Sure Shot Questions 2024
Chapter – 07
Alcohols, Phenols and Ethers
Questions
1. Write the IUPAC name of the given compound:
2. Write the preparation of phenol from cumene.
3. Write the structures of the main products in the
following reactions:
4. Write the product(s) in the following reactions:
5. Give one chemical test to distinguish between the
following:
(a) Phenol and 1-propanol
(b) Ethanol and dimethyl ether
(c) 1-propanol and 2-methyl-2-propanol
6. Write the equations for the following reactions:
(a) Salicylic acid is treated with acetic anhydride
in the presence of conc. H2SO4.
(b) tert-Butyl chloride is treated with sodium
ethoxide.
(c) Phenol is treated with chloroform in the
presence of NaOH.
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7. Write the IUPAC name of the given compound:
8. Give the strcture and IUPAC name of the product
formed when propanone is reacted with
methylmagnesium bromide followed by hydrolysis.
9. Write the structures of the main products in the
following reactions:
10. Give simple chemical tests to distinguish between
the following pairs of compounds:
(i) Ethanol and phenol
(ii) Propanol and 2-methylpropan – 2 –ol.
11. How do you convert
(i) phenol to toluene?
(ii) formaldehyde to ethanol?
12. Explain why p-nitrophenol is more acidic than
phenol.
13. Ortho and para - nitrophenols are more acidic than
phenol. Draw the resonance structures of the
corresponding phenoxide ions.
14. Write the main product (s) in each of the following
reactions:
15. (a) Arrange the following compounds in the
increasing order of their acid strength:
𝑝 − 𝑐𝑟𝑒𝑠𝑜𝑙, 𝑝 − 𝑛𝑖𝑡𝑟𝑜𝑝ℎ𝑒𝑛𝑜𝑙, 𝑝ℎ𝑒𝑛𝑜𝑙
(b) Write the mechanism (using curved arrow
notation) of the following reaction:
Page 1
 𝐻3 𝑂 +
𝐶𝐻2 = 𝐶𝐻2 → 𝐶𝐻3 − 𝐶𝐻2+ + 𝐻2 𝑂
16. Answer the following question:
(i) Dipole moment of phenol is smaller that the of
methanol. Why?
(ii) In Kolbe’s reaction, instead of phenol,
phenoxide ion is treated with carbon dioxide.
Why?
17. Explain the following behaviours:
(i) Alcohols are more soluble in water than the
hydrocarbons of comparable molecular masses.
(ii) Ortho-nitrophenol is more acidic than ortho-
methoxyphenol.
(iii) Cumene is a better starting material for the
preparation of phenol.
18. Write the main products (s) in each of the
following reactions:
19. How do you convert the following?
(i) Phenol to anisole
(ii) Propan – 2- oI to 2- Methyl propan – 2- oI
(i) Aniline to phenol.
20. A compound ‘A’ having molecular formula 𝐶4 𝐻10 𝑂
is found to be soluble in concentrated sulphuric
acid. It does not react with sodium metal or
potassium permanganate. On heating with excess
of HI, it gives a single alkyl halide. Deduce the
structure of compound A and explain all the
reactions.
21. Give reasons for the following:
(a) Protonation of phenols is difficult whereas
ethanol easily undergoes protonation.
(b) Boiling point of ethanol is ethanol is higher
than that of dimethyl ether.
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22. How do you convert the following:
(i) Phenol to anisole
(ii) Propan-2-ol to 2-methylpropan-2-ol
(ii) Aniline to phenol
23. Explain why is orthonitrophenol more acidic than
orthomethosyphenol?
24. Give Reasons:
(i) Relative ease of dehydration of alcohols is 30 >
20 > 10 .
(ii) 𝑜 − 𝑛𝑖𝑡𝑟𝑜𝑝ℎ𝑒𝑛𝑜𝑙 is more acidic than 𝑜 −
𝑚𝑒𝑡ℎ𝑜𝑥𝑦𝑝ℎ𝑒𝑛𝑜𝑙.
25. (a) Answer the following questions.
(i) Among HI, HBr, HCI, HI is most reactive towards
alcohols. Why?
(ii) Of the two alcohols: (a) 𝐶𝐻2 = 𝐶𝐻 −
𝐶𝐻2 𝑂𝐻 𝑎𝑛𝑑 (𝑏)𝐶𝐻2 = 𝐶𝐻 − 𝐶𝐻2 − 𝐶𝐻2 𝑂𝐻,
which one will react more easily with conc. HCI in
the presence of 𝑍𝑛𝐶𝐼2 ?
(b) Arrange the following compounds in the
increasing order of their acid strengths: 4-
nitrophenil, phenol, 2,4,6-trinitrophenol
26. How are the following conversions carried out?
(i) Propene → Propan – 2 - oI
(ii) Benzyl chloride → Benzyl alcohol
(iii) Ethyl magnesium chloride → Propan – 1- oI
(iv) Methyl magnesium bromide bromide → 2-
Methyl-propan -2-oI
27. Arrange the following sets of compounds in order
of their increasing boiling points:
(a) Pentan-1-oI, butan-1-oI, butan-2-oI,
ethanol, propan -1-oI, methanol
(b) Pentan -1-oI, n-butane, pentanal,
cthoxyethane.
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