SECTION-I (SINGLE CORRECT CHOICE)
1.
Which of the following phrases are not correctly associated with an SN1 reaction?
1. Rearrangement is possible.
2. Rate is affected by solvent polarity.
3. The strength of the nucleophile is important in determining the rate.
4. The reactivity series is tertiary > secondary > primary.
5. Proceeds with complete inversion of configuration.
(A) 3, 5
(B) 5 only
(D) 2, 3, 5
(D) 3 only
2.
Select the reagent that will yield the greater amount of substitution on reaction with 1-bromobutane.
(A) CH3CH2OK in dimethyl sulfoxide (DMSO)
(B) (CH3)3COK in dimethyl sulfoxide (DMSO)
(C) Both (A) and (B) will give comparable amounts of substitution.
(D) Neither (A) nor (B) will give any appreciable amount of substitution
3.
In the SN2 reaction of iodide ion with (CH3)2CHCH2CH2X what is the order of decreasing reactivity for the
following X substituents?
I X = OH- II X = CH3CO2- III X = CF3SO3- IV X = CCl3CO2(A) I > II > III > IV
(B) IV > III > II > I
(C) III > II > IV > I
(D) III > IV > II > I
4.
If the rate of reaction of 0.1 M sodium cyanide with 0.1M 1-bromoethane is 1.4 x 10-4, what effect will an
increase in NaCN concentration to [0.3] and alkyl bromide concentration to [0.2] have on the overall
reaction rate?
(A) increase by 2 times
(B) increase by 3 times
(C) increase by 6 times
(D) increase by 1.5 times
5.
Which of the following statements is true?
(A) CH3CH2S- is both a stronger base and more nucleophilic than CH3CH2O-.
(B) CH3CH2S- is a stronger base but is less nucleophilic than CH3CH2O-.
(C) CH3CH2S- is a weaker base but is more nucleophilic than CH3CH2O-.
(D) CH3CH2S- is both a weaker base and less nucleophilic than CH3CH2O-.
6.
Which of the following statements pertaining to an SN2 reaction are true?
1. The rate of reaction is independent of the concentration of the nucleophile.
2. The nucleophile attacks carbon on the side of the molecule opposite the group being displaced.
3. The reaction proceeds with simultaneous bond formation and bond rupture.
4. Partial racemization of an optically active substrate results.
(A) 1, 4
(B) 2, 3
(C) 1, 2, 3
(D) 2, 3, 4
7.
Optically pure (S)-2-butanol is treated first with TsCl and then with NaSCH3. The product has a specific
rotation   D   250 . If the same optically pure (S)-2-butanol is treated first with PBr3 and then with
NaSCH3, the optical rotation of the product would be
(A) – 250
(B) + 250
(C) 0
8.
CH3I
CH3ONa
CH3COOH
CH3I
(D) + 150
CH3COONa
CH3OH
Which of the following statements is true regarding the above two reactions?
(A) Dimethyl ether and methyl acetate are the major products in the two reactions respectively.
(B) Methyl acetate and dimethyl ether are the major products in the two reactions respectively.
(C) Dimethyl ether is the major product in both the reactions.
(D) Methyl acetate is the major product in both the reactions
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9.
In an experiment, Hughes studied the rate of racemisation of 2-iodooctane by sodium iodide (with
radioactive iodine) in acetone and compared it with the rate of incorporation of radioactive iodine into 2iodooctane.
acetone
RI  I*   RI*  I (I* is radioactive iodine)
How will the rate of racemisation compare with the rate of incorporation if
(I) Each act of exchange proceeds with retention (P) 2  rate of racemisation = 2rate of incorporation
of configuration
(II) Each act of exchange proceeds with
(Q) rate of racemisation = rate of incorporation
inversion of configuration
(III) Each act of exchange proceeds randomly in (R) no inversion
which retention and inversion are equally likely.
(A) I-P, II-Q, III-R
(B) I-R, II-P, III-Q
(C) I-P, II-R, III-Q
(D) I-R, II-Q, III-P
10.
Which of the following isomeric chlorides will undergo SN2 substitution most readily?
A) 4-chloro-1-butene
B) 1-chloro-1-butene (cis or trans)
C) 1-chloro-2-butene (cis or trans)
D) 2-chloro-1-butene
11.
A C7H13Br compound reacts with KOH in ethanol to form 3-methylcyclohexene as the major product.
What is a likely structure for the starting alkyl bromide?
A) cis-4-methylcyclohexyl bromide
B) trans-3-methylcyclohexyl bromide
C) cis-2-methylcyclohexyl bromide
D) trans-2-methylcyclohexyl bromide
12.
All of the following alkyl bromides react by SN2 substitution when treated with sodium cyanide in
methanol. Which one does not undergo an inversion of configuration?
A) (R)-1-bromo-2-methylbutane
B) (S)-2-bromo-3-methylbutane
C) (R)-1-bromo-3,3-dimethylcyclohexane
D) cis-4-ethyl-1-bromocyclohexane
13.
Consider the SN1 solvolysis of the following 1°-alkyl chlorides in aqueous ethanol.
I CH3CH2CH2Cl II CH2=CHCH2Cl III CH3OCH2Cl IV CF3CF2CH2Cl
What is the order of decreasing reactivity?
A) III > II > I > IV
B) II > III > I > IV
C) IV > III > II > I
D) I > II > III > IV
14.
The structures of two 3°-bicyclic chlorides (I and II) are shown below.
Which of the following statements is correct?
A) on treatment with KOH in ethanol, both compounds undergo E2 elimination.
B) on treatment with KOH in ethanol, I undergoes substitution and II undergoes elimination.
C) I is more reactive than II for both substitution and elimination
D) II is more reactive than I for both substitution and elimination
15.
Which of the following reaction sequences would best serve to convert 2-methyl-1-bromopropane to 4methyl-1-iodopentane?
A) (i) Mg in ether; .(ii) ethylene oxide (C2H4O); (iii) HI & heat
B) (i) NaC≡CH in ether; .(ii) H2 + Lindlar catalyst; (iii) HI
C) (i) KOH in alcohol; . (ii) C6H5CO3H in CH2Cl2; (iii) NaC≡CH in ether ; (iv) 2 H2 + Pt catalyst
D) (i) NaC≡CH in ether; .(ii) H3O+ + HgSO4; (iii) HI & heat
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16.
A C8H14 hydrocarbon (X) is reduced by sodium in liquid ammonia to a single C8H16 product (Y). Both of
these compounds undergo hydrogenation (Pt catalyst) to give 2,5-dimethylhexane. Ozonolysis of Y with
an oxidative workup produces a single C4H8O2 carboxylic acid. Reaction of Y with perbenzoic acid
(C6H5CO3H) gives a chiral C8H14O product, but reaction with bromine gives an achiral C8H14Br2 product.
What are X and Y?
A) X is 2,5-dimethyl-3-hexyne ; Y is cis-2,5-dimethyl-3-hexene.
B) X is 2,5-dimethyl-3-hexyne ; Y is trans-2,5-dimethyl-3-hexene.
C) X is 2.5-dimethyl-1,5-hexadiene ; Y is 2,5-dimethyl-3-hexyne.
D) X is 2,5-dimethyl-2,4-hexadiene ; Y is cis-2,5-dimethyl-3-hexene.
17.
Compound X reacts with HI. The product of this reaction, when treated with KOH in ethanol, gives Y (an
isomer of X). Ozonolysis of Y (H2O2 workup) produces two compounds: a two carbon carboxylic acid, and
a four carbon ketone. What is X?
A) 2-methyl-2-pentene
B) 4-methyl-1-pentene
C) 2,3-dimethyl-2-butene
D) 3-methyl-1-pentene
18.
Azide anion is a very good nucleophile. Predict the major product from the following reaction.
19.
Solvent Dielectric constants(  )
Methanol
32.6
H2O
78.5
Ethanol
42.7
CH 3CN
37.5

CH3CH2CH2Br + NaN3 
Above reaction is fastest in
(A) Methanol
(B) H2O
(C) CH3CN
(D) Ethanol
20.
OH
OH
OH
OCOCH3
A student tried to bring about the above conversion in the following two methods.
I) i. K ii. CH3COCl
II) i. TsCl/py ii. CH3COONa
Select the correct statement.
(A) I gives a better yield of the product. (B)II gives a better yield of the product.
(C) One is as good as the other.
(D) None of them gives satisfactory yield.
21.
22.
The reaction of (R)-1-chloro-3-methylpentane with sodium iodide in acetone will yield 1-iodo-3methylpentane that is
(A) R
(B) S
(C) A mixture of R and S
(D) Meso
Which of the following reacts faster in an SN1 reaction?
I. cis-4-tert-butylcyclohexyl bromide
II. trans-4-tert-butylcyclohexyl bromide
(A) I
(B) II
(C) both at equal rate
(D) both of them do not undergo SN1 reaction
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23.
Devise a series of reactions to convert benzene into meta-chlorobromobenzene. Select reagents and
conditions from the following table, listing them in the order of use.
1 sulfuric acid 2 Cl2 + FeCl3 3 NaNO2 + H3O(+)/0 ºC
(conc.)/ heat
& heat
4 H2/Pt catalyst
5 Mg in ether
6 PBr3
9 Cu2Br2 + HBr
10 (CH3CO)2O
+ pyridine
7 H3PO2
8 HNO3 (conc.) +
H2SO4 (conc.) & heat
(A) 1 then 2 then 6
(C) 8 then 4 then 10 then 2 then 3 then 9
24.
Stereoisomers I and II undergo E2 elimination on treatment with sodium ethoxide in ethanol. One isomer
reacts 500 times faster than the other. Also, one isomer gives X as the only product, whereas the other
gives Y together with some X.
Which of the following statements provides the best assignment of I and II?
(A) II reacts faster and gives both Y & X
(C) I reacts faster and gives both Y & X
25.
(B) 2 then 8 then 4 then 3 then 9
(D) 8 then 2 then 4 then 3 then 9
(B) II reacts faster and gives only X
(D) I reacts faster and gives only X
HBr  B+C (isomers having m.f.C H Br)
(A) C9 H10 
9 11
HBr/peroxide
D+E (isomers having m.f.C9 H11Br)
CH=CH-CH 3
Cold alk KMnO4
A 
 racemic mixture
A is
Which of the following is true about A ?
(A) A is cis isomer
(C) Data insufficient to decide
26.
(B) A is trans isomer
(D) None
Arrange the following species in the decreasing order of leaving tendency.
NO2
I. RSO 2 -O-
II. O2 N
-
O
-
III. O 2N
O
IV.
-
O
NO2
(A) I > II > III > IV
27.
(B) III > II > I > IV
A solution of pure (S)-2-iodobutane (
(C) I > III > II > IV
(D) III > I.> II > IV
  = +15.9 ) in water is allowed to react with radioactive iodide,
0
131 -
I,
until 1% of the iodobutane contains radioactive iodine. If the reaction proceeds with SN1 and there is
complete racemisation, what is the specific rotation of the recovered reaction mixture?
(A) 15.74
(B) 15.58
(C) 0
(D) 15
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28.
CH3
COOEt
Br
+
-
CN
DMSO

SN2
H
Choose the correct statement
(A) the product has S configuration
(C) the product is optically inactive
29.
(B) the product has R configuration
(D) None
A C6H14O chiral alcohol is converted to a bromide by treatment with PBr3. Reaction of this bromide, first
with Mg in ether, followed by quenching in 0.1 N HCl produces an achiral C6H14 hydrocarbon. Which of
the following is the original alcohol?
(A) 2-ethyl-1-butanol
(B) 4-methyl1-1-pentanol
(C) 3-methyl-3-pentanol
(D) 3-methyl-1-pentanol
CH2OH
30.
H2SO4

Br2
AlCl3
What is the major product of the above sequence of reactions?
CH3
CH3
(A)
(B)
(C)
(D)
Br
Br
Br
Br
Br
31.
Reaction of 1,1-dibromopentane with three equivalents of NaNH2 in ether is followed by treatment with
0.1M HCl at 0° C. What is the product?
(A) cyclopentene.
(B) 1,2-pentadiene.
(C) 2-pentyne. (D) 1-pentyne.
32.
Which of the following reagents and conditions would best serve to convert 1-butyne to 1,1dibromobutane?
(A) 2 equivalents of HBr, no peroxides. (B) 2 equivalents of HBr, with peroxides.
(C) 1 equivalent of Br2. (D) 2 equivalents of Br2 followed by i equivalent of KOH.
33.
Chloroethane, C2H5Cl, does not react with methanol under mild conditions. What reagent could be added
to the reaction mixture to increase the rate of substitution?
(A) HCl (conc.)
(B) NaOH
(C) NH4OH
(D) AgNO3
34.
Which of the following three compounds undergoes the fastest NAS (ArSN) reaction with hydroxide ion?
Cl
O
Cl
Cl
O
I
A) I
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II
B) II
III
C) III
D) I & II with equal ease
Page 5
OH
35.
H+

A
Number of dichloro isomers (including stetreoisomers) formed, when A is treated with Cl2/hv, is
(A) 6
36.
(B) 8
(C) 10
Which of the following compounds undergoes ArSN reaction fastest?
Cl
Cl
Me
Me
Me
Me
Me
Me
NO2
(A)
F
F
Me
CN
37.
(D) 12
CN
NO2
(B)
Me
(C)
(D)
The final product of the following sequence of reactions is
F
HBr
1 eq Mg
dry ether
H2O2
NO2
(A)
(B)
(C)
(D)
F
NO2
38.
NO2
NO2
NO2
The major product of the following reaction is
Cl
Cl 1 eq. NaOH

N
(A)
(B)
Cl
OH
N
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(C)
OH
Cl
Cl
N
(D)
Cl
+
N
OH
Cl
HO
Cl
N
Page 6
39.
Which of the following undergoes ArSN reaction most readily?
(A)
(B)
Cl
(D)
Cl
H
N
NO2
Cl
(C)
Cl
40.
(I) MeI  NaOH  MeOH  NaI
(II) MeI  MeOH  MeOMe  HI
(III) (CH3 )3 S   MeOH  MeOMe  (CH3 )2 S
In which of the above SN2 reactions, rate of the reaction increases on increasing the polarity of the
solvent?
(A) I
(B) II
(C) III
(D) I & II
41.
Br
AgNO3
H2O
Br
The major product of the above reaction is
Br
OH
OH
Br
(A)
42.
43.
(D)
(B)
If, in a SN2 reaction, water acts as solvent as well as nucleophile, the reaction order can be expected to
be
(A) 1
(B) 2
(C) 3
(D) 0
(C)
In ethanol/H2O mixture, isopropyl bromide reacts with hydroxide ion according to the following equation
rate  4.7  105 RX  OH   0.24  105 RX 
What percentage of isopropyl bromide reacts by SN2 mechanism when OH  = 0.1M?
(A) 90%
(B) 66%
(C) 98%
(D) 46%
44.
H
H
Br
CH3
NaOCH3
CH3OH/
Major product of the above reaction is
(A)
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(B)
(C)
(D)
Page 7
45.
Br CH2 (CH2 )6 CH2 Br
Na
CH  CH  ex.NaNH2  A 
 B 
C
liq.NH3
C is
(A)
(B)
(C)
(D)
46.
O2N
Pyridine
OH
Br
Major product of the above reaction is
O2N
O2N
O2N
N
N
N
O
O
N
OH
O
py
(A)
(B)
47.
(C)
(D)
Cl2
h
Number of monochlorinated isomers (including stereoisomers) formed in the above reaction is
(A) 4
(B) 6
(C) 3
(D) 8
48.
Cl
KNH2

CH3
Major product of the above reaction is
NH2
NH2
Cl
NH2
CH3
CH3
CH3
(A)
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(B)
(C)
CH3
(D)
Page 8
49.
Cl
KNH2
NH3
NH2
Major product of the above reaction is
NH2
Cl
NH2
NH2
NH2
NH2
NH2
(A)
50.
NH2
(B)
(C)
(D)
The major product of the following reaction is
Me
CH3
ONa + Br
C2H5
H
H3 C
C2 H5
H
H
O
Me
H
C2H5
CH3
H
H
(A)
C2H5
CH3
H
C2H5
O
O
Ph
DMSO
Ph
Me
H
O
Me
Ph
H
Ph
(B)
CH3
(C)
Me
Ph
H
(D)
51.
Reaction of 1,4-dibromobutane with Mg turnings in ether gives the bis-Grignard reagent,
BrMgCH2CH2CH2CH2MgBr. What is the product from the reaction of meso-2,3-dibromobutane with Mg
under the same conditions?
(A) trans-2-butene
(B) cis-2-butene
(C) meso-CH3CH(MgBr)CH(MgBr)CH3
(D) racemic-CH3CH(MgBr)CH(MgBr)CH3
52.
What is the order of reactivity of the following compounds in SN2 reaction?
(I) CH3CH2CH2Cl
(II) CH2=CH-CH2Cl
(III) CH3COCH2Cl
(A) I > II > III
(B) II > I > III
(C) III > II > I
(D) II > III > I
53.
Br2
CCl4
a mixture containing
A and B
The relation between A and B is
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54.
(A) Enantiomers
(B) Diastereomers
(C) Constitutional isomers
(D) None of the above.
Select the best combination of reagents for the following conversion
propane
2,2-dichloropropane
(A) i. ex. Cl2/hv ii. EtOH/KOH iii. Br2/CCl4 iv. 3 moles of NaNH2 followed by H+ v. 2 moles of HCl
(B) i. Cl2/hv and large excess of propane ii. EtOH/KOH iii. Br2/CCl4
iv. 3 moles of NaNH2 followed by H+ v. 2 moles of HCl
(C) i) i. Cl2/hv and excess of propane ii. ROH/ KOH iii. Br2/CCl4 iv. ROH/KOH KOH v. 2 moles of HCl
(D) i. 2 moles of Cl2 in the presence of light iv. 3 moles of NaNH2 followed by H+ v. 2 moles of HCl
55.
Mg
dry ether
*
CH3COOH
Mixture
Br
How many isomers does the mixture contain? (C* is C14)
(A) 6
(B) 3
(C) 4
SECTION-II (Multi Correct)
56.
Under the specified conditions, a substrate X undergoes substitution (with H2O) and elimination reactions
to give products A, B, C and D. A and B are stereoisomers but not enantiomers. C and D are
enantiomers. A and C are not isomers. Which of the following could be the starting material X?
Br
(A)
57.
(D) 5
(B)
Br
H
CH3
H
CH3
H
CH3
(C)
H3C
Br
(D)
Br
CH3
H3C
H3C
H
H
Cl2/hν
(S)-2-Chlorobutane 
 monochlorination
The product which is/are formed in the above reaction is
(A) (2S,3S)-2,3-dichlorobutane
( B) (2R,3R)-2,3-dichlorobutane
(C) (S)-1,2-dichlorobutane
(D) (R)-1,2-dichlorobutane
58.
CH3OH
CH2Cl
O
The products obtained in the above reaction is/are
OCH3
(A)
(B)
(C)
O
CH2OCH3
H3CO
O
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(D)
CH3
O
CH3
+
O
CH3
OCH3
Page 10
59.
60.
In which of the following options, all of which are SN2 reactions, the first reaction is faster than the
second?
CN
OH


(A) I. CH3 CH2 CH2I 
II. CH3 CH2CH2I 
DMSO
DMSO
I
Cl
(B) I.CH3 CH2CH2OTs 

II. CH3 CH2CH2 OTs 

DMSO
DMSO
NH3
PH3
(C) I. CH3CH2 CH2OTs 
II. CH3 CH2CH2 OTs 
CN
CN

(D) I. CH3 CH2CH2 OSO2 CH3 

II. CH3 CH2 CH2OSO2 CF3 
DMSO
DMSO
Which of the following is/are polar aprotic solvents?
(A) CH3COOH
(B) (CH3)3N
(C) CH3COCH3
(D) DMSO
61.
Under conditions of photochemical chlorination, (CH3)3CCH2C(CH3)3 gives a mixture of two
monochlorides. Select the correct statement(s) regarding the products.
(A) The major product is more reactive than the minor product toward SN1 solvolysis.
(B) The major product is less reactive than the minor product toward SN1 solvolysis.
(C) SN1 hydrolysis of the minor product gives 2,3,4,4-tetramethyl-2-pentanol as the major product.
(D) Major product is optically active.
62.
Which of the following give(s) white precipitate with aqueous AgNO3?
Br
Br
Br
Br
Br
(A)
63.
(B)
CH3-CH=CH-CH2Cl
(C)
(D)
NaCN
DMSO
The products formed in the above reaction is/are
(A) CH3CH=CHCH2CN
(B) CH2=CH-CH=CH2
(C) CH3-CH(CN)-CH=CH2
(D) CH3-CH=C(CN)-CH3
64.
B
HBr
H2O2
HBr
A
(R)
Select the correct statements regarding A and B.
(A) A is a mixture of diastereomers
(B) B is a mixture of enantiomers
(C) A is a mixture of enantiomers
(D) B is optically p
O
65.
B
CH3ONa
H3C
S Cl
O
Pyridine
H
H3C
C
OH
K
CH3I
C2H5
A
Select the
correct
statement(s)
(A) A and B are enantiomers
(C) B is (S)-2-methoxybutane
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(B) A is (R)-2-methoxybutane
(D) A and B are diastereomers.
Page 11
SECTION-III
Passage-I
The ratio of elimination to substitution is exactly the same (26% elimination) for 2-bromo-2-methylbutane
and 2-iodo-2-methylbutane in 80% ethanol + 20% water at 250C.
66.
By what mechanism does substitution most likely to occur in these compounds under these conditions?
(A) SN1
(B) SN2
(C)SNi
(D) None
67.
By what mechanism does elimination most likely to occur in these compounds under these conditions?
(A) E1
(B) E2
(C) E1CB
(D) None
68.
Which of the following best explains as to why the ratio of elimination to substitution is exactly the same in
these compounds?
(A) 80% ethanol + 20% water at 250C always gives the same ratio.
(B) The ratio is same because of the formation of same carbocation.
(C) Bromides and iodides always give the same ratio.
(D) None
Passage-II
An alkane (A) with the formula C6H14 reacts with chlorine to yield three compounds (excluding
stereoisomers) with the formula C6H13Cl: B, C, and D. Of these, only C and D undergo
dehydrohalogenation with sodium ethoxide in ethanol to produce an alkene. Moreover, C and D yield
same alkene E (C6H12). C is optically active. Hydrogenation of E produces A. Treating E with HCl
produces a compound (F) that is an isomer of B, C, and D. Treating F with Zn and acetic acid gives a
compound (G) that is isomeric with A.
69.
C is
(A)
Cl
(B)
(C)
(D)
Cl
Cl
70.
Cl
Correct statement regarding E is
(A) It is the least stable alkene possible for the molecular formula C6H12.
(B) It is the most stable alkene possible for the molecular formula C6H12.
(C) It has two degree of unsaturation.
(D) None of the above.
Passage-III
In the laboratories of the firm ‘Novartis’ has been found a compound labelled ‘achiral alkyl halide
C10H17Br’. The management feels that the compound might be useful as a pesticide, but they need to
know its structure. You have been called in as a consultant at a handsome fee. Compound A, when
treated with KOH in ethanol, yields two compounds B and C, each with molecular formula C10H16.
Compound A rapidly reacts in aqueous ethanol to give an acidic solution. Ozonolysis of A followed by
treatment with (CH3)2S gives (CH3)2C=O as one of the products plus an unidentified halogen containing
compound.
Hydrogenation of either B or C gives a mixture of both trans and cis 1-isopropyl-4-methylcyclohexane.
A reacts with one equivalent of Br2 to give a mixture of two separable compounds D and E, both of which
can be shown to be achiral. Finally, ozonolysis of B gives (CH3)2C=O and the following diketone.
O
O
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71.
72.
D and E are
(A) positional isomers
(C) functional isomers
B is
(A)
73.
(B) diastereomers
(D) None
(B)
(C)
(D)
Compound A, when reacts with ethanol, gives which of the following as the major organic compound?
OEt
OEt
EtO
EtO
(A)
(B)
CH3
(C)
(D)
Passage- IV
There are 5 isomers; A, B, C, D, & E with m.f. C7H7Cl of which A, B, C, & D are aromatic. E is quite
soluble in water. When treated with Mg/dry ether followed by H2O, A, B, C, and D give same compound F.
But when treated with Mg/dry ether followed by D2O, A, B, C, and D give four different compounds; G, H,
I, & J respectively.
A and E readily react with aq. NaOH. B, C, & D do not react with aq.NaOH under normal conditions.
74.
75.
F is:
(A) toluene
(B) cycloheptatriene
(C) benzene
E can be converted into an aromatic ion by treatment with
I. AgNO3
II. AlCl3
III. CH3MgBr
(A) II & IV
(B) I & II
(C) II & III
(D) none
IV. KH
(D) I & IV
Passage-V
There are three isomers, A,B and C having the m.f. C3H8O. Their boiling points are; A: 97.40C, B: -240C
and C: 82.40C. There is another compound, D , whose molecular weight is same as that of above
compounds but its m.f. is C2H4O2. The boiling point of D is 1180C.
76.
77.
78.
Treating A with PCl3 gives
(A) n-propyl chloride
(C) ethyl chloride
A and B are
(A) Functional isomers
(C) Diastereomers
(B) isopropyl chloride
(D) methyl chloride
(B) Enantiomers
(D) None
Treating D first with moist Ag2O and Br2 followed by heating gives which of the following as major product
(A) CH3Br
(B) CH3CH2Br
(C) CH4
(D) C2H6
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Passage-VI
Two compounds A and B have the molecular formula C10H10. Both absorb four mol of H2 in the presence
of Ni and give the following compound.
79.
80.
Both A and B give phthalic acid with hot KMnO4. A gives three monobromo isomers (excluding
stereoisomers) with NBS/CCl4. B gives two monobromo isomers (excluding stereoisomers) with
NBS/CCl4.
Including stereoisomers, how many isomers does A give with NBS/CCl4 ?
(A) 6
(B) 4
(C) 5
(D) 8
Including stereoisomers, how many isomers does B give with NBS/CCl4 ?
(A) 6
(B) 4
(C) 3
(D) 5
ANSWERS
1A
11 D
21 A
31 D
41 C
51 A
61 BC
71 B
2A
12 A
22 A
32 B
42 A
52 C
62 BD
72 B
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3D
13 A
23 D
33 D
43 B
53 B
63 AC
73 C
4C
14 D
24 A
34 B
44 B
54 A
64 AD
74 A
5C
15 A
25 C
35 C
45 C
55 B
65 ABC
75 B
6B
16 B
26 C
36 D
46 B
56 C
66 A
76 A
7B
17 D
27 A
37 A
47 D
57 AD
67 A
77 A
8D
18 D
28 A
38 B
48 B
58 ABC
68 B
78 A
9B
19 C
29 D
39 B
49 B
59 A
69 C
79 A
10 C
20 B
30 B
40 B
50 D
60 BCD
70 A
80 B
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