CPP

IIT-JEE
JEE, 2014
CPP Class - XII
ALCOHOL, ETHER & PHENOL
ALCOHOL : METHODS OF PREPARATION & PHYSICAL PROPERTIES
O
(i) 1eq.PhMgI
1. HO—CH2—CH2— C —H 
(ii) H3O
 (A) : If (A) is an alcohol, it is a

(A) 1° alcohol (B) 2° alcohol (C) 3° alcohol (D) none of the above

O O OH OH
(1) RMgX / Et 2O
2. HS–CH2–CH2– C –CH2– C –OEt       HS–CH2–CH2– C–CH2–C–R
(2) H3O 
R R
How many moles of grignards reagent is required for above conversion
(A) 3 (B) 4 (C) 2 (D) 5

3. Which of the following alcohols has the maximum b.p.?

Me

(A) CH3CH2CH2CH2OH (B) CH3CH2CHCH3 (C) Me—C—OH (D) CH3CHCH2OH

OH Me CH3

4. The relative order of acidity of alcohols in comparison to H2O and HCCH is

(A) H2O  ROH  HC  CH (B) H2O  HC  CH  ROH
(C) ROH  H2O  HC  CH (D) ROH > HCCH > H­2O

NBS(2eq) aq.KOH OH
5. (B)
A  (excess) OH

A and (B)

CH3
Br
(A) and HCHO (B) and
Br
CH3
Br

(C) and CH3OH (D) None

Br

6. Which of the following reaction are correct

 
(i) D (I) H
(A) CH3CH=CH2   CH3CHCH2 D (B)CH3 CH=CH2   CH3 CHCH3
(ii) H2O  ( II) D2 O

OH OD


(i) D
(C) CH3CH=CH2   CH3 CHCH2D (D) All are correct
( ii ) D2 O 
OD

FIITJEE 1
7. Power alcohol is :
(A) Absolute Alcohol : Petrol (20 : 80) (B) Absolute Alcohol : Petrol (80 : 20)
(C) Rectified spirit : Benzene (20 : 80) (D) Rectified spirit : Benzene (80 : 20)

8. For the conversion of

R R
O OH
R' R'
Which reducing agent may be used -
(A) NaBH4 (B) LiAlH4 (C) NaH (D) All of these

9. Which of the following reaction will give 2°–alcohol :

Me 1. Ether, 
(A) + MeMgBr
O 2. H3O+

O
1. Ether, 
(B) H–C–OMe + Et MgBr
2. H3O+

1. Ether, 
(C) Benzaldehyde + Phenyl magnesium bromide
2. H3O+
(D) All of these

10. Which diol is most stable

OH OH H H
Et OH H OH Et OH H OH

H H HO HO
(A) (B) (C) (D)
H H H H
H Et H ET

11. Choose the incorrect reaction -

1. B2H6/THF
(A) CH2 OH
1. H2O2/OH

1. Hg(OAC)2
(B) 2. H2O+NaBH4 OH

Ph
Ph OH
1. Ether, 
(C) O + MeMgBr
2. Hydrolysis Ph Me
Ph
(D) None of these

FIITJEE 2
12. Which of the following reaction will yield ethylene glycol :
O2 / Ag H2O
(A) CH2 = CH2 + KMnO 4 (dilute and alkaline)  (B) CH2  CH2 
473 K

575K
(C) Both A and B (D) None of these

CH3
2 (i ) Hg(OAc) , H O
CH3—C—CH=CH2 
2  X.
13. (ii )NaBH4
X is CH3

CH3 CH3
CH3—C—CH2—CH2OH CH3—C——CH—CH3
(A) (B)
CH3 CH3 OH

CH3 CH3

CH3—C——CH—CH3 H3C—C——CH—CH2OH
(C) (D)
OH CH3 CH3 OH

ALCOHOL : CHEMICAL REACTIONS AND CHEMICAL TESTS

14. Ph2CHCH2OH  HBr

 B, B is?
(A) Ph2CHCH2Br (B) PhCH(Br)CH2Ph (C) Ph2C(Br)CH3 (D) None of these

OH
Me

15. Conc.H2SO4 C (an alkene), where C is



Me
Me Me
Me
(A) (B) (C) (D)
Me
Me

16. The increasing order of dehydration of the following alcohols

OH —CH2OH —OH —OH

I II III IV

—OH
V

towards conc.H2SO4 is
(A) III  V  IV  II  I (B) III  V  IV  I  II (C) III  I  V  IV  II (D) II < I < III < V < IV

17. The dehydration of 1-butanol gives

(A) 1-butene as the main product (B) 2-butene as the main product
(C) equal amounts of 1-butene and 2-butene (D) 2-methyl propene

FIITJEE 3
 CH3
HBr
CH3——C——CH—CH3  A (predominant) , A is :
18.
CH3 OH
Br Br
| |
(A) (CH3)3C—CH—CH3 (B) (CH3)2C—CH(CH3)2 (C) both (D) none is correct

19. OH Hg (OAc) 2

    the major product is
NaBH 4
O
OH OH OH
(A) (B) (C) (D)
OH
OH
18
OH H+
20. The major product is
OH
18
(A) (B) (C) OH (D)
O O18 OH

HO OH

H
21.  ? The major product is:

O OH
CHO O

(A) (B) (C) (D)

OH
AgNO
22. CH3–C–CH2–I   3  ? The product is:
Ph
O
(A) CH3–C–CH2 (B) CH3–CH2–C
O
OH Ph
(C) CH3–C–CH3 (D) CH3–CH–CH2
Ph

NH 2
23. O HNO 2 ? The major product is
  
OH
O OH OH

(A) O (B) O (C) O (D) O

OH

FIITJEE 4
 ETHER : METHODS OF PREP. & PHYSICAL PROP.

HI
24. Ph – O – Ph  . The products of the reaction are
(A) PhOH and Ph I (B) Phenol only (C) PhI only (D) None of these

*
O–CH2–CH=CH2
Me
25. Organic compound  yields

OH OH OH OH
* * –CH=CH
CH * Me
CH2–CH=CH2 2 2 Me CH2–CH=CH2
(A) (B) (C) (D)
Me
CH 2–CH=CH2
*
CH3
CH3–C–I
CH2–OH NaH CH3
26.  A ? The major prouduct(s) is/are :

CH3
CH3
CH2–O–C–CH3 CH2–OH
(A) (B) (C) CH –C=CH (D) both (B) and (C)
3 2
CH3

27. Which of the following reaction can’t give ether

Br ONa
(A) Me–ONa+ (B) + CH3 – Br

E
(C) CH3ONa + (CH3)3CBr 
2
 (D) Both A and C

28. The products X and Y are –

O
SN2
CH3CH2O + (CH3O)2S (X) main product
(A)
O
HBF4
(B) CH3 CH2 – OH  CH2N2 (Y) main product

(A) X is methyoxy ethane and Y is acetone (B) X is ethoxy ethane and Y is ethene
(C) Both X and Y are methoxy ethane (D) Both X and Y are ethoxy ethane

29. Choose the correct statement

(A) dimethyl ether is soluble in water
(B) There is no large difference in the solubilities of ethoxy ethane and butanol in water
(C) All ethers one lighter than water
(D) All of these

30. Choose the correct solubility order

I. C2H5–O–C2H5 II. III. IV..

O O O
(A) IV > I > III > II (B) IV > III > I > II (C) III > IV > I > II (D) III > IV > II > I

FIITJEE 5
 OH
OC2H5(excess)
31. + C2H5I X, X is :
C2H5OH (anhyd)
(A) C2H5OC2H5 (B) C6H5OC2H5 (C) C6H5OC6H5 (D) C6H5I

ETHER : CHEMICAL REACTIONS

H O 
32. CH2 CH2 HCN
 A 3 B  C
H
O
(A) CH 2=CH–COOH (B) CH2=CH–CHO (C) CH2–CH2–COOH (D) OH–(CH2)2–CHO
OH

Ph
(1) LiAlH 4  AlCl3
33. Ph       the product is
O (2) H3O 
(3)PCC
Ph
(A) Ph–C–CH3 (B) Ph–CH–CHO (C) Ph–CH–CH 2OH (D) Ph–CH–COOH
OH Ph Ph Ph

CH3 CH 3
+
ex.H
34. CH3—C— C—CH3   ? The product is:
O
CH3 O CH3 CH3CH3
(A) CH3—CH—C—CH3 (B) CH3—C— C—CH3 (C) CH3—C C—CH3 (D) CH3—C— C—CH3
OH CH3 CH3 CH3 CH3 OH H

35. On boiling with concentrated hydrobromic acid phenyl ethyl ether yields
(A) phenol and ethyl bromide (B) bromobenzene and ethanol
(C) phenol and ethane (D) bromobenzene and ethane

36. Which one step is slow -

Me Me
(I)
O Me + H – I O Me + I
Me Me
Me H
Me
SN1 (II)

Me Me
I
I + MeOH
Me (III) Me
Me Me
(A) I (B) II (C) III (D) Both II and III

FIITJEE 6
37. Choose the correct statement regarding following reaction :
*
O OH
Me Me Me
Me 
Suitable Solvent

*
(A) The reaction is “Claisen rearrangement reaction”
(B) Substrate is heated in inert solvent (Benzene)
(C) Breaking and fermation of bond takes place simultaneously
(D) All of these

O
O C CH3 AlCl3
38. X+Y

(A) X is phenol Y is ethanal
(B) X is o - acylphenol and Y is p-acyl phenol
(C) X is Toluene and Y is CO 2
(D) X is benzene and Y is ethanoic acid.

PHENOL : METHODS OF PREPARATIONS AND PHYSICAL PROPERTIES

39. Phenol is obtained by which of the following reaction.

O
NH2
C–OH
(A) + OH aq. 
 ? (B) + OH aq. 
 ?

NH2 SO3H
NaNO 2 (1) NaOH / Fusion
(C) +     ? (D) +        ?
HCl , 0º C (2) H 3O

40. The most suitable method of the separation of 1 : 1 mixture of o-and p-nitrophenol is:
(A) distillation (B) crystallisation (C) sublimation (D) steam distillation

41. Which of the following phenols will show highest acidity?

Me
Me OH Me OH HO Me OH
(A) (B) (C) (D)
Me Me NO2 O2N CH3
NO2 NO2 Me

42. Intransolecular chelation is absent in

(A) Salicylic acid (B) S-nitrophenol
(C) P-Hydroxy acetophenone (D) None of these

Diazotisation 
43. Aniline  (A) 
Hydrolysis
(B) B is :
(A) Phenol (B) Aniline (C) Benzene (D) None of these

FIITJEE 7
 OH OH
OH OH

44. I. II. III. IV..

Cl Cl OCH3
Correct acidity order is :
(A) I > II > IV > III (B) II > I > IV > III (C) I > II > III > IV (D) II > I > III > IV

45. P-chlorophenol is more acidic than P - Fluoro Phenol due to :

(A) +R effect dominates in - F substituent
(B) Higher electronegativity of F.
(C) –I effect dominates in - F substituent
(D) All of these

46. Choose the incorrect order of acidity :

OH OH OH
CH3 OH
CH3 H3C CH3
> >
(A) (B)
CH3 CH3 H3C CH3
CN CN NO2 NO2
OH OH OH OH

> >
(C) (D)
NO2
Cl Br NO2

47. Which sequence represents the best synthesis of 4-tert-butylphenol?

(A) 1. Benzene + (CH3)3CCl, AlCl 3 (B) 1. Benzene + (CH3)3CCl, AlCl 3
2. Br2, FeBr3 2. HNO 3, H2SO 4
3. KOH, H2O, 50ºC 3. Fe, HCl
4. NaOH, heat
(C) 1. Benzene + HNO 3, H2SO 4 (D) 1. Benzene + (CH3)3CCl, AlCl3
2. Fe, HCl 2. HNO 3, H2SO 4
3. (CH3)CCl, AlCl 3. Fe, HCl
4. NaOH 4. NaNO 2, HCl, H2O
5. NaNO, HCl, H2O 5. H2O, heat

PHENOL : CHEMICAL REACTIONS AND CHEMICAL TESTS

48. Phenol reacts with bromine in carbon disulphide at low temperature to give
(A) m-bromophenol (B) p-bromophenol (C) o-and p-bromophenol (D) 2, 4, 6-tribromophenol

49. Phenol gives sym-tribromophenol (2, 4, 6-tribromophenol) when treated with bromine in aqueous solutions but
only o- and p-bromophenols in CCl4 solution because
(A) in aqueous solution the bromine is ionised
(B) in aqueous solution, phenol exists in equilibrium with phenoxide ion which has more activating effect
(C) In CCl4, the electrophilicity of Br2 increases
(D) in CCl4, the other positions of benzene rings are blocked by the solvent

50. An organic compound with molecular formula C7H8O dissolves in NaOH and gives characteristic colour with
FeCl3, On treatment with Br2 it gives tribromo product C7H5OBr3. The compound is
(A) p-cresol (B) 2-methoxy - 2 - phenyl propane
(C) m-cresol (D) o - cresol

51. Which of the following reagents can be used to distinguish a phenol and an alcohol?
(A) ammonical AgNO3 (B) ammonical Cu2Cl2
(C) aqueous ferric chloride (D) neutral ferric chloride

FIITJEE 8
52. Which of the following reagents is useful in separating benzoic acid from phenol?
(A) dil. HCl (B) dil. H2SO4 (C) 5% aq.NaOH (D) 5% aq. NaHCO3

53. Phenol can be distinguished from alcohol by all reagents except:

(A) Na (B) Alcoholic FeCl3 (C) Br2/HOH (D) NaOH

54. The active intermediates when phenol is reacted with concentrated H 2SO 4 and conc. HNO 3 respectively
are:
     
(A) HS O / NO2 (B) SO3 / NO2 (C) SO3 / NO (D) SO3 / NO

55. Reimer-Tiemann reaction is an example of electrophilic substitution reaction. The electrophile in the reaction is:

(A) (B) (C) : CCl2 (D)

56. is

(A) aldol condensation (B) Reimer-Tiemann reaction

(C) Kolbe reaction (D) Cannizzaro reaction

57. When sodium phenoxide is reacted with acetyl chloride, the major product obtained is:

OH OCOCH3 OH O Na

COCH3
(A) (B) (C) (D)

COCH3 COCH3

58. When excess phenol is reacted with PCl 3, the main product is:
Cl O OH Cl
(A) (B) (C) (D) (C6H5O)3P

59. Which of the following is not soluble in NaHCO3 Solun.

OH COOH OH SO3H
O2N NO2
(A) (B) (C) (D)

NO2

60. The end product in the following sequence is

CO 2 
NaOH CH 3COCl
Phenol   A   B H
 C     D
140C H 2O
(A) salicylic acid (B) salicylaldehyde (C) phenyl acetate (D) aspirin

*****
FIITJEE 9
 ANSWER KEY (AEP)

1. (A) 2. (B) 3. (A) 4. (A) 5. (B) 6. (D) 7. (A) 8. (D) 9. (D) 10. (D)
11. (D) 12. (C) 13. (B)

ALCOHOL : CHEMICAL REACTIONS AND CHEMICAL TESTS

14. (A) 15. (D) 16. (D) 17. (B) 18. (B) 19. (A) 20. (B) 21. (A) 22. (A) 23. (B)

ETHER : METHODS OF PREP. & PHYSICAL PROP.

24. (D) 25. (C) 26. (D) 27. (D) 28. (C) 29. (D) 30. (A) 31. (A)

ETHER : CHEMICAL REACTIONS

32. (A) 33. (B) 34. (B) 35. (A) 36. (B) 37. (D) 38. (B)

PHENOL : METHODS OF PREPARATIONS AND PHYSICAL PROPERTIES

39. (D) 40. (D) 41. (D) 42. (D) 43. (A) 44. (A) 45. (A) 46. (B) 47. (D)

PHENOL : CHEMICAL REACTIONS AND CHEMICAL TESTS

48. (B) 49. (B) 50. (C) 51. (D) 52. (D) 53. (A) 54. (B) 55. (C) 56. (B) 57. (B)
58. (D) 59. (C) 60. (D)

FIITJEE 10