ALCOHOLS, PHENOLS AND ETHERS

1. When ethylene oxide is reacted with 7. Which of the following has the highest
CH 3MgBr followed by hydrolysis then the solubility in water?
product formed is (a) Phenol (b) o-nitrophenol
(a) CH3OH (b) CH 3CH 2CH 2 − OH (c) p-nitrophenol (d) m-nitrophenol
OH 8. Which of the following has the highest boiling
|
(c) CH 3 CH − CH 3 (d) CH 3 − C − CH 3 point?
| | (a) Ethanol (b) Methanol
OH CH 3 (c) Ethylenoglycol (d) Glycerol

9. Which of the following is least acidic?

2. Which of the following is among phenols?
(a) o-oxylene (b) Resorcinol
(c) Anthrallic acid (d) p-benzoquinone

3. What is the I.U.P.A.C. name of

CH 3 − O − CH − CH 3 ?
| (a) CH 3 − COOH (b)
CH 3
(a) 1-Methoxy-1-methylethane
(b) 2-Methyl-2-methoxyethane
(c) 2-Metoxypropane
(d) 2-Propanone

4. Which of the following reagents can’t be used (c) (d)

for the reduction of
CH3COOH to CH3CH 2OH ? 10. Which of the following will react with
NaHCO3 to give salt, water and CO2 ?
(a) LiAlH 4 / H 2O (b) B2 H6 / H +
(c) H 2 / Pd (d) NaBH 4
5.
+
1.B2H6
CH3 − CH = CH 2 ⎯⎯⎯⎯
2.H O
2 2
(i)PCl5
→ A ⎯⎯⎯⎯
(ii)NaCN
H3O
→ B ⎯⎯⎯→ C (a) (b) CH 3 − COOH
(major)

What is C?
(a) CH 3 − CH − COOH
|
CH 3
(b) CH3 − CH 2 − CH 2 − COOH
(c) (d) Both (b) and (c)
(c) CH 3 − CH − COOH
| 11. In Victor-Meyer test the blue colouration is
COOH shown by
(d) HOOC − CH 2CH 2 − COOH (a) 1 − alcohol (b) 2 − alcohol
(c) di-ol (d) 3 -alcohol
6. Which of the following compound will form
2 -alcohol when treated with Grignard reagent 12. HBr reacts fastest with
followed by hydrolysis? (a) 2-methylpropan-2-ol (b) Propan-2-ol
O O (c) Propan-1-ol (d) Methanol
|| ||
(a) H − C − H (b) CH 3 − C − H 13. What is the result of following reaction?
O O CH3OH(aq) + NaOH(aq) ⎯⎯ →
|| ||
(c) CH 3 − C − CH 3 (d) CH 3 − C − OH (a) CH3ONa + H 2O (b) CO2 + 2H 2 + Na
O
|| 3
(c) H − C − ONa + H 2 (d) No reaction
2
14. Which of the following reagent attack on the 21. When ethyl alcohol is treated with
benzene ring in Reimer-Teimann reaction? H 2SO4at C, the product will be
(a) : CH 2 (b)  CCl2 (a) Ethyl oxonium hydrogen sulphate
(c) :CCl 2 (d) Diagram:- (b) Diethyl sulphate
(c) Ethyl hydrogen sulphate
(d) None of these
15. Which of the following group is the strongest
ring activator towards electrophilic aromatic
22. From Williamson’s synthesis, preparation of
substitution?
which of the following is possible?
(a) −OH (b) − NH 2
(a) Only symmetrical ethers
(c) −OCH 3 (d) −Cl (b) Only unsymmetrical ethers
(c) Both (A) and (B)
H2SO4
16. CH3 − CH2 − OH ⎯⎯⎯⎯ → A(Major). A is (d) None of these
410K
(a) CH 2 = CH 2 23. Which of the following produce violet colour
(b) CH3 − CH 2 − O − CH 2 − CH 3 with neutral FeCl3 solution?
(c) CH3 − CH 2 − OSO3H (a) Phenol (b) Ethanol
(d) All of these (c) Ethana (d) Alkyl halides

24. The O-H group is phenol in an electrophilic

17. CH 3 − O − CH − CH 3 + HI ⎯⎯ →A+B aromatic substitution is
| (alcohol)
(a) o-directing (b) p-directing
CH 3 (c) m-directing (d) o & p directing
Which of the following is major product A?
(a) CH 3 − OH 25. Which of the following gives negative
(b) HO − CH − CH 3 iodoform test?
| (a) CH3 − CH 2 − OH
CH 3 (b) CH3 − CH 2 − CH 2 − OH
(c) CH3 − CH 2 − OH (c) C6 H 5 − CH − CH 3
(d) CH3 − CH 2 − CH 2 − OH |
OH
18. The least reactive carboxylic acid in (d) CH 3 − CH − CH 3
esterification reaction is |
(a) CH 3COOH (b) (CH 3 )3 C − COOH OH
(c) HCOOH (d) (CH3 )CH − COOH 26. Phenol on treatment with bromine water in
the absence of a Lewis acid gives
19. Which of the following is used for the (a) o/p-bromophenol (b) m-bromophenol
fermentation of glucose to ethanol? (c) tribromophenol (d) none of these.
(a) Invertase (b) Zymase
(c) H 2SO4 (d) H 3PO4 27. In reaction of alcohols with alkali metal,
which of the following alcohols will react
20. What is the composition of an azeotropic fastest?
mixture of C2 H5OH and H 2O, known as (a) Secondary (b) Tertiary
rectified spirit? (c) Primary (d) All equally.
(a) 90% C2 H5OH + 10% H 2O 28. An organic compound (A) reacts with
(b) 95% C2 H5OH + 5% H 2O sodium metal and forms (B). On heating
(c) 5% C2 H5OH + 95% H 2O with conc. H 2SO4 (A) gives diethyl ether.
(d) 10% C2 H5OH + 90% H 2O (A) and (B) are respectively
(a) C2 H5OH and C2 H 5ONa
(b) C3H 7OH and CH 3ONa
(c) CH3OH and CH 3ONa
(d) C4 H9OH and C4 H 9ONa .
29. The compound (A) is Sodium isoprop 34. Select incorrect statement.
 (a) Reaction with Br2 and water gives 2,4,
oxide + A ⎯⎯ → 2-Ethoxy propane +
NaCl 6-tribromo phenol.
(a) C2 H 5ONa (b) C2 H5COCl (b) Reaction with dilute HNO3 gives
(c) C2 H 5Cl (d) CH 3ONa mixture of o-nitrophenol (minor) and
p-nitrophenol (major).
30. The correct order of relative acidic strength
of the following compounds is (c) Reaction with nitrating mixture gives
(a) phenol > o-nitrophenol > m-nitrophenol picric acid.
> p-nitrophenol (d) Reaction with conc. H 2SO4 at 300 K
(b) p-nitrophenol > m-nitrophenol > o-
nitrophenol > phenol gives o-phenolsulphonic acid.
(c) p-nitrophenol > o-nitrophenol > m- 35. One of the following statements regarding
nitrophenol > phenol Reimer-Tiemann reaction is false.
(d) o-nitrophenol > m-nitrophenol > p-
nitrophenol > phenol (a) Reaction of phenol with CHCl3 & KOH.
(b) CCl 2 acts as a nucleophile.
31. Phenol on sulphonation gives
(a) o-phenolsulphonic acid (c) Reaction of phenol with CCl 4 & NaOH.
(b) p-phenolsulphonic acid (d) Reaction of phenol with formaldehyde to
(c) m-phenolsulphonic acid form bakelite
(d) mixture of o- and p-phenolsulphonic
36. In which of the following first is more acidic
acids.
than second?
32. Isobutyl n-butyl ether when reacted with
cold conc. HI gives,
(a) CH3CH 2CH 2CH 2I + (CH3 )2 CHCH 2OH
(b) CH3CH 2CH 2CH 2OH + (CH 3 )2 CHCH 2I
(c) CH3CH 2CH 2CH 2 I + (CH3 )2 CHCH 2I
(a)
(d) CH3CH 2CH 2CH 2OH + (CH 3 )2 CHCH 2OH

33. The product A is

(b)

(c) ‘

(a) (b)

(d)
37. Which of the following compounds can
exist in optically active form?
(c) (d) (a) 1-Butanol (b) 2-Butanol
(c) 3-Pentanol (d) 4-Heptanol
38. Picric acid and benzoic acid can be 44. 4-Methoxy acetophenone is obtained from
distinguished by
(a) Aqueous NaHCO3
(b) Aqueous NaOH
(a)
(c) Aqueous FeCl3
(d) Aqueous Na 2CO3.

39. Dehydration of alcohol produces alkene, the (b)

reaction intermediate is
(a) Carbonium ion
(b) Carbanion
(c) Carbon free radical (c)
(d) Carbene.
40. The number of  and  -bonds present in
the molecule of carbolic acid respectively (d)
are
(a) 7, 3 (b) 2, 3 45. Which of the following is a phenol?
(c) 4, 3 (d) 13, 3 (a) Pentanoic acid (b) Phthalic acid
(c) Picric acid (d) Phosphoric acid
41. Cumene is
(a) o-methyl phenol
(b) p-cresol
(c) iso-propyl benzene
(d) phenyl-n-propane.
42. Which of the following statements is false in
case of epoxides?
(a) Epoxides are very reactive compounds
due to the ease of opening of highly strained
three membered ring.
(b) The C–O bonds in the epoxides are
weaker than in ordinary ethers.
(c) Epoxides are less stable than aliphatic
ether molecule.
(d) Epoxides are inert as compared to ethers.
43. The major product (B) formed in following
reaction is

(a) (b)

(c) (d)