CHAPTER – 11: ALCOHOLS, PHENOLS & ETHERS

SAI Type Questions (2 marks)

13. Anisole undergoes bromination with bromine and Ethanoic acid even in
absence of Iron Bromide Catalyst. Why?
14. Why are aromatic ethers o and p-directing?
15. Alcohols act as Bronsted acid and Bronsted base both. Explain.
16. Write the major product in the following reaction:

17. Complete the reaction:

(OR)

Predict the product of the following reaction:

SA II Type Questions (3 marks)

18. What happens when p-xylene is reacted with concentrated sulphuric acid and
the resultant product is fused with KOH?
19. How will you obtain 1-propanol from 2-propanol (in three steps)?
20. Provide a suitable explanation for the observation that when anisole reacts
with HI, it results in the formation of CH3I and not C6H5I.
21. How can the following conversions be carried out?
(i) Butene to butan-2-ol.
(ii) Anisole to phenol.

(OR)

What happens when C2H5OH is treated with conc. H2SO4 at 443 K? Explain the
mechanism of this reaction.

LA Type Questions (5 marks)

22 (i) Write the distinction test for ethyl alcohol and 2-propanol.
(ii) Of the two hydroxy organic compounds ROH and R'OH, the first one
reacts with acids and the other one reacts with bases to give salt. How
is R different from R'?

23. (i) What is absolute alcohol?

(ii) Arrange the following sets of compounds in order of their increasing boiling
points.
Pentan-1-ol, n-butane, pentanal, ethoxyethane.
(iii) Explain how an -OH group attached to a carbon in the benzene ring
activates benzene towards electrophilic substitution.

24. (a)How will you prepare picric acid from phenol?

(b) (i) Which of the following is an appropriate set of reactants for preparation of
1-methoxy-4 Nitrobenzene and why?
 (ii) Illustrate with examples the limitations of Williamson's synthesis for the
preparation of certain types of ethers.

25. (a) Upon treatment with sulphuric acid, a mixture of ethyl and n-propyl alcohols
yield a mixture of three ethers. What are they?
(b)A mixture of tert-butyl alcohol and ethyl alcohol gives a good yield of a
single ether. What ether is this likely to be? How do one account for this for this
good yield?
(OR)

(i) Between o-nitrophenol and p-nitrophenol, which one is steam volatile

and why?
(ii) The C-O bond length in phenol is less than that in methanol. Why?
(iii) What happens when di-alkyl ether is heated with excess of hydrogen
halide?