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ALCOHOLS, ETHERS AND PHENOLS E M RAO

SECTION-I (Single Correct Choice)



1. Arrange the following compounds in the decreasing of their boiling points.
(I) 3-hexanol (II) 1-hexanol (III) 2-methyl-2-pentanol (IV) 1-octanol
(A) I >II >III >IV (B) IV >II >I >III
(C) IV >III >II >I (D) II >III >I >IV

2. Which of the following reagents would be most effective for the following reaction sequence?

(A) KOH (B) Sodium ethoxide
(C) Sodium acetate (D) Butyl lithium

3. Which of the following is the best reagent to convert bromobenzene into benzene?
(A) LiAlH4 (B)NaBH4 (C) H2/Ni (D) Mg in ether ; water

4. Which sequence of steps describes the best synthesis of 2-phenylpropene?
(A) Benzene +2-chloropropene, AlCl3
(B) 1. Benzaldehyde +CH3CH2MgBr, diethyl ether 2. H3O
+
3. H2SO4, heat
(C) 1.Bromobenzene+Mg, diethyl ether 2. Propanal 3. H3O
+
4. H2SO4, heat
(D) 1. Bromobenzene +Mg, diethyl ether 2. Acetone 3. H3O
+
4. H2SO4, heat

5.

If A is an ester and only one alcohol is produced in the above reaction, which of the following could be the structure of A?
(A) CH3CH2COOCH3 (B) CH3COOC2H5
(C) HCOOCH2CH2CH3 (D) HCOOCH(CH3)CH3

6. 1,3-Propanediol can be distinguished from 1,2-ethanediol by
(A) KMnO4 (B) HCl+ZnCl2
(C) HIO4 followed by AgNO3 (D) Na

7. What sequence of steps represents the best synthesis of 4-heptanol?
(A) CH3CH2CH2MgBr +butanal in diethyl ether followed by H3O
+

(B) CH3CH2CH2CH2MgBr +acetone in diethyl ether followed by H3O
+

(C) (CH3CH2CH2)2CHMgBr +formaldehyde in diethyl ether followed by H3O
+

(D) CH3CH2CH2MgBr +ethyl acetate in diethyl ether followed by H3O
+


8. Which of the esters shown, after reduction with LiAlH4 and aqueous workup, will yield two molecules of only a single alcohol?
(A) CH3CH2CO2CH2CH3 (B) C6H5CO2C6H5
(C) C6H5CO2CH2C6H5 (D) None of these

9.











Which of the following can be X?
(A) CH3CHO; H
+
(B) Ethylene oxide; H
+

(C) CH3COCH3; H
+
(D) HCHO; H
+


10. Which of the following alcohols gives the best yield of dialkyl ether on being heated with a trace of sulfuric acid?
(A) 1-Pentanol (B) Cyclopentanol
(C) 2-Pentanol (D) 2-Methyl-2-butanol


HC CH
1.1eq NaNH
2
NaNH
2
NaNH
2
X X
H
2
/Pd
BaSO
4
Na/liq.NH
3
H
3
C
H H
CH
2
CH
2
OH
H
H
3
C H
CH
2
CH
2
OH
1. 1 eq NaNH
2
2. CH
3
I 2. CH
3
I
ALCOHOLS, ETHERS AND PHENOLS E M RAO



11. Which of the following is the best method to prepare (R)-2-butanol?
CH
3
CH
2
CCH
3
O
1. LiAlH
4
2. H
3
O
+
(A)

C H
3
C
H
H
3
CH
2
C
OCCH
3
O
1. LiAlH
4
2. H
3
O
+
(B)

CH
3
CH
2
CH
O
1. CH
3
MgBr/ether
2.H
3
O
+
(C)

C H
H
3
C
H
3
CH
2
C
1. LiAlH
4
2. H
3
O
+
OCCH
3
O
(D)


12. Which sequence of steps describes the best synthesis of 2-methyl-3-pentanone?
(A) 1. 1-Propanol +(CH3)2CHMgBr, diethyl ether 2. H3O
+
3. PDC, CH2Cl2
(B) 1. 1-Propanol +Na2Cr2O7, H2SO4, H2O, heat 2. SOCl2 3. (CH3)2CHCl, AlCl3
(C) 1. 1-Propanol +PCC, CH2Cl2 2.(CH3)2CHLi, diethyl ether 3.H3O
+
4.Na2Cr2O7, H2SO4
(D) 1. 2-Propanol +Na2Cr2O7, H2SO4, H2O, heat 2. CH3CH2CH2Li, diethyl ether 3. H3O
+
4. PCC, CH2Cl2

13. Which of the following compounds is unlikely to react with sodium metal?
(A) C2H5OC2H5 (B) C2H5OH (C) C2H5Br (D) C6H5OH


14.





Which of the following can be A?
(A) n-propyl alcohol (B) isopropyl alcohol (C) n-butyl alcohol (D) isobutyl alcohol

15. Which one of the following alcohols will be oxidized by J ones' reagent (CrO3 in 50% sulphuric acid) to a ketone having the
same number of carbon atoms ?
(A) 1-methylcyclohexanol (B) 3,3-dimethylcyclopentanol
(C) 3-methyl-1-hexanol (D) 3-ethyl-3-hexanol

16. What reagent would be suitable for distiguishing 1-methoxy-3-methyl-2-butene from its isomer 4-methyl-3-penten-1-ol?
A) bromine in methylene chloride B) KMnO4 in aqueous base
C) AgNO3 in dilute NH4OH D) sodium metal in hexane

17. A chiral C5H10O ether reacts with hot HI to give a C5H10I 2 product. Treatment of this with hot KOH in ethanol produces 1,3-
pentadiene. What is the structure of the original ether?
O O

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

18.


Select appropriate methods of preparing X and Y from 2-methylpropene.
(A) X- add HBr, then react with Mg in ether Y- add water, acid-catalysis
(B) X- add HBr/H2O2 , then react with Mg in ether Y- react with C6H5CO3H/CH2Cl2
(C) X- add HOBr Y- add B2H6in ether, then NaOH
(D) X- add HOBr Y- add HBr (peroxides) ,then react with Mg in ether

19.
CH
3
-CH-CH
2
Br
CH
3
CH
3
-C-CH
2
CH
2
CH
2
I
CH
3

Select the best series of reagents for the above conversion.
(A) (i ) Mg in ether; .(ii) ethylene oxide (C2H4O); (iii ) HI & heat
(B) (i ) NaCCH in ether; .(ii ) H2 +Lindlar catalyst; (ii i) HI
(C) (i ) KOH in alcohol; (ii) C6H5CO3H in CH2Cl2; (ii i) NaCCH in ; (iv) 2 H2 +Pt
(D) (i ) NaCCH in ether; .(ii ) H3O
+
+HgSO4; (i ii ) HI & heat
X +Y
2,5-dimethyl-2-hexanol
H
3
O
+
A
PBr
3
Mg
dry ether
B
CrO
3
/H
+
1. B
2.H
3
O
+
2,3-Dimethyl-2-butanol
ALCOHOLS, ETHERS AND PHENOLS E M RAO





20. Select the best combination of reagents for the following conversion.
OH
CH
2
OH
OH

(A) I. PBr3 II. NaNH2 III. O3; Zn/H2O (B) I. H
+
/D II. O3;Zn/H2O III. LiAlH4/ H
+

(C) I. K2Cr2O7 II. LiAlH4; H
+
(D) I. HIO4 II. LiAlH4; H
+

21. A chiral C7H16O2 diol is oxidized by PCC in CH2Cl2 to an achiral C7H12O2 compound. Which of the following would satisfy these
facts?
OH
OH

OH
OH

OH
OH

OH
OH

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

22. What product is expected from the following reaction?
O
O
excess HI
A

(A) 2 CH3CH2I B) 2 ICH2CH2OH
(C) 2 ICH2CH2I D) CH3CH2I +CH3CH2OH

23.





Which of the following might be A?
(A) 1-penten-3-ol (B) 3-penten-2-ol
(C) 3-methyl-2-buten-1-ol (D) 2-methyl-2-buten-1-ol

24. A C6H12O compound does not react with Br2 in CCl4, produces a flammable gas on treatment with LiAlH4, and reacts with
H2CrO4 changing the color from orange to green. Which of the following compounds best agrees with these facts?
(A) 1-methylcyclopentanol (B) methoxycyclopentane
(C) Hex-3-en-1-ol (D) cyclohexanol

25. Two equivalents of OsO4; H2O/NaHSO3 hydroxylate one equivalent of 1,5-cyclooctadiene. How many stereoisomeric
cyclooctane-1,2,5,6-tetraols will be formed?
(A) 1 (B) 2 (C) 3 (D) 4

26.
(A) CH3CH=CHCH2Cl (B) CH3CH(Cl)CH=CH2
(C) Both A and B (D) CH2=CH-CH=CH2

27.


Major product of the above reaction is
H
O

H
O

H
O

H
HO

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

A
H
2
Ni
B
chiral
achiral
MnO
2
C
an aldehyde
which is achiral
(C
5
H
10
O)
O
A
ALCOHOLS, ETHERS AND PHENOLS E M RAO

28.

(A) Cyclobutene (B) 1,3-Butadiene
(C) 1-Butyne (D) 2-Butyne

29 .

Major product of the above reaction is
(A) (S)-1,2-propanediol (B) (R)-1,2-propanediol (C) ( )-1,2-propanediol (D) (S)-1,3-propanediol

30.
B is
(A) Benzene (B) Benzoic acid (C) Phenol (D) Toluene

31. Cineole is the chief component of eucalyptus oil; it has the molecular formula C10H18O and contains no double or triple bonds.
It reacts with hydrochloric acid to give the dichloride shown:

Cineole +2 HCl
C H
3
C
Cl
CH
3
Cl CH
3
Which of the following can be the structure of cineole?



O



O

C H
3
C
OH
CH
3
H CH
3
C H
3
C
H
CH
3
HO CH
3
(A) (B) (C) (D)

32. Halohydrins, when treated with bulky bases like pyridine, form epoxides in a reaction that can be described as intramolecular
SN2. Identify the major product in the following reaction.








(A) O
CH
3
H
H
3
C
H
(B) O
H
CH
3
H
3
C
H

(C) Both A and B (D) Neither A or B

33. Select the best reactant to produce the following product.






CH
3
CH
3
H Cl
H OH
pyridine
O
CH
3
pyridine
Picric acid +NaHCO
3
A (a gas)
A +PhMgBr
followed by hydrolysis
B
O
CH
3
H
2
NaOH;H O

ALCOHOLS, ETHERS AND PHENOLS E M RAO



CH
3
OH
OH
CH
3
OH
OH
CH
3
OH
Cl
CH
3
OH
Cl
(A) (B) (C) (D)




34. The major product of the following reaction is

H
3
C CH
2
OOH
H
3
O
+


(A) p-methylbenzaldehyde (B) p-cresol
(C) Formadehyde (D) benzaldehyde

35.





Major products of the above reaction are
(I)p-cresol (II) p-nitrophenol (III) phenol (IV)


(A) II only (B) III only (C) I & IV (D) II and IV

36. Given below is the synthetic scheme for the preparation an analgesic, phenacetin.






Which of the following is the structure of phenacetin?
OEt
NH
2
CCH
3
O

OEt
NH
2
CCH
3
O

OEt
NHCCH
3
O
OCCH
3
NHCCH
3
O
O

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

37.



Major product is




C O-OH
C
6
H
4
-NO
2
-p
Ph
p-H
3
C-C
6
H
4
H
3
O
+
p-Nitrophenol
1.NaOH/ EtBr
2.Fe,HCl
CH
3
COCCH
3
O O
3.
Phenacetin
O
H
3
O
+
A
Ph-C-C
6
H
4
-NO
2
-p
O
ALCOHOLS, ETHERS AND PHENOLS E M RAO

OH H
3
C
H
3
C OH


CH
3
HO
CH
3
CH
3
CH
3
(A) (B) (C) (D)

38.
3 PhOH
PCl
3

Major product of the above reaction is
(A) 3 PhCl (B) (PhO)3P (C) 3 PhH (D) No reaction

39. A(C4H10O2) reacts with Na metal to liberate 1 mol of H2 gas per mol of A. Although A is inert toward periodic acid, it does react
with CrO3 to form B(C4H6O3). A can be

HO
OH

OH
OH
OH
OH

OH
HO

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

40. Diglyme(C6H14O3) is a liquid that is inert toward most common reagents like CH3Li, Br2/CCl4, aq.NaOH, m-CPBA, and Na.
When it is warmed with large excess of HI, it gives equimolar amounts of CH3I and C2H5I. Diglyme is
(A) CH3CH2OCH2 OCH2OCH2CH3 (B) CH3CH2OCH2OCH2CH2OCH3
(C)CH3OCH2CH2OCH2CH2OCH3 (D) CH3OCH2CH2OCH2OCH2CH3

41.



The above conversion can be brought by
(A) Red P/HI (B) i. ex HI ii. Na/dry ether (C) i. H
+
ii. Red P/HI (D) None

42. Compound Y, C7H8O, is insoluble in water, dilute HCl, and aqueous NaHCO3; it dissolves in dilute NaOH. When Y is treated
with bromine water it is converted into a compound, C7H5OBr3. What is the structure of Y?
(A) Phenol (B) Cyclohexanol (C) Cyclohexanone (D) None

43

Reactivity if A, B, and C toward H
+
is
(A) A >B >C (B) C >B >A (C) B >C >A (D) A >C >B


44.







B is
(A) p-methylphenylethanoate (B) methylp-methylbenzoate
(C) acetophenone (D) benzophenone

45. Observe the following reaction sequence.



RH
2
Br /hv
RBr
KOH
ROH
O
p-cresol
CH
3
COCl
AlCl
3
A
CH
3
COCl
B
AlCl
3
ALCOHOLS, ETHERS AND PHENOLS E M RAO

Above reaction sequence is good for preparing
(A) 1-butanol from butane (B) 2-methyl-1-propanol from 2-methylpropane
(C) benzyl alcohol from toluene. (D) (R)-1-phenylethanol from ethyl benzene

46.

OH
COOH
ex. Br
2
H
2
O
The major product of the reaction is


OH
Br
COOH
Br

OH
Br
Br
Br

OH
COOH
Br

OH
COOH
Br

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

47. Which of the following reactions is a more effective method for preparing phenyl propylether?
I: C6H5ONa +CH3CH2CH2Br
II: C6H5Br +CH3CH2CH2ONa
(A) Reaction I is more effective. (B) Reaction II is more effective.
(C) Both reactions I and II are effective. (D) Neither reaction I nor reaction II is effective.

48. Which of the following sets of reagents, used in the order shown, would enable preparation of p-chlorophenol from p-
chloronitrobenzene?
(A) 1. Fe, HCl; 2. NaOH; 3. NaNO2, H2SO4; 4. H3PO2
(B) 1. Fe, HCl; 2. NaOH; 3. NaNO2, H2SO4; 4. H2O, heat
(C) 1. Fe, HCl; 2. NaOH; 3. NaNO2, H2SO4; 4. ethanol
(D) 1. NaOH, heat; 2. HCl

49. Treating anisole with the following reagents will give, as the major product,
1. (CH3)3CCl, AlCl3; 2. Cl2, FeCl3; 3. HBr, heat
OH
C(CH
3
)
3
Cl

OH
C(CH
3
)
3
Cl

Br
C(CH
3
)
3
Cl

Br
C(CH
3
)
3
Cl

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

50.

O
HO
Cu
350
0
C
A


Compound A, when dissolved in H2O or ethanol, is converted cleanly into a compound B, which is an isomer of A. Compound
B is
ALCOHOLS, ETHERS AND PHENOLS E M RAO

(A)
O
O

(B) O
O
(C) OH
OH
(D) OH


51.

2 eq. of CH
3
COOH
O

Number of isomers (including stereoisomers) formed in the above reaction is
(A) 2 (B) 3 (C) 4 (D) 6

52.

O
A
A
KOH
A
B
1. O
3
Zn/H
+
C +D
*
(C* =C
14
)


C and D are
OH
CHO
+CH
3
CHO
*

OH
CHO
+CH
3
CHO
*

OH
CH
2
CHO
+HCHO
*

OH
CH
2
CHO
+HCHO
*

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

53. What is the major product of the following reaction?

OH
H
+
A






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

54. What is the major product of the following reaction?
OH
OH
H
+

ALCOHOLS, ETHERS AND PHENOLS E M RAO

O



O

O

O

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

55. Select the most appropriate sequence of reagents for the following conversion.
O
O

I. CH3MgBr; H
+
II. Cold dil. KMnO4 III. H
+
/A
(A) I, III, II (B) II, I, III (C) I, III, II, III (D) I, II, III

SECTION-II (Multi-correct)
56. Which of the following is/are soluble in aqueous NaHCO3?
(A) Phenol (B) Paranitrophenol
(C) 2,4-Dinitrophenol (D) 2,4,6-Trinitrophenol

57. An optically inactive mixture contains equal moles of A and B. There is another compound C which is isomeric with A and B.
All the three compounds have the molecular formula C4H10O2. All the three compounds give acetaldehyde when treated with
HIO4. Which of the conclusions can definitely be made from the above information?
(A) A and B are enantiomers (B) A and C are diastereomers
(C) A, B and C give same product with H
+
(D) C is optically inactive

58. (R)-2-butanol (R)-2-methoxybutane
The above conversion can be brought about by
(A) i. TsCl ii. CH3ONa (B) i. Na ii. CH3I
(C) CH2N2 (D) i. Na ii. (CH3)2SO4

59. Which of the following compounds give(s) phenol on heating strongly with NaOH?
A) Benzoic acid B) chloro benzene
C) sodium benzene sulfonate D) toluene

60. In which of the following reaction(s), given products are obtained as major products ?


61. Reaction of excess CH3MgBr with diethyl carbonate followed by hydrolysis yields
(A) isopropyl alcohol (B) tert.butyl alcohol (C) n-propyl alcohol (D) ethyl alcohol

62.




The above conversion can be brought about by
A) i. Cl2/H2O; ii. AgNO3 , iii. Red P/HI B) i. cold KMnO4 ii. H
+
/ A, iii. Zn-Hg/HCl
C) i. RCO3H ii. CH3MgX iii. PCC D) None

63. Which of the following combinations of reagents will yield a chiral product after hydrolysis in aqueous acid?


(A)
H
O
+CH
3
MgBr


(C)
CH
3
CH
2
COCH
3
O
+2 CH
3
MgBr

ALCOHOLS, ETHERS AND PHENOLS E M RAO


(C)
O
+CH
3
MgBr


(D)

CH3CHO +C2H5MgBr

64.


Select the correct option(s)
C(CH
3
)
2 HO
OH
X is


OH
CH
2
OH
X is


O
Y is




O
CH
3
CCH
3
Z is

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




65.


Select the correct sequence(s) of reagents for the above conversion?
(A) H3O
+
(B) I.B2H6;THF II.H2O2;NaOH
(C) I.Hg(OAc)2;H2O II. NaBH4 (D) I. PhCO3H II.LiAlH4 III. H3O
+


66. In which of the following reactions, an aldehyde is obtained as a major product?

(A) CH
3
CH
2
CH
2
-O-OH (B) CH
3
-O-CH=CH
2
(C) CH
3
CH
2
CHCl
2 (D)
OH
CHCl
3
KOH
H
+
H
+
NaOH


67.

Select the correct statement(s) regarding A, B, C and D.
(A) A and B are enantiomers (B) C and D are enantiomers
(C) A and B are diastereomers (D) C and D are diastereomers

68. Which of the following give(s) an aldehyde as a major product with CHCl3/KOH?
(A) Phenol (B) Aniline (C) Pyrrole (D) Benzene




(CH
3
)
3
CCH=CH
2
(CH
3
)
3
CCHCH
3
OH
O
Mixture of A and B
Mixture of C and D
1.CH
3
MgBr/
dry ether
2.H
3
O
+
H
3
O
+
A
COCH
3
O O
1. ex.CH
3
MgBr
X +(CH
3
)
3
COH
2. H
3
O
+
X
Y +Z (C
3
H
6
O) +HIO
3
H
3
CCO
HIO
4
ALCOHOLS, ETHERS AND PHENOLS E M RAO

69.

A (C
14
H
12
O)
Optically active
B (C
14
H
14
O
2
)
Optically inactive
HIO
4
only benzaldehyde
H
3
O
+

Select the correct statement(s).
(A) A is trans-2,3-diphenylepoxyethane (B) B is meso-1,2-diphenylethane-1,2-diol
(C) A is cis-2,3-diphenylepoxyethane (D) B is racemic-1,2-diphenylethane-1,2-diol

70. Select the product(s) formed in the following reaction.

OH
1. NaOH
2.CH
3
I

OCH
3

OH

OH

OH

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

SECTION-III (Passages)
Passage :1 (Q.NO: 71-73)
+
3 4
7 14 2 4 2 2 4
4
7 14 2
1.O 2.Zn/H KMnO
A C 3-hexanol
A(C H )decolorisesBr /CCl andreactswithHg(OAc) /H O;NaBH toformB,whichisresolvable
KMnO
HBO
D(isomerof A&G) E(chiral) F,C H O (chiral carboxylicacid)
G(i


+
3 4
1.O 2.Zn/H KMnO /
somerof A&D) H 2-methyl-3-pentanol

71. A is
(A) 1-heptene (B) 2-ethyl-1-pentene (C) 3-methyl-2-hexene (D) 3-heptene

72. D is
(A) 3-methyl-3-hexene (B) 3-methyl-1-hexene
(C) 3-methyl-2-hexene (D) 4-methyl-2-hexene

73. When G is treated with Hg(oAc)2/H2O; NaBH4
(A) a chiral alcohol is produced
(B) a primary alcohol is produced as a major product.
(C) an achiral alcohol is produced
(D) None

Passage:2 (Q.No 74-75) : Phenacetin(PHT) and Acetyl salicylic acid (ASS) are well-known analgesics (pain relievers). See the
following reaction sequences.














74. Select the correct statement.
(A) ASS is more soluble in H2O at P
H
2 than at P
H
9
(B) A further ArSE in ASS occurs at ortho to COOH.
(C) The conjugate base of ASS is less water soluble than the acid.
ONa
0
+
2
9 8 4
CO /100C
H
A B ASS(C H O )
(CH
3
CO)
2
O
H
3
PO
4
NO
2
0
3 2 4 2 2
SO/H SO SnCl /HCl Ac O
NaOH/300C
C D E F
10 13 2
EtBr
F PHT(C H NO )
ALCOHOLS, ETHERS AND PHENOLS E M RAO

(D) ASS is more acidic than benzoic acid.

75. Select the correct statement regarding PHT and ASS.
. (A) At P
H
9 PHT is more polar than ASS
(B) Both can be deprotonated by NaHCO3.
(C) The ring in PHT is more electron rich than in ASS.
(D) PHT is chiral.

Passage:3 (Q.No: 76-78)


76. M contains
(A) Enantiomers (B) Diastereomers
(C) Positional isomers (D) Functional isomers

77. O contains
(A) Enantiomers (B) Diastereomers
(C) Positional isomers (D) Functional isomers

78. Select the incorrect statement.
(A) S is optically inactive as a result of internal compensation
(B) S has two chiral centers
(C) R has two chiral centers
(D) S is optically inactive as a result of external compensation

Passage:4 (Q.No 79-81)






















79. Select the correct statement about E.
(A) It is a racemic mixture. (B) It gives turbidity with Lucas reagent in 5-10 minutes
(C) It is a pure compound and optically inactive. (D) It gives red color with FeCl3.

80. Select the correct statement about B.
(A) It is a racemic mixture. (B) It gives turbidity with Lucas reagent in 5-10 minutes
(C) It is a pure compound and optically inactive. (D) It liberates H2 with Na.
A (C
8
H
16
)
E
n-octane
1. OsO
4
2. NaHSO
3
D
(isomer of C
and non-resolvable)
m-CPBA
B (C
8
H
16
O)
1. LiAlH
4
2. H
2
O
C (C
8
H
18
O
2
)
H
3
O
+
C can be resolved.
1. B
2
H
6
;THF
2. H
2
O
2
,OH
-
E
H
2
/Ni
3 2 2 2
3
3 2
3
2 13 28 13 28
(R)-1-bromo-2,4-dimethylpentane+Mg L
L+(CH ) CHCH CHO,thenH O M,amixture
M+CrO N
N+CH MgBr,thenH O O,amixrure
O+POCl /py P(amixture)+Q(amixture)
PorQ+H /Ni R(C H ) + S(C H )
opt.active opt.ina

ctive
ALCOHOLS, ETHERS AND PHENOLS E M RAO


81. Select the correct statement.
A) D is a racemic mixture. B) A is 4-octene
C) A is 3-octene D) E is 5-octanol


SECTION-IV (Matching)
82.
COLUMN-I COLUMN-II (Distinguishing reagents)
(A) OH
NO
2
NO
2
O
2
N
OH
&

(P) Na
(B) OH
C
2
H
5
OH
&

(Q) NaHCO3
(C) C2H5OH & CH3OCH3 (R) FeCl3
(D) CH2=CHCH2OH & CH3CH2CH2OH (S) MnO2
(T) Br/H2O

83. Match column-I (containing pairs of compounds) with column-II (containing distinguishing reagents)
COLUMN-I COLUMN-II
(A) CH3CH=CH2 and (CH3)3COH
(P)
| |
3 2
Ag(NH )
+

(B) CH3CH=CH2 and CH3CHOHCH3 (Q) Br2/H2O
(C) CH3CH=CH2 and CH3C CH (R) KMnO4
(D) CH3CH2CH2OH and CH3OCH3 (S) Na

84.
COLUMN-I COLUMN-II (Products with HIO4)
(A)
HO
OH
O
OH
(P) CH3CH2COOH and OHCCH2CHO
(B)
HO
OH
O
O
(Q) HCOOH, CO2 and OHCCH2CHO
(C)
O
O
OH

(R) 2 HCOOH and OHCCH2CHO
(D)
HO
OH
OH
OH
(S) CO2, HCOOH, and OHCCH2COOH









ALCOHOLS, ETHERS AND PHENOLS E M RAO

85.
COLUMN-I COLUMN-II
(A)
H
3
O
+

(P)
OH

(B)
1.Hg(OAc)
2
/H
2
O
2. NaBH
4

(Q) OH

(C)
*
1.B
2
H
6
/THF
2. H
2
O
2
;NaOH

(R) OCH
3

(D)
1.Hg(OAc)
2
/CH
3
OH
2. NaBH
4

(S)
OH












ANSWERS
1.B 2.D 3.D 4.D 5.D 6.C 7.A 8.C 9.B 10.A
11.B 12.C 13.A 14.B 15.B 16.D 17.B 18.B 19.A 20.D
21.B 22.A 23.A 24.D 25.B 26.B 27.B 28.B 29.A 30.B
31.B 32.B 33.D 34.A 35.C 36.C 37.B 38.B 39.B 40.C
41.B 42.A 43.A 44.A 45.C 46.B 47.A 48.B 49.B 50.C
51.C 52.A 53.B 54.A 55.C 56.CD 57.ABCD 58.BCD 59.BC 60.AC
61.BD 62.AB 63.AD 64.ACD 65.CD 66.ABCD 67.BC 68.A 69.AB 70.AB
71.B 72.B 73.A 74.D 75.C 76.B 77.B 78.D 79.A 80.C
81.B
82. A-QT B-RT C-P D-ST
83. A-QRS B-QS C-PS D-RS
84. A-Q B-S C-P D-R
85. A-P B-Q C-S D-R