CHEMISTRY

Halogen Derivatives, Oxygen Containing Compound

BENGALURU, KARNATAKA

CHEMISTRY Me
|
48. Me  C  H 
KMnO 4
A,
|
O
Me
.
CH 3  CH 2  CH  OH 
PCC
B
46. H 
 A . The product A can be
Zn,NaOH

|
CH 3
O
Relation between A and B is
OH (1) Functional isomers (2) Homologous
O (3) Metamers (4) None
Ans. 4
H
(1) (2)
OH OH
O
49.
Cu / 
  X  then which is true about X

O
OH (1) X can give 2, 4 - DNP test
(2) X is an alkene
OH (3) X can give tollen’s reagent test
(3) (4)
OH
(4) X can give lucas reagent test
O Ans. 1
Ans. 4 OH O
Sol. Zn/NaOH is a reducing agent that converts
aldehyde to ketone in to alcohol Sol.
Cu / 
 , 
2,4DNP
 ve test
47. The order of boiling point for n-Butylalcohol,
isopropyl carbinol and sec - butylalcohol is
Me Me Me
(1) n - Butylalcohol > isopropyl carbinol >
sec-butylacohol HX
X+
50.
(2) isopropyl carbinol > n - Butylalcohol >
OH (Major) X
sec-butylacohol
(3) sec-butylacohol > isopropyl carbinol > In given reaction reactivity of HX will be follow
n - Butylalcohol order as
(4) n - Butylalcohol > sec-butylacohol > (1) HF > HCl > HBr > HI
isopropyl carbinol (2) HI > HBr > HCl > HF
Ans. 1 (3) Reactivity will only depend type of alcohol hence
for HX it will be same
(4) HF > HI > HBr > HCl
Ans. 2
51. Carbinol and Fromaldehyde can be distinguished by
(1) Lucas reagent (2) Tollen’s reagent
(3) Iodoform test (4) Both (1) and (2)
Ans. 4
Sol. Carbinol = CH3OH
Formaldehyde  HCHO
BENGALURU, KARNATAKA

(4) None
CH 3
H CH 3 Ans. 2
52. C HI Sol. Pinacol - Pinacolone rearragement
C major product
H 3C
H OCH 3
OH HI
54. OCH 3 (Excess) P + Q then

P & Q is
(1) (2)
I I OH
(1) OH + CH 3I
I

(3) (4) None I

(2) I + CH 3OH
Ans. 2
Sol. I
(3) I + CH 3I
HI H 2O H-shift +
+ OH
OH  (4) OH + CH 3OH
OH 2 I
Ans. 3

I 55.
 CH3 2 O ,
H2O
,
 H C 3 3
C  O
2 will have bond
I II III
angle in the order
CH
3 Ph (1) I > II > III (2) II > III > I
| |
H 2 SO 4 / 
53. Ph  C  C  CH 3   product, then (3) III > I > II (4) III > II > I
| | Ans. 3
OH OH .. ..
O O
..

..
product will be
Sol. , ,
H 3C 110 CH 3 H 105 H
(1) Ph  C  C  Ph
| | ..
O
..

CH3 CH3

Me 3 C 132 C Me 3

CH
3
|
(2) Ph  C  C  CH 3
| ||
 
KOH aq
Ph O 56.   X , X will be
18
O
CH
3
|
(3) Ph  C  C  Ph (1) OH (2) OH
| || 18 OH OH 18
CH 3 O
BENGALURU, KARNATAKA

59. Phenol(2eq) + Phthalic annhydride(1 eq)

OH

Conc.H 2SO 4

 P then what is true about P..
(3) (4) All of these (1) It is a redox indicator
OH (2) It is an acid - base indicator
Ans. 1 (3) P is phenophthalein and it becomes colourless
57. Which of the ether can not be prepared by in acidic medium
williamsons synthesis : (4) Both (2) and (3)
Ans. 4
CH 3
Sol.
|
(1) H 3C  C  O  CH 3 OH
OH
|
CH 3 HO H

+ O 
Conc.H2 SO 4



C
C
CH 3 HO H O C O
| O C

(2) H 3C  C  O  CH 2  CH 3 O
phenophthalein
|
CH 3
OH
(3) Ph  O  CH 2  CH 3
60. 
Br2
 X , then X may be
CS2
CH 3
|
(4) H3C  C  O  Ph
OH
| Br
CH 3 Br OH
Br
Ans. 4 (1) (2)

Sol. R 1  ONa   R  X  R1  O  R

Br
R1 may be bulky but R should be 1° or 2° not
vinylic
OH
58. R  CH  CH  R 
 R  CH  CH  R . Then
X

(3) (4) Both (2) and (3)

O
X can be
(1) MCPBA (2) PAA Br
(3) O2 (4) Both (1) and (2) Ans. 4
Ans. 4 61. A compound having molecular formula C8H10O
Sol. Per acid will lead to form epoxide gives neutral FeCl3 test then number of possible
MCPBA - meta chloroperbenzoic acid compounds for given molecular formula are
PAA - peracetic acid (1) 3 (2) 6
(3) 4 (4) 9
Ans. 4
BENGALURU, KARNATAKA

Sol. Phenots will give neutral FeCl3 test (2) Fries rearrangement
OH OH (3) Electrophilic substitution reaction
Et OH Me
Me (4) Friedal craft reaction
Ans. 2

(o, m, p) 3 Me Me CH
3
|
64. H 3C  CH  O  Ph  A  B then A and B
HI
OH
OH are
Me (1) H 3 C  CH  I  PhOH
Me
Me |
CH
3
Me
(2) Ph - I, CH3  CH  OH
OH |
CH
3
total = 3+6 = 9 (3) Both (1) and (2)
Me
(4) None
Me Ans. 1
62. CaC 2 
H O
 Ca OH 2  A gas  
2 Hot
Fe Tube
B Aromatic  
Br / Fe
C 2 O
dry
Mg t o 

H  A   B   C  CH 2  OH

2 ethylene NH 2 NH2 H3 O

H 3PO 2
65. glycol KOH

D (1 eq)
E CH 2  OH
O
Then the relation between B and E will be
Identify incorrect choice for A, B and C
(1) Homologues (2) Functional isomers
(3) Identical (4) None O
Ans. 3
Sol. (1) A is O
Br
O
C 2 H 2 (A)  Benzene 
Hot Fe Br2 / Fe  PhMgBr D 

Mg
dryehter
Tube

H 3 PO 2 O O
(E) PhH (Benzene)
(2) A is H
O O
||
O  C  CH 3 OH O OH
C
CH 3
63. AlCl3 / 
  +

C
CH3
O

Above reaction is called as

(1) Beckmann rearrangement
BENGALURU, KARNATAKA

CH 2  Br OH
(3) C is H
69.

aq.CH3 COOH

O
Reaction involves
(4) B is O (1) Carbanion intermediate
(2) Carbocation as intermediate
O (3) SN1 Reaction mechanism
Ans. 2 (4) Both (2) and (3)
O
Ans. 4
O
OH
CH 2  Br +
Sol. OH OH NH 2 NH2
 
+
H (1 eq) O KOH O
Sol. 
aq.CH3 COOH
 
Ring
Expansion
 
H2 O
 H

O O
O
H3O 
OH Br
+
H
 
OH O F
RO K
X , then X will be
70.
66. Order of PKa for given phenols is O2N

OH OR
OH OH OH OR
NO 2
F OR
(1) (2)
NO 2 O2N O2 N
(I) (II) (IV)
NO 2
(III) R
Br
(1) I > III > II > IV (2) IV > II > I > III
(3)
(3) IV > I > III > II (4) II > I > III > IV
Ans. 2 RO
67. Order of acidic strength for given compounds
OR
Carbolic acid, Methanol
(I) (II) (4) Br
Methyl carbinol, Cresol NO 2
(III) (IV)
Ans. 1
(1) I > IV > II > III (2) I > IV > III > II 2
Sol. (SN Ar Mechanism)
(3) IV > I > II > III (4) IV > I > III > II
71. In which of the following reaction retention of
Ans. 1 configuration is observed?
Sol. Phenol > methyl phenol > methanol > ethanol
(Acidic strength) H
68. Incorrect order for the given property will be
(1) Me Br 
NaI
(1) F– > Cl– > Br– > I– (Nucleophilicity in Acetone

aq.medium)
(2) F– > Cl– > Br– > I– (Basic strength) D
(3) F– > Cl– > Br– > I– (Leaving group ability
(4) Both (1) and (3)
Ans. 4
BENGALURU, KARNATAKA

C2H5 I Cl

O O
(1) (2)
(2) H oNa  CH 3 I 


Me Cl Br

C 3H 7 O
(3) (4)

(3) H C O
3 Br  H 2O 

Ans. 1
C2H5 Sol. Leaving group ability of I- and stability of
carbocation
74. CH3  C CH3 
I
  X  Ag
 Y 
2 Hot
Z .
CH 3 Na CO
||
Powder
2 3FeTube

O
(4) H OH  SOCl 2 
pyridine
Product X, Y and Z are
(1) Tri iodo methane, ethane,ethyle
C2H5 (2) Iodoform, acetylene, benzene
(3) Iodoform, acetic acid, acetaldehyde
Ans. 2
(4) Acetic acid, acetylene, benzene
Sol. As nucleophilic carbon remain in same
Ans. 2
configuration
CH 3  C  CH 3 I2
 CH3COONa   CHI3 Ag
 HC  CH 
Hot
Benzene
72. In which case SN2 Ar reaction is fastest? Sol. ||
Na 2 CO3 Powder FeTube

Cl 75. Tear gas is

Cl NO 2 (1) C(NO2) Cl3 (2) COCl2
(3) CHCl3 (4) CH3COCl
(1) (2) Ans. 1
76. The oxidation of CHCl3 by air and light is prevented
NO 2 by adding
(1) CH3COOH (2) C2H5OH
Br Cl (3) CH3CHO (4) CH3COOCH3
NO 2 Ans. 2
77. Which of the following will be most reactive for 1
(3) (4) reaction
NO 2 NO 2 Br

Ans. 2 (1) C CH 2  CH 3

Sol. -M of NO2 group is more as well as chlorobenzene
is more reactive towards SN2Ar than that of bromo
73. Which of the following will be most reactive for (2) C6 H 5  CH  Br
SN1 |
CH
3
BENGALURU, KARNATAKA

Ans. 2
(3) CH 2  CH  CH  CH3 81. Which of the following compounds will undergo
| racemisation when solution of KOH hydrolyses?
Br
(1) PhCH2Cl (2) CH 3  CH  Cl
Br |
| CH
(4) CH 2  CH  CH  CH 3 3
|
CH 3 CH3
|
Ans. 1 H  C  Cl
(3) (4) None
Sol. Stability of carbocation is most |
78. Most reactive and least reactive for  2 reaction C2 H5

Ans. 3
Cl Cl
Sol. The carbon to which halogen is attached should be
Cl Cl Cl chiral
Cl
82. Ozone in stratosphere is depleted by
Cl Cl Cl Cl (1) CF2Cl2 (2) C6F6
Cl Cl (3) C7H16 (4) C6H6Cl6
I II Ans. 1
Sol. (ChloroFluoroCarbons)
Cl
83. 
i Mg,ether
Cl 
1eq  A 
HBr
ii CO , H O
X
Cl 2 3

O
Cl Cl (1)
OH
Cl
III OH
(2)
(1) I - least & II - most O
(2) II - least & I - most OH
(3) III - least & I - most
(3)
(4) III - least & II - most
O
Ans. 2
Sol. (   H and Cl should be Anti periplanar) OH

79. Isocyanide can be prepared from alkyl halide on (4)

treatment with O
(1) KNC (2) AgNC Ans. 2
(3) KCN (4) AgCN Sol.
Ans. 4
80. Which of following are arranged in the decreasing
order of dipole moment
(1) CH3Cl, CH3Br,CH3F
(2) CH3Cl, CH3F, CH3Br
(3) CH3Br, CH3Cl, CH3F
(4) CH3F, CH3Cl, CH3Br
BENGALURU, KARNATAKA

88. Which of the following when heated with KOH and

H Br Br Mg, ether
primary amine gives carbyl amine test
MgBr
CO 2 (1) CHCl3 (2) CH2Cl2
OH
 O- (3) CH3COH (4) CCl4

H3 O

O Ans. 1
O
89. The compound used as refrigerant is
84. If CHCl3 is one of the products in the following
(1) N2 (2) CCl4
reaction then A is, A  Cl2  NaOH 

 (3) CF4 (4) CF2Cl2
O Ans. 4
|| 90. The final product in the reaction
H
(1) 3 C  C OH (2) CH 3  CH  CH 3
| PhOH  CCl 4 
KOH
 product
OH (1) Salicylaldehyde (2) Salicyclic acid
(3) CH3CH2OH (4) Both (2) and (3)
(3) Methyl salicylate (4) Benzyl chloride
Ans. 4
Ans. 2
Sol. H 3C  CH  H / R will give chloroform test Sol. (Reimer - Timann carboxylation)
|
OH

85. 
Br2

H 2 / Pt
 
KCN
H2O
 P . The end product of

the reaction is
(1) Propanoic acid (2) Adipic acid
(3) Malonic acid (4) Succinic acid
Ans. 2
Sol.

Br Br CN COOH


Br2

H2 / Pt
 
KCN
 
H 2O


Br Br CN

86. Which of the following is used as insecticide

(1) D.D.T (2) Chloritone
(3) Chloropicrin (4) All of them
Ans. 1
87. Pyrene is used as
(1) Fire explosive (2) Fire extinguisher
(3) In lighter gas (4) In cooking gas
Ans. 2