CHAPTER 11

ALCOHOL,PHENOL AND ETHER

I.Write chemical equations for the following name reactions.

1. Riemer Tiemann reaction

2. Williamson’s synthesis

3. Kolbe’s reaction

4. Hydroboration –oxidation reaction

II. Write IUPAC names for the following compounds:

5. CH3-O-CH2-CH2-CH3

6. CH2=CH-CH(OH)CH2-CH2-CH3

7.

8.

9. CH3-O-CH2-CH(OH) -CH3

10.

III. Give reason for the following or / Account the following

11. Phenols are much more acidic than alcohols. Why?

12. The boiling points of ethers are much lower than those of the alcohols of comparable
molar masses.

13. Ortho-nitrophenol is more acidic than ortho-methoxyphenol.

14. Alcohols are comparitively more soluble in water than hydrocarbon of comparable
molecular masses.

15. Bond angle C-O-C in ethers is slightly higher than the tetrahedral angle (1090280)

16. O-nitrophenol has lower boiling point than p-nitrophenol.

17. Alcohols have higher boiling point than corresponding hydrocarbons. Or

propanol has higher boiling point than that of butane
 18. Boiling point of ethanol is higher than that of methanol

19. Acid catalysed dehydration of t-butanol is faster than that of n-butanol .

20. The boiling point of ethers are lower than isomeric alcohols. Or
Boiling point of ethanol is higher than that of methoxymethane

21. Phenyl methyl ether reacts with HI to give phenol and methyl iodide and not
iodobenzene and methyl alcohol . why?

22. (CH3)3C-Br on reaction with NaOCH3 gives an alkene instead of ether.

IV. How will you distinguish the following pair of compounds ? OR Write a chemical test to
distinguish the following compounds.
23. 1-propanol and 2-propanol

24. Phenol and benzoic acid

25. Propanol and t-butylalcohol

 26. 2-pentanol and 3-pentanol

27. Propan-2-ol and 2-methylpropan-2-ol

28. Ethanol and methanol

V. Arrange the following in the increasing order of property indicated in brackets

29. p-cresol, p-nitrophenol, phenol (acidic strength)

30. 2-methylpropan-2-ol, butan-1-ol, propan-2-ol (rate of acid catalysed dehydration)

31. CH3CH2OH, CCl3CH2OH, CF3CH2OH ( Acid strength)

32. Pentan-1-ol, butan-1-ol, ethanol, propan-1-ol, methanol (boiling point)

33. Pentan-1-ol, n-butane, pentanal, ethoxyethane (boiling point)

34. Propan-1-ol, 2,4,6-trinitrophenol, 4-nitrophenol, 3-nitrophenol, 3,5 dinitrophenol,

phenol, p-cresol, 4-methoxyphenol (Acid strength)
VI. Other miscellaneous questions
35. Write the preparation of phenol from benzene using oleum and sodium hydroxide. OR
You are given benzene, Conc.H2SO4, NaOH and dil HCl.Write the preparation of phenol
using these reagents.

36. Write the structures of the products when butan-2-ol reacts with (i) CrO3 (ii) SOCl2

37. Write the equations for the following reactions:

i) Bromine in CS2 with phenol
ii) Treating phenol with CHCl3 in presence of NaOH
iii) Anisole react with HI
iv) nitration of anisole
v) phenol reaction with dilute nitric acid
38. Write the equation involved in the acetylation of salycylic acid.

39. O-nitrophenol or p-nitrophenol, which is more volatile and why?

40. How is toluene obtained from phenol?

41. Name the reagents used in the following reactions :

i) bromination of phenol to 2,4,6- tribromophenol
ii) butan-2-one to butan-2-one
iii) oxidation of primary alcohol to carboxylic acid

42. Write the major product of the following reaction and explain why/
 43. The following is not an appropriate reaction for the preparation of t-butyl ethyl ether.

i) What would be the major product of this reactionand why?

ii) Write a suitable reaction to prepare t-butyl ethyl ether.

44. Write chemical equation for the preparation of Aspirin starting from phenol.

VII. Complete the following chemical equations:

45. CH2 == CH—CH2 OH

46.

47.

48. CH3 – CH = CH2 + H2O

49.

50.

51.
 52.

53.

54. CH3CH2CH2-O- CH3 + HBr →

IX. How will you carry out the following conversions

55. Ethanol to Ethene

56. Propanol to 2-methylpropan-2-ol

57. Propene to Propan-2-ol

58. Phenol to 2,4,6-trinitrophenol(picric acid)

59. Benzyl chloride to benzyl alcohol

60. Methyl magnesium bromide to 2-methylpropan-2-ol

61. Butanol to butanoicacid

62. Propanol to propan-2-ol

63. Phenol to toluene

 64. Ethanol to ethane-1,2-diol

65. Phenol to acetophenone

66. Phenol to benzoquinone

67. Phenol to anisole

68. Aniline to phenol

69. Anisole to p-bromoanisole

70. Cumene to phenol

71. Chlorobenzene to phenol

72. An organic compound A with molecular formula C6H6O gives a characteristic colour
with aqueous solution of FeCl3. When A is treated with CO2 and NaOH at 410 K under
pressure, it gives compound B,which upon acidification gives compound C. Compound
C reacts with acetyl chloride to give D ,which is a popular pain killer. Deduce the
structures of A,B, C and D with equations.

X. Write the mechanism of the following reaction:

73. Write the main product when Ethanol heated with conc.H2SO4 at 443 K . Write its
mechanism. Or
Write the mechanism to convert ethanol to ethene.
74. Write the main product when Ethanol heated with conc.H2SO4 at 413 K . Write its
mechanism. Or
Write the mechanism to convert ethanol to ethoxyethane.

75. Write the mechanism to convert ethene to ethanol.

76. Write the mechanism for acid catalysed hydration of propene.