ALCOHOLS,PHENOLS AND ETHERS

GIVE REASON: (3)

1.i)Bond angle in methanol is slightly less than the tetrahedral angle

ii)Bond length in phenol is slightly less than methanol
iii)Phenol has smaller dipole moment than methanol.
2.Primary and also secondary alkyl halide on treatment with aq.KOH gives ----------
3. Tertiary alkyl halide on treatment with aq.KOH undergoes ------------- and gives -----------
4. Aldehyde to primary alcohol (Write the reagents used)
5. Ketone to sec.alcohol (Write the reagents used)
6. Write reactions for Bouveault Blane reduction. (2)
7. Write hydroboration oxidation reaction of propene.(2)
8. Write the preparation of primary,secondary and tertiary alcohol using Grignard reagent.(3)
9. Convert i)ethanal to ethanol ii) Propanone to 2-propanol (2)
10. Convert i)ethanoic acid to ethanol ii) ethanol ,methanol from ester. (2)
11. Write the preparation of phenol from chlorobenzene(Dow’s process) benzene,aniline and
cumene (4)
12. (5 m)

13. Write the mechanism for the acid catalysed hydration of an alkene. (3)
14. Convert i) sodium salicylate to phenol ii) benzene diazonium salt to phenol iii) benzene to
phenol
15. (3m)

16. Arrange the following in the increasing order of boiling point. Give reason (2)
Butan -2-ol, 2-methyl propan-1-ol, butan-1-ol,2-methyl propan-2-ol
17. Ethoxy ethane has less boiling point than ether. Give reason (1)
18. Give reactions to prove that alcohols and phenols are acidic in nature. (3)
19. Covert salicylic acid to aspirin (1)
20. How can you identify the formation of primary,sec,ter,alcohol using lucas reagent.
21. Write the dehydration reactions of alcohol using phosphoric acid to prepare alkene.(3)
22. Write the mechanism of dehydration of ethanol (3)
23. Write the mechanism for the reaction of ether with HI(3)
24. Write dehydrogenation reactions of three types of alcohol using Cu
25. Convert i)isopropyl alcohol to acetic acid ii) Pentan-2-ol to propionic acid iii)2-propanol to
propanone (3)
26.Write acylation reactions of phenol.(2)
27. Convert i) phenol to aniline ii) phenol to methane (2)
28. Write i)benzoylation (Schotten baumann )ii) Friedel crafts alkylation iii) Kolbe’s
iv) Reimer-Tiemann reaction of phenol .
29. Oxidation of alcohol into aldehyde is arrested at this stage by some reagents. Name them(1)
30. Write the reactions: phenol with i) dil HNO3 ii)con. HNO3 iii)Br2 iv) Br2/CS2 v)Zn dust
vi)oxidation
31. Write the structures of the major products expected from the following reactions:
(a) Mononitration of 3-methylphenol (b) Dinitration of 3-methylphenol
(c) Mononitration of phenyl methanoate
32. Give structures of the products you would expect when each of the following alcohol reacts
with
(a) HCl –ZnCl2 (b) HBr and (c) SOCl2.
(i) Butan-1-ol (ii) 2-Methylbutan-2-ol
33. Predict the major product of acid catalysed dehydration of
(i) 1-methylcyclohexanol and (ii) butan-1-ol
34. Ortho and para nitrophenols are more acidic than phenol. Draw the resonance
structures of the corresponding phenoxide ion
35. Write the mechanism of dehydration of alcohol using sulphuric acid to give alkene(3)
36. Write reaction for coupling reaction and also for the preparation of phenolphthalein
37.Give reaction for ferric chloride test and Libermann’s test for phenol.
38. Write the condition for iodoform test. Give chemical reaction to support.
39. Distinguish between primary,secondary and tertiary alcohol
40. Distinguish between phenol and alcohol
41. Interconversions of alcohol(11/46 &47)
42. Solved examples (from 11/48 …..)
43. Write Williamson’s synthesis reaction.
44. Williamson’s synthesis prefer primary alkyl halide and ter.alkoxide ,but not ter.halide
and primary alkoxide.Give rreason and give chemical reactions to support this
statement.
45. Convert phenol to methyl phenyl ether.
46.

47. Learn All book back questions & conceptual questions.

48. Out of ter.butyl alcohol and n-butyl alcohol,which one will undergo acid catalysed
dehydration faster and why?
49. Arrange the following compounds in the increasing order of their property indicated.
i)P-nitrophenol,ethanol,phenol(acidic character) ii) propanol,propane,propanal(boiling
point)
50. Ter.butyl chloride on heating with sodium methoxide gives 2-methyl propene instead of
ter butyl methyl ether. Account for this statement.

ALCOHOLS,PHENOLS AND ETHERS – REASONING OUT

(BOOK AND BOOK BACK )

1. Bond angle in alcohol is less is slightly less than the tetrahedral angle.
2. The Carbon-Oxygen bond length in phenol is slightly less than that in methanol.
3. The bond angle in ether is slightly greater than the tetrahedral angle.
4. Order of acidity of alcohols is 10 > 20 > 30
5. Alcohols are weaker acid than water.
6. Alcohols and phenols are soluble in water.
7.Alcohols and phenols are bronsted acid.
8.Alcohols can act as bronsted base.
9. o-Nitro phenol is steam volatile and p-nitro phenol is less volatile.
10. Polarisation of bromine molecule in phenol takes place even in the absence of lewis
acid.
11. Dehydration of 20 & 30 alcohol form alkene and not ether.
12. In phenol,electrophilic substitution favours at ortho and para position .
13. Propanol has higher boiling point than butane
14. o-Nitrophenol is more acidic than o-methoxy phenol
15. Ethanol has higher boiling point than methoxy methane
MTG
16. Phenol is more acidic than ethanol.
17. Ethanol has higher boiling point than methanol
18. Acid catalysed dehydration of tert.butanol is faster than that of n-butanol.
19. Phenol undergoes electrophilic substitution easily than benzene.
20. Ter.butyl chloride on heating with sodium methoxide gives 2-methyl propene
Instead of ter.butyl methyl ether
TOGETHER
21. Ortho and para nitro phenols are more acidic than phenol
22. Phenols does not give protanation reaction readily.
23. phenyl methyl ether reacts with HI to give phenol and methyl iodide and not
iodo benzene and methyl alcohol
24. (CH3)3 C-O- CH3 reacts with HI gives (CH3)3 C-I and methyl alcohol as main products and
not
(CH3)3 C-OH and CH3-I
25. Dipole moment of phenol is smaller than that of methanol.
26. Di-ter.butyl ether can’t be prepared by Williamson synthesis.
27. In Kolbe’s reaction , instead of phenol , phenoxide ion is treated with CO 2
28. p-Nitro phenol is more acidic than p-methyl phenol

MODERN ABC
29. 0rtho and para nitro phenol is more acidic than meta nitro phenol.- 1175
30. 0rtho nitro phenol is slightly weaker acid than p- nitro phenol
31. Cresols are weaker acid than phenol
32. o and p – cresols are less acidic than m-cresols
33. m-aminophenol is more acidic than o and p amino phenol
34. Acidic strength: m-methoxy phenol > o-methoxy phenol> p-methoxy phenol
35. Sodium metal is used to dry diethyl ether and benzene and not to dry ethanol. 1195
36. Out of phenol and benzene,which can be nitrated easily. 1196
37.Phenol has smaller dipole moment than methanol.
38. Alcohols are easily protonated than phenol.
39. Alkoxide ion is more basic than hydroxide ion
40. Order of acidity o-cresol < phenol <o-nitro phenol (Exempler)
41. –OH group in phenols more strongly held as compared to –OH group in alcohols
42. O=C=O non polar while R-O-R is polar---1236
43. The reactivity of all the three classes of alcohols with Lucas reagent is different .
44. In Kolbe’s reaction, instead of phenol , phenoxide ion is treated with CO2
45. Ter.butyl ether can’t be prepared by Williamson synthesis. 1236