QUESTION BANK

CLASS XII (CHEMISTRY)

UNIT 5 : ALCOHOLS, PHENOLS & ETHERS
CASE/SOURCE BASED QUESTIONS
Read the passage given below and answer the following questions

Case1: An efficient, aerobic catalytic system for the transformation of alcohols into carbonyl
compounds under mild conditions, copper-based catalyst has been discovered. This copper-based
catalytic system utilizes oxygen or air as the ultimate, stoichiometric oxidant, producing water as
the only by-product

A wide range of primary, secondary, allylic, and benzylic alcohols can be smoothly oxidized to
the corresponding aldehydes or ketones in good to excellent yields. Air can be conveniently used
instead of oxygen without affecting the efficiency of the process. However, the use of air requires
slightly longer reaction times. This process is not only economically viable and applicable to
large-scale reactions, but it is also environmentally friendly. (Reference:Ohkuma, T., Ooka, H.,
Ikariya, T., &Noyori, R. (1995). Preferential hydrogenation of aldehydes and ketones. Journal of
the American Chemical Society, 117(41), 10417-10418.) The following questions are multiple
choice questions. Choose the most appropriate answer:
1 The Copper based catalyst mention in the study above can be used to convert:
(A) propanol to propanonic acid
(B) propanone to propanoic acid
(C) propanone to propan-2-ol
(D) propan-2-ol to propanone
2 The carbonyl compound formed when ethanol gets oxidised using this copper-based catalyst can
also be obtained by ozonolysis of:
a) But-1-ene
b) But-2-ene
c) Ethene
d) Pent-1-ene
3 Which of the following is a secondary allylic alcohol?
A) But-3-en-2-ol
B) But-2-en-2-ol
C) Prop-2-enol
D) Butan-2-ol
4 Benzyl alcohol on treatment with this copper-based catalyst gives a compound ‘A’ which on
reaction with KOH gives compounds ‘B’ and ‘C’. Compound ‘B’ on oxidation with KMnO4-
KOH gives compound ‘C’. Compounds ‘A’, ‘B’ and ‘C’ respectively are :
(A) Benzaldehyde, Benzyl alcohol, potassium salt of Benzoic acid
(B) Benzaldehyde, potassium salt of Benzoic acid, Benzyl alcohol
(C) Benzaldehyde, Benzoic acid, Benzyl alcohol
(D) Benzoic acid, Benzyl alcohol, Benzaldehyde
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5 An organic compound ‘X’ with molecular formula C3H8O on reaction with this copperbased
 catalyst gives compound ‘Y’ which reduces Tollen’s reagent. ‘X’ on reaction with sodium metal
gives ‘Z’ . What is the product of reaction of ‘Z’ with 2-chloro-2-methylpropane?
a) CH3CH2CH2OC(CH3)3
b) CH3CH2OC(CH3)3
c) CH2=C(CH3)2
d) CH3CH2CH=C(CH3)2
CASE/SOURCE BASED QUESTIONS:2
Whether an alcohol is primary, secondary or tertiary can be determined by taking advantage of
the relative rates at which the three classes of alcohols react with HCl/ ZnCl2 . This is known as
Lucas test. The alcohol is added to a mixture of concentrated HCl and ZnCl2 (the Lucas reagent).
Low molecular weight alcohols are soluble in the Lucas reagent, but the alkyl halide products are
not, so the solution turns cloudy as the alkyl halide is formed. When the test is carried out at
room temperature, the solution turns cloudy immediately if alcohol is tertiary, in about five
minutes if the alcohol is secondary, and remains clear if the alcohol is primary. Because test
relies on the complete solubility of the alcohol in the Lucas reagent, it is limited to alcohols with
fewer than six carbon atoms. Now, the answer following questions
6 The intermediate formed during Lucas Test is ___________________.
(A)Carbocation
(B)Carbanion
(C)Free radical
(D)Carbene
7 Which of the following is least soluble in water?
(A) C2H5OH
(B) C3H4 OH
(C) C4H9 OH
(D) C5H11OH
8 The reaction of Lucas reagent is fastest with:
(A) (CH3)3C-OH
(B) (CH3)2CHOH
(C) CH3CH2CH2OH
(D) CH3CH2OH
9 Excess of ethanol when heated with cone. H2SO4 at 140°C, thecompound obtained is:
(A) ethene
(B) diethyl sulphate
(C) ethoxyethane
(D) ethyl hydrogensulphate
Case 3
Phenols are widely used in household products and as intermediates for industrial synthesis. For
example, phenol itself is used (in low concentrations) as a disinfectant in household cleaners and
in mouthwash. Phenol may have been the first surgical antiseptic. In 1865 the British surgeon
Joseph Lister used phenol as an antiseptic to sterilize his operating field. With phenol used in
this manner, the mortality rate from surgical amputations fell from 45 to 15 percent in Lister’s
ward. Phenol is quite toxic, however, and concentrated solutions cause severe but painless burns
of the skin and mucous membranes. Less-toxic phenols, such as n-hexylresorcinol, have
supplanted phenol itself in cough drops and other antiseptic applications. Butylated
hydroxytoluene (BHT) has a much lower toxicity and is a common antioxidant in foods.

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 Source :https://www.britannica.com/science/phenol
10 Phenol can be used as
a) a disinfectant only
b) a antiseptic only
c) disinfectant as well as antiseptic by changing concentration
d) a antipyretic
11 Butylated hydroxytoluene is a derivative of
a) butanol
b) butanoic acid
c) butane
d) phenol
Case Study – 4
A compound (X) containing C, H and O is unreactive towards sodium. It also does not react with Schiff’s
reagent. On refluxing with an excess of hydroiodic acid, (X) yields only one organic product (Y). On
hydrolysis, (Y) yields a new compound (Z) which can be converted into (Y) by reaction with red phosphorous
and iodine. The compound (Z) on oxidation with potassium permanganate gives a carboxylic acid. The
equivalent weight of this acid is 60.
The following questions are multiple choice questions. Choose the most appropriate answer:
12. The compound (X) is an
(a) acid (b) aldehyde
(c) alcohol (d) ether
13. The IUPAC name of the acid formed is
(a) methanoic acid (b) ethanoic acid
(c) propanoic acid (d) butanoic acid
14. Compound (Y) is
(a) ethyl iodide (b) methyl iodide
(c) propyl iodide (d) mixture of (a) and (b)
15. Compound (Z) is
(a) methanol (b) ethanol
(c) propanol (d) butanol

Case Study – 5

Alcohols and phenols are formed when a hydrogen atom in a hydrocarbon, aliphatic and aromatic respectively,
is replaced by –OH group. These classes of compounds find wide applications in industry as well as in day-to-
day life. For instance, have you ever noticed that ordinary spirit used for polishing wooden furniture is chiefly a
compound containing hydroxyl group, ethanol. The sugar we eat, the cotton used for fabrics, the paper we use
for writing, are all made up of compounds containing –OH groups. Just think of life without paper; no note-

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books, books, newspapers, currency notes, cheques, certificates, etc. The magazines carrying beautiful
photographs and interesting stories would disappear from our life. It would have been really a different world.
An alcohol contains one or more hydroxyl (OH) group(s) directly attached to carbon atom(s), of an aliphatic
system (CH3OH)

Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important
intermediates in organic synthesis. A multistep synthesis may use Grignard-like reactions to form an alcohol
with the desired carbon structure, followed by reactions to convert the hydroxyl group of the alcohol to the
desired functionality. The most common reactions of alcohols can be classified as oxidation,
dehydration, substitution, esterification, and reactions of alkoxides.
Alcohols are versatile compounds. They react both as nucleophiles and electrophiles. The bond between O–H is
broken when alcohols react as nucleophiles.
16. Which of the Following is true?

a. Lower alcohols are liquid at room temperature and the higher ones are solid

b. Lower alcohols and higher alcohols, both are liquid at room temperature

c. Higher alcohols are liquid at room temperature and the lower ones are solid

d. Both lower and higher alcohols are solid at room temperature

17. Identify the nucleophile that attacks the carbocation in the second step of acid catalysed hydration of
alkene?

(a) OH- (b) H2O

(c) H+ (d) H3O+

18. Which of the following is a dihydric alcohol?

(a) Glycerol (b) Catechol
(c) Resorcinol (d) Ethylene glycol
19. Which of the following terms does not describe CH2=CH-CH2OH?
(a) Primary (b) Monohydric
(c) Allylic (d) Vinylic
Case 5 :Read the passage given below and answer the following questions:
Dehydration of alcohols can lead to the formation of either alkenes or ethers. This dehydration can be carried
out either with protonic acid such as conc. H2SO4, H3PO4 or catalysts such as anhydrous ZnCl2or Al2O3. When
primary alcohols are heated with conc. At 433K-443K, they undergo intramolecular dehydration to form
alkenes. Secondary and tertiary alcohols undergo dehydration under milder n. The ease of dehydration of
alcohols follows the order : 3o>2o>1o. The dehydration of alcohols always occurs in accordance with the
Saytzeff’s rule. Primary alcoholswhen heated with protic acid at 413K, gives dialkyl ether.

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20.. Which one of the following alcohols undergoes acid-catalysed
acid catalysed dehydration to alkenes most readily
(a) (CH3)2CHCH2OH (b) (CH3)3COH
(c) CH3CHOHCH3 (d) CH3CH2CH2OH
21.. Dehydration of alcohol is an example of which type of reaction
(a) substitution(b) elimination
(c) addition (d) rearrangement
22.. The alcohol which does not give a stable compound on dehydration is
(a) ethyl alcohol (b) methyl alcohol
(c) n-propyl alcohol (d) n-butyl
butyl alcihol

Case 6: Read the passage given below and answer the following questions:
Alcohols consist of two parts, s, an alkyl group and a hydroxyl group. The properties of alcohols are chiefly due
to the hydroxyl group. The nature of alkyl group simply modify these properties. The boiling points of alcohols
increase with increase in the number of carbon atoms (increase
(increase in van der Waals forces).In alcohols, the boiling
points decrease with increase of branching in carbon chain. Boiling points of alcohols are higher in comparison
to other classes of compounds of comparable molecular masses. The high boiling points of alcohols
alc are mainly
due to the presence of intermolecular hydrogen bonding in them which is lacking in ethers and hydrocarbons.
Solubility of alcohols in water is due to their ability to form hydrogen bonds with water molecules. The
solubility decrease with increase
ncrease in size of alkyl groups.
23.. The properties of alcohols are chiefly due to
(a) alkyl group (b) aryl group
(c) hydroxyl group (d) all of these
24.. Propanol has higher boiling point than that of of the hydrocarbon, butane due to
(a) hydrogen bonding (b) covalent bonding
(c) ionic bonding (d) all of these
25.Solubility
.Solubility of alcohols in water is due to presence of
(a) carbon (b) hydrogen
(c) hydrogen bonding (d) none of these
26.Solubility of alcohols decreases with increase in size of
(a) alkyl group(b) aryl group
(c) carbonyl group (d) all of these

Case-7

We define alcohols as organic compounds that contain a hydroxyl group that is covalently bonded to a
carbon atom. The general formula of alcohol is R – OH where R is the alkyl group. We can classify alcohols
into three types as primary, secondary and tertiary alcohols.
We know that alcohol is soluble in water. This is because the hydroxyl group in the alcohol has the ability to
form
orm hydrogen bonds with water molecules.
Alcohols that contain smaller hydrocarbon chains are highly soluble in water.
As the hydrocarbon chain length increases, the solubility in water decreases.

Q.27.In
In alcohols hydroxyl group is _________bonded to a carbon atom.
(i) Covalently
(ii)Ionic

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(iii)both (i) and (ii)
(iv) None of the above

Q.28.As the hydrocarbon chain length increases the solubility in water ____________
(i) increases
(ii) decreases
(iii) reamains same
(iv) None of the above
Case 8- When alcohol reacts with protic acids it tends to lose a molecule of water in order to form alkenes.
These reactions are generally known as dehydration of alcohols. It is a basic example of an elimination reaction.
The rates differ for the primary, secondary and tertiary alcohols. The carbocation is very much stable in the case
of tertiary alcohols; hence the rate of dehydration is highest for tertiary alcohols as compared to secondary and
primary alcohols. Dehydration can be performed in a 3 step mechanism:
1. Formation of protonated alcohol
2. Formation of carbocation
3. Formation of alkenes

Q.29. Dehydration of alcohols is which type of reaction-

(i) Substitution biomolecular reaction
(ii) Substitution unimolecular reaction
(iii) Elimination reaction
(iv) All of the above
Q.30. Which is the most stable Carbocation?
(i) Primary Carbocation
(ii) Secondary Carbocation
(iii) Tertiary Carbocation
(iv) both (i) and (iii)
Case 9: Phenol is the organic compound containing benzene ring bonded to a hydroxyl
group. They are also known as carbolic acids. Phenols reacts with active metals like sodium,
potassium to form phenoxide .This reaction of phenol with metals indicates its acidic nature .Phenol
reacts with aqueous NaOH to produce phenoxide ions .This indicates that the acidity of phenol is
higher in comparison to the alcohol and water molecules.
31 Select the incorrect statement
(A) Phenol is acidic due to polar nature of -OH group
(B) An electron withdrawing group increases the electron density on oxygen
(C) An electron releasing group increases the electron density on oxygen
(D) Alcohols are less acidic than phenol.

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32 Phenol is acidic, so it react with metal like
(A) Iron
(B) zinc
(C) sodium
(D) cobalt

Case 10: Read the passage given below and answer the following questions-

Ethers are readily cleaved by HI or HBr at 373K to form an alcohol and alkyl halide

R-O-R + HX →R-X + R-OH

R-OH +HX→R-X + H2O

Mixed ether containing primary,or secondary alkyl group when heated with hydrogen halide,the lower alkyl
group forms halide and higher will form an alcohol.Tertiary alkyl ether when heated with hydrogen halide gives
tertiary alkyl halide.

33. Among the following ethers,which one will produce methyl alcohol on treatmaent with hot concentrated HI

a) b)

c) d)

34. When reacts with one mole of HI ,one of the products formed is

a)ethane
b)ethanol
c)iodoethene
d)ethanol
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35. Which of the following cannot be made by using Williamson Synthesis:
(a) Methoxybenzene
(b) Benzyl p-nitrophenyl ether
(c) tert. butyl methyl ether
(d) Ditert. butyl ether

36. The ether

H2
O C

37. when treated with HI produces

Case 11: An organic compound (A) having molecular formula C6H6O gives a characteristic colour with
aqueous FeCl3 solution.On treatment with CO2 and NaOH at 400K under pressure gives B,which on
acidification gives a compound C.The compound C reacts with acetyl chloride
chloride to give D which is popular pain
killer.
38. Compound A is
a)2-hexanol
b)dimethyl ether
c)phenol
d)2-methyl pentanal

39. Number of carbon atoms in compound D is

a)7
b)6
c)8
d)9
40. The conversion of compound A to C is known as
a)Reimer Tiemann reaction
b)Kolbe’s reaction
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c)Schmidt reaction
d)Swarts reaction
41. Compound C is
a)salicylic acid
b)salicylaldehyde
c)benoic acid
d)benaldehyde
ANSWER KEY
1 D 11 D 21 b 31 B
2 B 12 (d) ether 22 b 32 C
3 A 13 (b) ethanoic acid 23 C 33 a
4 A 14 (a) ethyl iodide 24 A 34 d
5 C 15 (b) ethanol 25 C 35 d
6 A 16 (i) 26 a 36 a
7 D 17 (b) H2O 27 (i) 37 c
8 A 18 (d) Ethylene glycol 28 (ii) 38 d
9 C 19 (d) Vinylic 29 (iii) 39 b
10 C 20 B 30 (iii) 40 a

The questions submitted by the PGTs (Chemistry) of KVs of Bhubaneswar, Guwahati,

Kolkata, Ranchi, Silchar and Tinsukia Regions.
Vetted by: Tinsukia Region

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