1. General formula of primary alcohol is [CPMT 1975]

(a) CHOH (b) OHC − (c) OHCH2 (d)

OH

C

OH

=

2. Butane –2–ol is [CPMT 1977, 89]

(a) Primary alcohol (b) Secondary alcohol (c) Tertiary alcohol (d) Aldehyde

3. The characteristic grouping of secondary alcohols is [ Delhi PMT 1984]

(a) OHCH 2− (b) CHOH (c) OHC−|

| (d)

OH

C

OH

4. Which of the following is tertiary alcohol [Delhi PMT 2000]

(a)

OHCH

OHCH

OHCH

−

−

−

2

|

|

2

(b) OH

CH

CH

CH

CCH −−3

3

2

|

|

3

|

(c) OHCH

CH

CH

CCH −−− 2

3

3

|

|

3 (d) OHCHCH −− 23

5. Which is primary alcohol [CPMT 1980]

(a) Butane–2–ol (b) Butane–1–ol (c) Propane–2–ol (d) Isopropyl alcohol

6. Cyclohexanol is a

(a) Primary alcohol (b) Secondary alcohol (c) Tertiary alcohol (d) Phenol

7. 1,2,3-trihydroxybenzene is also known as

(a) Pyrogallol (b) Phloroglucinol (c) Resorcinol (d) Quinol

8. Glycerine has [MP PMT/PET 1988; MP PMT 1989, 91; AIIMS 1997]

(a) One primary and two secondary – OH groups (b) One secondary and two primary – OH groups

(c) Three primary – OH groups (d) Three secondary – OH

groups

9. Ortho-dihydroxy benzene is

(a) Carvacrol (b) Resorcinol (c) Catechol (d) Orcinol

10. The compound OHCHHOCH 22 − is

(a) Ethane glycol (b) Ethylene glycol (c) Ethylidene alcohol (d) Dimethyl alcohol

11. 3-pentanol is a [Raj. PET 2002]

(a) Primary alcohol (b) Secondary alcohol (c) Tertiary alcohol (d) None of these

12. Cresol has [CPMT 2003]

(a) Alcoholic –OH (b) Phenolic – OH (c) – COOH (d) – CHO

13. Glycerol is a [Delhi PMT 1984, 2000; MP PET 2001]

(a) Primary alcohol (b) Monohydric alcohol (c) Secondary alcohol (d) Trihydric alcohol

14. Carbinol is [Raj. PMT 2000]

(a) OHHC 52 (b) OHCH 3 (c) CHOHCH 23)( (d) 323 )( CHOHCHCHCH

15. Which of the following are isomers

(a) Methyl alcohol and dimethyl ether (b) Ethyl alcohol and dimethyl ether

BBaassiicc LLeevveell

General Introduction of hydroxy compounds

(c) Acetone and acetaldehyde (d) Propionic acid and propanone

16. 733 HCOCH −− and 5252 HCOHC −− exhibit which type of isomerism [MP PMT 1989]

(a) Metamerism (b) Position (c) Chain (d) Functional

17. Dimethyl ether and ethyl alcohol are

[CPMT 1986; Manipal MEE 1995]

(a) Branched isomer (b) Position isomer (c) Functional isomer (d) Tautomer

18. Which of the following shows optical isomerism [MP PET 1989]

(a) COOHCHCHCH 223 (b) COOHOHCHCH )(3 (c) CHCOOHCHCH =3 (d) None

19. Isomeric forms of propyl alcohols are

(a) 1 (b) 2 (c) 3 (d) 4

20. The isomerism shown by acetic acid and methyl formate is called

(a) Functional isomerism (b) Chain isomerism (c) Geometric isomerism (d) Metamerism

21. Molecular formula of amyl alcohol is

(a) OHC 147 (b) OHC 136 (c) OHC 125 (d) OHC 105

22. The structural formula of cyclohexanol is [Bihar CEE 1995]

(a) (b) (c) (d)

23. How many isomers of OHHC 115 will be primary alcohols

(a) Four (b) Five (c) Three (d) Two

24. If two –OH groups are attached to 1,4 carbon atoms, it is

(a) α-glycol (b) β-glycol (c) γ-glycol (d) ∆-glycol 25. Total number of isomeric alcohols with formula OHC 104 is

(a) 2 (b) 1 (c) 3 (d) 4

26. Picric acid is a yellow coloured compound, its chemical name is [CPMT 1981, 92]

(a) m-nitrobenzoic acid (b) 2, 4, 6-trinitrophenol (c) Trinitrotoluene (d) Trinitroaniline

27. Which does not have a carboxyl group [MLNR 1984]

(a) Picric acid (b) Ethanoic acid (c) Aspirin (d) Benzoic acid

28. Phenol is also called [MP PMT 1993, 2004]

(a) Salicylic acid (b) Benzyl alcohol (c) Carbolic acid (d) Salol

29. Ethanol is prepared industrially by [MP PMT 1989]

(a) Hydration of ethylene (b) Fermentation of sugars (c) Both of these (d) None of these

30. The process of manufacture of absolute alcohol from rectified spirit is [CPMT

1986, 87; Kurukshetra CEE 2002]

(a) Fractional distillation (b) Steam distillation (c) Azeotropic distillation (d) Vacuum distillation

31. Which of the following is boiled with ethyl chloride to form ethyl alcohol

(a) Alcoholic KOH (b) Aqueous KOH (c) OH 2 (d) 22OH

32. Which of the following reagents convert the propene to 1-propanol

(a) 422 , SOHOH (b) Aqueous KOH (c) OHNaBHMgSO 244 /, (d) −OHOHHB ., 2262

33. Acetic acid and OHCH 3 are obtained on large scale by destructive distillation of

(a) Wood (b) Coal (c) Turpentine (d) Crude oil

CH2

CH2

CH2

H2C

H2C

CHOH

CH2

CH2

CH2

H2C

H2C

CHOH

CH2OH

BBaassiicc LLeevveell

Preparation of Hydroxy compounds

34. In fermentation by zymase, alcohol and 2CO are obtained from [BVP 2003]

(a) Invert sugar (b) Glucose (c) Fructose (d) All

35. Which enzyme converts glucose and fructose both into ethanol [MP PMT 1989, 90, 96; CPMT 1983, 84, 86, 94;

KCET 1989; MNR 1978; MP PET 1994, 99]

(a) Diastase (b) Invertase (c) Zymase (d) Maltase

36. Fermentation is an [CPMT 1977; Raj. PMT 1999]

(a) Endothermic reaction (b) Exothermic reaction (c) Reversible reaction (d) None of these

37. Fermentation of starch solution to ethyl alcohol does not require

(a) Invertase (b) Diastase (c) Zymase (d) Maltase

38. Ethyl alcohol is industrially prepared from ethylene by [CPMT 1985]

(a) Permanganate oxidation (b) Catalytic reduction

(c) Absorbing in 42SOH followed by hydrolysis (d) Fermentation

39. Oil + → ∆)(aqNaOH Glycerol + Soap

Above reaction is called [UPSEAT 2001]

(a) Saponification (b) Esterification (c) Hydrogenation (d) None of these

40. Conversion of glucose into ethyl alcohol is made by [MP PMT 1995]

(a) Acid (b) Enzyme (c) Hydroxylamine (d) Phenyl hydrazine

41. Which reagent can convert acetic acid into ethanol [BVP 2003]

(a) Na + alcohol (b) LiAlH4 + ether (c) H2 + Pt (d) HClSn+

42. Glucose → ethyl alcohol in this reaction enzyme is [Raj. PMT 2002; BHU 2002]

(a) Zymase (b) Invertase (c) Maltase (d) Diastase

43. The fermentation of starch to give alcohol occurs mainly with the help of

(a) 2O (b) Air (c) 2CO (d) Enzymes

44. Methyl alcohol is industrially prepared by the action of [KCET (Med.) 2000]

(a) 2HCO + (b) OHHC 52 (c) 33COCHCH (d) COOHCH 3

45. Alcoholic fermentation is brought about by the action of [CPMT 1977, 79, 88; DPMT 1983]

(a) 2CO (b) 2O (c) Invertase (d) Yeast

46. Benzyl alcohol is obtained from benzaldehyde by [CPMT 1983; MLNR 1993]

(a) Fittig's reaction (b) Cannizaro's reaction (c) Kolbe's reaction (d) Wurtz's reaction

47. Primary alcohols can be obtained from the reaction of the RMgX with

(a) 2CO (b) HCHO (c) CHOCH 3 (d) OH 2

48. RMgBr on reaction with an excess of oxygen followed by hydrolysis gives [Roorkee Qualifying 1998]

(a) RH (b) RCOOR (c) RCOOH (d) ROH

49. When MgICH 3 reacts with acetone, an addition compound is formed which on hydrolysis gives

(a) A primary alcohol (b) A secondary alcohol (c) A tertiary alcohol (d) An aldehyde

50. The reaction between an ester and excess of Grignard reagent shall finally result in a [UPSEAT 2000]

(a) Primary alcohol (b) Secondary alcohol (c) Tertiary alcohol (d) Ketone

51. Action of nitrous acid with ethylamine produces [BHU 2000]

(a) Ethane (b) Ammonia (c) Ethyl alcohol (d) Nitroethane

52. Which one of the following will produce a primary alcohol by reacting with MgICH 3 [MP PET 1991]

(a) Acetone (b) Methyl cyanide (c) Ethylene oxide (d) Ethyl acetate

53. Ethylene reacts with Baeyer's reagent to give [CPMT 1988]

(a) Ethane (b) Ethyl alcohol (c) Ethylene glycol (d) None of these

54. If formaldehyde and potassium hydroxide are heated, then we get

(a) Acetylene (b) Methane (c) Methyl alcohol (d) Ethyl formate

55. Which gas is eliminated in fermentation [Raj. PMT 1997]

(a) 2O (b) 2CO (c) 2N (d) 2H

56. Acetone on treatment with IMgCH −−3 and on further hydrolysis gives [UPSEAT 2000]

(a) Isopropyl alcohol (b) Primary alcohol (c) Acetic acid (d) 2-methyl 1,-2-propanol

57. The Bouveault-Blanc reduction involves [MP PET 1991]

(a) NaOHHC /52 (b) 4LiAlH (c) −MgXHC 52 (d) HClZn /

58. Alkenes convert into alcohols by

(a) Hydrolysis by dil. 42SOH (b) Hydration of alkene by alkaline 4KMnO

(c) Hydrolysis by water vapours and conc. 42SOH (d) Hydration of alkene by aqueous KOH

59. Coconut oil upon alkaline hydrolysis gives [MP PET 1991; AFMC 2000; KCET 2001]

(a) Glycol (b) Alcohol (c) Glycerol (d) Ethylene oxide

60. Which one is not synthesized by Grignard reagent [MP PET 1991]

(a) Primary alcohol (b) Secondary alcohol (c) A ketone (d) An ester

61. Methanol is manufactured by passing (under pressure) a mixture of water gas and excess hydrogen over heated

(a) Platinized asbestos (b) Cobalt chloride (c) Zn and Cr oxides (d) Finely divided metal

62. The conversion OHCHCHCHCHOCHCH 222 =→−= can be effected by

(a) +Na alcohol (b) Zn + HCl (c) NiH /2 (d) 4LiAlH

63. The conversion OHCHCHCHCHOCHCH 22323 → can be effected by

(a) 4NaBH (b) HClZn / (c) NiH /2 (d) Na + alcohol

64. Which of the following reactions are used in the preparation of alcohol

(a) →+ KOHaqBrHC .52 (b) →= 423)( LiAlHOCCH

(c) →−− OHEtNaOCH

O

CCH /||33 (d) → OHClCHCH 2

23

65. In the commercial manufacture of ethyl alcohol from starchy substances by fermentation method, which enzymes stepwise

complete the fermentation reaction

(a) Diastase, maltase and zymase (b) Maltase, zymase and invertase

(c) Diastase, zymase and lactase (d) Diastase, invertase and zymase

66. Absolute alcohol can be obtained from rectified spirit [KCET 1985]

(a) By removing the water in it using concentrated sulphuric acid (b) By removing the water

using phosphorus pentaoxide

(c) By distilling with the appropriate amount of benzene (d) By distilling over plenty of quick lime

67. Absolute alcohol cannot be prepared by fractional distillation of rectified spirit since

(a) It forms azeotropic mixture (b) It is used as power alcohol (c) It is used in wines (d)

68. Commercially methanol is prepared by [IIT 1984; MP PMT 1990; KCET 1992]

(a) Reduction of CO in presence of 32.2 OCrZnO

(b) Methane reacts with water vapours at 900oC in presence of Ni catalyst

(c) Reduction of HCHO by 4LiAlH

(d) Reduction of HCHO by aqueous NaOH

69. The reaction, water gas 22)( HHCO ++ 673 K, 300 atmosphere in presence of the catalyst ZnOOCr /32 is used for the

manufacture of [MP PMT 1989]

(a) HCHO (b) HCOOH (c) OHCH 3 (d) COOHCH 3

70. Propan-1-ol can be prepared from propene by action of [AIIMS 2003]

(a) 422 / SOHOH (b) OHOAcHg 22 /)( followed by 4NaBH

(c) 62HB followed by 22OH (d) 4223 / SOHHCOCH

71. Which of the following reaction shows industrial method of preparation of OHCH 3 [CPMT 1996; MP PET 1989]

(a) C

Catalyst

oHCO

3002 →+ (b) OHOHCH 23 +

(c) 223 HNONHCH + (d) KOHaqBrCH .3 +

72. Formaldehyde gives an additive product with methyl magnesium iodide which on aqueous hydrolysis gives[MP PMT / PET 1988]

(a) Isopropyl alcohol (b) Ethyl alcohol (c) Methyl alcohol (d) Propyl alcohol

73. The reaction of CHCHCH =3 OH with HBr gives [IIT 1998]

(a) 23CHBrCHCH OH (b) CHBrCHCH 23 OH

(c) 23CHBrCHCH Br (d) CHBrCHCH 23 Br

74. From which of the following tertiary butyl alcohol is obtained by the action of methyl magnesium iodide

(a) HCHO (b) CHOCH 3 (c) 33COCHCH (d) 2CO

75. 22

6222OH

NaOHHBCHCH →+= Product.

Product in above reaction is [Raj. PMT 2003]

(a) CHOCHCH 23 (b) OHCHCH 23 (c) CHOCH 3 (d) None of the above

76. In the reaction ACH

O

CHMgBrHC OH →−+ 22252

A is [MP PET 1994, 2003; CBSE 1998]

(a) CHOCHHC 252 (b) OHCHCHHC 2252 (c) OHCHHC 252 (d) CHOHC 52

77. The product of reduction of benzaldehyde is

(a) Benzoic acid (b) Benzyl alcohol (c) Benzene (d) Catechol

78. The factor adversely affecting the fermentation process is

(a) Presence of air (b) Low concentration of sugar

(c) High concentration of sugar (d) Presence of an enzyme

79. Pyroligneous acid obtained during destructive distillation of wood contains

(a) Acetone and methyl alcohol (b) Methyl alcohol and ethyl

alcohol

(c) Acetone and acetic acid (d) Methyl alcohol, acetone and acetic acid

80. Action of water in the presence of sulphuric acid with the following alkenes

(i)

3

3

3

CH

CCHCH

CH

=− and (ii) 23 CHCHCH =− gives

AAddvvaannccee LLeevveell

(a) (i)

3

23

3

| CHOH

CCHCH

CH

−− and (ii) 33|

CH

OH

CHCH −−

(b) (i)

3

3

3

| CHCH

OH

CHCH

CH

−− and (ii) OHCHCHCH 223 −−

(c) (i)

3

3

3

| CHCH

OH

CHCH

CH

−− and (ii) 33|

CH

OH

CHCH −−

(d) (i)

3

23

3

| CHOH

CCHCH

CH

−− and (ii) OHCHCHCH 223 −−

81. Which one of the following reactions would produce secondary alcohol

(a)

+ →

H

MgBrCHCCHHC

O

.2

.1356

3

.|| (b)

+ →

H

LiAlHCCHHC

O

.2

.1356

4

.|| (c)

+ →

H

LiAlHCHOCH.2

.13

4 (d)

2.2

.1356

.||

Br

OHCCHHC

O

→+

82. Propene, 23 CHCHCH =− can be converted to 1-propanol by oxidation. Which set of reagents among the following is

ideal to effect the conversion [ CBSE 1991]

(a) Alkaline 4KMnO (b) 62HB and alkaline 22OH

(c) ZnO /3 dust (d) 244 ,/ ClCHOsO

83. Chlorination of toluene in the presence of light and heat followed by treatment with aqueous NaOH gives

(a) o-cresol (b) p-cresol (c) 2, 4-dihydroxy toluene (d) Benzyl alcohol

84. The compound that will react most readily with NaOH to form methanol is [IIT Screening 2001]

(a) −+ INCH 43 )( (b) 33OCHCH (c) −+ ISCH 33 )( (d) ClCH 33 )(

85. Which is hydrolysed at the fastest rate

(a) (b) (c) (d)

86. HBO, oxymercuration-demercuration and acid catalysed hydration will give same product in

(a) (b) (c) (d)

87. ,2 ASeO → A is

(a) (b) (c) (d)

88. → A A is

Cl Cl Cl

Cl

OH OH OH

OH

COOH

O

O

CH2OH

O

O

(a) OHHB 262 / (b) 4LiAlH (c) NaOHCH /3 (d) HIP /

89. →=+OHCHCH

CHCH

CHCHCH 33

32

3

|

Major product of this reaction

(a) Is optical isomer (b) Gives white turbidity with HBr immediatly

(c) Is dehydrated easily (d) All correct

90. Consider the following methods

I : Hydration of olefins II : Hydrolysis of cyanides

III : Reduction of carbonyl compounds

Which of these can be used to prepare alcohols

(a) I, II and III (b) I and II (c) II and III (d) I and III

91. Rate of hydration of

,2CHCH = ,3CHCHCH = ,|

2

3

CH

CH

C =

(I) (II) (III)

will be in order

(a) I<II<III (b) I<III<II (c) II<I<III (d) III<II<I

92. +

→OH

excessMgBrCH

3

3 )( X, X is

(a) CH

OHCH

3

3 (b)

CH

OHCH

3

3

(c) (d)

93. →=+OH

CHCHCH 33 A (major)

(a) 32|

CH

OH

CHCH (b) 32|

CHCH

OH

CH

(c) 3||

CH

OH

CH

OH

CH (d) OHCHCHCH 222

94. .)(

)(3

3252 A

OH

excessMgBrCHCOOHC

+ → A (alcohol) can also be obtained by

(a) +

→OH

molMgBrCHCHOCHCH

3

323

)2( (b)

+ →

OH

molMgBrCHHOC

O

CCH3

3523

)2(||

(c) +

→OH

molMgBrCHCH

O

CCH3

333

)1(|| (d) As in (b) and (c)

95. Ester

)()2(

)( 1043

3284

Balcohol

OHCOH

parts

MgBrCHOHCA →++

Alcohol B reacts fastest with Lucas reagent. Hence A and B are

O O

OH OH

O O OH

CH3

(a) COHCHHOC

O

CCH 33523 )(,||

(b) CHOHCHHOC

O

CH 2373 )(,||

(c) CHOHCHHOC

O

CCH 23523 )(,||

(d) COHCHHOC

O

CH 3373 )(,||

96. Which one of the following compounds is most rapidly hydrolysed by SN 1 mechanism

(a) CHClCHCH =3 (b) ClCHCHCH 22 = (c) ClCH 2 (d) CClHC 356 )(

97.

O

XOHCH

ONaCHCHCCH

CH

,3

323

3

→− X is

(a) |

|

323

3

OH

OCHCCHCH

CH

(b) |

|

3

23

3

OCH

OHCCHCH

CH

(c) ||

33

3

CHOCH

CHOHCHCH − (d) None is correct

98. → A

Reagent A used in this change is

(a) 62HB (b) 4LiAlH (c) HClSn / (d) NaOHCH /3

99.

O

AH

OHCHCCH

CH

,18

223

3

+ →− A(with position of

18 O) is

(a) ||

|

18

23

3

OHOH

CHCCH

CH

− (b) ||

|

18

23

3

OHOH

CHCCH

CH

− (c)

18

23

2

O

CHCCH

OHCH

− (d) No reaction

100. ← Y → X

Select X and Y out of I : −− OHMnO /4 II : HHCO3

(a) I, II (b) II, I (c) II, II (d) I, I

101. H2C = = CH2 will form terminal doil by

(a) Oxymercuration-demercuration (b) Hydroboration oxidation

(c) Acid-catalysed hydration (d) All given above

102. Sodium benzene sulphonate reacts with NaOH and then on acidic hydrolysis, it gives [Roorkee 1995; KCET 1998; MHCET 2001]

(a) Phenol (b) Benzoic acid (c) Benzene (d) Disodium benzaldehyde

103. Which of the following does not form phenol or phenoxide [AFMC 2000]

(a) ClHC 56 (b) COOHHC 56 (c) ClNHC 256 (d) NaSOHC 356

104. Benzene diazonium chloride on hydrolysis gives [CPMT 1989]

(a) Benzene (b) Benzylalcohol (c) Phenol (d) Chlorobenzene

105. Which of the following represents Raschig’s method for the preparation of phenol

O

O

O

OH OH OH

HO OH HO OH

(a) (b)

(c) (d) None of these

106. Phenetole reacts with HI to produce

(a) OHCHCHIHC 2356 + (b) OHHCICHCH 5623 + (c) ICHCHOHCHHC 23256 + (d) OHHCICHCH 5623 +

107. The compound with the highest boiling point is [MLNR 1985]

(a) 4CH (b) OHCH 3 (c) ClCH 3 (d) BrCH 3

108. The boiling point of ethyl alcohol should be less than that of [Punjab CET 1985]

(a) Propane (b) Formic acid (c) Dimethyl ether (d) None of these

109. Boiling point of alcohol is comparatively higher than that corresponding alkane due to [MH CET 2002]

(a) Intermolecular hydrogen bonding (b) Intramolecular hydrogen bonding

(c) Volatile nature (d) None of these

110. Methanol and ethanol are miscible in water due to [MP PET/PMT 1988; CPMT 1989; CBSE 1991]

(a) Covalent character (b) Hydrogen bonding character (c) Oxygen bonding character (d)

111. If ethanol dissolves in water, then which of the following would be done

(a) Absorption of heat and contraction in volume (b) Emission of heat and contraction in volume

(c) Absorption of heat and increase in volume (d) Emission of heat and increase in volume

112. Ethylene glycol is a (at 25oC)

(a) Solid compound (b) Liquid (c) Gas (d) Brown solid

113. Low molecular weight alcohols are [CPMT 1976, 89; Pb. PMT 2000]

(a) Soluble in water (b) Soluble on heating (c) Insoluble in water (d) Insoluble in all solvents

114. Liquor poisoning is due to [CPMT 1971]

(a) Presence of bad compound in liquor (b) Presence of methyl alcohol

(c) Presence of ethyl alcohol (d) Presence of carbonic acid

115. Picric acid is (at 25oC)

(a) A white solid (b) A colourless liquid (c) A gas (d) A bright yellow solid

116. Widespread deaths due to liquor poisoning occurs due to [Delhi PMT 2001]

(a) Presence of carbonic acid in liquor (b) Presence of ethyl alcohol in liquor

(c) Presence of methyl alcohol in liquor (d) Presence of lead compounds in liquor

117. Absolute ethanol cannot be obtained by simple fraction of a solution of ethanol and water because [KCET 1984; MP PMT

1987]

(a) Their B.P.'s are very nearer (b) Ethanol remains dissolved

in water

(c) They form a constant boiling mixture (d) Ethanol molecules are solvated

118. The correct order of the solubility of the different alcohols in water is

(a) n-propyl alcohol > ethyl alcohol > n-butyl alcohol (b) Ethyl alcohol > n-butyl alcohol > n-propyl alcohol

(c) n-butyl alcohol > n-propyl alcohol > ethyl alcohol (d) Ethanol > n-propanol > n-butyl alcohol

119. Methyl alcohol is toxic. The reason assigned is [Raj. PET 2000]

(a) It stops respiratory track (b) It reacts with nitrogen and forms CN– in the lungs

(c) It increases 2CO content in the blood (d) It is a reduction product of formaldehyde

BBaassiicc LLeevveell

Physical Properties of Hydroxy compounds

Cl

+ NaOH salt

200,623

Cu

atmK → CH – CH3 |

CH3 + →H

O

(ii)

(i) 2

K

SiOOHCl X800

)air( 22 → → ++

120. Which of the following is not characteristic of alcohols [AIIMS 1980; AFMC 1997]

(a) They are lighter than water

(b) Their boiling points rise fairly uniformly with increasing molecular weight

(c) Lower members are insoluble in water and organic solvents but solubility regularly increases with molecular weight

(d) Lower members have pleasant smell and burning taste, while higher members are odourless and tasteless

121. The order of solubility of alkanols in water is

(a) Propanol < Butanol > Pentanol (b) Propanol > Butanol > Pentanol

(c) Propanol > Butanol < Pentanol (d) Propanol = Butanol = Pentanol

122. Power alcohol is [KCET 1990]

(a) An alcohol of 95% purity (b) A mixture of petrol hydrocarbons and ethanol

(c) Rectified spirit (d) A mixture of methanol and ethanol

123. In order to make alcohol undrinkable pyridine and methanol are added to it. The resulting alcohol is called

(a) Power alcohol (b) Proof spirit (c) Denatured spirit (d) Poison alcohol

124. The boiling point of alcohol are ..... than corresponding thiols [Pb. PMT 2000]

(a) More (b) Same (c) Either of these (d) Less

125. Which compound has the highest boiling point [MP PET 2003]

(a) Acetone (b) Diethyl ether (c) Methanol (d) Ethanol

126. Methylated spirit is

(a) Methanol (b) Methanol + ethanol (c) Methanoic acid (d) Methanamide

127. The correct order of boiling point for primary (1o), secondary (2

o) and tertiary (3

o) alcohols is [CPMT 1999; Raj. PMT 2002]

(a) 1o>2

o>3

o (b) 3

o>2

o>1

o (c) 2

o>1

o>3

o (d) 2

o>3

o>1

o

128. The vapour pressure of aqueous solution of methanol is [UPSEAT 2000]

(a) Equal to water (b) Equal to methanal (c) More than water (d) Less than water

129. The boiling point of glycerol is more than propanol because of [CPMT 1997, 2002]

(a) Hydrogen bonding (b) Hybridisation (c) Resonance (d) All the above

130. Which compound is soluble in water

(a) 2CS (b) OHHC 52 (c) 4CCl (d) 3CHCl

131. Which of the following is most soluble in water [MP PMT 1995]

(a) Normal butyl alcohol (b) Isobutyl alcohol (c) Tertiary butyl alcohol (d) Secondary butyl alcohol

132. Which of the following is not characteristic of alcohols [AFMC 1992]

(a) Lower alcohols are stronger and have bitter taste

(b) Higher alcohols are stronger and have bitter taste

(c) The boiling points of alcohols increase with increasing molecular mass

(d) The lower alcohols are soluble in water

133. Which of the following explains the viscous nature of glycerol [JIPMER 1997]

(a) Covalent bonds (b) Hydrogen bonds (c) Vander Wall's forces (d) Ionic forces

134. Glycerol boils at 290oC with slight decomposition. Impure glycerine can be purified by [CPMT 1983, 94]

(a) Steam distillation (b) Simple distillation (c) Vacuum distillation (d) Extraction with a

solvent

135. Maximum solubility of alcohol in water is due to [MP PMT / PET 1988; MP PMT 1989]

(a) Covalent bond (b) Ionic bond (c) H–bond with H2O (d) None of the above

136. In cold countries ethylene glycol is added to water in the radiators to [CPMT 1971;

NCERT 1971; MP PMT 1993]

(a) Bring down the specific heat of water (b) Lower the viscosity

(c) Reduce the viscosity (d) Make water a better lubricant

137. When glycerine is added to a litre of water which of the following behaviour is observed [NCERT 1977; BHU 1979]

(a) Water evaporates more easily (b) The temperature of water is increased

(c) The freezing point of water is lowered (d) The viscocity of water is lowered

138. Which of the following statements are not correct

(a) All alcohols are soluble in water (b) Only the lower alcohols are

soluble in water

(c) All alcohols are poisonous (d) Methanol is not poisonous

139. Which of the following are correct

(a) Ordinary ethyl alcohol is known as rectified spirit

(b) The alcohol sold in the market for polishing, etc., is known as methylated spirit

(c) Absolute alcohol is 100% ethanol

(d) Power alcohol is 100% ethanol

140. Which of the following alcohols is the least soluble in water

(a) Ethyl alcohol (b) OHHC 94 (c) OHHC 115 (d) OHHC 2512

141. Which of the following exhibits maximum hydrogen bonding

(a) Ethyl alcohol (b) Diethyl ether (c) Ethyl chloride (d) Triethylamine

142. Which has larger value of dipole moment

(a) Methanol (b) Phenol (c) Equal (d) No dipole moment

143. Dipole moment of )(),( 23323 IIOHCHCHICHCHCH and )(23 IIIFCHCH is in order

(a) I<II<III (b) I>II>III (c) I<III<II (d) III<I<II

144. Which decomposes below its boiling point

(a) Glycerol (b) Benzene (c) Toluene (d) Chlorobenzene

145. Which is the most stable conformation of butane-2,3-diol

(a) (b) (c) (d)

146. The dimer of alcohol will have the structure

(a) 3|

.....|

|CH

H

OH

H

H

COH −−−− (b) 33|

.....|

CH

H

O

H

OCH −−−

(c) HOCHCHOH −−−− 33........ (d) 33 .....|

CHOH

H

OCH −−−

147. For which of the following parameters the structural isomers OHHC 52 and 33OCHCH would be expected to have the

same values (assume ideal behaviour)

(a) Boiling points (b) Vapour pressure at the same temperature

(c) Heat of vaporization (d) Gaseous densities at the same temperature and

pressure

148. The boiling point of methanol is greater than that of methyl thiol because

(a) There is intramolecular hydrogen bonding in methanol and intermolecular hydrogen bonding in methyl thiol

(b) There is inter molecular hydrogen bonding in methanol and no hydrogen bonding in methyl thiol

(c) There is no hydrogen bonding in methanol and intermolecular hydrogen bonding in methyl thiol

(d) There is intramolecular hydrogen bonding in methanol and no hydrogen bonding in methyl thiol

(e) There is no hydrogen bonding in methanol and intramolecular hydrogen bonding in thiol

149. Phenol at Co25 is

OH

OH

H

H

CH3

CH3

OH

HO

H

H

H3C

CH3

CH3

OH

OH

H

H H3C

OH

HO

H CH3

CH3

H

(a) A white crystalline solid(b) A transparent liquid (c) A gas (d) Yellow solution

150. Which compound has hydrogen bonding [MP PMT 1992; MP PET 1991]

(a) Toluene (b) Phenol (c) Chlorobenzene (d) Nitrobenzene

151. The order of melting point of ortho, para, meta-nitrophenol is [Orissa JEE 2003]

(a) o > m > p (b) p > m > o (c) m > p > o (d) p > o > m

152. Which of the following has lowest boiling point [MH CET 1999]

(a) p-nitrophenol (b) m-nitrophenol (c) o-nitrophenol (d) Phenol

153. ortho-nitrophenol is steam volatile whereas para-nitrophenol is not. This is due to [CBSE 1989]

(a) Intramolecular hydrogen bonding present in ortho-nitrophenol

(b) Intermolecular hydrogen bonding

(c) Intramolecular hydrogen bonding present in para-nitrophenol

(d) None of these

154. For phenol, which of the following statements is correct [MP PMT 1995]

(a) It is insoluble in water

(b) It has lower melting point compared to aromatic hydrocarbons of comparable molecular weight

(c) It has higher boiling point than toluene

(d) It does not show acidic property

155. Maximum ionisation constant is of

(a) (b) (c) (d)

156. Which has maximum pKa value in phenols

(a) (b) (c) (d)

157. Which of the following compounds will have the highest dipole moment

(a) (b) (c) (d)

158. Order of reactivity of alcohols towards sodium metal is [PU CET 1985]

(a) Pri > Sec > Ter (b) Pri > Sec < Ter (c) Pri < Sec > Ter (d) Pri < Sec < Ter

159. In ,23 OHCHCH which bond dissociates heterolytically [IIT 1988; CPMT 1996]

(a) C – C (b) C – O (c) C – H (d) O – H

160. Which of the following statements is correct regarding case of dehydration [CPMT 1985]

(a) Primary > Secondary (b) Secondary > Tertiary (c) Tertiary > Primary (d) None of these

161. Methanol and ethanol are distinguished by the [MP PET 1999]

(a) Action of HCl (b) Iodoform test (c) Solubility in water (d) Sodium

BBaassiicc LLeevveell

Chemical Properities of Hydroxy compounds

OH OH

OH

OH

CH3

OH

NO2 O2N

NO2

OH

CH3 H3C

OH OH

N

NO2 OH

NO2

OH

NO2 NO2

OH

162. Which of the following can work as a dehydrating agent for alcohols

(a) 42SOH (b) 32OAl (c) 43POH (d) All the these

163. Primary, secondary and tertiary alcohols may be distinguished by employing [CPMT 1980, 84; MP PMT / PET 1988;

Raj. PMT 2000; MP PMT 2001]

(a) Hoffmann's test (b) Fehling solution test (c) Victor Meyer's test (d) None of the above

164. In reaction of alcohols with alkali metal, acid etc. which of the following alcohol will react fastest

(a) Secondary (b) Tertiary (c) Primary (d) All equal

165. Methyl alcohol (methanol), ethyl alcohol (ethanol) and acetone (propanone) were treated with iodine and sodium hydroxide

solution. Which substances will give iodoform test

(a) Only ethyl alcohol (b) Only methyl alcohol and ethyl alcohol

(c) Only ethyl alcohol and acetone (d) Only acetone

166. The – OH group of methyl alcohol cannot be replaced by chlorine by the action of [KCET 1989]

(a) Chlorine (b) Hydrogen chloride (c) Phosphorus trichloride (d) Phosphorus

pentachloride

167. In esterification, the reactivity of alcohols is [Delhi PMT 2000]

(a) 1o > 2

o > 3

o (b) 3

o > 2

o > 1

o (c) Same in all cases (d) None of these

168. Which of the following is acidic [MH CET 2001; CBSE

2001]

(a) OHCH 3 (b) OHHC 56 (c) −CHOHCH 23)( (d) OHCHCH 23

169. The compound which will give negative iodoform test is [CPMT 1993, 99]

(a) CHOCH 3 (b) OHCHCH 23 (c) Isopropyl alcohol (d) Benzyl alcohol

170. Methyl alcohol can be distinguished from ethyl alcohol using [KCET 1984]

(a) Fehling solution (b) Schiffs reagent

(c) Sodium hydroxide and iodine (d) Phthalein fusion test

171. In '';350

22223 XOHCHCHC

XOHCHCHo

+=→ is [MP PAT 1996]

(a) NaCl (b) 2CaCl (c) 52OP (d) 32OAl

172. Lucas test is used for [CBSE 1990; AIIMS 2002]

(a) Alcohols (b) Amines (c) Diethyl ether (d) Glacial acetic acid

173. An alcohol solvates anions due to

(a) Oxygen and its electron pairs (b) Hydrogen bonding

(c) Alkyl group (d) Alkoxide formation

174. Alcohol which gives red colour with Victor Meyer test is [Raj. PMT 2003]

(a) OHHC 52 (b) 33|

CH

OH

CHCH −− (c) OHCHC 33)( (d) None of the above

175. Iodoform test is not given by [CPMT 2003]

(a) 2-pentanone (b) 3-pentanone (c) Ethanol (d) None of these

176. At higher temperature, iodoform reaction is given by [AIIMS 2003]

(a) 323 CHCOCH (b) 5223 HCCOCH (c) 3256 CHCOHC (d) 5623 HCCOCH

177. 4LiAlH converts acetic acid into

[CPMT 1977; MP PMT 1990, 92]

(a) Acetaldehyde (b) Methane (c) Ethyl alcohol (d) Methyl alcohol

178. Which of the following compound dehydrates most easily [MP PMT 1994; BHU 2002]

(a) COHR3 (b) CHOHR2 (c) OHCHCH 23 (d) OHCHCHCH 223

179. Which of the following differentiate between OHHC 52 and OHCH 3

(a) HCl (b) 3NH (c) OH 2 (d) KOHI +2

180. At room temperature the alcohol that do not reacts with Lucas reagent is

(a) Primary alcohol (b) Secondary alcohol (c) Tertiary alcohol (d) All these three

181. Ethyl alcohol exhibits acidic character on reacting with [MP PMT 1995]

(a) Acetic acid (b) Sodium metal

(c) Hydrogen iodide (d) Acidic potassium dichromate

182. The reagent which easily reacts with ethanol and propanol is [MP PET 1989]

(a) Fehling solution (b) Grignard reagent (c) Schiffs reagent (d) Tollen's reagent

183. Iodoform is formed on warming I2 and NaOH with [MP PET 1995; DCE 1999; Raj. PET 1999; Raj. PMT 2002]

(a) OHHC 52 (b) OHCH 3 (c) HCOOH (d) 66HC

184. Which reagent is useful in converting 1-butanol to 1-bromobutane

(a) 3CHBr (b) 2Br (c) BrCH3 (d) 3PBr

185. Which of the following compound will give positive iodoform test [MP PMT 1986,

99; SCRA 1991; CPMT 1994]

(a) OHCH 3 (b)

3

3

CH

OHCCH

H

(c)

3

3

3

CH

OHCCH

CH

(d) OHCHCHCH 223

186. The compound which gives the most stable carbonium ion on dehydration is [MNR 1995; DCE 2000]

(a) OHCH

CH

CHCH 2

3

3|

−− (b)

3

3

3

CH

OHCCH

CH

(c) OHCHCHCHCH 2223 −−− (d) 32

3

3

|CHCH

CH

CHCH −−−

187. OHXRHXOHR 2+−→+−

In the above reaction, the reactivity different alcohols is [CPMT 1997]

(a) Tertiary > Secondary > Primary (b) Tertiary < Secondary <

Primary

(c) Tertiary < Secondary > Primary (d) Secondary < Primary <

Tertiary

188. Which easily reacts fastest with lucas reagent at room temperature [IIT 1981, 86;

MP PMT 1989; CBSE 1989;

CPMT 1989; MP PET 1997; JIPMER 1999; MP PMT 1999, 2000]

(a) Butane-1-ol (b) Butane-2-ol (c) 2-methyl propane-1-ol (d) 2-methyl propane-2-ol

189. When ethyl alcohol and KI reacted in presence of ,32CONa yellow crystals of ......... are formed [AFMC 1989]

(a) 3CHI (b) ICH 3 (c) 22 ICH (d) IHC 52

190. Which of the following is responsible for iodoform reaction [CPMT 1980; Raj. PMT 1997]

(a) Formalin (b) Methanol (c) Acetic acid (d) Ethanol

191. Maltose on hydrolysis gives [BHU 1996; CPMT 2001]

(a) Mannose + glucose (b) Galactose + glucose (c) Glucose (d) Mannose + fructose

192. Which of the following produces violet colour with 3FeCl solution

(a) Enols (b) Ethanol (c) Ethanal (d) Alkyl halides

193. The reaction between an alcohol and an acid with the elimination of water molecule is called [MH CET 1999]

(a) Esterification (b) Saponification (c) Etherification (d) Elimination

194. By means of calcium chloride which of following can be dried

(a) Methanol (b) Ethanol (c) Both (a) and (b) (d) None of these

195. Which compound does not form iodoform with alkali and iodine [IIT 1985]

(a) Acetone (b) Ethanol (c) Diethyl ketone (d) Isopropyl alcohol

196. Which is most acidic [Raj. PET 1999]

(a) OH 2 (b) OHHC 52 (c) 33OCHCH (d) OHHC 56

197. Lucas test is used to distinguish between [MP PET 1994]

(a) 1o, 2

o and 3

o alcohols (b) 1

o, 2

o and 3

o amines (c) Aldehydes and ketones (d) Alkenes and alkynes

198. The conversion of alcohols into chloro-compounds by reaction with 2SOCl follows the order

(a) 1o > 2

o > 3

o (b) 3

o > 2

o > 1

o (c) 2

o > 1

o > 3

o (d) 1

o = 2

o > 3

o

199. When ethanol is passed over red hot copper at 300oC, the product formed is [EAMCET 1987, 93; MP PET

1995]

(a) CHOCH 3 (b) 33COCHCH (c) 42HC (d) COOHCH 3

200. Reduction of acetyl chloride with H2 in presence of Pd gives [MP PMT 2001]

(a) 33COCHCH (b) OHHC 52 (c) COOHCH 3 (d) CHOCH 3

201. Alcohols combine with acetylene in the presence of mercury compounds as catalyst to form

(a) Acetals (b) Xanthates (c) Vinyl ethers (d) None of the above

202. Ethyl alcohol on oxidation with 722 OCrK gives [MLNR 1987; Bihar CEE 1995; UPSEAT 2000]

(a) Acetic acid (b) Acetaldehyde (c) Formaldehyde (d) Formic acid

203. When ethyl alcohol reacts with bromine in presence of red phosphorus the compound formed is

(a) 62HC (b) 3PBr (c) BrCH3 (d) BrHC 52

204. Ethylene may be obtained by dehydration of which of the following with concentrated 42SOH at Co170160 −

[Delhi PMT 2000; MP PET 2001]

(a) OHHC 52 (b) OHCH 3 (c) OHCHCHCH 223 (d) OHCHCHCH 223)(

205. The alcohol which does not give a stable compound on dehydration is

(a) Ethyl alcohol (b) Methyl alcohol (c) n-propyl alcohol (d) n-butyl alcohol

206. In presence of air, fermentation of ethyl alcohol by azotobactor bacteria forms [MP PMT 1989]

(a) 22 CHCH = (b) 62HC (c) CHOCH 3 (d) COOHCH 3

207. The fatty acid, that shows reducing property, is [KCET (Med.) 2000]

(a) Acetic acid (b) Formic acid (c) Oxalic acid (d) Ethanoic acid

208. The alcohol that produces turbidity immediately with HClconcZnCl .2 + at room temperature [EAMCET 1997]

(a) 1-hydroxybutane (b) 2-hydroxybutane

(c) 2-hydroxy-2-methylpropane (d) 1-hydroxy-2-methylpropane

209. In the esterification reaction of alcohols [Bihar CEE 1995]

(a) OH– is replaced by COOCH 3 group (b) OH

– is replaced by chlorine

(c) H+ is replaced by RCO group (d) OH

– is replaced by OHHC 52

210. During dehydration of alcohols to alkenes by heating with conc. 42SOH the initiation step is [AIEEE 2003]

(a) Protonation of alcohol molecule (b) Formation of carbocation

(c) Elimination of water (d) Formation of an ester

211. Which of the following are the starting materials for the Grignard's synthesis of ter-butanol [EAMCET 1989]

(a) 333 COCHCHMgBrCH + (b) 3323 COCHCHMgBrCHCH +

(c) 333 CHOHCHCHMgBrCH + (d) CHCHMgBrCH 333 )(+

212. The reaction of OHHC 52 with 42SOH does not give [MP PET 1996]

(a) Ethylene (b) Diethyl ether (c) Acetylene (d) Ethyl hydrogen

sulphate

213. Alcohols can be distinguished from alkenes by

(a) Dissolving in cold concentrated 42SOH (b) Decolourizing with bromine in 4CCl

(c) Oxidizing with neutral permanganate solution (d) None of the above

214. The alcohol which easily reacts with conc. HCl is [MP PMT 1985]

(a) 323 CHCHCHOHCH −−− (b) OHCCH −−33)(

(c) OHCHCHCHCH −−−− 2223 (d) OHCHCHCH 223)( −−

215. Which of the following gives ketone on oxidation [EAMCET 1987; BIT 1992]

(a) COHCH 33)( (b) OHCHCHCH 223 (c) OHCHCHCH 223)( (d) 33CHOHCHCH

216. Conc. 42SOH reacts with OHHC 52 at 170oC to form [MP PMT /PET 1991; IIT 1981; EAMCET 1979; KCET 2001]

(a) 33COCHCH (b) COOHCH 3 (c) CHOCH 3 (d) 42HC

217. When primary alcohol is oxidised with chlorine, it produces [AFMC 1999]

(a) HCHO (b) CHOCH 3 (c) CHOCCl3 (d) CHOHC 73

218. Which of the following compounds is oxidised to prepare methyl ethyl ketone [DCE 2001]

(a) 2-propanol (b) 1- butanol (c) 2-butanol (d) Tert – butyl alcohol

219. Primary alcohols on dehydration give

(a) Alkenes (b) Alkanes (c) Both (a) and (b) (d) None of these

220. Which one of the following compounds gives a positive iodoform test

(a) Pentanal (b) 1-phenyl ethanol (c) 2-phenyl ethanol (d) 3-pentanol

221. Alcohols react with Grignard reagent to form [Delhi PMT 1986]

(a) Alkanes (b) Alkenes (c) Alkynes (d) All the above

222. Which form complex with calcium chloride

(a) Methanol (b) Ethanol (c) Both (d) None

223. Which of the following is the most suitable method for removing the traces of water from ethanol

(a) Heating with Na metal (b) Passing dry HCl through it (c) Distilling it (d) Reacting with Mg

224. Alcohols (i) ,223 OHCHCHCH (ii) 33 CHCHOHCH −− and (iii) 333 ))(( CHOHCHCCH −− were treated with Lucas reagent

(Conc. ).2ZnClHCl + What results do you expect at room temperature

(a) (ii) and (iii) react immediately and (i) in about 5 minutes

(b) (iii) react immediately, (ii) reacts in about 5 minutes and (i) not at all

(c) (i) reacts immediately, (ii) reacts in about 5 minutes and (iii) not at all

(d) (i) reacts in about 5 minutes, (ii) reacts in about 15 minutes and (iii) not at all

225. The dehydration of 1o, 2

o and 3

o alcohols follows the order

(a) 1o> 2

o > 3

o (b) 3

o> 2

o > 1

o (c) 2

o> 1

o > 3

o (d) There is no such order

226. The reaction 322323 4132 CHOCHCHCH

KHOHCHCH →

+ is believed to occur through the formation of

(a) 223 HOCHCH+

(b) 23

+HCCH (c) 3223

|CHCH

H

OCHCH −−+••

(d) None of these

227. Ethyl iodide reacts with moist silver oxide to produce

(a) ethane (b) Propane (c) Ethyl alcohol (d) Diethyl ether

228. The alkaline hydrolysis of esters is known as

(a) Hydration (b) Esterification (c) Dehydration (d) Saponification

229. Which of the following is the most reactive with HCl in the presence of 2ZnCl

(a) COHCH 33)( (b) OHCHCHCH 223)( (c) CHOHCH 23)( (d) OHHC 56

230. Ethyl alcohol is less acidic than phenol because

(a) The phenoxide ion is more resonance stabilized than phenol

(b) There is more hydrogen bonding in phenol than in ethyl alcohol

(c) The ethoxide ion is less resonance stabilized than ethyl alcohol

(d) Phenol has a higher b.p. than ethyl alcohol

231. OHHC 52 reacts with halogen acids in the presence of 2ZnCl to form RX. Its reactivity with HI, HBr and HCl follows the

order

(a) HI > HBr > HCl (b) HCl > HBr > HI (c) HCl > HI > HBr (d) HBr = HCl > HI

232. Which of the following exhibit hydrogen bonding

(a) Chloroform (b) Ethyl alcohol (c) Acetic acid (d) Dimethyl ether

233. The intermediate formed during the dehydration of alcohol is

(a) Carbanion (b) Carbonium ion (c) Free radical (d) Carbene

234. Which of the following compounds are easily oxidized by 722 OCrK and 42SOH

(a) OHCHCH 23 (b) CHOHCH 23)( (c) CHOCH 3 (d) COHCH 33)(

235. 333233|

)()( CH

OH

CHCCHXCHCCHCH →= , X can be

(a) −OHOHTHFBH ./. 223 (b) +OH3 (c) NaOHNaBHOAcHg ,/)( 42 (d) None

236. Oxo process

(a) Is simply carbonylation or hydroformylation reaction (b) Uses cobalt carbonyl hydride ])([ 4COCoH as catalyst

(c) Both statements are correct (d) Both statements are

incorrect

237. → ∆− ,||

|42

3

3

3

3SOHCH

OH

CH

CH

CH

CCH

33

33

||CHCH

CCHCCH =

This is called

(a) Retropinacol rearrangement (b) Wagner-rearrangement

(c) Both correct (d) None is correct

238. Upon oxidation, alcohol gave a corbonyl compound containing same number of carbon atoms. The alcohol are

(a) Primary alcohol (b) Secondary alcohol

(c) Tertiary alcohol (d) Primary and secondary alcohols

239. Ethyl alcohol is denaturated by adding [CEE Bihar 1989]

(a) Glycerol (b) Methanol and pyperidine (c) Aniline (d) Ether and ethanol

240. When wine is put in air, it becomes sour due to

(a) Oxidation of OHHC 52 (b) Reduction of OHHC 52 (c) Formation of 252 NHHC (d) Dissolution of 2CO

241. The order of reactivity of the following alcohols

32|

CH

OH

CHFCH − 322|

CH

OH

CHCHFCH − 33|

CH

OH

CHCH − OHCHHC 256

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

(a) I > II > III > IV (b) I > III > II > IV (c) IV > III > II > I (d) IV > III > I > II

242. When ethyl alcohol reacts with acetic acid, the products formed are

(a) Sodium ethoxide + hydrogen (b) Ethyl acetate + water

(c) Ethyl acetate + soap (d) Ethyl alcohol + water

243. When rectified spirit and benzene are distilled together, the first fraction obtained is

(a) A ternary azeotrope (b) Absolute alcohol (c) A binary azeotrope (d) Denatured spirit

244. Oxidation of ethanol by chromic acid forms [MP PET 1992]

(a) Ethanol (b) Methanol (c) 2-propanone (d) Ethanoic acid

245. When vapours of an alcohol are passed over hot reduced copper, alcohol is converted into alkene quickly, the alcohol is [CPMT 1985]

(a) Primary (b) Secondary (c) Tertiary (d) None of these

246. Isopropyl alcohol heated at 300oC with copper catalyst to form [AFMC 1990; MP PMT 1986, 89, 92; JIPMER 2000]

(a) Acetone (b) Dimethyl ether (c) Acetaldehyde (d) Ethane

247. Primary and secondary alcohols on action of reduced copper give

(a) Aldehydes and ketones respectively (b) Ketones and aldehydes respectively

(c) Only aldehydes (d) Only ketones

248. When a solution of sodium chloride containing ethyl alcohol is electrolysed, it forms

(a) Ethyl alcohol (b) Chloral (c) Chloroform (d) Acetaldehyde

249. Methyl alcohol on oxidation with acidified 722 OCrK gives [MLNR 1987]

(a) 33COCHCH (b) CHOCH 3 (c) HCOOH (d) COOHCH 3

250. Which will dehydrate easily [Roorkee 1995]

(a) 3-methyl-2-butanol (b) Ethyl alcohol (c) 2-methyl propane-2-ol (d) 2-methyl butanol-2

251. The final product of the oxidation of ethyl alcohol is [KCET (Med.) 1999]

(a) Ethane (b) Acetone (c) Acetaldehyde (d) Acetic acid

252. Which alcohol reacts with fatty acids to form fats [MP PMT / PET 1988; MP PET 1991]

(a) Ethanol (b) Glycerol (c) Methanol (d) Isopropanol

253. 23 g of Na will react with methyl alcohol to give [NCERT 1972; MP PMT 1990]

(a) One mole of oxygen (b) One mole of H2 (c) 22

1Hofmole (d) None of these

254. Dehydration of ethanol gives [CPMT 1985; BHU 1989]

(a) Acetic acid (b) Ethane (c) Ethylene (d) Acetylene

255. Ethyl alcohol reacts with methyl magnesium bromide to form [CPMT 1990]

(a) Methane (b) Ethane (c) Propane (d) Butane

256. Which compound gives yellow ppt. with iodine and alkali [IIT 1984]

(a) 2-hydroxy propane (b) Acetophenone (c) Methyl acetone (d) Acetamide

257. Dehydrogenation of 33|

CH

OH

CHCH −− gives [MP PMT 2002]

(a) Acetone (b) Acetaldehyde (c) Acetic acid (d) Acetylene

258. When 2-ethylanthraquinol dissolved in a mixture of benzene and cyclohexanol is oxidised, the product is

(a) Ethanol (b) Hydrogen peroxide (c) Anthracene (d) None of these

259. The final product obtained by distilling ethyl alcohol with the excess of chlorine and 2)(OHCa is

(a) CHOCH 3 (b) CHOCCl3 (c) 3CHCl (d) OCH 23)(

260. Ethyl orthoformate is formed by heating with sodium ethoxide [EAMCET 2003]

(a) 3CHCl (b) OHHC 52 (c) HCOOH (d) CHOCH 3

261. Glycerol reacts with conc. 3HNO and conc. 42SOH to form [CPMT 1983]

(a) Glycerol mononitrate (b) Glycerol dinitrate (c) Glycerol trinitrate (d) Acrolein

262. With oxalic acid, glycerol at 260oC gives [BHU 1996]

(a) Allyl alcohol (b) Glyceryl mono-oxalate (c) Formic acid (d) Glyceraldehyde

263. Glycerol was distilled with oxalic acid crystals and the products were led into Fehling solution and warmed. Cuprous oxide

was precipitated. It is due to [KCET 1987]

(a) CO (b) HCHO (c) CHOCH 3 (d) HCOOH

264. On heating glycerol with conc. 42SOH , a compound is obtained which has a bad odour. The compound is [CPMT 1974; CBSE 1994]

(a) Glycerol sulphate (b) Acrolein (c) Formic acid (d) Allyl alcohol

265. The reaction of ethylene glycol with 3Pl gives [MP PMT 2000]

(a) ICHICH 22 (b) 22 CHCH = (c) CHICH =2 (d) ICH = CHI

266. Glycerol heated with oxalic acid at 110oC to form [CPMT 1986, 90, 91, 97; JIPMER 1997]

(a) Formic acid (b) Oxalic acid (c) Allyl alcohol (d) Glycerol trioxalate

267. Ethylene glycol, on oxidation with per-iodic acid, gives [NCERT 1983; CPMT 1983]

(a) Oxalic acid (b) Glycol (c) Formaldehyde (d) Glycollic acid

268. Glycerol react with potassium hydrogen sulphate to form [CPMT 1974; MP PMT 1990]

(a) Ethanol (b) Propane (c) Acryldehyde (d) Acrylic acid

269. Dehydration of glycerol gives [CPMT 1985; MP PET 1992; MP PMT 1992, 94]

(a) Propane (b) Propene (c) Acrolein (d) Benzene

270. Acrolein is formed from glycerol by heating with [MP PMT / PET 1988]

(a) Acidic 4KMnO (b) 2Br water (c) 4KHSO (d) 3HNO

271. Final product formed on reduction of glycerol by hydroiodic acid is

(a) Propane (b) Propanoic acid (c) Propene (d) Propyne

272. When glycerol is heated with ,4KHSO it gives [MP PMT 1991]

(a) 32 CHCHCH −= (b) OHCHCHCH 22 −= (c) CHOCHCH −=2 (d) 22 CHCCH ==

273. Glycerol reacts with 24 IP + to form

(a) Aldehyde (b) Allyl iodide (c) Allyl alcohol (d) Acetylene

274. When glycol is heated with dicarboxylic acid, the products are

(a) Polyesters (b) Polyethers (c) Polyethylene (d) No reaction at all

275. By distilling glycol with fuming sulphuric acid, which of following is obtained

(a) Glycerol (b) Pinacol (c) Dioxan (d) Ethylene oxide

276. When glycerol is heated with an excess of HI, it produces

(a) Allyl iodide (b) Propene (c) Glycerol triiodide (d) 2-iodopropane

277. When ethylene glycol is heated with a mixture of conc. 3HNO and conc. ,42SOH it produces

(a)

COOH

COOH|

(b) 22 HCO + (c)

22

22|

ONOCH

ONOCH (d)

OHCH

ONOHC

2

22|

278. With anhydrous zinc chloride, ethylene glycol gives [MP PMT 2004]

(a) Formaldehyde (b) Acetylene (c) Acetaldehyde (d) Acetone

279. Rate of substitution reaction in phenol is [MP PMT 1989]

(a) Slower than the rate of benzene (b) Faster than the rate of benzene

(c) Equal to the rate of benzene (d) None of these

280. Which statement is true [MP PMT 1991]

(a) OHHC 56 is more acidic than OHHC 52 (b) OHHC 56 is less acidic than OHHC 52

(c) OHHC 56 react with 3NaHCO (d) OHHC 56 gives oxime with OHNH2 and HCl

281. The – OH group in phenol in an electrophilic aromatic substitution is

(a) ortho-orienting (b) para-orienting (c) meta-orienting (d) ortho and para-orienting

282. Because of resonance the oxygen atom of – OH group of phenol

(a) Acquires positive charge (b) Acquires negative charge (c) Remains uneffected (d)

283. Which of the following compounds will be most easily attacked by an electrophile [CBSE 1998, 99; MP PMT 2004]

(a) (b) (c) (d)

284. Phenol is less acidic than [UPSEAT 2003; IIT 1986]

(a) Acetic acid (b) p-methoxy phenol (c) p-nitro phenol (d) Ethanol

285. Which of the following is phenolic

(a) Phthalic acid (b) Phosphoric acid (c) Picric acid (d) Phenylacetic acid

286. Phenol is less acidic than [UPSEAT 1999; MNR 1995]

(a) Ethanol (b) Methanol (c) ortho nitrophenol (d) para methyl-phenol

287. Phenol is [CPMT 1980]

(a) Acidic (b) Basic (c) Neutral (d) None of these

288. Which of the following is most acidic [CPMT 1999]

(a) Phenol (b) Benzyl alcohol (c) m-chlorophenol (d) Cyclohexanol

289. The ring deuteration of phenol

(a) Lowers the acidity (b) Increases the acidity (c) Imparts no effect (d) Causes amphoteric nature

290. The bad smelling substance formed by the action of alcoholic caustic potash on chloroform and aniline is

Cl OH CH3

[MP PMT 1971, 92, 2001; CPMT 1971, 86; AFMC 2002]

(a) Phenyl isocyanide (b) Nitrobenzene (c) Phenyl cyanide (d) Phenyl isocyanate

291. In presence of NaOH, phenol react with 3CHCl to form o-hydroxy benzaldehyde. This reaction is called

[BIT 1992; MP PMT 1990, 2002; AIIMS 1992; MP PET 1994;JIPMER 1999]

(a) Reimer-Tiemann’s reaction (b) Sandmeyer’s reaction

(c) Hoffmann’s degradation reaction (d) Gattermann’s aldehyde synthesis

292. acidSalicylic 4 →++ KOHCClA ’A’ in above reaction is [RPMT 2003]

(a) (b) (c) (d)

293. Which of the following does not gives effervescence with 3NaHCO [MP PET 1992]

(a) Phenol (b) Benzoic acid (c) 2, 4-dinitrophenol (d) 2, 4, 6-trinitrophenol

294. Salicylic acid can be prepared using Riemer-Tiemann’s reaction by treating phenol with [KCET 1989]

(a) Methyl chloride in the presence of anhydrous aluminium chloride

(b) Carbon dioxide under pressure in sodium hydroxide solution

(c) Carbon tetrachloride and concentrated sodium hydroxide

(d) Sodium nitrite and a few drops of concentrated sulphuric acid

295. Reaction is called [MP PET 2003]

(a) Lederer Manasse reaction (b) Claisen condensation (c) Benzoin condensation (d)

296. At low temperature phenol reacts with 2Br in 2CS to form [MP PET 1991; CPMT 1981; MP PMT 1990;IIT 1982; RPMT 2000]

(a) m-bromophenol (b) o- and p-bromophenol (c) p-bromophenol (d) 2, 4, 6-tribromophenol

297. Phenol+

→H

NaOHCHCl /3 Salicylaldehyde. This reaction is known as [Pb. PMT 2002]

(a) Riemer Tiemann reaction (b) Bucherer reaction (c) Gattermann synthesis (d)

298. An organic halide is shaken with aqueous NaOH followed by the addition of dil. 3HNO and silver nitrate solution gave

white ppt. The substance can be [JIPMER 1997]

(a) BrCHHC )( 346 (b) ClCHHC 256 (c) ClHC 56 (d) None of these

299. Phenol and benzoic acid is distinguished by [BHU 2003]

(a) NaOH (b) 3NaHCO (c) 32CONa (d) 42SOH

300. Benzenediazonium chloride on reaction with phenol in weakly basic medium gives [IIT 1998]

(a) Diphenyl ether (b) p-hydroxyazobenzene (c) Chlorobenzene (d) Benzene

301. Kolbe-Schmidt reaction is used for [CBSE 1991]

(a) Salicylic acid (b) Salicylaldehyde (c) Phenol (d) Hydrocarbon

302. What is the reagent used for testing fluoride ion in water [EAMCET 2003]

(a) Alizarin-S (b) Quinalizarin (c) Phenolphthalein (d) Benzene

303. With excess bromine, phenol reacts to form [BHU 2001]

(a) (b) (c) (d) Mixture of (a) and (b)

304. Phenol reacts with 3CHCl and NaOH (at 340 K) to give [MP PMT 1997; CBSE 2002]

OH NO2 CHO

OH OH

CH2OH

OH

CH2OH

+ → or base acid2OCH +

OH

Br

OH

Br

OH

Br Br

Br

(a) o-chlorophenol (b) Salicylaldehyde (c) Benzaldehyde (d) Chlorobenzene

305. Phenol is heated with phthalic anhydride in the presence of concentrated 42SOH . The product gives pink colour with

alkali. The product is [KCET (Med.) 2000; CPMT 1981; CBSE 1988; MP PET 1997]

(a) Bakelite (b) Fluorescein (c) Salicylic acid (d) Phenolphthalein

306. When phenol reacts with 3CHCl and KOH, the product obtained would be [RPMT 1997]

(a) Salicylaldehyde (b) p-hydroxy benzaldehyde (c) Both (a) and (b) (d) Chloretone

307. The most suitable method of the separation of a 1 : 1 mixture of ortho and para nitrophenols is [CBSE 1994, 99; CPMT 1997]

(a) Distillation (b) Sublimation (c) Crystallization (d) Chromatography

308. 356 aq.

356 OCOCHHCClCOCHOHHC NaOH →+ is an example of [BHU 1984]

(a) Dow’s reaction (b) Reimer-Tiemann reaction (c) Schotten-Baumann reaction (d) Kolbe’s reaction

309. Phenol is heated with 4CCl and alc. KOH when salicylic acid is produced. The reaction is known as

[CPMT 1986; DPMT 1983; KCET 1993]

(a) Friedel-Craft’s reaction (b) Riemer-Tiemann reaction (c) Rosenmund reaction (d) Sommlet reaction

310. Among the following, the compound that undergoes nitration readily is [NCERT 1984]

(a) Benzoic acid (b) Toluene (c) Phenol (d) Nitrobenzene

311. To obtain m-chloronitrobenzene, the first compound is [Roorkee 1995]

(a) Benzene (b) Nitrobenzene (c) Chlorobenzene (d) Benzaldehyde

312. Benzene diazonium chloride on boiling with dilute sulphuric acid gives [MP PMT 1983]

(a) Toluene (b) Benzoic acid (c) Benzene (d) Phenol

313. A compound that easily undergoes bromination is [KCET (Engg.) 2002]

(a) Phenol (b) Toluene (c) Benzene (d) Benzoic acid

314. Reaction of phenol with dil. 3HNO gives [KCET 1993; RPMT 1997]

(a) p- and m-nitrophenols (b) o- and p-nitrophenols (c) Picric acid (d) o- and m-nitrophenols

315. Oxidation of which of the following by air in presence of vanadium pentoxide gives phenol

(a) Toluene (b) Benzene (c) Benzaldehyde (d) Phenyl acetic acid

316. Action of diazomethane on phenol liberates

(a) 2O (b) 2H (c) 2N (d) 2CO

317. Which of the following reacts with phenol to give salicylaldehyde after hydrolysis [MP PMT 1995]

(a) Dichloromethane (b) Trichloromethane (c) Methyl chloride (d) None of these

318. Liebermann’s test is answered by [KCET 1998]

(a) Aniline (b) Methylamine (c) Ethyl benzoate (d) Phenol

319. Which is formed when benzalamine react with nitrous acid [KCET (Med.) 2001]

(a) OHHC 56 (b) ONHC 56 (c) OHNHC 252 (d) OHCHHC 256

320. Phenol on distillation with zinc dust gives [MP PET 1991; CPMT 1997; MP PMT 1999, 2001; Pb. PMT 2000]

(a) 66HC (b) 126HC (c) 5656 HOCHC (d) 5656 HCHC −

321. Phenol is converted into salicylaldehyde by [CPMT 1986; MP PMT 1990; BIT 1992; KCET 1999]

(a) Etard’s reaction (b) Kolbe’s reaction (c) Reimer Tiemann’s reaction (d) Cannizzaros reaction

322. Which of the following are known as mercaptans [Pb. PMT 2002]

(a) Thio-alcohols (b) Thio-ethers (c) Thio-acids (d) Thio-aldehydes

323. Phenol reacts with aqueous bromine to give [MP PMT 2003]

(a) (b) (c) (d)

324. Which is obtained on treating phenol, with dilute 3HNO [BVP 2003]

OH

Br

OH

Br

OH

Br Br

Br

OH

Br

OH

Br

+

OH

NO2

OH

NO2

OH

NO2 O2N

NO2

(a) (b) (c) (d) None of these

325. Phenol reacts with dilute 3HNO at normal temperature to form [MP PMT 1989]

(a) (b) (c) (d)

326. Which of the following statements is correct [BHU 1997]

(a) Phenol is less acidic than ethyl alcohol (b) Phenol is more acidic than ethyl alcohol

(c) Phenol is more acidic than carboxylic acid (d) Phenol is more acidic than carbonic acid

327. The reaction of conc. 3HNO and phenol forms [MP PMT/PET 1988; BHU 1988; MP PMT 1999; Pb. PMT 2000]

(a) Benzoic acid (b) Salicylic acid (c) o- and p-nitrophenol (d) Picric acid

328. Phenol is treated with bromine water and shaken well. The white precipitate formed during the process is [KCET (Med.) 2001]

(a) m-bromophenol (b) 2, 4-dibromophenol

(c) 2, 4, 6-tribromophenol (d) A mixture of o- and p-bromophenols

329. When heated with 3NH under pressure alone or in presence of zinc chloride phenols are converted into [RPMT 1997]

(a) Aminophenols (b) Aniline (c) Nitrobenzene (d) Phenyl hydroxylamine

330. When phenol is heated with phthalic anhydride in concentrated sulphuric acid and the hot reaction mixture is poured into a dilute solution of sodium hydroxide, the product formed is [MP PET 2003]

(a) Alizarin (b) Methyl orange (c) Fluorescein (d) Phenolphthalein

331. Phenol is [MP PMT 1990; UPSEAT 1999]

(a) A weaker base than 3NH (b) Stronger than carbonic acid

(c) Weaker than carbonic acid (d) A neutral compound

332. + )( Anhydrous

5252

52

OHHC

HCOIHC →−

[IIT Screening 2003]

(a) 5256 HOCHC (b) 5252 HOCHC (c) 5656 HOCHC (d) IHC 56

333. Azo-dyes are prepared from [CPMT 2001]

(a) Aniline (b) Benzaldehyde (c) Benzoic acid (d) Phenol

334. Which will undergo a Friedel-Craft’s alkylation reaction [Pb PMT 1998]

(a) 1, 2 and 4 (b) 1 and 3 (c) 2 and 4 (d) 1 and 2

335. This reaction + HCl + HCN2

Anhydrous

ZnCl → is known as [MP PET 1997]

(a) Perkin reaction (b) Gattermann reaction (c) Kolbe reaction (d) Gattermann-Koch reaction

336. Bakelite is prepared by the reaction between [CBSE 1995]

(a) Urea and formaldehyde (b) Tetramethylene glycol and hexamethylene di-isocyanate

OH

NO2 O2N

NO2

OH

NO2

OH

NO2

+

OH

NO2

OH

NO2

OH

CH3

NO2 1

CH2CH3

2

COOH

3

OH

4

OH OH

CHO

(c) Phenol and formaldehyde (d) Ethylene glycol and dimethyl terephthalate

337. 2Br water react with phenol to form [BIT 1992; AIIMS 1996; KCET 2001; MP PMT 1993; IIT 1984]

(a) 2-bromophenol (b) 4-bromophenol (c) 2, 4-dibromophenol (d) 2, 4, 6-tribromophenol

338. The reaction of aromatic acyl chloride and phenol in the presence of a base NaOH or pyridine is called [AFMC 19985]

(a) Kolbe’s reaction (b) Perkin’s reaction (c) Sandmeyer’s reaction (d) Schotten-Baumann

reaction

339. Sodium phenoxide when treated with 2CO under pressure [JIPMER 1999]

(a) (b) (c) (d) None of these

340. The compound obtained by heating salicylic acid with phenol in the presence of phosphorus oxychloride is [KCET (Med.) 1999]

(a) Salol (b) Aspirin (c) Oil of wintergreen (d) o-chlorobenzoyl chloride

341. In the Liebermann’s nitroso reaction, sequential changes in the colour of phenol occurs as [AFMC 1998; BHU 1999]

(a) Brown or red → green → red → deep blue (b) Red → deep blue → green (c) Red → green → white (d) White → red → green

342. Phenol is obtained by heating aqueous solution of [MP PMT 1995]

(a) Aniline (b) Benzene diazonium chloride (c) Benzoic acid (d) None of these

343. Phenolphthalein is obtained by heating phthalic anhydride with conc. 42SOH and [BHU 1996]

(a) Benzyl alcohol (b) Benzene (c) Phenol (d) Benzoic acid

344. When phenol reacts with ammonia in presence of 2ZnCl at Co300 , it gives [AFMC 2001]

(a) Primary amine (b) Secondary amine (c) Tertiary amine (d) Both (b) and (c)

345. Sodium phenoxide when heated with 2CO under pressure at Co125 gives [DPMT 1983; MP PMT 1997]

(a) Sodium benzoate (b) Salol (c) Sodium salicylate (d) Salicylaldehyde

346. Phenols react with ferric chloride solution to give (a) Blue colouration (b) Purple colouration (c) Green colouration (d) All of these

347. Which of the following groups will increase the basicity of phenol (a) 2NH− (b) 3CH− (c) 2NO− (d) None of these

348. Which of the following groups will increase the acidity of phenol (a) 2NO− (b) – CN (c) – X(halogen) (d) None of these

349. In the reaction of phenol with 3CHCl and aqueous NaOH at 345 K, the species attacking the ring is

(a) 3CHCl (b) 2CHCl (c) 2COCl (d) 2CCl

350. In the Libermann test for phenols, the blue or green colour produced is due to the formation of

(a) (b)

(c) (d)

351. OHCH

KOH

3

aq. → product, product is

(a) and OKCH3 (mixture) (b) b

COOH

OH

OH

COOH

OH HOOC

NOH O

N O OH N O O– Na+

OH

OCH3 OCH3

OH

OCH3

OH

OCH3

OH

OH ON

(c) (d)

352. Read the following statements carefully

(1) A secondary alcohol on oxidation gives a ketone

(2) Ethanol reacts with conc. 42SOH at 180oC to yield ethylene

(3) Methanol reacts with iodine and sodium hydroxide to give a yellow precipitate of iodoform

(4) Hydrogen gas is liberated when sodium is added to alcohol

Select the correct statements from the above set

(a) 1, 2 (b) 3, 4 (c) 1, 2, 4 (d) 1, 3, 4

353. Rectified spirit obtained by fermentation contains 4.5% of water. So in order to remove it, rectified spirit is mixed with

suitable quantity of benzene and heated. Benzene helps because

(a) It is dehydrating agent and so removes water

(b) It forms the lower layer which retains all the water so that alcohol can be distilled off

(c) It forms an azeotropic mixture having high boiling point and thus allows the alcohol to distill over

(d) It forms low boiling azeotropic mixtures which distill over, leaving behind pure alcohol which can then be distilled

354. Assertion : A triester of glycerol and palmitic acid on boiling with aqueous NaOH gives a solid cake having soapy touch

Reason : Free glycerol is liberated which is a greasy solid [AIIMS 1996]

(a) Both assertion and reason are true statements and reason is the correct explanation of assertion

(b) Both assertion and reason are true statements and reason is not the correct explanation of assertion

(c) Assertion is true but reason is a false statement

(d) Both assertion and reason are false statements

355. In methyl alcohol solution, bromine reacts with ethylene to yield 322 OCHCHBrCH in addition to 1,2-dibromoethane

because

[Punjab PMT 1998]

(a) The ion formed initially may react with Br– or OHCH 3 (b) The methyl alcohol solvates the bromine

(c) The reaction follows Markownikoffs rule (d) This is a free-radical mechanism

356. When ethyl alcohol )( 52 OHHC is mixed with ammonia and passed over heated alumina, the compound formed is

[Delhi PMT 1981; CBSE 1989]

(a) 252 NHHC (b) 42HC (c) 5252 HOCHC (d) 33OCHCH

357. Which one of the following will most readily be dehydrated in acidic condition [IIT Screening 2000]

(a) (b) (c) (d)

358. ,)(Re

'33 XCHOHCHCHCHCH

agent

sJon →−−=−

Product X is [Raj. PET 2000]

(a) 3223 )( CHOHCHCHCHCH (b) 33 CHCOCHCHCH =

(c) Both the above (d) 3223 COCHCHCHCH

359. An alcohol on oxidation is found to give COOHCH 3 and COOHCHCH 23 . The structure of the alcohol is [BIT 1990]

(a) OHCHCHCH 223 (b) 3223 )()( CHCHOHCCH (c) 323 CHOHCHCHCH (d)

3223 )( CHCHCHOHCHCH

360. Conc. 42SOH heated with excess of OHHC 52 at 140oC to form [MP PMT 1990; Raj. PMT 2000; AFMC 2002]

O OH OH O

OH

OH

OH

AAddvvaannccee LLeevveell

(a) 323 CHOCHCH −− (b) 3223 CHCHOCHCH −−

(c) 3223 CHCHCHOCH −−−− (d) 22 CHCH =

361. When vapour of ethanol are passed over platinised asbestos in excess of air, the compound formed is

(a) CHOCH 3 (b) 33COCHCH (c) 22HC (d) COOHCH 3

362. When but –3-en-2-ol reacts with aq. HBr, the product formed is [DCE 2001]

(a) 3-bromobut – 1 - ene (b) 1 – bromobut – 2 – ene (c) A mixture of both a and b (d) 2 – bromobut – 2-ene

363. Reaction : Ag

Co

OOHCH →+ 60023 product

The product is [Raj. PET 2000]

(a) OCCH ==2 (b) OCH =2 (c) 42HC (d) 22HC

364. Which of the following would undergo dehydration most readily

(a) 1-phenyl-1 butanol (b) 2-phenyl-2-butanol

(c) 1-phenyl-2-butanol (d) 2-phenyl-1-butanol

365. Butanal with dilute NaOH gives

(a) CHOCHCHCHH

OH

C

H

CCHCHCH 2222223

|

| (b) CHOCHCHCH

O

CCHCHCH 222223

||

(c) CHOCHCHCHCHCHOHCCH 222222 (d) HO

OH

C

CH

CH

CH

H

CCHCHCH

3

2

223

|

|

|

|−

366. Which of the following is not true in case of reaction with heated copper at 300oC [CPMT 1999]

(a) Phenol → Benzyl alcohol (b) Primary alcohol → Aldehyde (c) Secondary alcohol → Ketone (d) Tertiary alcohol → Olefin 367. A mixture of methanol vapours and air is passed over heated copper. The products are [KCET 1988]

(a) Carbon monoxide and hydrogen (b) Formaldehyde and water

vapour

(c) Formic acid and water vapour (d) Carbon monoxide and water vapour

368. Which is more reactive with HBr [IIT 1986, 87; JIPMER

2000]

(a) 2-methyl propane-2-ol (b) Propane-1-ol (c) Propane-2-ol (d) 2-methyl propane-1-ol

369. Propene is the product obtained by dehydration of [KCET (Engg.) 2001]

(a) 2-propanol (b) 1-propanol (c) Propanal (d) n-propyl alcohol

370. Isopropyl alcohol on oxidation forms

(a) Acetone (b) Ether (c) Ethylene (d) Acetaldehyde

371. Which of the following vapours passed over heated copper to form acetone [BIT 1992]

(a) OHCHCHCH 223 −− (b) 33|

CH

OH

CHCH −− (c) OHC

CH

CH

CH −3

3

3 (d) OHCHCHCH 22 −=

372. The acidity of the compounds ROHOHHCCOHRCOOH ,,, 5632 decreases in the order

(a) ROHOHHCCOHRCOOH >>> 5632 (b) ROHCOHRCOOHOHHC >>> 3256

(c) 3256 COHRCOOHOHHCROH >>> (d) ROHOHHCRCOOHCOH >>> 5632

373. The acidic character of 1o, 2

o, 3

o alcohols, OH 2 and CHRC ≡ is in the order

(a) CHRCOH ooo ≡>>>> 3212 (b) OHCHRC ooo2123 >>>>≡

(c) CHRCOHooo ≡>>>> 2321 (d) CHRCOHooo ≡>>>> 2123

374. The acid strengths of ethanol, isopropanol and tert. butanol decrease in the order

(a) Ethanol >isopropanol>tert. butanol (b) Tert. butanol >isopropanol>Ethanol

(c) Isopropanol>tert. butanol> Ethanol (d) Tert. butanol > Ethanol >isopropanol

375. Dehydration of alcohols

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

will be in order

(a) I<II<III<IV (b) I>II>III>IV (c) III<II<I<IV (d) II<III<IV<I

376. In the following case configuration about chiral C(*) is retained

(a) → → BrCHNa

Et

OHH

Me3* (b) → → ONaCHTsCl

Et

OHH

Me3*

(c) → → ONaCHPCl

Et

OHH

Me35* (d) In none case

377. →− 42.

3

33

3|

||

SOHconc

OHCH

CHCHCCH

CH

A (predominant), A is

(a) 233)( CHCCHCH = (b) 2323 )()( CHCCCH = (c) 322

3

2|

CHCHH

CH

CCCH = (d) None is correct

378. ,2 AMnO → A is

(a) (b) (c) (d)

379. → 42. SOHconc products can be

(a) (b) (c) Both correct (d) None is correct

380. .|

2222 AOHCHCH

OH

CHCHCH MnO →= A is

(a) OHCHH

O

H

CCCHCH 22

||

2||

= (b) CHOCH

OH

CHCHCH 22|

= (c) CHOH

O

CCCHCH 22||

= (d) OH

O

CH

O

CCCHCH||

||22 =

381. ZnCuo

H

pressure

COCoHHCOCHCHCH

− → →= 242

23,125

])([,, Product

This represents oxo method of alcohol synthesis. Product can be

(a) OHCHCHCHCH 2223 (b) OHCH

CH

CHCH 2

3

3|

(c) Both are true (d) None is true

382. → 43POH

OH OH OH OH

OH

OH

OH

O

O

OH

O O

O OH OH

OH

18

OH

+ H2O

O

A

In this dehydration reaction O18 will be in

(a) OH 2 (b) A (c) Both (d) None

383. → 4LiAlH A, A is

(a) OHCH

CH

CHCH 2

3

3|

(b) OHCHCHCHCH 2223 (c) OH

CH

CH

CCH

3

3

3

|

|− (d) No reaction

384. 3

3

3

32

3

3

3|

|

|

|

|CH

OH

CH

CH

CH

CCHCHCH

CH

CH

CCH −−−→=−−

This change can be done by

(a) Acid catalysed hydration (b) Oxymercuration-demercuration

(c) Hydroboration-oxidation (d) Any method mentioned above

385. →− HBrCH

OH

CH

CH

CH

CCH 3

3

3

3|

|

| A (predominant), A is

(a) 333

|)( CH

Br

CHCCH (b) 2323 )(|

)( CH

Br

CCHCH (c) Both (d) None is correct

386. In this diol

(a) OH at C2 is more basic than that of at C5 (b) OH at C2 is more acidic than at C5

(c) Both behave as a base (d) Both behave as an acid

387. Which is not cleaved by 4HIO

I : Glycerol II : Glycol III : 1,3-propanediol IV : Methoxy-2-propanol

(a) I, II, III, IV (b) I, II (c) II, III (d) III, IV

388. →= HClOClCHCHCH 22 X is

(a)

OHClCl

CHCHCH|||

22 (b)

ClClOH

CHCHCH|||

22 (c) ClCHCH

O

CH 22 − (d) 33|

CH

Cl

CHCH

389. Periodiate oxidation of 1,2-cyclopentanediol is

(a) (b) (c) (d) H

O

CCHCHHCH

O

C||||

222

390. )( 444 OHCA does not decolorise 2Br water and is also neutral to litmus. Hence, A is

(a) CHCOOH

CHCOOH|| (b) 22 )(COOHCCH = (c) (d) None is correct

391. OHH

OHH ← B

→ A HHO

OHH and enantiomer A and B are

(a) −− OHMnOHHCO /, 43 (b) −− OHMnOSONaOsO /,/ 4324

(c) HHCOOHMnO 34 ,/ −− (d) MCPBAOHMnO ,/4−−

O

H3C

H3C C H2

OH OH 2 5

O

O O

O

O

O O

O O

392. ,%2.0 4 ABuOOHt

OsO−

→ A is

(a) (b) (c) (d)

393. Dehydration product of 1,4-diol given below will be

→ 432223

18

||

POH

OH

CHCHCH

OH

CHCH

(a) (b) (c) (d)

394. 2-butene

3

3

3

CH

OHH

OHH

CH

HHCO → , Hence, 2-butene is

(a) Cis- (b) Trans- (c) Both (d) None is correct

395. Glycerol + cold

SOHHNO → 42

3 product, product is

(a) Trinitro glycerine (b) Glyceryl trinitrate (c) T.N.T. (d) Glycerol mono nitrate

396. → ONaCHClCHCH

O

HC 322

14

A, A is

(a) 322

14

OCHCHCH

O

HC (b) 22

14

3 CH

O

CHHOCCH (c) ClCHH

OCH

CHC 22

3

2

14

| (d) ClCHH

OH

CHC 222

14

|

397. An organic liquid A containing C, H and O has a pleasant odour with a boiling point of 78oC. On boiling A with conc.

42SOH a colourless gas is produced which decolourises bromine water and alkaline 4KMnO . One mole of this gas also

takes one mole of H2. The organic liquid A is

(a) ClHC 52 (b) CHOHC 52 (c) 62HC (d) OHHC 52

398. In the following series of chemical reactions, identify Z [Manipal MEE 1995]

(a)

2

2

2

3||NH

CH

NH

CHCH −− (b)

OH

CH

OH

CHCH||

23 −− (c) 23|

CH

OH

CCH =− (d) CHCCH ≡−3

399. A compound X with molecular formula OHC 83 can be oxidised to a compound Y with the molecular formula .263 OHC X is

most likely to be [MP PMT 1991]

(a) Primary alcohol (b) Secondary alcohol (c) Aldehyde (d) Ketone

400. Identify X

XOH

teIntermedia

CH

MgICHOC

CH

2

etherdry → →=

3

3

3

[CPMT 1988]

(a) OHCH 3 (b) Ethyl alcohol (c) t-butyl alcohol (d) Methyl iodide

401. If there be a compound of the formula 33 )(OHCCH which one of the following compounds would be obtained from it

without reaction with any reagent

HO C

H OH

H OH

(meso)

H OH

HO H

and enantiomer

(racemic)

H3C

18

O

H3C

18

O

CH3

18

OCH3

18

O

(a) OHCH 3 (b) OHHC 52 (c) COOHCH 3 (d) HCHO

402. In the sequence of the following reactions COOHCHXOHCHCHAcidChromic

O

AcidChromic

O3

||||23 → →

X is [MP PMT 2002]

(a) 33COCHCH (b) CHOCH 3 (c) 33OCHCH (d) COOHCHCH 23

403. Compound 'A' reacts with 5PCl to give 'B' which on treatment with KCN followed by hydrolysis give propanoic acid as the

product. What is 'A' [CBSE 2002]

(a) Ethane (b) Propane (c) Ethyl chloride (d) Ethyl alcohol

404. An organic compound A reacts with sodium metal and forms B. On heating with conc. .42SOH A gives diethyl ether. A and

B are

[AFMC 1998]

(a) OHHC 52 and ONaHC 52 (b) OHHC 73 and ONaCH 3 (c) OHCH 3 and ONaCH 3 (d) OHHC 94 and

ONaHC 94

405. .3223 BOHCHCHA OAlCu

∆∆ → ← A and B respectively are [Raj. (Engg./Med.) 2000]

(a) Alkene, alkanal (b) Alkyne, alkanal (c) Alkanal, alkene (d) Alkene, alkyne

406. An unknown compound 'D' first oxidised to aldehyde and then acitic acid by a dilute solution of 722 OCrK and .42SOH The

unknown compound 'D' is [BHU 2000]

(a) CHOCH 3 (b) OHCHCHCH 232 (c) OHCHCH 23 (d) 323 CHCHCH

407. A compound A on oxidation gave acetaldehyde, then again on oxidation gave acid. After first oxidation it was reacted with

ammonical ,3AgNO then silver mirror was produced. A is likely to be

(a) Primary alcohol (b) Tertiary alcohol (c) Acetaldehyde (d) Acetone

408. An organic compound X on treatment with acidified 722 OCrK gives a compound Y which reacts with I2 and sodium

carbonate to form triodomethane. The compound X is [KCET 1996]

(a) OHCH 3 (b) 33 CHCOCH −− (c) CHOCH 3 (d) 33 )( CHOHCHCH

409. The compound 'A' when treated with cerric ammonium nitrate solution gives yellow ppt. The compound 'A' is [MP PET 2002]

(a) Alcohol (b) Aldehyde (c) Acid (d) Alkane

410. A compound X of formula OHC 83 yields a compound ,63 OHC on oxidation. To which of the following classes of

compounds could X being [Pb. PMT 2000]

(a) Secondary alcohol (b) Alkene (c) Aldehyde (d) Tertiary alcohol

411. From the reaction OHMgICH

BSOHDILOCrK

A2

3

42

722

. → → 3

3

3

|

|CH

CH

OH

CCH −−

The reactant A is [MH CET 2002]

(a) 33CHOHCHCH (b) 33COCHCH (c) OHHC 52 (d) COOHCH 3

412. The adduct of the compound 'A' obtained by the reaction with excess of isopropyl magnesium iodide, upon hydrolysis

gives a tertiary alcohol. The compound 'A' is

(a) An ester (b) A secondary alcohol (c) A primary alcohol (d) An aldehyde

413. An organic compound dissolved in dry benzene evolved hydrogen on treatment with sodium. It is

(a) A ketone (b) An aldehyde (c) A tertiary amine (d) An alcohol

414. An alcohol, on oxidation, produces a ketone with the same number of carbon atoms. When the ketone is oxidized, it yields

an acid with a fewer number of carbon atoms. The alcohol could be a

(a) Primary alcohol (b) Secondary alcohol (c) Tertiary alcohol (d) None of these

415. An organic compound gives hydrogen on reacting with sodium metal. It also gives iodoform test and forms an aldehyde of

molecular formula OHC 42 on oxidation with acidified dichromate. The compound is

(a) OHCH 3 (b) COOHCH 3 (c) CHOCH 3 (d) OHHC 52

416. A compound with molecular formula 3104 OHC is converted by the action of acetyl chloride to a compound with molecular

weight 190. The original compound has

(a) One-OH group (b) Two-OH group (c) Three-OH group (d) nO-OH group

417. Compound X has molecular formula .384 OHC It evolves 2CO with aq. XNaHCO3 reacts with 4LiAlH to give an achiral

product. The structure 'X' is

(a) COOH

OH

CHCHCH|

23 (b) OH

OCH

CHCOCH

3

| (c) COOHCH

OH

CHCH 23|

(d) H

OHCH

CHCOOCH

2

3|

418. +MgBrCH3 ,3

/3 DOH

HCHOCBHBrAOH etherMg

+

+ → → → → D is

(a) (b) (c) (d)

419. → ←+

+

OHA

OH

moltwoMgBrCHB 3

3

3 )( OOH

CH

CHCCH

3

3|

, B is

(a) 323)( CHCOCHCH (b) 2323 )|()( H

OH

CCCHCH (c) 2323 )()( CHCHCOCHCH (d) 2323 )|

()( H

OH

CCHCHCHCH

420. ← C → A

Schemes A, B, C are

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

421. ,3

4

BCrO

AOHAcKMnOAlkaline

Cold → → A and B are

(a) , (b) ,

(c) , (d) No formation of A and B

422. ← 4NaBHB CHCHOCH = ,/2 APtH → A and B are

(a) ,22 CHOCHCH OHCHCHCH 2= (b) ,222 OHCHCHCH

OHCHCHCH 2=

O

H3C CH2OH CH3

CH2OH

CH3

CH3

OH

CH2OH

OH CH2CH3 CH2CH2OH

OH

CH=CH2

CHCH3

B

CH3

CH3 OH

OH

CH3 OH

OH

CH3 OH

OH

CH3

OH

CH3 OH

O

CH3 O

O

(c) OHCHCHCH 2= in both cases (d) ,222 OHCHCHCH in both cases

423. ,/2 AHNaOHI → → → ∆

∆

+ A is

(a) (b) (c) (d)

424. ,3

/ AOH

HCHOetherMg

+ → → A is

(a) (b) (c) (d)

425. ,2233 OHCHCHCHOHARMgBr →+

+ R and A are

(a) −23CHCH and HCHO (b) −3CH and 22 H

O

CHC − (c) Both are correct (d) None is correct

426. ./.2

)(.122

3

22

62 XCHCHOH

YOHOH

excessHB

− → ←

+ X and Y are

(a) , (b) II, I

(I) (II)

(c) I in both case (d) II in both case

427. ,3

3

|2

|2

AOH

MgBrCH

CHCH

OHOH

+ → →

−

A is

(a) (b) (c) (d)

428. ,||

32 /23 ACHCCH

O

CCH HICHNaNHOHHO → → →≡+

A is

(a) 32223

||CHCHCHCH

O

CCH (b) 32223

||CHCHCH

O

CCHCH (c) 323

||CCHCCH

O

CCH ≡ (d) 323

||CHCHHCCH

O

CCH =

429. Glycerol ,4 BHClOAKHSO → → A and B respectively are

(a) H

O

C

OH

CHH

Cl

CH

O

CCHCH||

||,

||22 = (b) H

O

C

Cl

CH

OH

CHH

O

CCHCH||

||,

||22 =

CH3

OH O

O

OH

O

C

O

OH C

O

OCH3 C

O

Cl Br

Br CH2OH Cl CH2OH HOH2C CH2OH OHC CHO

HOH2C CH2OH H3C CH3

HO OH

CHO

O

CH

O

OH

CH3

CH

OH

OH

CH3

H3C

CHO

HO CH3

CH

HO

O

O

CH3

CH2

CH2

(c)

Cl

CHCHCHCHOCHCH

OH

2323 , (d) CHOCH

ClO

CHH

O

CCHCH 222|

,||

=

430. When phenol is reacted with 3CHCl and NaOH followed by acidification, salicylaldehyde is obtained. Which of the

following species are involved in the above mentioned reaction as intermediate [DCE 2000]

(a) (b) (c) (d) All of these

431. When phenol is allowed to react with 2Br in (i) 2CS solution and (ii) in aqueous solution, the resulting compounds are

(a) (i) 2, 4, 6-tribromophenol and (ii) o- and p-bromophenol

(b) (i) m-bromophenol and (ii) 2, 3, 4-tribromophenol

(c) (i) o- and p-bromophenol and (ii) 2, 4, 6-tribromophenol

(d) (i) o- and m-bromophenol and (ii) 2, 3, 4-tribromophenol

432. Assertion (A): Phenol is more reactive than benzene towards electrophilic substitution reaction.

Reason (R) : In the case of phenol, the intermediate carbocation is more resonance stabilized. [IIT Screening 2002]

(a) Both A and R are true and R is a correct explaination of A (b) Both A and R are true but R is not a correct

explaination of A

(c) A is true but R is false (d) Both A and R are false

(e) A is false but R is true

433. Assertion (A): Phenol is a weak acid than ethanol.

Reason (R) : Groups with + M effect and – I effect decrease acidity at p-position [AIIMS 2002]

(a) Both A and R are true and R is a correct explaination of A

(b) Both A and R are true but the R is not a correct explaination of A

(c) A is true but R is false

(d) Both A and R are false

(e) A is false but R is true

434. When phenol reacts with chloroform and an alkali like NaOH, the compound formed is salicyldehyde. If we use pyrene in place of chloroform the product obtained is [MH CET 1999]

(a) Salicylic acid (b) Cyclohexanol (c) Phenolphthalein (d) Salicylaldehyde

435. What is the product formed in the following reaction + →+

H

NaOHCClOHHC (2)

(1)456 [KCET 1998]

(a) p-hydroxybenzoic acid (b) o-hydroxybenzoic acid (c) Benzaldehyde (d) Salicylaldehyde

436. Which of the following is most acidic [MP PET 2004]

(a) Picric acid (b) p-nitrophenol (c) m-nitrophenol (d) o, p dinitrophenol

437. One mole of phenol reacts with bromine to form tribromophenol. How much bromine is used [MP PMT 1989]

(a) 1.5 mol (b) 3 mol (c) 4.5 mol (d) 6 mol

438. What amount of bromine will be required to convert 2 g of phenol into 2, 4, 6-tribromophenol [MP PET/PMT 1998]

(a) 4.00 (b) 6.00 (c) 10.22 (d) 20.44

439. In the following compounds

The order of acidity is [IIT 1996]

(a) III >IV > I > II (b) I > IV > III > II (c) II > I > III > IV (d) IV > III > I > II

H

CCl3

O

CHCl2

O

H

CHCl |

OH

O

OH

(I)

CH3

NO2 (IV) (II

)

OH

CH3

OH

NO2

(III)

440. The increasing order of acidity among phenol, p-methylphenol, m-nitrophenol and p-nitrophenol is [CBSE 1995; RPMT 2002]

(a) m-nitrophenol, p-nitrophenol, phenol, p-methylphenol (b) p-methylphenol, m-nitrophenol, phenol, p-nitrophenol

(c) p-methylphenol, phenol, m-nitrophenol, p-nitrophenol (d) Phenol, p-methylphenol, p-nitrophenol, m-nitrophenol

441. Arrange the following in decreasing order of acidic strength. 2, 4, 6-trinitrophenol (I), 2, 4-dinitrophenol (II), p-nitrophenol (III),phenol (IV)

(a) I > II > III > IV (b) I > III > II > IV (c) IV > III > II > I (d) III > II > I> IV

442. In which case coupling takes place

(a) (b)

(c) In both cases (d) In none cases

443. Consider following statements

I : is more stable than II : is more stable than

(a) I and II both are correct (b) I and reverse of II are correct

(c) II and reverse of I are correct (d) I and II both are incorrect

444. ANO →

+2 , A can be

(a) (b) (c) (d) No SE reaction is possible

445. X can be

(a) 2Br water (b) 22 / CSBr (c) Both (a) and (b) are correct (d) None is correct

446. The compound X in the reaction is [Roorkee 1999]

(a) (b) (c) (d)

447. What is the end product in the following sequence of operations Phenol CBACo

→ → → HCl

140

CONaOH 2 [CBSE 1991; AIIMS 1999]

(a) Salicylaldehyde (b) Benzoic acid (c) Chlorobenzene (d) Salicylic acid

448. Phenol DCB OSOH → → → NaOHH/NaNO 2422 . Name of the reaction is [KCET 2003]

(a) Liebermann’s reaction (b) Phthalein fusion test (c) Reimer Tiemann reaction (d) Schotten-Baumann

reaction

N2C

l O2N OH + →base

N2C

l H3C OH + →base

NO2 H

OH

⊕

NO2 H

⊕

OH

CH3

OH

NO2

CH3

OH

NO2

CH3

OH

NO2

OH OH

Br

→ X

Cl HO

−

NO2

Cl

OH

−

NO2

ONa

COONa

COONa ONa

COOH

OCOONa

ONa

+ → → HClK XCO 3902

OH

COOH

449. Phenol CBA OOH

CCO o → → →

+22

2

AC/H

140/ (ii)

NaOH (i). In this reaction, the end product C is

(a) Salicylaldehyde (b) Salicylic acid (c) Phenyl acetate (d) Aspirin

450. . A, B, C and D are respectively are

(a) Salicylic acid, salol, aspirin and oil of winter green

(b) Salicylic acid, aspirin, salol and oil of winter green

(c) Salicylic acid, oil of winter green, salol and aspirin

(d) None is correct

451. Salol can be used as [MP PMT 1983]

(a) Antiseptic (b) Antipyretic (c) Both (a) and (b) (d) None of these

452. Substances used in bringing down the temperature in high fevers are called [Delhi PMT 1983]

(a) Pyretics (b) Antipyretics (c) Antibiotics (d) Antiseptics

453. Which one is used in the preparation of explosives [MP PMT /PET 1988]

(a) OHCH 3 (b) 2)(COOH (c) Glycerol (d) Urea

454. Glycerol as a triester present in

(a) Petroleum (b) Kerosene (c) Vegetable oil and fat (d) Naphtha

455. Wine (alcoholic beverages) contains [CPMT 1972,

77; BHU 1996; AFMC 2001]

(a) OHCH 3 (b) Glycerol (c) OHHC 52 (d) 2-propanol

456. Glycerol is not used in which of following cases

(a) Explosive making (b) Shaving soap making (c) As an antifreeze for water (d) As an antiseptic agent

457. Aspirin is also known as [CPMT 1989, 94; MP PET 1995]

(a) Methyl salicylic acid (b) Acetyl salicylic acid (c) Acetyl salicylate (d) Methyl salicylate

458. Glycerol is used in the manufacture of [SCRA 1991]

(a) Dynamite (b) Varnish (c) Paints (d) Soft drinks

459. Which is used as an antifreeze [AFMC 1992]

(a) Glycol (b) Ethyl alcohol (c) Water (d) Methanol

460. Aspirin is [Delhi PMT 1982, 83; BHU 1998]

(a) Antibiotic (b) Antipyretic (c) Sedative (d) Antiseptic

461. Tonics in general contain [MNR 1995]

(a) Ether (b) Methanol (c) Ethanol (d) Rectified spirit

462. Rectified spirit is a mixture of [Delhi PMT 1982; MP PMT 1976, 77, 96;

CPMT 1976, 77, 90; KCET 1990]

(a) 95% ethyl alcohol + 5% water (b) 94% ethyl alcohol + 4.53% water

(c) 94.4% ethyl alcohol + 5.43% water (d) 95.57% ethyl alcohol + 4.43% water

463. Glycerol is used [Kurukshetra CET 2002]

(a) As a sweetening agent (b) In the manufacture of good quality soap

(c) In the manufacture of nitro glycerine (d) In all of the above

464. Which is used in alcoholic beverages

(a) Methanol (b) Ethanol (c) Phenol (d) Glycerol

465. Denatured spirit is mainly used as a

(a) Good fuel (b) Drug

(c) Solvent in preparing varnishes (d) Meterial in the preparation of oil

466. Absolute alcohol is [Raj. PMT 1997]

(a) 100% pure ethanol (b) 95% alcohol + 5% H2O

(c) Ethanol + water + phenol (d) 95% ethanol + 5% methanol

BBaassiicc LLeevveell

Uses of Hydroxy compounds

OH BAH

KOHCCl → → ∆∆+

,,4

D

COHCH

COClCH

→ →

3

3

467. Glycerine is used in car radiators to

(a) Facilitate evaporation (b) Increase the temperature of the water in the radiator

(c) Lower the freezing point of the water in the radiator (d) Lower the viscosity of the water in the radiator

468. Cordite is a mixture of

(a) Nitroglycerine, gun cotton and vaseline (b) Borax, glycerine

(c) Carborundum and charcoal (d) Glycerol and / 4KMnO

469. Dynamite is prepared by mixing nitroglycerine with

(a) Saw dust and ammonium nitrate (b) Cellulose nitrate

(c) Saw dust alone (d) Conc. sulphuric acid

470. Grain alcohol is common name of [MP PMT 1987]

(a) Amyl alcohol (b) Ethyl alcohol (c) Methanol (d) None

471. Bakelite is a [Kerala (Engg.) 2002]

(a) Urea-formaldehyde resin (b) Phenol formaldehyde resin (c) Polyethylene (d) Artificial rubber

472. Cresol is [BHU 1996]

(a) A mixture of three cresols with little phenol (b) Used as dye for wood

(c) A soapy solution of cresols (d) Having an aldehyde group

473. Phenol is used in the manufacture of [AIIMS 1996]

(a) Bakelite (b) Polystyrene (c) Nylon (d) PVC

474. High contents of phenol is found in (a) Light oil (b) Middle oil (c) Heavy oil (d) Pitch

29. An example of a compound with the functional group – O – is [CPMT 1983]

(a) Acetic acid (b) Methyl alcohol (c) Diethyl ether (d) Acetone

30. In ethers, the C – O – C bond angle is

(a) o180 (b) o90 (c) o110 (d) o160

31. Which of the following is a simple ether [AFMC 1997]

(a) 33OCHCH (b) 352 OCHHC (c) 356 OCHHC (d) 5256 HOCHC

32. Name of 32223)( CHCHCHOHCCH −−−− is [MP PMT 1992]

(a) Isopropyl propyl ether (b) Dipropyl ether (c) Di-isopropyl ether (d) Isopropyl propyl ketone

33. Etherates are

(a) Ethers (b) Solution in ether

(c) Complexes of ethers with Lewis acid (d) Complexes of ethers with Lewis base

34. Which of the following do not contain an acyl group

(a) Acid chloride (b) Amide (c) Ester (d) Ether

35. This polyether is known as

(a) 12-crown-4 (b) 18-crown-6 (c) 8-crown-4 (d) 4-crown-8

36. Sulphuric ether is

(a) 5252 HCOHC −− (b) 33 CHOCH −− (c) 5252 HCSHC −− (d) 33 CHSCH −−

37. The compound which is not isomeric with diethyl ether is

(a) Methyl n-propyl ether (b) Butanone (c) Butan-1-ol (d) 2-methylpropan-2-ol

38. Ethers are isomeric with monohydric alcohols. Both have the general formula

(a) OHC nn 22 + (b) OHC nn 2 (c) OHC nn 42 + (d) OHC nn 22 −

39. Ether is

Basic Level

General introduction of ethers

O

O

O

O

(a) OC

H

R

= (b) OC

R

R

= (c) O

R

R

(d) OC

RO

R

=

40. Epoxides are

(a) Unsaturated ethers (b) Mixed ethers

(c) Cyclic ethers with C – C ring (d) Not ethers

41. OHC 104 is the molecular formula of diethyl ether. The metamers represented by this formula is/are

(a) 1 (b) 2 (c) 3 (d) 4

42. Crown ethers are

(a) Cyclic ethers (b) Ethers with several other functional groups

(c) Mixed ethers (d) Not ethers

43. OHHC 52 and 33OCHCH are [CPMT 1990]

(a) Position isomers (b) Functional isomers (c) Metamers (d) Chain isomers

44. The IUPAC name of 523 HOCCH is [MNR 1986]

(a) Ethoxy methane (b) Methoxy ethane (c) Ethyl methyl ether (d) Methyl ethyl ether

45. Diethyl ether may be regarded as an anhydride of

(a) OHHC 52 (b) COOHHC 52 (c) CHOHC 52 (d) 5252 HCOOCHC

46. In [18]-crown-6, the number of oxygen atoms is

(a) 18 (b) 6 (c) 12 (d) 24

47. Ether is prepared by [DPMT 76, 81, 82, 83, 84; CPMT 1976, 82, 84, 89, 2000; MP PET 1990] (a) Williamson’s synthesis (b) Wurtz’s reaction (c) Friedel Craft’s reaction (d) Hoffmann bromide reaction

48. On boiling with concentrated hydrobromic acid, phenyl ethyl ether will yield [AIIMS 1992] (a) Phenol and ethyl bromide (b) Phenol and ethane (c) Bromobenzene and ethanol (d) Bromobenzene and ethane

49. By the action of ICH3 on sodium ethoxide, we get [CPMT 1979]

(a) 33COOCHCH (b) 523 HCOCCH (c) 523 HOCCH (d) Ethyl acetate

50. Heating together of sodium ethoxide and ethyl chloride will give [CPMT 1971, 81; NCERT 1984; Roorkee 1990; MP PMT 1994]

(a) Ether (b) Ethyl alcohol (c) Acetaldehyde (d) Acetic acid

51. The compound formed when ethyl bromide is heated with dry silver oxide is [MP PET/PMT 1988] (a) Dimethyl ether (b) Diethyl ether (c) Methyl alcohol (d) Ethyl alcohol

52. Ether is formed when ethyl alcohol is heated with conc. 42SOH . The conditions are [KCET 1984]

(a) Excess of 42SOH and Co170 (b) Excess of OHHC 52 and Co140

(c) Excess of OHHC 52 and Co180 (d) Excess of conc. 42SOH and Co100

53. When a mixture of ethanol and methanol is heated in the presence of concentrated 42SOH , the resulting organic product or products is/are[Manipal MEE 1995]

(a) 523 HOCCH (b) 33OCHCH and 5252 HOCHC

(c) 523 HOCCH and 33OCHCH (d) 523 HOCCH , 33OCHCH and 5252 HOCHC

54. The reagent used for the preparation of higher ether from halogenated ethers is [Tamil Nadu CET 2001]

(a) conc. 42SOH (b) Sodium alkoxide (c) Dry silver oxide (d) Grignard reagent

55. In Williamson’s synthesis, ethoxyethane is prepared by [MP PMT 1995]

(a) Passing ethanol over heated alumina (b) Sodium ethoxide with ethyl bromide

(c) Ethyl alcohol with sulphuric acid (d) Ethyl iodide and dry silver oxide

56. Ethyl chloride is converted into diethyl ether by [CBSE 1999; CPMT 1999; BHU 2000]

O

Basic Level

Preparation of ethers

(a) Wurtz synthesis (b) Grignard reaction (c) Perkin’s reaction (d) Williamson’s synthesis

57. The products formed in the following reaction →+−− heat356 HICHOHC are [IIT 1995]

(a) IHC −56 and OHCH −3 (b) OHHC −56 and ICH −3

(c) 356 CHHC − and HOI (d) 66HC and OICH3

58. Structure of diethyl ether is confirmed by [DPMT 1985]

(a) Kolbe’s synthesis (b) Frankland’s synthesis (c) Wurtz’s synthesis (d) Williamson’s synthesis

59. The reaction, Sodium alkoxide + alkyl halide → Ether + sodium halide is called [CPMT 1990]

(a) Wurtz reaction (b) Kolbe’s reaction (c) Williamson’s synthesis (d) Perkin’s reaction

60. Which of the following pairs of reagents will not form ether

(a) COONaCHBrHC 352 + (b) ONaHCBrHC 5252 + (c) CHONaCHBrHC 2352 )(+ (d) ONaCHCHBrCH 323)( +

61. When vapours of alcohol are passed under pressure over heated 32OAl at Co250 , the product obtained is

(a) Dimethyl ether (b) Ethyl methyl ether (c) Diethyl ether (d) None of these

62. Ethanol reacts diazomethane to produce

(a) 33 CHOCH −− (b) 352 CHOHC −− (c) 5252 HCOHC −− (d) None of these

63. To prepare phenyl t-butyl ether, best synthesis is

(a) (b)

(c) → →= 42)(232 )( NaBHOAcHgCHCCH (d) None is suitable

64. Which route provides a better synthesis of ether

(a) I (b) II (c) Of equal importance (d) None of these

65. Consider the following synthesis

I : → → 4

3

2)( NaBH

OHCH

OAcHg II : →→ →+ BrCHNaOH 33 III : →→ →

−

BrCHNa

OHOH

THFBH 3

22

3

/

.

This change

3

3

3|

|

32

3|

3

CH

OCH

CHCHCHCHCHCH

CH

CHCH →= can be made by using

(a) I, II and III (b) I and II (c) I and III (d) I only

66. To convert 23 CHCHCH = into 3223 OCHCHCHCH , process given above

(a) I (b) II (c) III (d) I and II

67. Which of the following reactions can be used for the preparation of tert. butylmethyl ether

(a) →++−aNOCCHBrCH 333 )( (b)

+−+ aNOCHCClCH 333)(

(c) →+ ClCHCOHCH 333)( (d) →+ OHCHCClCH 333)(

68. An ether is more volatile than an alcohol having the same molecular formula. This is due to [AIEEE 2003]

ONa + (CH3)3C–Cl Br + (CH3)3CONa

OH

CH2 – O−

+ →I32

|

3 CHCH

Br

CHCH ,

CH2Br

+ → II32

|

3 CHCH

O

CHCH

�

Basic Level

Physical properties of ethers

AAddvvaannccee LLeevveell

(a) Dipolar character of ethers (b) Alcohols having resonance structures

(c) Inter-molecular hydrogen bonding in ethers (d) Inter-molecular hydrogen binding in alcohols

69. Ether which is liquid at room temperature is [BVP 2002]

(a) 352 OCHHC (b) 33OCHCH (c) 5252 HOCHC (d) None of these

70. The compound which has lowest boiling point among the following is (a) Diethyl ether (b) Ethanol (c) Methanol (d) Water

71. The boiling point of thio ether are ……. Than those of ethers (a) Higher (b) Lower (c) Equal (d) Nearly same

72. Inter-molecular hydrogen bonding is not present in

(a) COOHCH3 (b) OHHC 52 (c) 33OCHCH (d) 252 NHHC

73. Ether form peroxide in contact with air and light and it may cause explosion, since the boiling point of peroxide is (a) Equal to ether (b) Lower than ether (c) Higher than ether (d) None of these

74. Ether is always purified before distillation because (a) It is very poisonous (b) It is converted into explosive peroxide (c) Both (a) and (b) (d) None of these

75. Oxygen atom in ether is [MP PMT/PET 1988] (a) Very active (b) Replaceable (c) Comparatively inert (d) Active

76. Acetyl chloride does not react with [MNR 1995] (a) Diethyl ether (b) Aniline (c) Phenol (d) Ethanol

77. Diethyl ether can be decomposed by heating with [CPMT 1980, 81, 89]

(a) HI (b) NaOH (c) Water (d) 4KMnO

78. At Co0 diethyl ether reacts with gaseous HI to form [MP PMT 1989]

(a) OHIHC 252 + (b) OHCHIHC 352 + (c) OHHCIHC 5252 + (d) Only IHC 52

79. The ether that undergoes electrophilic substitution reactions is [JIPMER 2001]

(a) 523 HOCCH (b) 356 OCHHC (c) 33OCHCH (d) 5252 HOCHC

80. Methyl-terbutyl ether on heating with HI of one molar concentration gives [MP PET 1997]

(a) COHCHICH 333 )(+ (b) CICHOHCH 333 )(+ (c) ClCHICH 333 )(+ (d) None of these

81. When ether is exposed in air for sometime an explosive substance produced is [RPMT 2002;CPMT 1996] (a) Peroxide (b) TNT (c) Oxide (d) Superoxide

82. In this reaction OHXHHOCHC HIP2

Red5252 2][4 + →+ + , X is [MP PMT 2002]

(a) Ethane (b) Ethylene (c) Butane (d) Propane

83. Which of the following is obtained when 5252 HOCHC is heated with conc. 42SOH [CPMT 1996]

(a) 22 CHCH = (b) OHHC 52 (c) HSOHC 452 (d) 3223 CHCHCHCH

84. The compound which does not react with sodium is [CBSE PMT 1994]

(a) OHHC 52 (b) 33 CHOCH −− (c) COOHCH3 (d) 33 CHCHOHCH −−

85. Dimethyl ether when heated with excess HI gives [CPMT 1996; IIT 1983]

(a) ICH3 and OHCH3 (b) ICH3 and OH2

(c) ICHHC 362 + and OHCH3 (d) ICH3 and HCHO

86. Diethyl ether absorbs oxygen to form [DPMT 1984] (a) Red coloured sweet smelling compound (b) Acetic acid (c) Ether suboxide (d) Ether peroxide

87. Which of the following statements about ethers are correct (a) Peroxide is obtained in the presence of air (b) Ethers are weakly acidic (c) Ethers forms oxonium salts (d) Ethers form stable complexes with Lewis acids

88. An ethers reacts with 42SOH to form a/an

Basic Level

Chemical properties of ethers

(a) Alkyl free radical (b) Zwitter ion (c) Oxonium ion (d) Oxy anion

89. Acetic anhydride reacts with diethyl ether in the presence of anhydrous 3AlCl to give

(a) 33COOCHCH (b) 323 COOCHCHCH (c) 323 CHCOOCHCH (d) OHCHCH 23

90. Ether can be freed from peroxide by shaking with (a) Ferrous salt solution (b) Copper sulphate solution (c) Ferric salt solution (d) None of these

91. Ethers in contact with air for a long time form peroxides. The presence of peroxide can be tested by adding +2Fe ions followed by the addition of

(a) KCNS (b) 2SnCl (c) 2HgCl (d) KI

92. Diethyl ether does not react with

(a) Sulphuric acid (b) Hydrochloric acid (c) Hydroiodic acid (d) Acetic acid

93. Ethers are not distilled to dryness for fear of explosion. This is due to formation of

(a) Oxides (b) Peroxides (c) Alcohols (d) Ketones

94. Diethyl ether combines with CO under specific conditions to form

(a) Ethyl propanoate (b) Acetic acid (c) Carbon dioxide (d) Acetone

95. When diethyl ether is heated with excess of sulphuric acid, it forms

(a) Propionic acid (b) Acetic acid (c) Ethyl hydrogen sulphate (d) Ethyl alcohol

96. Ether on heating with acetyl chloride in presence of anhydrous 2ZnCl gives

(a) Ethyl alcohol (b) Ethyl chloride

(c) Ethyl acetate (d) Ethyl chloride and ethyl acetate

97. Formation of peroxide in ether can be prevented by

(a) By adding small amount of OCu2 (b) Shaking with ferrous salt solution

(c) Distilling with conc. 42SOH (d) All of the above

98. When diethyl ether is treated with chlorine in dark, it forms

(a) Perchloro diethyl ether (b) Ethyl chloride (c) Acetyl chloride (d) 1, 1-dichloro ether

99. )(422 ALiAlH

O

CHCH →+− , (A) is

(a) CHOCH3 (b) OHCHCH 23 (c) 22 CHCH = (d) OHCHOHCH 22 −

100. + →+

H

OHMgICH 2.......3 Propanol-1. The missing reagent is

(a) HCHO (b) OHHC 52 (c) ClHC 52 (d) Ethylene oxide

101. The hybrid state of central oxygen atom in ether is

(a) 2sp (b) 3sp (c) sp (d) dsp3

102. According to Lewis concept of acids and bases, ethers are

(a) Neutral (b) Acidic (c) Basic (d) Amphoteric

103. Complete combustion of ether gives

(a) OHHC 52 (b) 2CO and OH 2 (c) 42 HC (d) 22HC

104. Which is correct

(a) OHCHIHCHIHCOCH 352523 +→+−− (b) OHICHHIHCOCH 23523 2 +→+−−

(c) OHOHHCHIHCOCH 252523 2 +→+−− (d) OHHCICHHIHCOCH 523523 +→+−−

105. When an ether is treated with 52SP , it gives

(a) Thio-alcohol (b) Thio-ether (c) Thio-ester (d) Thio-acetal

106. When diethyl ether is treated with chlorine in presence of sun light, it forms

(a) ClHC 52 (b) 62HC (c) COClCH 3 (d) OClC 252 )(

107. Which of the following reactions gives an oxonium salt

(a) Ethyl alcohol + sodium metal (b) Diethyl ether + hydrochloric acid

(c) Tertiary amine + alkyl halide (d) Nitromethane + sodium metal

108. Decreasing order of reactivity of following alkyl halides in the Williamson’s ether synthesis is

BrCCHCH 233 )( (A), 22 CHCHClCH = (B), 322 CHCHClCH (C), 322 CHCHBrCH (D)

(a) B > D > C > A (b) A > B > C > D (c) D > C > B > A (d) C > D > B > A

109. )mix()()mix( anhydrous333

conc. ACOCHCHB HIHI → ←

(a) A and B are identical mixture of ICH 3 and COHCH 33 )(

(b) A and B are identical mixture of ClCH 33 )( and OHCH 3

(c) A is a mixture of ICH 3 and COHCH 33 )( and B is a mixture of OHCH 3 and ClCH 33 )(

(d) A is a mixture of OHCH 3 and ClCH 33 )( and B is a mixture of ICH 3 and COHCH 33 )(

110. The mixture of ethanol and sulphuric acid is heated in a closed flask at Co140 . The flask would then contain

(a) 42SOH and 5252 HOCHC only

(b) OH 2 , 42SOH and 452 HSOHC only

(c) OH 2 , 452 HSOHC , 5252 HOCHC and 42SOH

(d) OH 2 , 5252 HOCHC , 452 HSOHC , 42SOH and OHHC 52 only

111. The ether when treated with HI to produces [IIT 1999]

(a) I and II (b) I and III (c) I, II and III (d) All of the above

112. An organic compound of molecular formula OHC 104 does not react with sodium. With excess of HI, it gives only one type of alkyl halide.

The compound is [SCRA 2001]

(a) Ethoxyethane (b) 2-Methoxypropane (c) 1-Methoxypropane (d) 1-Butanol

113. The product (D) in the following sequence of reactions is )()()()( 3)aq(42 DCBAHC ICHNaNaOHHBr → → → →

(a) Butane (b) Ethane (c) Propane (d) Ethyl methyl ether

114. Ether can be used [CPMT 1982]

(a) As a general anaesthetic (b) As a refrigerant (c) In perfumery (d) All of the above

115. Indicate the incorrect statement

(a) Diethyl ether is used as anesthetic (b) Diethyl ether is used as a fuel

(c) Diethyl ether is an inert compound (d) Diethyl ether is insoluble in water

116. The compound which is mixed with alcohol to get a substitute for petrol is

(a) Acetaldehyde (b) Diethyl ether (c) Propanol (d) Ethanolp

O – CH2

CH2I

(I)

CH2OH

(II)

I

(III)

OH

(IV)

Basic Level

Uses of ethers

AAddvvaannccee LLeevveell

BBaassiicc aanndd AAddvvaannccee Level

Answer Sheet

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BBaassiicc aanndd AAddvvaannccee Level

Answer Sheet

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