BAKLIWAL TUTORIALS

ORGANIC CHEMISTRY ALCOHOLS-PHENOLS-ETHERS Assignment-2

One or more than one answer type questions:

OH
Con.H2SO4
?

1. OH The possible product(s) in the above reaction is/are:

A) B) C) D) O

2.
OH HBr , boiling Product

Which of the following are possible product(s) (in the significant amounts)?
A) CH2Br B)
Br

C) D)
Br

3. Identify compound (X) in the following oxidation reaction :

( X ) 
K 2Cr2O7
H 2 SO4

 O O

NH2 OH

(A) (B)

NH2 NH2
OH CH3

(C) (D)

OH CH3
4. Which of the following reactions are correctly interpreted?
CH 3 CH 3
(A) CH 3  C  CH  CH 2  Hg  OAc 2  CH 3  C  CH 2  CH 2  OH
H 2O
NaBH 4

CH 3 CH 3

CH 3 CH 3 CH 3 O

(B) C C + Ag C C CH 3
OH Cl (aq)

CH 3CH 2 SH
(C) OH + TsCl A SCH 2CH 3
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Pt
(D) O O + H2 HO OH

5.
O
O C CH3
O  CH 3 COOH

(A) (B)

(Aspirin)
(Anisole)
OH
OH
COOCH 3
COOC6 H 5
(C)
(D)

(oil of winter green) (Salol)

6.

Which of the following statement is/are correct regarding above reaction

a)The reaction mechanism involves initial formation of alkyl chlorosulfite

  

b)  from C6 H 5 N HCl  can bring SNi displacement of very good leaving group
 
ClSO2
c) overall 100% retention takes place during the reaction
d) overall 50% retention and 50% Inversion takes place during the reaction.

7.
H3CO CH2 O CH2 NO2

One mole
of HI

Product
Products are

H3CO CH2I O2N CH2I

a) b)

H3CO CH2OH O2N CH2OH

c) d)
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8. Which of the following ether cannot be prepared by using Williamson’s
synthesis
CH3 CH3

H3C C O C CH3

CH3 CH3
a) b) H 2C  CH  O  CH  CH 2

O
c) d) CH 2  CH  CH 2  O  CH 2  CH  CH 2

9.

CH3
KMnO4 Phenol
A B (Product)
 H+
CH3

Which of the following is correct regarding product ‘B’

a) ‘B’ is colourless in acidic medium

b) ‘B’ is pink colour in basic medium

c) ‘B’ has Benzenoid form in Basic medium

d) ‘B’ exists in Ionic form in Basic medium

10. Which of the following statements are correct
a) Phenol on treating with K 2 S2O8 / OH  produces quinol
b)Phenol on treating with CH 3  C  Cl / AlCl3 produces meta hydroxy acetophenone
||
O
c) Acylation of salicylic acid in basic medium occurs on phenolic oxygen
d)

gives effervescence with NaHCO3

11.
H3O+
A
BH3,THF
B
H2O2, OH
Hg(AcO)2, H2O
C
NaBH4,OH
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Which of the statements given is / are not correct
a) ‘C’ is primary alcohol
b) ‘B’ form turbidity with lucas reagent after 5-10 minutes and gives yellow ppt
with aqueous bleaching powder
c) ‘A’ is tertiary alchohol and gives Red ppt during victor mayer reaction
 PI3 , AgNO2 , HNO2 , Base 
d) Both ‘B’ and ‘C’ are 20 alcohols respond to haloform reaction
12.
CH 3 CH3 CH 3 H
C C C C
H H H CH 3
per acid per acid

A C
+ +
H /H2O H /H2O

B D
Which of the following statements is/are true:
a) B is a single compound and optically inactive
b) D is a single compound and optically inactive
c) B is an equimolar mixture of two enantiomeric compounds
d) D is an equimolar mixture of two enantiomeric compounds
13. FeCl3 gives positive test with
OH

(A) (B) acetylacetone

(C) acetoacetic ester (D) acrolein

14. Compound (X) C 4H8O decolorizes Baeyer’s reagent. It undergoes hydrolysis in

dil H 2SO 4 to give (Y) and (Z) where both Y and Z give positive iodoform test while
only ‘Y’ responds to Tollens test but (Z) doesn’t. Choose the correct statements
of the following :
OH/ 
(A) Y  CH  CH  CH  CHO
3
PCC/CH Cl
2 2 Y
(B) Z 
Br
Br /CCl |
(C) 2
X  4  BrCH  CH  O  CH CH
2 2 3
O /H O/z
(D) 3 2
X  2 Y other product

15. The reagent (s) used to convert phenol in to Anisole is/are.

a) NaOH , CH 3 I b) CH 2 N 2 , BF3 c)  CH 3 2 SO4 , NaOH d) NaHCO3 , CH 3 I
16. Predict which two reactions give the same alcohol among the following reactions:

a) b)
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c) d)
17. Alcohol A (C10H18O) is converted to mixture of alkene B and C on heating
with conc. H3PO4. Catalytic hydrogenation of B and C yields the same
product. Assume that dehydration of alcohol A proceeds without
rearrangement. Alkene B on ozonolysis forms cyclopentanone. Identify
the correct option.

(A) (B)
A is OH B is

(C) (D)
C is C is
18. A (C5H12O) ether, on reaction with PCl5 form alkyl chloride B and C. B
and C both on reaction with aqueous KOH form alcohol D and E. Both D
and E give iodoform test. Identify correct answers.
CH 3 - CH - CH 3
(A) A is CH 3CH 2 - O - CH(CH 3 ) 2 (B) C is |
Cl
CH 3 - CH - CH 3
(C) C is CH3CH2CH2Cl (D) E is |
OH
19.

20. Compare the properties of two isomeric products x and y formed in the
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OH
1. CCl4 + KOH/ x + y

Following reaction. 2. H

Acid strength H2O solubility Volatility M. point

(a) y  x y  x x  y yx
(b ) x y x y yx x y
(c ) yx x y yx yx
(d ) x y yx x y yx

HO *
CH2NH2
NaNO2 + HCl
(0-5° C)
21. The product P (major) of the following reaction is
*
O O CH = O
O
* *
*
(a) (b) (c) (d)

22. Which of the following compounds undergoes Reimer-Tiemann reaction ?

OH
(A) (B) N
H
CH2 OH NH 2

(C) (D)

23.

The conversion can be performed suitably by

A) I .BH 3  THF II .H 2O2,OH 
B) I .HBr peroxide II . OH 
C) I .Cl2, H 2O II . LiAIH 4
D) I . HBr II . OH 
24. Luca’s test is used to make distinction between 1, 2 and 3 alcohols
2 anhydrous ZnCl
ROH  HCl  RCl   H2O
conc . White turbidity

A) ROH behaves as a Lewis base

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B) Greater the value of pKa (alcohol), greater the reactivity and faster the
formation of white turbidity.
C) Alcohol which readily reacts with Na metal, will give turbidity readily

D) Alcohol which gives red colour in Victor Meyer test, will give turbidity at slower
rate than those giving blue or white colour in Victor Meyer test.
25.

One or more than one Answers

1 ABCD 2 BC 3 ABC 4 BCD 5 BCD 6 A
7 AD 8 ABC 9 ABD 10 ACD 11 ABCD 12 BC
13 ABC 14 ABC 15 ABC 16 AB 17 ABD 18 ABD
19 BD 20 D 21 B 22 AB 23 AB 24 ABD
25 AB