CHAPTER : 11 ALCOHOL , PHENOL & ETHER

2022 TERM I
Q1 Which of the following intermediates is formed in the reaction in shown
below-
Ans. Both CH3CH2OH2 cation and CH3-CH2 carbocation
Q2 The reaction is an example of

And Reimer Tiemann reaction

Q3 In the following reaction,
PhCH=CH2 + B2H6 (H2O2/OH—) ---- (?)
The product formed is ?
Ans. PhCH2-CH2-OH
Q4 Phenol is more acidic than ethanol because ?
Ans. Phenoxide ion is more stable than ethoxide ion.
Q5 The structure of the major product expected from the mononitraton of 3-
methylphenol will be
Ans 4-Nitro-3-methylphenol
Q6 Phenylethanol may be prepared by the reaction of C6H5MgBr with
Ans CH3-CHO
Q7 Assertion (A)Reaction of (CH3)3-C-Br with CH3-ONa gives majorily 2-
methylpropene.
Reason (R) CH3-ONa acts as a strong base.
Q8 Complete the following analogy
o-nitrophenol:A::o-cresol:B
ans A more acidic than phenol B less acidic than phenol
2021 exam suspended due to covid 19
2020 SET 1
For question 1 choose any one option from following four options.
(A) Both Assertion (A) and Reason (R) are correct statements, and Reason (R) is the correct
explanation of the Assertion (A).
(B) Both Assertion (A) and Reason (R) are correct statements, but Reason (R) is not the correct
explanation of the Assertion (A).
(C) Assertion (A) is correct, but Reason (R) is wrong statement.
(D) Assertion (A) is wrong, but Reason (R) is correct statement.

Q1 Assertion (A): (CH3)3C-O-CH3gives (CH3)3C-I and CH3-OH on treatment with HI.

Reason (R) :.The reaction occurs by SN1 mechanism. Ans. A
Q2 Write the product(s) of the following reactions;
(i)
 + PCC ------------------- ?

(ii) + (CH3CO)2O/CH3COOH------------ ?

(iii) + CH3MgBr/H3O+ ---------------- ?

OR
(a) Write the mechanism of the following SN1 reaction.
(CH3)3-C-Br + Aq. NaOH -------------------- (CH3)3-OH + NaBr
(b) Write the equation for the preparation of 2-methyl-2-methoxypropane by
Williamson synthesis.

2019
Q1(a)Give equations of the following reactions
(i) Phenol is treated with conc. HNO3.
(ii) Propene is treated with B2H6 followed by H2O2/OH-.
(iii) Sodium t-butoxide is treated with CH3Cl.
(b) How will you distinguish between butan-1-ol and butan-4-ol?
(c) Arrange the following in increasing order of acidity?
Phenol, ethanol, water
OR
(a) How can you obtain Phenol form (i) Cumene (ii) Benzene sulphonic acid
(iii) Benzene diazoniumchoride?
(b) Write the structure of the major product obtained from dinitration of 3-
methylphenol/
(c) Write the reaction involed in Kolbe’s reaction.
2018
1. Write the structure of the main products in the following reaction:

(i) ?
?

(ii)

(iii) ------------ ?
2017
1.(a) Arrange the following compound in increasing order of their acidic
strength :
p-cresol; p-nitrophenol& phenol
(b) Write the mechanism (using curved arrow notation) of the following
reaction:
CH2=CH2 H3O+ CH3-CH2+ + H2O

OR
Write the structure of the products when Butan-2-ol reacts with the following:
(i)CrO3
(ii)SOCl2
2016
Q1. Write the chemical equations involved in
1. Kolbe’s reaction
2. Friedal craft Acetylation of Anisole
OR
Q. How do you convert
1. Phenol to Toluene
2. Formaldehyde to Ethanol
Q2. Give reasons for the following :
1. Protonation of phenols is difficult whereas ethanol easily undergoes protonation.
2. Boiling point of ethanol is higher than that of CH 3-O-CH3
3. Anisole on reaction with HI gives phenol and CH 3-I as main products and not
Iodobenzene and CH3-OH.
2015

Q1. IUPAC name of

Q2 Give reasons for the following :
1. p – nitrophenol is acidic than p – methyl phenol.
2. Bond length of C-O in phenol is shorter than that in methanol.
3. (CH3)3 C-Br on reaction with sodium methoxide (Na +- O-CH3) gives alkene as the main
product and not an ether.

2014
Q1. Write the equations involved in the following reactions:
1. Reimer – Tieman reaction
2. Williamson Synthesis
Q2. Write the mechanism of the following reaction.
CH3-CH2-OH + HBr ----------------CH3-CH2-Br + H2O
2013
Q1. Explain the mechanism of the following reaction:
H+ (443K)
CH3-CH2-OH ----------------- CH2=CH2+ H2O

Q2. Write the equations involved in the following reactions:

 1. Reimer – Tiemann reaction
2. Williamson’s ether synthesis
2012
Q1. Explain the mechanism of acid catalysed hydration of an alkene to form corresponding alcohol.
Q2. Explain the following behaviours
1. Alcohols are more soluble in water than the hydrocarbons of the comparable molecular
masses.
2. Ortho nitrophenol is more acidic than orthomethoxy phenol.
2011
Q1. How would you obtain the following:-
1. Benzoquinone from phenol
2. 2 methyl propan2ol from methyl Magnesium bromide
3. Propan2ol from propene
4. Ethanol to ethene

2010
Q1. Convert following:
1. Phenol to Benzoquinone
2. Propanone to 2 methyl propan2ol
3. Propene to propan2ol

2009
Q1. Explain
1. The boiling point of ethanol is higher than that of methoxymethane
2. Phenol is more acidic than ethanol
3. O & P nitrophenols are more acidic than phenol.

2008
Q1. (a) Name the reagents and write the chemical equations for the preparation of the following
compounds by Williamson’s synthesis
1. Ethoxy – Benzene
2. 2-methyl-2-methoxy propane

(b) Why do phenols not give the protonation reaction readily?

Q2 IUPAC name of
CH3-O-CH2-CH(CH3)-CH2-CH3
2007
Q1. How can the following conversion be carried out
1. Propene to Propan2ol
2. Anisole to Phenol
Q2 Write one chemical reaction for Fischer esterification.
2007 SET II
Q1 How is if that alcohol and water are miscible in all proportion?
2007 SET III
Q1 convert (i)methanol to ethanol and (ii) ethanol to acetone
2006
Q1. Give reason: 1. Ortho-nitrophenol is more acidic than ortho-methoxyphenol
2 Glycerol is used in cosmetics
Q2 Give equation for coupling reaction.
2005
Q1. Explain how an –OH group attached to a carbon in the benzene ring activates benzene towards
electrophilicsubstitution.
Q2. Write the equations involved in the following reactions:
a. Reimer – Tiemann reaction
b. Williamson’s ether synthesis
2004
Q1. What happens when ethanol is heated with con.Sulphuric acid at 473K. Explain the mechanism
of this reaction?
Q2. Conversion:
1. Methanal to propan1ol
2. Benzyl alcohol to benzoic acid
2003
Q1 Complete the following reaction
1

Q2 Write the reactions and their conditions only for the preparation of phenol to salicylic acid.
2003 SET II
Q1 Complete the following reactions
1. (CH3)2CH-OH + PCl5 ----------- ?
2. (CH3)3C-X +NaOH ------------ ?

2002
Q1 Conversions
1. Ethene to ethanol ii. Chlorobenzene to phenol iii ethanal to 2-propanol
OR
1. Chlorobenzene to phenol 2. Phenol to 4-bromophenol 3. Phenol to 2acetoxybenzoic acid
Q2 Write the reactions and their conditions only for the commercial preparation of phenol from
cumene
Q2 Arrange the following sets of compounds in order of their increasing boiling points.
Q3 Write one distinguish test between ethyl alcohol and 2-propanol.
Q4 IUPAC name of
-

2002 SET II
Q1 Mention two important uses of methanol
Q2Give the structural formula and name of the product when phenol is treated with an excess of
aqueous bromine.
Q3 Give suitable reason for the statement
1. Ether possess a dipole moment even if the alkyl radicals in the molecule are identical.
Q4 IUPAC name of

2001
Q1 Why it is that phenol is acidic and hexanol is neutral toward a solution of NaOH.
Q2. Find out A and B in following reaction
---------
2001 SET II
Q1. Explain why phenols do not undergo substitution of the –OH group like alcohols.
2000
Q1 IUPAC name of (CH3)3COH.
Q2 Account for followings
2. Alcohols act as weak bases.
3. Phenols exhibit an acidic character.
4. Ether possess a dipole moment ecen if the alkyl radicals in the molecule are identical.
5. Identify A,B,C and D in the following reaction.

--------
Q4 Describe following with an example
1. Protonation 2. Acetylation
2000 SET II
Q1. Account for followings
1. Phenol has a smaller dipole moment than methanol.
2. Phenols do not give protonation reactions readily.
Q2 Describe following with an example 1. Trans-esterification