Previous HSE questions and answers for the chapter “Alcohols, Phenols and Ethers”

1. The bond angle in C-O-H in alcohols is slightly less than tetrahedral angle.
a) Give the reason for the difference in the bond angle observed in alcohol. (1)
b) What is the bond angle in C-O-H in phenol? Give the reason for the variation. (2)
c) Alcohols undergo dehydration. How is ethanol converted to ethene? (1) [March 2008]
Ans: a) It is due to the repulsion between the 2 unshared electron pairs of oxygen.
b) The C-O-H bond angle in phenol is 1090. It is due to the repulsion between unshared electron pair on
oxygen atom and due to the presence of bulky phenyl group.
c) Ethanol on heating with concentrated H2SO4 at 443 K, undergoes dehydration to form ethene.

2. Williamson’s synthesis is an important method of ether synthesis.

a) To synthesis tertiary butyl ether, which of the following reagent sets are better? Justify.
i) (CH3)3C-Br + CH3ONa
ii) (CH3)3C-ONa + CH3-Br. (2)
b) Explain the cleavage of C-O in CH3-CH2-O-CH3 when treated with HI. (1) [March 2009]
Ans: a) The set of reagents (CH3)3C-ONa & CH3-Br are suitable for the preparation of tert-butyl ether. If
the alkoxide used is primary, dehydrohalogenation occurs and the product formed is an alkene. This is
because of the strong basic character of 10 alkoxide.
b) In the case of ethers containing two different alkyl groups, the lower alkyl group forms the alkyl
halide.
CH3-O-CH2-CH3 + HI CH3-I + CH3-CH2-OH
3. Phenols are more acidic than alcohols.
a) Name the product obtained when phenol is treated with chloroform in the presence of NaOH. (½)
b) Name the above reaction. (½)
c) What is the product obtained when phenol is treated with Conc. HNO 3? (½)
d) Write the structure and IUPAC name of the above product. (1)
e) Ethanol and propane have comparable molecular masses, but their boiling points differ widely.
Which of them have higher boiling points? Substantiate your answer. (1½) [March 2010]
Ans: a) Salycylaldehyde (o-hydroxybenzaldehyde)
b) Reimer-Tiemann reaction
c) Picric acid
d) 2,4,6-trinitrophenol

e) Ethanol has higher boiling point than propane. This is due to inter molecular hydrogen bonding
in ethanol.
4. Ethanol can be prepared by treating HCHO and CH3CH2MgBr.
a) Is the above statement true? (1)
b) Justify your answer. (2) [March 2010]
Ans: a) This is not true.
 b) For the preparation of ethanol, treat formaldehyde (HCHO) with methyl magnesium bromide
(CH3MgBr).
H-CHO + CH3MgBr CH3-CH2-OMgBr H2O CH3-CH2-OH + MgBr(OH)
5. Ethers are generally non-reactive compounds. One of the important reactions of ethers is the action of
HI.
C6H5-O-CH3 HI A + B
Identify A and B. explain the reaction. (4) [March 2011]
Ans: A is phenol (C6H5-OH) and B is iodomethane (CH3-I)
C6H5-O-CH3 HI C6H5-OH + CH3-I
Here the O-CH3 bond is weaker than the O–C6H5 bond. This is because the carbon of phenyl
group is sp2 hybridised and there is a partial double bond character.
6. Mixture of Conc. HCl and anhydrous ZnCl2 is an important reagent which helps to distinguish between 10,
20 and 30 alcohols.
a) Give the name of the above reagent. (½)
b) Give one example each for 10, 20 and 30 alcohols. (1½)
c) Explain how the above reagent helps to distinguish above three types of alcohols. (2) [SAY 2011]
Ans: a) Lucas Reagent
b) 10 alcohol – methanol (CH3-OH), 20 alcohol – isopropylalcohol [(CH3)2CHOH] and 30 alcohol – tert-
butyl alcohol [(CH3)3C-OH]
c) Lucas Test: Tertiary alcohols react with Lucas reagent and form immediate turbidity; secondary
alcohols form a turbidity within 5 minutes while primary alcohols do not produce turbidity at room
temperature. But they give turbidity on heating.
7. a) Write the name or structure of the compounds A and B in the following reactions:
A CHCl3 + NaOH C6H5OH NaOH/CO2 B
H + H+ (2)
b) Vapours of an alcohol ‘C’ on passing over heated copper produce compound ‘D’. ‘D’ on reaction with
CH3MgCl followed by hydrolysis produces 2-methylbutan-2-ol. Write the name or structure of
compounds ‘C’ and ‘D’. (2) [March 2012]
Ans: a) A is salicylaldehyde and B is salicylic acid

Salicylic Acid
b) C is butan-2-ol and D is butanone.
CH3-CH2-CHOH-CH3 hot Cu CH3-CH2-CO-CH3 CH3MgCl/H2O CH3-CH2-C(OH)-CH3
Butan-2-ol Butanone
CH3
8. Methanol and ethanol are two commercially important alcohols.
i) Write one method of preparation of methanol and ethanol. (2)
ii) Name the products obtained when ethanol is treated with CrO3 in anhydrous medium. (1)
iii) The boiling point of ethanol is higher than that of methoxy methane. Give reason. (1) [SAY 2012]
Ans: i) Formaldehyde on reduction using LiAlH4, gives methanol, while acetaldehyde gives ethanol.
R-CHO + [H] LiAlH4 R-CH2OH
R2CO + [H] LiAlH4 R2CH-OH
ii) Ethanal or acetaldehyde [CH3-CH2-OH CrO3 CH3-CHO]
iii) This is due to the presence of inter molecular hydrogen bonding in ethanol.
9. a) Write the IUPAC names of all the possible isomers with molecular formula C3H8O (1½)
 b) Phenol is usually manufactured from cumene. Write the structure of cumene. (½)
c) Primary, secondary and tertiary alcohols can be distinguished by Lucas test.
i) What is Lucas reagent? (½)
ii) Write the observations, for primary, secondary and tertiary alcohols in Lucas test. (1½) [March 2013]
Ans: a) CH3-CH2-CH2OH – Propan-1-ol, CH3-CHOH-CH3 – Propan-2-ol and CH3-O-CH2-CH3 –
Methoxyethane
b) Cumene is isopropylbenzene (2-phenyl propane). Its structure is:

c) i) Lucas reagent is a mixture of Conc. HCl and anhydrous ZnCl2

ii) Tertiary alcohols react with Lucas reagent and form immediate turbidity; secondary alcohols
form turbidity within 5 minutes while primary alcohols do not produce turbidity at room
temperature.
10. How are the following conversions carried out? Represent the chemical reactions.
a) Ethanol to ethanal (1)
b) Phenol to picric acid (1)
c) Phenol to benzene (1)
d) Phenol to tribromophenol (1) [June 2013]
Ans: a) By oxidation using CrO3.
CH3-CH2-OH CrO3 CH3-CHO
b) By nitration using nitrating mixture.

c) By heating with zinc dust.

d) Bromination using bromine water.

11. a) How will you prepare the following compounds using a Grignard reagent?
i) Primary alcohol
 ii) Secondary alcohol (2)
b) How will you distinguish primary and secondary alcohols using Luca’s test? (1)
c) Write the correct pair of reactants for the preparation of t-butyl methyl ether by Williamson
synthesis. (1) [March 2014]
Ans: a) Formaldehyde (methanal) reacts with Grignard reagent followed by hydrolysis gives primary
alcohols.
H-CHO + RMgX R-CH2-OMgX H2O R-CH2-OH + MgX(OH)
Formaldehyde adduct 10 alcohol
Aldehydes other than formaldehyde, react with Grignard reagent followed by hydrolysis gives secondary
alcohols.
R-CHO + RMgX R2CHOMgX H2O R2CHOH + MgX(OH)
Aldehyde adduct 20 alcohol
b) Refer the answer of question no. 6 (c).
c) Refer the answer of question no. 2 (a).
12. a) Write the name or formula of the following:
i) A simple ether
ii) A mixed ether
iii) A dihydric alcohol
iv) A trihydric alcohol (2)
b) Phenol on treatment with Br2 in CS2 at low temperature gives two isomeric monobromophenols ‘X’
and ‘Y’. But phenol on treatment with bromine water gives a white precipitate ‘Z’. Identify the
products ‘X’, ‘Y’ and ‘Z’. (2) [SAY 2014]
Ans: a) i) CH3 – O – CH3 (Methoxymethane)
ii) CH3-CH2-O-CH3 (Methoxyethane)
iii) HO-CH2-CH2-OH (Ethane-1,2-dial)
iv) HO-CH2-CHOH-CH2OH (Propane-1,2,3-trial)
b) X is 2-Bromophenol, Y is 4-Bromophenol and Z is 2,4,6-tribromophenol.

X = o-bromophenol Y= p-bromophenol Z = 2,4,6-tribromophenol

13. Alcohols are compounds with general formula R-OH.
a) Alcohols are soluble in water. Give reason? (1)
b) i) Explain a method for the manufacture of ethanol. (2)
ii) How will you convert phenol to benzene? (1) [March 2015]
Ans: a)This is because alcohols can form inter molecular hydrogen bonding with water.
b) i) Ethanol can also be manufactured by hydration of ethene in acidic medium.
CH2=CH2 + H2O H+ CH3-CH2-OH
ii) By heating with zinc dust.

Phenol Benzene
14. a) Write a test to distinguish between phenol and alcohol. (1)
b) Write suitable reagent(s) used for the following conversions:
i) CH3-CH2-Cl CH3-CH2-OH
ii) CH3-CH2-OH CH3-CH2-O-CH2-CH3
iii) OH OH
CHO
(3) [SAY 2015]
Ans: a) Phenol gives a white precipitate with bromine water, but alcohol does not. [Phenol gives a
violet colouration with neutral ferric chloride, while alcohol does not].
i) Aq. KOH or NaOH
ii) Conc. H2SO4/413 K
iii) Chloroform (CHCl3) + aq. NaOH followed by acidification
15. a) Complete the following:

(2)
b) Explain the following:
i) Esterification
ii) Williamson Synthesis (2) [March 2016]
Ans: a)

b) i) Esterification: Alcohols and phenols react with carboxylic acids, acid chlorides and acid anhydrides to
form esters.
ii) Williamson Synthesis: Alkyl halide reacts with sodium alkoxide to form ether. This reaction is
called Williamson’s ether synthesis.
R-X + R’-ONa → R-O-R’ + NaX
16. a) Phenol when treated with Conc. HNO3 gives,
(i) o-Nitrophenol (ii) p-Nitrophenol (iii) 2,4,6-Trinitrophenol (iv) a mixture of
o-nitrophenol and p-nitrophenol (1)
b) Methanol and ethanol are two commercially important alcohols. Write one method each for the
preaparation of methanol and ethanol. (3) [SAY 2016]
 Ans: a) 2,4,6-Trinitrophenol
b) Refer the answer of question no. 8 (i)
17. a) Arrange the following compounds in the order of increasing boiling points:
Ethanol, Propan-1-ol, Butan-1-ol, Butan-2-ol (1)
b) In the lab, students were asked to carry out the reaction between phenol and conc. HNO 3. But one
student, ‘A’ carry out the reaction between phenol and dil. HNO3. Do you think the student ‘A’ got the
same result as others. Substantiate with suitable explanations. [also write the chemical equations
wherever necessary]. (3) [March 2017]
Ans: a) Ethanol < Propan-1-ol < Butan-2-ol < Butan-1-ol
b) With dil. HNO3, phenol gives a mixture of ortho and para nitrophenols, but with conc. HNO3, it gives
2,4,6 –trinitrophenol (Picric acid)

18. a) Identify the product:

HCHO CH3MgX/H2O ……………..

i) CH3OH ii) CH3CH2OH iii) CH3-CH-CH3 iv) CH3-CH-CH2-CH3 (1)

OH OH
b) Complete the following:

(3) [SAY 2017]

Ans: a) CH3-CH2-OH

b) (i) Picric acid OR, 2,4,6-Trinitrophenol OR,

(ii) Salicylaldehyde OR, o-hydroxybenzaldehyde OR,

 (iii) C6H5-OH + CH3-I [Phenol + Methyl iodide]

19. (a) Grignard reagents are important class of organometallic compounds used to prepare alcohols.
Identity the compounds A and B and write the formula.

(b) Write the name of products formed when salicylic acid is treated with acetic anhydride in acid
medium. (4) [March 2018]
Ans: a) (i) A : CH3CH2OH
(ii) B: CH3-CHO
(b) Acetylsalicylic acid (aspirin) and acetic acid

20. (a) Predict the products A and B.

3CH3 - CH =CH2 + (H - BH2)2 A H2O2/OH- B

(b) How methanol is prepared industrially? (4) [SAY 2018]

Ans: a) A is triethylborane [(CH3-CH2-CH2)3B] and B is propan-1-ol [CH3-CH2-CH2-OH]
b) Methanol is industrially prepared by the catalytic hydrogenation of carbon monoxide at about 573-
673 K temperature and 200-300 atm pressure and in the presence of ZnO – Cr2O3 catalyst.

21. Write the chemical equation representing Reimer-Tiemann reaction. (2)

Ans: Phenol when treated with chloroform in the presence of sodium hydroxide, followed by
acidification, we get salicylaldehyde (o-hydroxybenzaldehyde). This reaction is known as Reimer -
Tiemann reaction.

22. Give the structural formula and IUPAC name of the product formed by the reaction of propanone with
CH3MgBr in dry ether, followed by hydrolysis. (2)
Ans: The product formed is (CH3)3C-OH.
Its IUPAC name is 2-Methylpropan-2-ol
23. Predict the products obtained by the reaction of 2-methoxy-2-methylpropane with HI. (2) [March 2019]
Ans: (CH3)3C-I (tert-butyl iodide or 2-Iodo-2-methylpropane) and CH3-OH (methyl alcohol or methanol)
24. Write the preparation of propan-2-ol from a Grignard reagent. (2)
Ans: Acetaldehyde (ethanal) reacts with methyl magnesium bromide followed by acidification, we get
propan-2-ol.
CH3-CHO + CH3MgBr CH3-CH-OMgBr H2O/H+ CH3-CHOH-CH3 + MgBr(OH)
25. Phenols are acidic. Why? (2)
Ans: In phenols, the –OH group is directly bonded to an sp2 hybridized carbon atom of the benzene ring.
Due to the greater electronegativity of sp2 hybridized carbon, the benzene ring acts as an electron
withdrawing group. So it is easy to remove the hydrogen atom as H+ ion and thus phenol is acidic in
nature.
26. (a) What is cumene? Explain the preparation of phenol from cumene. (3)
(b) Identify the compound A.
OH
A
Na2Cr2O7/H2SO4 (1) [SAY 2019]

Ans: (a) Cumene is isopropylbenzene (2-phenyl propane).

When cumene is oxidised in presence of air followed by hydrolysis in presence of acid, we get phenol.

(b) A is benzoquinone.

27. Ethanol and methoxymethane are functional isomers. But ethanol has higher boiling point than
methoxymethane. Give reason. (2)
Ans: This is due to the presence of inter molecular hydrogen bonding in ethanol, which is absent in
methoxymethane.
28. (a) A mixture of anhydrous ZnCl2 and conc. HCl is an important reagent used to distinguish primary,
secondary and tertiary alcohols. How the above reagent is used to distinguish the three types of
alcohols? (3)
(b) Predict the product formed in the reaction CH3-CH2-OH Conc. H2SO4 ? (1) [March 2020]
443K
Ans: (a) Refer the answer of question no. 6 (c)
(b) Ethene (CH2=CH2)
OH
29. (a) X NaOH + CHCl3 CHO
340 K
o – Hydroxybenzaldehyde
Identify X and name the reaction. (2)
(b) How can the following conversions be effected:
(i) Phenol Benzene (1)
(ii) Phenol 2, 4, 6-Trinitrophenol (1) [SAY 2020]
Ans: (a) X is phenol (C6H5-OH) and the reaction is Reimer-Tiemann reaction.
(b) Refer the answer of question no. 10.
30. Explain the following reactions (i) Reimer-Tiemann reaction (ii) Williamson's synthesis. (3)
 Ans: (i) Reimer-Tiemann Reaction: Phenol when treated with chloroform in the presence of
NaOH, followed by acidification, we get salicylaldehyde (o-hydroxybenzaldehyde).

(ii) Williamson’s synthesis: Alkyl halide reacts with sodium alkoxide to form ether. This reaction
is called Williamson’s ether synthesis.
R-X + R’-ONa → R-O-R’ + NaX
31. (i) How are the following conversions carried out?
A. Propene to Propan-2-ol.
B. Ethanal to Ethanol. (2)
(ii) Name the enzyme which converts glucose to ethanol. (1) [March 2021]
Ans: (i) A. Propene reacts with water in the presence of acid as catalyst to form propan-2-ol.
CH3-CH=CH2 + H2O H+ CH3-CH(OH)-CH3
B. Ethanal when reduced using lithium aluminium hydride (LiAlH4) or sodium borohydride
(NaBH4) or on catalytic hydrogenation, we get ethanol.
CH3-CHO + [H] LiAlH4 CH3-CH2OH
(ii) Zymase
32. (i) Which among the following alcohols has the highest boiling point?
(A) CH3OH (B) CH3 – CH2 – CH2 – CH2 – OH (C) CH3 – CHOH– CH2 – CH3 (D) CH3 – CH2 – CH2 – OH (1)
(ii) Phenol is more acidic than ethanol. Why? (2)
Ans: (i) (B) CH3 – CH2 – CH2 – CH2 – OH
(ii) This is due to the following reasons:
In alcohol, the O-H group is directly bonded to an sp3 hybridized carbon atom, but in phenol, it is
bonded to more electronegative sp2 hybridized carbon. So the ease of cleavage of O-H bond is greater
on phenol and hence it is more acidic than alcohol.
The alkoxide ion (R-O-) formed by the ionization of alcohol is not resonance stabilized. But the phenoxide ion
(C6H5-O-) formed by the ionization of phenol is resonance stabilized. SO phenol readily loses H+ and hence it is
more acidic.
[OR, This is due to the greater electronegativity of sp2 hybridised carbon atom to which –OH group is
attached in phenol and the greater stability of the phenoxide ion formed during the ionisation of
phenol.]
33. Explain Lucas test to distinguish primary, secondary and tertiary alcohols. (3) [SAY 2021]
Ans: Refer the Answer of the Question number 6 (c).
34. Give a reagent which is used to distinguish 10, 20 and 30 alcohols. (1)
Ans: Lucas reagent (Conc. HCl and anhydrous ZnCl2)
35. (i) Alcohols and phenols have higher boiling points. Why? (1)
(ii) What is aspirin? How is it prepared from salicylic acid? (2)
Ans: (i) This is due to the inter molecular hydrogen bonding in alcohols and phenols.
(ii) Aspirin is acetyl salicylic acid. It is prepared by the acetylation of salicylic acid.
36. (i) Identify A and B in the following reaction (1)

(ii) What is meant by hydroboration - oxidation reaction? Illustrate it with an example. (2) [March 2022]
Ans: (i) A is Phenol (C6H5-OH) and B is Methyl iodide (CH3-I)
(ii)Alkenes add diborane to give trialkyl boranes as addition product. This on oxidation by
hydrogen peroxide in the presence of aqueous sodium hydroxide to form alcohols. This reaction
is known as Hydroboration-oxidation reaction.

37. On heating phenol with chloroform in the presence of NaOH product formed is ________. (1)
Ans: Salicylaldehyde
38. (i) What is “Wood spirit”? (1)
(ii) Explain the commercial preparation of wood spirit. Give the chemical equation. (2)
Ans: (i) Wood spirit is Methanol or Methyl alcohol.
(ii) It is manufactured by the catalytic hydrogenation of carbon monoxide at about 573-673 K
temperature and 200-300 atm pressure and in the presence of ZnO – Cr2O3 catalyst.

39. Predict A and B

(2) [SAY 2022]

Ans: A is CH3-CH2-CH2-OH (Propan-1-ol or n-Propyl alcohol and
B is CH3-CH2-CH2-CHO [Butanal]