl3 + KOH (alc.)
H2 N S—N (Carbylamine
Foul smell
(3) H N Test) (P) of isocyanide
Primary O
amine (-NH2) Sulphapyridine
O
H H
S CH3
(4) R—C—NH NaHCO3(aq)
CH3 (Sodium
Becomes soluble
Hydrogen With effervescence
N COOH carbonate) Of CO2 gas
O
Penicillin H (Q)
Thus, the correct match is :
A  R; B  S; C  P; D Q
13. The correct match is :
A  (Q), B  (P), C  (R)
(a) Norethindrone It is an antifertility drug(Q) containing synthetic progesterone derivative.
[Other similar drug, is ethinylestradiol (novestrol)].
(b) Ofloxacin It is an antibiotic (P), i.e. produced wholly or partly by chemical synthesis with
low concentration of microorganism. [Some other similar drugs : Penicillin, chloramphenicol,
salvarsan etc.]
(c) Equanil (meprobamate) It is a mild tranquilizer for relieving hypertension. It relieve anxiety,
stress, excitement by inducing a sense of well being.
(Other similar drug is chlordiazepoxide.)

CHEMISTRY

CPP
ST

List-I List-II



List-I List-II

List-I List-II

List-I List-II

(e) Analgesic

suggested?

N
(CH2)2
N
(Brompheniramine)
Br


(S) Analgesics
(1) (a)  (Q); (b)  (R); (c)  (S) (2) (a)  (Q); (b)  (P); (c)  (R)
(3) (a)  (R); (b)  (P); (c)  (S) (4) (a)  (R); (b)  (P); (c)  (R)




(4) All of these



reaction
(3) Both (1) and (2)
(4) None
(3) Both (1) and (2) (4) None










(iii) equanil

(1) (2)
(3) (4)



ANSWER KEY
1. (2) 2. (2) 3. (3) 4. (2) 5. (1)
6. (3) 7. (3) 8. (2) 9. (3) 10. (4)
11. (3) 12. (2) 13. (2) 14. (1) 15. (4)
16. (1) 17. (4) 18. (3) 19. (1) 20. (3)
21. (3) 22. (3) 23. (2) 24. (2,3) 25. (1)
26. (1) 27. (3) 28. (2) 29. (1) 30. (3)
31. (4) 32. (1) 33. (4) 34. (3) 35. (4)
36. (1) 37. (3) 38. (2) 39. (1) 40. (3)
SOLUTION
Active site with
Active shape change
site

Inhibitor site
(non-competitive)




7. Correct match is
itchy eyes etc.]
Phenolic
OH -OH group
FeCl3
Violet colouration
(R)
H3C CH3
Cl

H3C OH CCH
H H
–
Dil. KMnO4/5°C/OH
Pink colour of
O (S) KMnO4 gets
C=C
(Double bond)
O
CHCl3 + KOH (alc.)
Foul smell
Primary O
O
H H
S CH3
CH3 (Sodium
Becomes soluble
O
Penicillin H (Q)
A  R; B  S; C  P; D Q
A  (Q), B  (P), C  (R)
salvarsan etc.]

CHEMISTRY

CPP
ST

List-I List-II



List-I List-II

List-I List-II

List-I List-II

(e) Analgesic

suggested?

N
(CH2)2
N
(Brompheniramine)
Br


(S) Analgesics
(1) (a)  (Q); (b)  (R); (c)  (S) (2) (a)  (Q); (b)  (P); (c)  (R)
(3) (a)  (R); (b)  (P); (c)  (S) (4) (a)  (R); (b)  (P); (c)  (R)




(4) All of these



reaction
(3) Both (1) and (2)
(4) None
(3) Both (1) and (2) (4) None










(iii) equanil

(1) (2)
(3) (4)



ANSWER KEY
1. (2) 2. (2) 3. (3) 4. (2) 5. (1)
6. (3) 7. (3) 8. (2) 9. (3) 10. (4)
11. (3) 12. (2) 13. (2) 14. (1) 15. (4)
16. (1) 17. (4) 18. (3) 19. (1) 20. (3)
21. (3) 22. (3) 23. (2) 24. (2,3) 25. (1)
26. (1) 27. (3) 28. (2) 29. (1) 30. (3)
31. (4) 32. (1) 33. (4) 34. (3) 35. (4)
36. (1) 37. (3) 38. (2) 39. (1) 40. (3)
SOLUTION
Active site with
Active shape change
site

Inhibitor site
(non-competitive)




7. Correct match is
itchy eyes etc.]
Phenolic
OH -OH group
FeCl3
Violet colouration
(R)
H3C CH3
Cl

H3C OH CCH
H H
–
Dil. KMnO4/5°C/OH
Pink colour of
O (S) KMnO4 gets
C=C
(Double bond)
O
CHCl3 + KOH (alc.)
Foul smell
Primary O
O
H H
S CH3
CH3 (Sodium
Becomes soluble
O
Penicillin H (Q)
A  R; B  S; C  P; D Q
A  (Q), B  (P), C  (R)
salvarsan etc.]

CHEMISTRY

CPP
ST

List-I List-II



List-I List-II

List-I List-II

List-I List-II

(e) Analgesic

suggested?

N
(CH2)2
N
(Brompheniramine)
Br


(S) Analgesics
(1) (a)  (Q); (b)  (R); (c)  (S) (2) (a)  (Q); (b)  (P); (c)  (R)
(3) (a)  (R); (b)  (P); (c)  (S) (4) (a)  (R); (b)  (P); (c)  (R)




(4) All of these



reaction
(3) Both (1) and (2)
(4) None
(3) Both (1) and (2) (4) None










(iii) equanil

(1) (2)
(3) (4)



ANSWER KEY
1. (2) 2. (2) 3. (3) 4. (2) 5. (1)
6. (3) 7. (3) 8. (2) 9. (3) 10. (4)
11. (3) 12. (2) 13. (2) 14. (1) 15. (4)
16. (1) 17. (4) 18. (3) 19. (1) 20. (3)
21. (3) 22. (3) 23. (2) 24. (2,3) 25. (1)
26. (1) 27. (3) 28. (2) 29. (1) 30. (3)
31. (4) 32. (1) 33. (4) 34. (3) 35. (4)
36. (1) 37. (3) 38. (2) 39. (1) 40. (3)
SOLUTION
Active site with
Active shape change
site

Inhibitor site
(non-competitive)




7. Correct match is
itchy eyes etc.]
Phenolic
OH -OH group
FeCl3
Violet colouration
(R)
H3C CH3
Cl

H3C OH CCH
H H
–
Dil. KMnO4/5°C/OH
Pink colour of
O (S) KMnO4 gets
C=C
(Double bond)
O
CHCl3 + KOH (alc.)
Foul smell
Primary O
O
H H
S CH3
CH3 (Sodium
Becomes soluble
O
Penicillin H (Q)
A  R; B  S; C  P; D Q
A  (Q), B  (P), C  (R)
salvarsan etc.]

CPP 20220411175711706233

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

CPP 20220411175711706233

Uploaded by

Copyright:

Available Formats

CHEMISTRY

RANK BOOSTING COURSE-2022

IUPAC NOMENCLATURE NO. 01

2. In the following molecules,

Hybridisation of carbon a, b and c respectively are :

Type-2 (Alkane, alkene, alkyne and cyclic compounds)

3. The IUPAC name for the following compound is

5. The IUPAC name of the following compound is

(1) 3-bromo-5-methylcyclopentane carboxylic acid

6. The IUPAC name of the compound shown below is

(1) 2-bromo-6-chlorocyclohex-1-ene (2) 6-bromo-2-chlorocyclohexene

Type-3 (Monofunctional and Polyfunctional compounds)

9. Which of the following compounds has incorrect IUPAC nomenclature?

(3) CH3CHCCH2CH3 (4) CH3CH–CH–CH3

Type-4 (Aromatic compound)

10. The IUPAC name of the following compounds is

11. The correct IUPAC name of the following compounds is

(1) 4-methylchlorobenzene (2) Methylchloro benzene

(3) 1-chloro-4-methylbenzene (4) 1-methyl-4-chlorobenzene

Type-5 (Common name)

13. Mesityl oxide is a common name of :

(1) 2,4-Dimethyl pentan-3-one

(2) 3-Methyl cyclohexane carbaldehyde

(3) 2-Methyl cyclohexanone

(4) 4-Methyl pent-3-en-2-one

[IUPAC, JEE Main 2021]

1. (3) 2. (3) 3. (4) 4. (4) 5. (4)

6. (3) 7. (2) 8. (3) 9. (4) 10. (3)

11. (3) 12. (3) 13. (4)

3. The IUPAC name for the given compound is 3, 5-dimethyl-4-propylhept-1-en-6-yne.

5. The IUPAC name of the given compound.

IUPAC name is 2, 5-dimetyl-6-oxo-3-enoic acid.

8. The IUPAC name of the given compound is 3-hydroxy-4-mehylpentanoic acid.

11. The IUPAC name of the given compounds is

RANK BOOSTING COURSE-2022

GENERAL ORGANIC CHEMISTRY NO. 02

1. Given below are two statements :

Csp2  H1s bond with empty 2p orbital of other carbon.

Choose the correct option :

2. Which of the following compounds does not exhibit resonance?

(3) CH3CH2CH2CONH2 (4) CH3CH2CH=CHCH2NH2

3. Which one among the following resonating structures is not correct?

5. Which of the following has the shortest C—Cl bond ?

Type-2 (Stability of intermediates)

8. The order of stability of the following carbocations:

(I) (II) (III)

10. Which of the following is an aromatic compound ?

11. Which one of the following compounds is nonaromatic ?

12. Among the following, the aromatic compounds are :

(A) CH2 (B) (C) (D)

Choose the correct answer from the following options :

(1) (2) (3) (4)

Type-4 (Acidic Strength)

(1) CHBr3 (2) CHl3 (3) CHCl3 (4) CH(CN)3

CHCH,CH3—CCH and CH2CH2 is as follows :

16. Which among the following is the strongest acid ?

(1) CHCH2CH2CH3 (2) (3) (4)

17. The correct order of acid character of the following compounds is :

Type-5 (Basic Strength)

19. A. Phenyl methanamine B. N,N-Dimethylaniline

21. The increasing order of pKb values of the following compounds is

22. The decreasing order of basicity of the following amines is

23. The increasing order of basicity of the following compounds is