JEE (Main + Adv.

) Division

Daily Practice Problems

Chemistry

ALCOHOL, PHENOL,
ETHER

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ALCOHOL, PHENOL, EHTER
DPP - 1
JEE [MAIN + ADV.] DIVISION
Single Correct Question

1. In the reaction : Me3C – O – CH2CH3 + HI 
(1 mole )
(A) Me3C OH + CH3CH2I (B) Me3C – I + CH3CH2OH
(C) Me3C – I + CH3CH2I (D) Me3C – OH + CH3CH2OH

2. How many alcohols having the molecular formula C5H12O are chiral ?
(A) 0 (B) 2 (C) 4 (D) 6

OH OH
3. How many optically active compounds are possible from the given structure?
(A) 2 (B) 3 (C) 1 (D) 4

4. Which of the following reactions would give pentan-2-ol?

Me O
(i ) EtMgBr (i ) MeMgBr
(i)   
 (ii)   

(ii ) H 3O  (ii ) H3O
O Me
Br
(i ) Mg / Ether Pr MgBr / Ether
(iii) Me Me   
(ii ) O 2
(iv) MeCHO   



H 3O
(iii ) H3O
(A) (i), (ii) (B) (i), (ii), (iii) (C) (ii), (iii) (D) all of these

5. Ph – O – CH2 – Ph + HI 
Which of the following is formed in the above reaction ?
(A) Ph – I (B) Ph – CH2– OH (C) PhOH (D) Ph – O – CH2 – I
Ph

H 2O18
6. H/  A (Major) A is
O
18 18
Ph OH Ph OH Ph OH Ph OH
(A) (B) (C) (D)
18 18
OH OH OH OH

7. RMgX
 ? Product Obtained is:
H O 2

R R' R R
| | | |
(A) R 'C  CH 2 OH (B) RCH 2  C  OH (C) R ' CH 2  C  OH (D) R ' ' CH 2  C  OH
| | | |
R' ' R'' R'' R'

8. H/
H 2O
 J (Major) J is
OH
OH OH OH
(A) (B) (C) (D)

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 Et Et O
|| 18
( i ) CH3 C O O H
9.     
(ii ) H  / H 2O
D D
Major product(s) of the above reaction is :
Et 18 Et
D OH D OH
(A) + en (B)
18
+ en
HO D D OH
Et Et
Et
D OH Et
D OH
(C) D (D) + en
OH
HO D
Et
Et
10. Dehydration of the alcohols

will be in order
(A) IV > III > II > I (B) I > II > III > IV (C) IV > II > III > I (D) II > IV > I > III

11. To prepare 3-ethylpentane-3-ol, the reactants needed are -

(A) CH3CH2MgBr +CH3COCH2CH3 (B) CH3MgBr +CH3CH2CH2COCH2CH3
(C) CH3CH2MgBr +CH3CH2COCH2CH3 (D) CH3CH2CH2MgBr +CH3COCH2CH3

CH2CH3 CH=CH2
C
OH

B A
12.
CHCH3 CH 2CH2OH
OH

Select schemes A, B, C out of

I acid catalysed hydration II HBO III oxymercuration-demercuration
(A) I in all cases (B) I, II, III (C) II, III, I (D) III, I, II
13. Propene, CH3–CH=CH2 can be converted to 1-propanol by oxidation. Which set of reagents among
the following is ideal to effect the conversion -
(A) Alkaline KMnO4 (B) B2H6 and alkaline H2O2
(C) O3 /Zn dust (D) OsO4 / NaHSO3
14. In the reaction sequence, CaC2 H
2O
 A   2
 B H
dil. H 2SO 4 2
C, the product C is -
Hg Ni

(A) CH3OH (B) CH3CHO (C) C2H5OH (D) C2H4

MgBr CH2CH2OH
15. forms on reaction with -

CH 2 – CH2
(A) CH3–CHO (B) (C) CH3–CH2–CHO (D) O
O

Answer Key
1. B 2. D 3. A 4. D 5. C 6. A 7. B
8. B 9. D 10. C 11. C 12. C 13. B 14. C
15. B
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 ALCOHOL, PHENOL, EHTER
®
DPP - 2
JEE [MAIN + ADV.] DIVISION
Single Correct Question
conc. H 2SO 4
110°C
X (Major)

conc. H 2SO 4
1. C2H5OH 140°C Y (Major)

conc. H 2SO 4
Z (Major)
160°C – 170°C

Major products X, Y, Z are respectively.

(A) C2H5HSO4, C2H5OC2H5, C2H4 (B) C2H4 , C2H5OC2H5 , C2H5HSO4
(C) C2H5OC2H5 , C2H4 , C2H4 (D) C2H4 in all cases

conc .HCl
2. Me OH  
ZnCl 2
Which statement is correct ?
Cl

(A) Both Me Cl (I) and Me (II) are formed

(B) Only (I) is formed
(C) Only (II) is formed
(D) Both are not formed
CH3
conc. H2SO4 LiAlH4
3. CH3 P Q
OH OH
Identify P and Q respectively.
CH3 CH3
CH 3 CH3 CH 3 CH3
(A) , (B) ,
CH3 O CH3OH
O OH
CH 3 CH3 CH3 CH 3 CH3 CH3

(C) CH3 , CH3 (D) ,

O OH O OH
4. Acetaldehyde can be obtained from ethanol by reaction with :
(A) H2 / Ni (B) Acidified KMnO4
(C) CrO3 in anhydrous medium (D) Jones Reagent

PCC 'X'
Me–CH2–OH

5. CH–OH PCC 'Y'

CH3
'X' and 'Y' can't be differentiated by -
(A) Tollen's Reagent (B) Fehling solution (C) Schiff's Reagent (D) Iodoform test
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 dil.alk.KMnO 4
6.      Product(s)
Product(s) is / are
CH3 CH3
(A) OH (B) OH + en
OH H
H OH
CH3
CH3
OH
(C) H (D) H + en
OH
H
H

7. CH 2  CHCHCH 2CH 2OH MnO

2  A. A is

|
OH

(A) CH 2  CHCCH 2 CH 2 OH (B) CH 2  CHCHCH 2 CHO

|| |
O OH

O
||
(C) CH 2  CHCCH 2 CHO (D) CH  CHCCH COH
2 2
|| ||
O O

HO
CrO
3
8.
OH  M,
OH
M is gS &
O OH HO H
(A) (B)
O O
OH
O H
O H
(C) O (D)
O
OH

9. Among the given compounds, the correct dehydration order is:

(I) (II) (III) (IV)

(A) I < II < III < IV (B) II < III < IV < I (C) I < III < IV < II (D) I < II < III = IV

10. Which of the following alcohols does not give a red colour in Victor Meyer test-
(A) Isobutyl alcohol (B) Isoamyl alcohol
(C) Diethyl carbinol (D) Phenylcarbinol

11. Which of the following alcohols gives a red colour in victor Meyer test :
(A) n–Propyl alcohol (B) Isoproyl alcohol (C) (CH3)3C–OH (D) Sec. Butyl alcohol

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12. Alcohol which gives red colour with Victor Meyer test is :
(A) C2H5OH (B) CH3–CH(OH)–CH3
(C) C(CH3)3OH (D) None of the above

13. In the Victor-Meyer’s test, the colour given by 1°, 2° and 3° alcohols are respectively.
(A) red, colourless, blue (B) red, blue, colourless
(C) blue, red, violet (D) red, blue, violet

14. Which of the following is produced when an aqueous solution of butan-2-ol is refluxed with
dilute acidic KMnO4?
(A) butanol (B) butanoic acid
(C) potassium butanoate (D) butanone

15. The reagent most suitable for converting a primary alcohol into an aldehyde is -
(A) K2Cr2O7and H2SO4 (B) KMnO4 and NaOH
(C) ClCrO3–, CH2Cl 2 (D) HNO3

16. Methanol and ethanol are distinguished by-

(A) Treating with Schiff’s reagent (B) Treating with Lucas reagent
(C) Heating with iodine and alkali (D) Treating with CrO3 in dil. H2SO4

Answer Key
1. A 2. A 3. C 4. C 5. D 6. B 7. A
8. C 9. A 10. C 11. A 12. A 13. B 14. D
15. C 16. C
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