204

$IBQUFS "MDPIPMT
1IFOPMT

"% BOE
&UIFST
1. The heating of phenyl methyl ether with HI (a) –COOH (b) –CHCl2
(c) –CHO (d) –CH2Cl (2015)
produces
(a) iodobenzene (b) phenol 5. Which of the following reaction(s) can be used
(c) benzene (d) ethyl chloride. for the preparation of alkyl halides?
(NEET 2017)
(I) CH3CH2OH + HCl o
Anh. ZnCl
2

2. Which one is the most acidic compound? (II) CH3CH2OH + HCl ⎯→

(III) (CH3)3COH + HCl ⎯→
0) 0) (IV) (CH3)2CHOH + HCl o
Anh. ZnCl2

(a) (I) and (II) only

(a) (b) (b) (IV) only
(c) (III) and (IV) only
(d) (I), (III) and (IV) only (2015)
/0
6. The reaction,
&+
0) &+ & 21D  &+&+&O 1D&O
0)
0/ /0
&+ &+
(c) (d) &+ & 2 &+ &+
/0 &+
$) is called
(NEET 2017) (a) Etard reaction
3. The reaction (b) Gattermann-Koch reaction
(c) Williamson synthesis
0) /B) 0o/B .Fo* (d) Williamson continuous etherification
process. (2015, Cancelled)
.F
0 7. Among the following sets of reactants which
one produces anisole?
can be classified as (a) CH3CHO ; RMgX
(a) dehydration reaction (b) C6H5OH ; NaOH ; CH3I
(b) Williamson alcohol synthesis reaction (c) C6H5OH ; neutral FeCl3
(c) Williamson ether synthesis reaction (d) C6H5CH3 ; CH3COCl ; AlCl3 (2014)
(d) alcohol formation reaction.
8. Which of the following will not be soluble in
(NEET-I 2016)
sodium hydrogen carbonate?
4. Reaction of phenol with chloroform in (a) 2,4,6-Trinitrophenol
presence of dilute sodium hydroxide finally (b) Benzoic acid
introduces which one of the following (c) o-Nitrophenol
functional group? (d) Benzenesulphonic acid (2014)
Alcohols, Phenols and Ethers 205

9. Among the following ethers, which one will 

produce methyl alcohol on treatment with hot

concentrated HI? 




›
(a) 

(b) 
 

Š—
(b) 


 


(c) CH3—CH2—CH2—O—CH3 ›
(d)


(c) 
 

Š—
(NEET 2013) 

10. Number of isomeric alcohols of molecular 

 


formula C6H14O which give positive iodoform

test is ›
(a) three (b) four 

(c) five (d) two

(Karnataka NEET 2013) (d) 
 

Š—
11. In the following sequence of reactions 





(2011)
the end product (C) is ›
(a) acetone (b) methane 14. Given are cyclohexanol (I), acetic acid (II),
(c) acetaldehyde (d) ethyl alcohol 2,4,6-trinitrophenol (III) and phenol (IV). In these
(2012) the order of decreasing acidic character will be
(a) III > II > IV > I (b) II > III > I > IV
12. Which of the following compounds can be
(c) II > III > IV > I (d) III > IV > II > I
used as antifreeze in automobile radiators? ( 2010)
(a) Methyl alcohol (b) Glycol
(c) Nitrophenol (d) Ethyl alcohol 15. Which of the following compounds has the
(Mains 2012) most acidic nature?
13. In the following reactions,
(a) (b)

(i)
(c)

(d) (2010)
(ii)
› Š›”
 ’— Š‹œŽ—ŒŽ  
˜ ™Ž›˜¡’Ž Š“˜› ’—˜›
™›˜žŒ ™›˜žŒ 16. Among the following four compounds
(i) Phenol
the major products (A) and (C) are respectively (ii) Methyl phenol

(iii) Meta-nitrophenol
(iv) Para-nitrophenol
(a) 
 

Š—
206

The acidity order is (b) CH3 – CH2 – O – SO3H

(a) (iv) > (iii) > (i) > (ii) (c) CH3CH2OH
(b) (iii) > (iv) > (i) > (ii) (d) CH2 CH2 (2009)
(c) (i) > (iv) > (iii) > (ii)
(d) (ii) > (i) > (iii) > (iv) (2010) 21. HOCH2·CH2OH on heating with periodic acid
gives
17. When glycerol is treated with excess of HI,
it produces CHO
(a) 2-iodopropane (b) allyl iodide (a) 2HCOOH (b)
CHO
(c) propene (d) glycerol triiodide
(Mains 2010) H
(c) 2 C O (d) 2CO2 (2009)
18. Following compounds are given H
(i) CH3CH2OH (ii) CH3COCH3 22. Consider the following reaction:
(iii) (iv) CH3OH Zn dust CH Cl
Phenol X Anhyd.3AlCl Y
3
Alkaline KMnO4
Z
Which of the above compound(s), on being the product Z is
warmed with iodine solution and NaOH, will (a) benzaldehyde (b) benzoic acid
give iodoform? (c) benzene (d) toluene (2009)
(a) (i), (iii) and (iv) (b) Only (ii)
23. In the reaction:
(c) (i), (ii) and (iii) (d) (i) and (ii)
(Mains 2010) CH3
heated
19. Match the compounds given in List I with CH3 – CH – CH2 – O – CH2 – CH3 + HI
their characteristic reactions given in List II.
Select the correct option. Which of the following compounds will be
List I List II formed?
(Compounds) (Reactions)
A. CH3(CH2)3NH2 (i) Alkaline hydrolysis (a) CH3 – CH – CH3 + CH3CH2OH
B. CH3C CH (ii) With KOH (alcohol)
CH3
and CHCl3 produces
bad smell
(b) CH3 – CH – CH2OH + CH3CH3
C. CH3CH2COOCH3 (iii) Gives white ppt.
with ammoniacal CH3
AgNO3
D. CH3CH(OH)CH3 (iv) With Lucas reagent
CH3
cloudiness appears
after 5 minutes (c) CH3 – CH – CH2OH + CH3CH2I
(a) A-(ii), B-(i), C-(iv), D-(iii)
(b) A-(iii), B-(ii), C-(i), D-(iv) CH3
(c) A-(ii), B-(iii), C-(i), D-(iv)
(d) CH3 – CH – CH2 – I + CH3CH2OH
(d) A-(iv), B-(ii), C-(iii), D-(i)
(Mains 2010) (2007)
20. Consider the following reaction: 24. The general molecular formula, which represents
PBr3 alc. KOH the homologous series of alkanols is
Ethanol X Y (a) CnH2n+2O (b) CnH2nO2
(i) H2SO4, room temperature (c) CnH2nO (d) CnH2n + 1O
Z
(ii) H2O, heat (2006)
the product Z is 25. Ethylene oxide when treated with Grignard
(a) CH3CH2 – O – CH2 – CH3 reagent yields
Alcohols, Phenols and Ethers 207

(a) primary alcohol 32. Iodoform test is not given by

(b) secondary alcohol (a) ethanal (b) ethanol
(c) tertiary alcohol (c) 2-pentanone (d) 3-pentanone
(d) cyclopropyl alcohol. (2006) (1998)
26. The major organic product in the reaction is 33. Reaction of CH2 – CH 2 with RMgX leads to

CH3 – O – CH(CH3)2 + HI ® products O

(a) CH3I + (CH3)2CHOH the formation of
(b) CH3OH + (CH3)2CHI (a) RCH2CH2OH (b) RCHOHCH3
(c) ICH2OCH(CH3)2 (d) CH3OC(CH3)2 R
(c) RCHOHR (d) CHCH2OH
R
I
(1998)
(2006)
27. Which one of the following compounds is 34. Which one of the following compounds is
most acidic? resistant to nucleophilic attack by hydroxyl
(a) Cl – CH2 – CH2 – OH ions?
(a) Diethyl ether (b) Acetonitrile
OH OH (c) Acetamide (d) Methyl acetate
(b) (c) (1998)
NO2
35. When 3,3-dimethyl-2-butanol is heated with
OH H 2SO4, the major product obtained is
(d) (2005) (a) 2,3-dimethyl-2-butene
CH3 (b) cis and trans isomers of 2,3-dimethyl-2-butene
(c) 2,3-dimethyl-1-butene
28. Which one of the following will not form a (d) 3,3-dimethyl-1-butene. (1995)
yellow precipitate on heating with an alkaline
solution of iodine? 36. On heating glycerol with conc. H 2SO 4 , a
(a) CH3CH(OH)CH3 compound is obtained which has bad odour.
(b) CH3CH2CH(OH)CH3 The compound is
(c) CH3OH (a) acrolein (b) formic acid
(d) CH3CH2OH (2004) (c) allyl alcohol
(d) glycerol sulphate. (1994)
29. n-propyl alcohol and isopropyl alcohol can
be chemically distinguished by which reagent 37. The compound which does not react with
sodium is
(a) PCl5 (b) reduction
(a) CH3COOH (b) CH3CHOHCH3
(c) oxidation with potassium dichromate
(c) C2H5OH (d) CH3OCH3
(d) ozonolysis. (2002)
(1994)
30. When phenol is treated with CHCl3 and NaOH,
38. Ethanol and dimethyl ether form a pair of
the product formed is
functional isomers. The boiling point of
(a) benzaldehyde (b) salicylaldehyde ethanol is higher than that of dimethyl ether,
(c) salicylic acid (d) benzoic acid. due to the presence of
(2002) (a) H-bonding in ethanol
31. Which of the following is correct? (b) H-bonding in dimethyl ether
(a) On reduction, any aldehyde gives (c) CH3 group in ethanol
secondary alcohol. (d) CH3 group in dimethyl ether. (1993)
(b) Reaction of vegetable oil with H2SO4 gives 39. Increasing order of acid strength among
glycerine. p-methoxyphenol, p-methylphenol and
(c) Alcoholic iodine with NaOH gives iodoform. p-nitrophenol is
(d) Sucrose on reaction with NaCl gives invert (a) p-nitrophenol, p-methoxyphenol,
sugar. (2001) p-methylphenol
208

(b) p-methylphenol, p-methoxyphenol, 46. When phenol is treated with excess bromine
p-nitrophenol water. It gives
(c) p-nitrophenol, p-methylphenol, (a) m-bromophenol
p-methoxyphenol (b) o-and p-bromophenols
(d) p-methoxyphenol, p-methylphenol, (c) 2,4-dibromophenol
p-nitrophenol. (1993) (d) 2,4,6-tribromophenol. (1992)
40. Which one of the following on oxidation gives 47. The compound which reacts fastest with Lucas
a ketone? reagent at room temperature is
(a) Primary alcohol (a) butan-1-ol
(b) Secondary alcohol (b) butan-2-ol
(c) Tertiary alcohol (c) 2-methylpropan-1-ol
(d) All of these. (1993) (d) 2-methylpropan-2-ol. (1989)
41. What is formed when a primary alcohol 48. Which one of the following compounds will
undergoes catalytic dehydrogenation? be most readily attacked by an electrophile?
(a) Aldehyde (b) Ketone (a) Chlorobenzene (b) Benzene
(c) Alkene (d) Acid (1993) (c) Phenol (d) Toluene
42. When hydrochloric acid gas is treated with (1989)
propene in presence of benzoyl peroxide, it 49. Propene, CH3CH==CH2 can be converted into
gives 1-propanol by oxidation. Indicate which set
(a) 2-chloropropane of reagents amongst the following is ideal
(b) allyl chloride for the above conversion?
(c) no reaction (a) KMnO4 (alkaline)
(d) n-propyl chloride. (1993) (b) Osmium tetroxide (OsO4/CH2Cl2)
43. How many isomers of C5H11OH will be primary (c) B2H6 and alk. H2O2
alcohols? (d) O3/Zn. (1989)
(a) 5 (b) 4 50. Phenol is heated with CHCl3 and aqueous KOH
(c) 2 (d) 3 (1992) when salicylaldehyde is produced. This
44. Methanol is industrially prepared by reaction is known as
(a) oxidation of CH4 by steam at 900ºC (a) Rosenmund’s reaction
(b) reduction of HCHO using LiAIH4 (b) Reimer-Tiemann reaction
(c) reaction HCHO with a solution of NaOH (c) Friedel-Crafts reaction
(d) reduction of CO using H2 and ZnO–Cr2O3. (d) Sommelet reaction. (1989,88)
(1992)
51. Lucas reagent is
45. HBr reacts fastest with (a) conc. HCl and anhydrous ZnCl2
(a) 2-Methylpropan-1-ol (b) conc. HNO3 and hydrous ZnCl2
(b) Methylpropan-2-ol (c) conc. HCl and hydrous ZnCl2
(c) propan-2-ol (d) conc. HNO3 and anhydrous ZnCl2.
(d) propan-1-ol. (1992) (1988)

Answer Key

1. (b) 2. (c) 3. (c) 4. (c) 5. (d) 6. (c) 7. (b) 8. (c) 9. (a) 10. (b)
11. (d) 12. (b) 13. (b) 14. (a) 15. (b) 16. (a) 17. (a) 18. (c) 19. (c) 20. (c)
21. (c) 22. (b) 23. (c) 24. (a) 25. (a) 26. (a) 27. (c) 28. (c) 29. (c) 30. (b)
31. (c) 32. (d) 33. (a) 34. (a) 35. (a) 36. (a) 37. (d) 38. (a) 39. (d) 40. (b)
41. (a) 42. (a) 43. (b) 44. (d) 45. (b) 46. (d) 47. (d) 48. (c) 49. (c) 50. (b)
51. (a)