Organic Chem. Sr. (2020-22) Alcohol Ether Phenol 29.06.

2021

SINGLES
1. During the zeisel estimation of Aromatic ether (C 9H12O3) of 1.68gr produces 4.70gr of
yellow precipitate. What is the structure of the ether
OCH3 OCH3
OCH3 OCH3

CH2OH OCH3
(a) (b)
OH
OCH3 CH2OH

H3C
HOH2C CH2OH OCH3
(c) (d)
O O H

H 2SO 4
Ph Me A  B ; A and B are
2. Me
Me OH COMe
O

CH3 and
and

a) OH b) Me
Me Me
O
and MeOH +
Me Me
c) OPh d) OPh

3. Cumene (iso-Propylbenzene) on oxidation with alkaline KMnO4 gives

A) Phenol B) Acetone
C) Both (A) & (B) D) Benzoic acid
Zn C2 H 5Cl
4. Phenol X Y ; number of structural isomers of Y are
Dust Anhydrous AlCl3
a) 2 b) 3 c) 4 d) 0
5. Study following reactions
O
HBr
  CH3 CH CH2 OH [Major]
(only)
H 3C
(I) Br

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Organic Chem. Sr. (2020-22) Alcohol Ether Phenol 29.06.2021

O
1. BF Ph

3

CH3OH OH [Major]
Ph 2. H  / H 2 O
(1eq) OCH3
(II)
OH
O
CH3 H SO

2 4
(CH3)2 C CHCH3 [Major]
MeOH
CH3 OCH3
CH3
(III)
O OH
CH3 
H CH O

3
 (CH3)2 C CH CH3 [Major]

CH3 CH3 OCH3

(IV)
Correct reactions are
a) I & II b) II & III c) III & IV d) I & IV
OCH3


Ph  CH  CH 2 H ,
 HF
 P 
O 2 / Pt
 Q   X  Y,
6.
Where X is a compound that forms azodye with benzene diazoniumchloride in
faintly basic medium. Hence the products P, X and Y are respectively
Ph CH3 CH2Ph
OH OH

, and PhCOCH 3 , and PhCH2CHO

OCH 3 OCH 3 OCH3 OCH3

(A) (B)
CH2Ph
Ph CH3 OH CH2CHO
OH O

CH3
, and , and
OCH 3

OCH 3 OCH3 OCH3

(C) (D)
7. Which of the following geminal diols is most unstable :
OH OH
F 3C H3C
C C
OH OH
a) F3C b) H3C
ClCH2 OH Cl 3C OH
C C
OH H
c) ClCH2 c) OH
8. The product formed during the trifluoro acetolysis of labeled phenethyl tosylate is
H H
OTs
CF COOH

3

D D

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Organic Chem. Sr. (2020-22) Alcohol Ether Phenol 29.06.2021

H H D D
O CF3 O CF3

D D O H H O
A) Only B) Only
D D
CF3

H H O
C) A 1 : 1 mixture of A&B D) Only

9.

10. Final product of the following sequence is

A) Phenyl cyclohexyl ketone B) Diphenyl ketone

C) Cyclohexane carboxylic acid D) Cyclohexane carbaldehyde
11. Which one of the following compound is most likely to give effervescence of CO2
with NaHCO3 ?
OH OH OH
OH NO2
a. d.

OH
CH3 NO2
(a) (b) (c) (d)
12. Bromination of salicyclic acid with Br2 water gives

a) b) c) d)
13. In the reaction
CH3 Conc.H 2 SO4
CH3 A The product A is
OH

OH

CH3 CH3

O CH3 CH3
A) B)

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Organic Chem. Sr. (2020-22) Alcohol Ether Phenol 29.06.2021

CH3
CH3
CH3

=
COCH3 O
C) D)
NaOH
14. PhOH 
 P, in given reaction product P is :
Me2SO4
A) Ph  O  SO2OMe B) PhOMe C) PhOSO2OPh D)PhMe
15. Identify the substance that does not undergo oxidation to give corresponding
quinone.
OH OH
OH
OH
OH

OH OH OH
A) B) C) D)
16. The first formed carbocation in the following acid catalysed rearrangement is,
OH H+
Product

OH OH OH
+
+ + +
A) B) C) D)
OH
H
 X  ;  X  is
17. CH2

(A) (B)

(C) (D)
18. A chiral C5H10O ether reacts with HI to give a C5H10I2 product. Treatment of this
with hot KOH in ethanol produces 1,3  pentadiene . What is the structure of original
ether ?
CH3
O (C) O
(B)
(D)
CH3 O
O CH3
CH3 CH3
CH3
(A) (B) (C) (D)

19.

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Organic Chem. Sr. (2020-22) Alcohol Ether Phenol 29.06.2021

a) b) c) d)
20. Identify the end product in the given sequence of reaction
O


H  A  Me SO Conc. HNO


2 4  B 
Conc. H SO  C
3
2 4

H3C CH3
CO2 H O2 N CH3

OCH3 CO2 H OCH3 CH3

(A) (B)
OCH3
NO2
CH3
CH3
OCH3 NO2
(C) (D) CH3